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Revision as of 12:24, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 472074449 of page Rifampicin for the Chem/Drugbox validation project (updated: 'ChEBI', 'ChemSpiderID', 'DrugBank', 'ChEMBL', 'StdInChI', 'StdInCh...  Latest revision as of 05:12, 30 October 2024 edit Tsarivan613 (talk | contribs)Extended confirmed users4,888 editsm →Mechanism of action: Copy editing per MOS:NUMERAL 
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{{short description|Antibiotic medication}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400305846
| verifiedrevid = 477172778
| IUPAC_name = (7''S'',9''E'',11''S'',12''R'',13''S'',14''R'',15''R'',16''R'',17''S'',18''S'',19''E'',21''Z'')-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclotriaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate
| IUPAC_name = (7''S'',9''E'',11''S'',12''R'',13''S'',14''R'',15''R'',16''R'',17''S'',18''S'',19''E'',21''Z'')-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(''E'')-methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclotriaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate
| image = Rifampicin.svg
| image = Rifampicin structure.svg
| width = 220
| width = 275
| alt =
| image2 = Rifampicin 3D 1i6v.png | image2 = Rifampicin 3D 1i6v.png
| width2 = 225
| alt2 =
| USAN = Rifampin


<!--Clinical data--> <!--Clinical data-->
| pronounce = {{IPAc-en|r|ɪ|ˈ|f|æ|m|p|ə|s|ɪ|n}}
| tradename = Rifadin
| tradename = Rifadin, others
| Drugs.com = {{drugs.com|international|rifampicin}}
| Drugs.com = {{drugs.com|monograph|rifampin}}
| MedlinePlus = a682403 | MedlinePlus = a682403
| DailyMedID = Rifampin
| pregnancy_AU = C | pregnancy_AU = C
| routes_of_administration = ], ]

| legal_AU = S4 | legal_AU = S4
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Drug and medical device highlights 2018: Helping you maintain and improve your health | website=] | date=14 October 2020 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/drug-medical-device-highlights-2018.html| access-date=17 April 2024}}</ref>
| legal_UK = POM | legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = Oral, ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 90 to 95% | bioavailability = 90 to 95% (by mouth)
| protein_bound = 80%
| metabolism = ] and intestinal wall
| metabolism = ] and intestinal wall
| elimination_half-life = 1.5 to 5 hours
| elimination_half-life = 3–4 hours
| excretion = 15 to 30% ]<br />60% ]
| excretion = Urine (~30%), faeces (60–65%)


<!--Identifiers--> <!--Identifiers-->
Line 29: Line 41:
| ATC_suffix = AB02 | ATC_suffix = AB02
| ATC_supplemental = {{ATCvet|J54|AB02}} | ATC_supplemental = {{ATCvet|J54|AB02}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28077 | ChEBI = 28077
| PubChem = 5360416 | PubChem = 5381226
| IUPHAR_ligand = 2765
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = <!-- blanked - oldvalue: APRD00207 -->
| DrugBank = DB01045
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10468813 | ChemSpiderID = 10468813
| UNII_Ref = {{fdacite|correct|FDA}}
| NIAID-AIDS = 007228
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = VJT6J7R4TR | UNII = VJT6J7R4TR
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00211 | KEGG = D00211
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 180 --> | ChEMBL = 374478
| NIAID_ChemDB = 007228 | NIAID_ChemDB = 007228
| PDB_ligand = RFP


<!--Chemical data--> <!--Chemical data-->
| C=43 | H=58 | N=4 | O=12 | C=43 | H=58 | N=4 | O=12
| smiles = CN1CCN(CC1)/N=C/c2c(O)c3c5C(=O)4(C)O/C=C/(OC)(C)(OC(C)=O)(C)(O)(C)(O)(C)\C=C\C=C(\C)C(=O)Nc2c(O)c3c(O)c(C)c5O4
| molecular_weight = 822.94 g/mol
| smiles = O=C/2c3c5C(=O)4(O/C=C/(OC)((OC(=O)C)(C)(O)(C)(O)(/C=C\C=C(/C(=O)NC(/C\2=C\NN1CCN(C)CC1)=C(\O)c3c(O)c(c5O4)C)C)C)C)C
| InChI = 1/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,44,49-51,53H,15-18H2,1-10H3,(H,45,55)/b12-11-,19-14+,22-13+,28-20+/t21-,23-,24-,25-,29-,34+,35+,39-,43-/m0/s1
| InChIKey = FZYOVNIOYYPUPY-KMBRGFCMBT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1 | StdInChI = 1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JQXXHWHPUNPDRT-WLSIYKJHSA-N | StdInChIKey = JQXXHWHPUNPDRT-WLSIYKJHSA-N
| synonyms =
| synonyms = <small>5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8--2,7-(epoxypentadecatrienimino)-naphthofuran-1,11(2''H'')-dione 21-acetate</small>
| melting_point = 183 | melting_point = 183
| melting_high = 188 | melting_high = 188
| boiling_point = 937
| boiling_notes = <ref>{{cite web|title=Rifampicin (CAS 13292-46-1)|url=http://www.scbt.com/datasheet-200910-rifampicin.html|website=Santa Cruz Biotechnology Product Block|publisher=Santa Cruz Biotechnology|access-date=14 November 2014|url-status=live|archive-url=https://web.archive.org/web/20141127235842/http://www.scbt.com/datasheet-200910-rifampicin.html|archive-date=27 November 2014}}</ref>
}} }}

<!-- Definition and medical uses -->
'''Rifampicin''', also known as '''rifampin''', is an ] ] used to treat several types of ], including ] (TB), ], ], and ].<ref name=AHFS2015>{{cite web|title=Rifampin|url=https://www.drugs.com/monograph/rifampin.html|publisher=The American Society of Health-System Pharmacists|access-date=Aug 1, 2015|url-status=live|archive-url=https://web.archive.org/web/20150907012311/http://www.drugs.com/monograph/rifampin.html|archive-date=2015-09-07}}</ref> It is almost always used together with other antibiotics with two notable exceptions: when given as a "preferred treatment that is strongly recommended"<ref name=CDC2020>{{cite journal | vauthors = Sterling TR, Njie G, Zenner D, Cohn DL, Reves R, Ahmed A, Menzies D, Horsburgh CR, Crane CM, Burgos M, LoBue P, Winston CA, Belknap R | display-authors = 6 | title = Guidelines for the Treatment of Latent Tuberculosis Infection: Recommendations from the National Tuberculosis Controllers Association and CDC, 2020 | journal = MMWR. Recommendations and Reports | volume = 69 | issue = 1 | pages = 1–11 | date = February 2020 | pmid = 32053584 | pmc = 7041302 | doi = 10.15585/mmwr.rr6901a1 | publisher = Centers for Disease Control, Atlanta, GA, USA }}</ref> for latent TB infection; and when used as post-exposure prophylaxis to prevent ] and ] in people who have been exposed to those bacteria.<ref name=AHFS2015 /> Before treating a person for a long period of time, measurements of liver enzymes and blood counts are recommended.<ref name=AHFS2015 /> Rifampicin may be given either ] or intravenously.<ref name=AHFS2015 />

<!-- Side effects and mechanism-->
Common side effects include nausea, vomiting, diarrhea, and loss of appetite.<ref name=AHFS2015 /> It often turns urine, sweat, and tears a red or orange color.<ref name=AHFS2015 /> Liver problems or allergic reactions may occur.<ref name=AHFS2015 /> It is part of the recommended treatment of active tuberculosis during pregnancy, though its safety in pregnancy is not known.<ref name=AHFS2015 /> Rifampicin is of the ] group of antibiotics.<ref name=AHFS2015 /> It works by decreasing the production of ] by bacteria.<ref name=AHFS2015 />

<!-- History, society and culture -->
Rifampicin was discovered in 1965, marketed in Italy in 1968, and approved in the United States in 1971.<ref name=Sensi1983>{{cite journal | vauthors = Sensi P | title = History of the development of rifampin | journal = Reviews of Infectious Diseases | volume = 5 | issue = Suppl 3 | pages = S402–S406 | date = 1983 | pmid = 6635432 | doi = 10.1093/clinids/5.supplement_3.s402 | jstor = 4453138 }}</ref><ref name=Ox2009>{{cite book|title=Oxford Handbook of Infectious Diseases and Microbiology|date=2009|publisher=OUP Oxford|isbn=978-0-19-103962-1|page=56|url=https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56|url-status=live|archive-url=https://web.archive.org/web/20151124232554/https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56|archive-date=2015-11-24}}</ref><ref name=Mc2011 /> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> The World Health Organization classifies rifampicin as critically important for human medicine.<ref>{{cite book | vauthors=((World Health Organization)) | year=2019 | title=Critically important antimicrobials for human medicine | edition=6th revision | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | isbn=9789241515528 | hdl-access=free }}</ref> It is available as a ].<ref name=AHFS2015 /> Rifampicin is made by the soil bacterium '']''.<ref name=Mc2011>{{cite book| vauthors = McHugh TD |title=Tuberculosis: diagnosis and treatment|date=2011|publisher=CAB International|location=Wallingford, Oxfordshire|isbn=978-1-84593-807-9|page=219|url=https://books.google.com/books?id=YAGnWQUsCKcC&pg=PA219}}</ref>

== Medical uses ==
]

=== Mycobacteria ===
Rifampicin is used for the treatment of ] in combination with other antibiotics, such as ], ], and ].<ref>{{Cite book | vauthors = ((World Health Organization)) |title=Treatment of tuberculosis: guidelines | edition=Fourth | year=2010 |isbn=978-92-4-154783-3 |publisher=World Health Organization | hdl=10665/44165 }}</ref> For the treatment of tuberculosis, it is administered daily for at least six months.<ref name="isbn0-06-273090-8">{{cite book|author=Long, James W.|title=Essential Guide to Prescription Drugs 1992|url=https://archive.org/details/essentialguidetolong00long|url-access=registration|publisher=HarperCollins Publishers|location=New York|year=1991|pages=|isbn=978-0-06-273090-9}}</ref> Combination therapy is used to prevent the development of resistance and to shorten the length of treatment.<ref name="Erlich">{{cite book | vauthors = Erlich H, Doolittle WF, Neuhoff V | title = Molecular Biology of Rifamycin | location = New York, NY | publisher = MSS Information Corporation | date = 1973 | pages = 44–45, 66–75, 124–130 }}</ref> ] of '']'' to rifampicin develops quickly when it is used without another antibiotic, with laboratory estimates of resistance rates from 10<sup>−7</sup> to 10<sup>−10</sup> per tuberculosis bacterium per generation.<ref name=pmid25118103/><ref name=pmid4991927>{{cite journal | vauthors = David HL | title = Probability distribution of drug-resistant mutants in unselected populations of Mycobacterium tuberculosis | journal = Applied Microbiology | volume = 20 | issue = 5 | pages = 810–814 | date = November 1970 | pmid = 4991927 | pmc = 377053 | doi = 10.1128/aem.20.5.810-814.1970 }}</ref>

Rifampicin can be used alone in patients with ] infections to prevent or delay the development of active disease because only small numbers of bacteria are present. A ] found no difference in efficacy between a 3- to 4-month regimen of rifampicin and a 6-month regimen of isoniazid for preventing active tuberculosis in patients not infected with HIV, and patients who received rifampicin had a lower rate of ].<ref name=pmid23828580/> However, the quality of the evidence was judged to be low.<ref name=pmid23828580>{{cite journal | vauthors = Sharma SK, Sharma A, Kadhiravan T, Tharyan P | title = Rifamycins (rifampicin, rifabutin and rifapentine) compared to isoniazid for preventing tuberculosis in HIV-negative people at risk of active TB | journal = The Cochrane Database of Systematic Reviews | volume = 2013 | issue = 7 | pages = CD007545 | date = July 2013 | pmid = 23828580 | pmc = 6532682 | doi = 10.1002/14651858.CD007545.pub2 }}</ref> A shorter 2-month course of rifampicin and pyrazinamide had previously been recommended but is no longer recommended due to high rates of hepatotoxicity.<ref name=pmid12904741>{{cite journal | title = Update: adverse event data and revised American Thoracic Society/CDC recommendations against the use of rifampin and pyrazinamide for treatment of latent tuberculosis infection--United States, 2003 | journal = MMWR. Morbidity and Mortality Weekly Report | volume = 52 | issue = 31 | pages = 735–739 | date = August 2003 | pmid = 12904741 | url = https://www.cdc.gov/mmwr/preview/mmwrhtml/mm5231a4.htm | author1 = Centers for Disease Control Prevention (CDC) | author2 = American Thoracic Society }}</ref>

Rifampicin should be taken on an empty stomach with a glass of water. It is generally taken either at least one hour before meals or two hours after meals.<ref>{{cite web|title=Rifampin oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing – WebMD|url=http://www.webmd.com/drugs/2/drug-1744/rifampin-oral/details#uses|website=WebMD|access-date=13 November 2014|url-status=live|archive-url=https://web.archive.org/web/20141122113749/http://www.webmd.com/drugs/2/drug-1744/rifampin-oral/details#uses|archive-date=22 November 2014}}</ref>

Rifampicin is also used to treat nontuberculous ] infections including ] (Hansen's disease) and '']''.<ref>{{Cite book|title=The Sanford Guide to Antimicrobial Therapy 2015|year=2015|isbn=978-1-930808-84-3| vauthors = Chambers HF, Gilbert DN, Eliopoulos GM, Saag MS |publisher=Antimicrobial Therapy; 41 edition |url-access=registration|url=https://archive.org/details/sanfordguidetoan00davi_0}}</ref>

With multidrug therapy used as the standard treatment of Hansen's disease, rifampicin is always used in combination with ] and ] to avoid causing drug resistance.{{cn|date=August 2022}}

It is also used in the treatment of '']'' infections as associated with ], usually in combination with ] or other antibiotics.<ref name="pmid26332541">{{cite journal | vauthors = Yotsu RR, Murase C, Sugawara M, Suzuki K, Nakanaga K, Ishii N, Asiedu K | title = Revisiting Buruli ulcer | journal = The Journal of Dermatology | volume = 42 | issue = 11 | pages = 1033–41 | date = November 2015 | pmid = 26332541 | doi = 10.1111/1346-8138.13049 | s2cid = 39768846 | doi-access = free }}</ref>

=== Other bacteria and protozoans ===
In 2008, tentative evidence showed rifampicin may be useful in the treatment of methicillin-resistant ''Staphylococcus aureus'' (]) in combination with other antibiotics, including in difficult-to-treat infections such as osteomyelitis and prosthetic joint infections.<ref>{{cite journal | vauthors = Perlroth J, Kuo M, Tan J, Bayer AS, Miller LG | title = Adjunctive use of rifampin for the treatment of Staphylococcus aureus infections: a systematic review of the literature | journal = Archives of Internal Medicine | volume = 168 | issue = 8 | pages = 805–819 | date = April 2008 | pmid = 18443255 | doi = 10.1001/archinte.168.8.805 | doi-access = free }}</ref> As of 2012, if rifampicin combination therapy was useful for pyogenic vertebral osteomyelitis was unclear.<ref>{{cite journal | vauthors = Pola E, Logroscino CA, Gentiempo M, Colangelo D, Mazzotta V, Di Meco E, Fantoni M | title = Medical and surgical treatment of pyogenic spondylodiscitis | journal = European Review for Medical and Pharmacological Sciences | volume = 16 | issue = Suppl 2 | pages = 35–49 | date = April 2012 | pmid = 22655482 }}</ref> A meta-analysis concluded that adding adjunctive rifampicin to a β-lactam or vancomycin may improve outcomes in staphylococcus aureus bacteremia.<ref>{{cite journal | vauthors = Russell CD, Lawson McLean A, Saunders C, Laurenson IF | title = Adjunctive rifampicin may improve outcomes in Staphylococcus aureus bacteraemia: a systematic review | journal = Journal of Medical Microbiology | volume = 63 | issue = Pt 6 | pages = 841–848 | date = June 2014 | pmid = 24623637 | doi = 10.1099/jmm.0.072280-0 | doi-access = free }}</ref> However, a more recent trial found no benefit from adjunctive rifampicin.<ref>{{cite journal | vauthors = Thwaites GE, Scarborough M, Szubert A, Nsutebu E, Tilley R, Greig J, Wyllie SA, Wilson P, Auckland C, Cairns J, Ward D, Lal P, Guleri A, Jenkins N, Sutton J, Wiselka M, Armando GR, Graham C, Chadwick PR, Barlow G, Gordon NC, Young B, Meisner S, McWhinney P, Price DA, Harvey D, Nayar D, Jeyaratnam D, Planche T, Minton J, Hudson F, Hopkins S, Williams J, Török ME, Llewelyn MJ, Edgeworth JD, Walker AS | display-authors = 6 | title = Adjunctive rifampicin for Staphylococcus aureus bacteraemia (ARREST): a multicentre, randomised, double-blind, placebo-controlled trial | journal = Lancet | volume = 391 | issue = 10121 | pages = 668–678 | date = February 2018 | pmid = 29249276 | pmc = 5820409 | doi = 10.1016/S0140-6736(17)32456-X }}</ref>

It is also used as preventive treatment against ''Neisseria meningitidis'' (]) infections. Rifampicin is also recommended as an alternative treatment for infections by the tick-borne pathogens '']'' and '']'' when treatment with ] is contraindicated, such as in pregnant women or in patients with a history of allergy to tetracycline antibiotics.<ref name=pmid17029130>{{cite journal | vauthors = Wormser GP, Dattwyler RJ, Shapiro ED, Halperin JJ, Steere AC, Klempner MS, Krause PJ, Bakken JS, Strle F, Stanek G, Bockenstedt L, Fish D, Dumler JS, Nadelman RB | display-authors = 6 | title = The clinical assessment, treatment, and prevention of lyme disease, human granulocytic anaplasmosis, and babesiosis: clinical practice guidelines by the Infectious Diseases Society of America | journal = Clinical Infectious Diseases | volume = 43 | issue = 9 | pages = 1089–1134 | date = November 2006 | pmid = 17029130 | doi = 10.1086/508667 | doi-access = free }}</ref><ref name=pmid19681699>{{cite journal | vauthors = Thomas RJ, Dumler JS, Carlyon JA | title = Current management of human granulocytic anaplasmosis, human monocytic ehrlichiosis and Ehrlichia ewingii ehrlichiosis | journal = Expert Review of Anti-Infective Therapy | volume = 7 | issue = 6 | pages = 709–722 | date = August 2009 | pmid = 19681699 | pmc = 2739015 | doi = 10.1586/eri.09.44 }}</ref>

It is also sometimes used to treat infections by '']'' species, '']'', '']'', and '']''. For these nonstandard indications, antimicrobial susceptibility testing should be done (if possible) before starting rifampicin therapy.{{cn|date=December 2022}}

The ], '']'' species, and '']'' species are intrinsically resistant to rifampicin.{{cn|date=August 2022}}

It has been used with ] in largely unsuccessful attempts to treat ] caused by '']''.{{cn|date=August 2022}}

Rifampicin can be used as monotherapy for a few days as prophylaxis against meningitis, but ] develops quickly during long-term treatment of active infections, so the drug is always used against active infections in combination with other antibiotics.<ref>{{cite web|url=http://dermnetnz.org/treatments/rifampicin.html|title=Rifampicin|access-date=August 22, 2014|url-status=live|archive-url=https://web.archive.org/web/20141002044503/http://www.dermnetnz.org/treatments/rifampicin.html|archive-date=October 2, 2014}}</ref>

Rifampicin is relatively ineffective against ], which has led to its use as a selective agent capable of isolating them in materials being cultured in laboratories.<ref name=pmid7309842>{{cite journal | vauthors = Leschine SB, Canale-Parola E | title = Rifampin as a selective agent for isolation of oral spirochetes | journal = Journal of Clinical Microbiology | volume = 12 | issue = 6 | pages = 792–795 | date = December 1980 | pmid = 7309842 | pmc = 273700 | doi = 10.1128/jcm.12.6.792-795.1980 }}</ref>

=== Viruses ===
Rifampicin has some effectiveness against ] virus.<ref name=pmid17055024>{{cite journal | vauthors = Charity JC, Katz E, Moss B | title = Amino acid substitutions at multiple sites within the vaccinia virus D13 scaffold protein confer resistance to rifampicin | journal = Virology | volume = 359 | issue = 1 | pages = 227–232 | date = March 2007 | pmid = 17055024 | pmc = 1817899 | doi = 10.1016/j.virol.2006.09.031 }}</ref><ref name=pmid8289340>{{cite journal | vauthors = Sodeik B, Griffiths G, Ericsson M, Moss B, Doms RW | title = Assembly of vaccinia virus: effects of rifampin on the intracellular distribution of viral protein p65 | journal = Journal of Virology | volume = 68 | issue = 2 | pages = 1103–1114 | date = February 1994 | pmid = 8289340 | pmc = 236549 | doi = 10.1128/JVI.68.2.1103-1114.1994 | author1-link = Beate Sodeik }}</ref>

=== Pathogen susceptibility ===
The minimum inhibitory concentrations of rifampicin for several medically significant pathogens are:
* ''Mycobacterium tuberculosis'' — 0.002 – 64&nbsp;μg/mL
* ''Mycobacterium bovis'' — 0.125&nbsp;μg/mL
* ''Staphylococcus aureus'' (methicillin resistant) — ≤ 0.006–256&nbsp;μg/mL<ref>{{cite web|url=http://antibiotics.toku-e.com/antimicrobial_1018.html|title=Rifampicin (Rifampin) - The Antimicrobial Index Knowledgebase—TOKU-E|work=toku-e.com|url-status=live|archive-url=https://web.archive.org/web/20141209203837/http://antibiotics.toku-e.com/antimicrobial_1018.html|archive-date=2014-12-09}}</ref>
* ''Chlamydia pneumoniae'' — 0.005&nbsp;μg/mL<ref name=pmid9756794>{{cite journal | vauthors = Gieffers J, Solbach W, Maass M | title = In vitro susceptibilities of Chlamydia pneumoniae strains recovered from atherosclerotic coronary arteries | journal = Antimicrobial Agents and Chemotherapy | volume = 42 | issue = 10 | pages = 2762–2764 | date = October 1998 | pmid = 9756794 | pmc = 105936 | doi = 10.1128/AAC.42.10.2762 }}</ref>

===Primary biliary cholangitis===

Rifampicin is used to treat ] caused by ]. The treatment-related adverse effects include ], ], ], and interactions with other drugs.<ref name=Trivedi2017>{{cite journal | vauthors = Trivedi HD, Lizaola B, Tapper EB, Bonder A | title = Management of Pruritus in Primary Biliary Cholangitis: A Narrative Review | journal = The American Journal of Medicine | volume = 130 | issue = 6 | pages = 744.e1–744.e7 | date = June 2017 | pmid = 28238692 | doi = 10.1016/j.amjmed.2017.01.037 | doi-access = free }}</ref> For those reasons as well as some ethical concerns regarding off-label use of antibiotics, rifampin as a very effective preventive antibiotic for meningitis, is not considered appropriate for itchiness.<ref>{{cite journal | vauthors = Parsonage B, Hagglund PK, Keogh L, Wheelhouse N, Brown RE, Dancer SJ | title = Control of Antimicrobial Resistance Requires an Ethical Approach | journal = Frontiers in Microbiology | volume = 8 | pages = 2124 | date = 2 November 2017 | pmid = 29163414 | pmc = 5673829 | doi = 10.3389/fmicb.2017.02124 | doi-access = free }}</ref><ref>{{Cite web | url=https://www.aboutkidshealth.ca/Article?contentid=232&language=English | title=AboutKidsHealth}}</ref><ref>{{cite journal | vauthors = Littmann J, Viens AM | title = The Ethical Significance of Antimicrobial Resistance | journal = Public Health Ethics | volume = 8 | issue = 3 | pages = 209–224 | date = November 2015 | pmid = 26566395 | pmc = 4638062 | doi = 10.1093/phe/phv025 }}</ref>

=== Hidradenitis suppurativa ===
Rifampicin with ] has been used to treat the skin disease ].<ref>{{cite journal | vauthors = Saunte DM, Jemec GB | title = Hidradenitis Suppurativa: Advances in Diagnosis and Treatment | journal = JAMA | volume = 318 | issue = 20 | pages = 2019–2032 | date = November 2017 | pmid = 29183082 | doi = 10.1001/jama.2017.16691 | s2cid = 5017318 }}</ref>

== Adverse effects ==
The most serious ] is hepatotoxicity, and people receiving it often undergo baseline and frequent ] to detect early liver damage.<ref name=":0">{{Cite book|title=Medical-surgical nursing : assessment and management of clinical problems| vauthors = Lewis SM, Dirksen SR, Heitkemper MM, Bucher L, Harding M |date=5 December 2013|isbn=978-0-323-10089-2|edition=9th|location=St. Louis, Missouri | publisher = Elsevier/Mosby |oclc=228373703}}</ref>

The more common side effects include fever, gastrointestinal disturbances, rashes, and immunological reactions. Taking rifampicin usually causes certain bodily fluids, such as urine, sweat, and tears, to become orange-red in color, a benign side effect that nonetheless can be frightening if it is not expected. This may also be used to monitor effective absorption of the drug (if drug color is not seen in the urine, the patient may wish to move the drug dose farther in time from food or milk intake). The discolorization of sweat and tears is not directly noticeable, but sweat may stain light clothing orange, and tears may permanently stain soft contact lenses. Since rifampicin may be excreted in breast milk, breastfeeding should be avoided while it is being taken.{{citation needed|date=May 2018}}

Other adverse effects include:
* Liver toxicity—], liver failure in severe cases
* Respiratory—breathlessness
* Cutaneous—flushing, pruritus, rash, hyperpigmentation,<ref>{{cite journal| vauthors = Thangaraju P, Singh H, Punitha M, Giri VC, Ali MS |journal= Sudan Medical Monitor|title=Hyperpigmentation, a marker of rifampicin overuse in leprosy patient: An incidental finding|volume=10|issue=1|pages=25–26|year=2015|doi=10.4103/1858-5000.157506|s2cid=74136252 |doi-access=free }}</ref> redness and watering of eyes
* Abdominal — ], vomiting, abdominal cramps, ]
* ]—chills, fever, headache, ], and ]. Rifampicin has good penetration into the brain, and this may directly explain some malaise and ] in a minority of users.
* Allergic reaction—rashes, itching, swelling of the tongue or throat, severe dizziness, and trouble breathing<ref>{{cite web|title=Rifampin oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing—WebMD|url=http://www.webmd.com/drugs/2/drug-1744/rifampin-oral/details#uses|website=WebMD|access-date=13 November 2014|url-status=live|archive-url=https://web.archive.org/web/20141122113749/http://www.webmd.com/drugs/2/drug-1744/rifampin-oral/details#uses|archive-date=22 November 2014}}</ref>

== Chemical structure ==
Rifampicin is a ] belonging to the chemical class of compounds termed ]s, so named because of their heterocyclic structure containing a ] core spanned by an aliphatic ansa chain. The naphthoquinonic ] gives rifampicin its characteristic red-orange crystalline color.{{cn|date=August 2022}}

The critical functional groups of rifampicin in its inhibitory binding of bacterial RNA polymerase are the four critical ] groups of the ansa bridge and the naphthol ring, which form ]s with amino acid residues on the protein.<ref name=pmid11290327>{{cite journal | vauthors = Campbell EA, Korzheva N, Mustaev A, Murakami K, Nair S, Goldfarb A, Darst SA | title = Structural mechanism for rifampicin inhibition of bacterial rna polymerase | journal = Cell | volume = 104 | issue = 6 | pages = 901–912 | date = March 2001 | pmid = 11290327 | doi = 10.1016/s0092-8674(01)00286-0 | s2cid = 8229399 | doi-access = free }}</ref>

Rifampicin is the {{Not a typo|3-(4-methyl-1-piperazinyl)-iminomethyl}} derivative of ].<ref>{{Cite book|title=Principles and Practice of Infectious Diseases| vauthors = Bennett J |publisher=Elsevier Health Sciences|year=2015|page=339 }}</ref>

== Interactions ==
Rifampicin is the most powerful known ] of the ] ] enzyme system, including isoenzymes ], ], ], ], ], ], and ].<ref name=drug-interactions.com>{{cite web|url=http://medicine.iupui.edu/clinpharm/DDIs/table.aspx|title=Division of Clinical Pharmacology &#124; Indiana University Department of Medicine|publisher=Medicine.iupui.edu|date=2011-09-27|access-date=2011-11-07|url-status=live|archive-url=https://web.archive.org/web/20111105041126/http://medicine.iupui.edu/clinpharm/ddis/table.aspx|archive-date=2011-11-05}}</ref> It increases metabolism of many drugs<ref>{{Cite web|date=2012-12-26|title=Division of Clinical Pharmacology {{!}} Indiana University Department of Medicine|url=http://medicine.iupui.edu/clinpharm/DDIs/table.aspx|access-date=2021-07-22|archive-url=https://web.archive.org/web/20121226190830/http://medicine.iupui.edu/clinpharm/DDIs/table.aspx|archive-date=2012-12-26}}</ref> and as a consequence, can make them less effective, or even ineffective, by decreasing their levels.<ref name="Collins">{{cite book | vauthors = Collins RD | title = Atlas of Drug Reactions. | location = New York, NY | publisher = Churchill Livingstone | date = 1985 | pages = 123 }}</ref> For instance, patients undergoing long-term anticoagulation therapy with ] have to increase their dosage of warfarin and have their clotting time checked frequently because failure to do so could lead to inadequate anticoagulation, resulting in serious consequences of thromboembolism.<ref>{{cite book | vauthors = Stockley IH | chapter = Anticoagulant Drug Interactions. | title = Drug Interactions | edition = 3rd | location = Boston | publisher = Blackwell Scientific Publications | date = 1994 | pages = 274–275 }}</ref>

Rifampicin can reduce the efficacy of ] or other ] by its induction of the cytochrome P450 system, to the extent that ] have occurred in women who use oral contraceptives and took rifampicin even for very short courses (for example, as prophylaxis against exposure to bacterial meningitis).{{cn|date=August 2022}}

Other interactions include decreased levels and less effectiveness of ], ], ], ], ], ], ], ], ], and ].<ref name=pmid18384456>{{cite journal | vauthors = Riss J, Cloyd J, Gates J, Collins S | title = Benzodiazepines in epilepsy: pharmacology and pharmacokinetics | journal = Acta Neurologica Scandinavica | volume = 118 | issue = 2 | pages = 69–86 | date = August 2008 | pmid = 18384456 | doi = 10.1111/j.1600-0404.2008.01004.x | s2cid = 24453988 | doi-access = free }}</ref>

Rifampicin is antagonistic to the microbiologic effects of the antibiotics gentamicin and amikacin. The activity of rifampicin against some species of mycobacteria can be potentiated by isoniazid (through inhibiting mycolate synthesis)<ref name=pmid9570407>{{cite journal | vauthors = Mdluli K, Swanson J, Fischer E, Lee RE, Barry CE | title = Mechanisms involved in the intrinsic isoniazid resistance of Mycobacterium avium | journal = Molecular Microbiology | volume = 27 | issue = 6 | pages = 1223–1233 | date = March 1998 | pmid = 9570407 | doi = 10.1046/j.1365-2958.1998.00774.x | s2cid = 13764717 | doi-access = free }}</ref> and ambroxol (through host directed effects in autophagy and pharmacokinetics).<ref name=pmid30012752>{{cite journal | vauthors = Choi SW, Gu Y, Peters RS, Salgame P, Ellner JJ, Timmins GS, Deretic V | title = Ambroxol Induces Autophagy and Potentiates Rifampin Antimycobacterial Activity | journal = Antimicrobial Agents and Chemotherapy | volume = 62 | issue = 9 | pages = AAC.01019–18 | date = September 2018 | pmid = 30012752 | pmc = 6125555 | doi = 10.1128/AAC.01019-18 }}</ref>

== Pharmacology ==

=== Mechanism of action ===
]
Rifampicin inhibits bacterial DNA-dependent RNA synthesis by inhibiting bacterial DNA-dependent ].<ref name=pmid4957347>{{cite journal | vauthors = Calvori C, Frontali L, Leoni L, Tecce G | title = Effect of rifamycin on protein synthesis | journal = Nature | volume = 207 | issue = 995 | pages = 417–418 | date = July 1965 | pmid = 4957347 | doi = 10.1038/207417a0 | s2cid = 4144738 | bibcode = 1965Natur.207..417C }}</ref>

Crystal structure data and biochemical data suggest that rifampicin binds to the pocket of the RNA polymerase β subunit within the DNA/RNA channel, but away from the active site.<ref name=pmid11290327/> The inhibitor prevents RNA synthesis by physically blocking elongation, and thus preventing synthesis of host bacterial proteins. By this "steric-occlusion" mechanism, rifampicin blocks synthesis of the second or third ] between the nucleotides in the RNA backbone, preventing elongation of the 5' end of the RNA transcript past more than two or three nucleotides.<ref name=pmid11290327/><ref name=pmid18787125>{{cite journal | vauthors = Feklistov A, Mekler V, Jiang Q, Westblade LF, Irschik H, Jansen R, Mustaev A, Darst SA, Ebright RH | display-authors = 6 | title = Rifamycins do not function by allosteric modulation of binding of Mg2+ to the RNA polymerase active center | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 105 | issue = 39 | pages = 14820–14825 | date = September 2008 | pmid = 18787125 | pmc = 2567451 | doi = 10.1073/pnas.0802822105 | doi-access = free | bibcode = 2008PNAS..10514820F }}</ref>

In a recent study rifampicin was shown to bind to ] and alter its conformation as well as activity towards supporting metabolism of ] via ].<ref>{{cite journal | vauthors = Jensen SB, Thodberg S, Parween S, Moses ME, Hansen CC, Thomsen J, Sletfjerding MB, Knudsen C, Del Giudice R, Lund PM, Castaño PR, Bustamante YG, Velazquez MN, Jørgensen FS, Pandey AV, Laursen T, Møller BL, Hatzakis NS | display-authors = 6 | title = Biased cytochrome P450-mediated metabolism via small-molecule ligands binding P450 oxidoreductase | journal = Nature Communications | volume = 12 | issue = 1 | pages = 2260 | date = April 2021 | pmid = 33859207 | pmc = 8050233 | doi = 10.1038/s41467-021-22562-w | doi-access = free | bibcode = 2021NatCo..12.2260J }}</ref>

=== Mechanism of resistance ===
Resistance to rifampicin arises from mutations that alter residues of the rifampicin binding site on RNA polymerase, resulting in decreased affinity for rifampicin.<ref name=pmid18787125/> Resistance mutations map to the '']'' gene, encoding the beta subunit of RNA polymerase. The majority of resistance mutations in ] are in 3 clusters on ''rpoB''.<ref name=pmid25118103>{{cite journal | vauthors = Goldstein BP | title = Resistance to rifampicin: a review | journal = The Journal of Antibiotics | volume = 67 | issue = 9 | pages = 625–630 | date = September 2014 | pmid = 25118103 | doi = 10.1038/ja.2014.107 | doi-access = free }}</ref> Cluster I is amino acids 509 to 533, cluster II is amino acids 563 to 572, and cluster III is amino acid 687.{{cn|date=December 2022}}

When describing mutations in ''rpoB'' in other species, the corresponding amino acid number in ''E. coli'' is usually used. In ''Mycobacterium tuberculosis'', the majority of mutations leading to rifampicin resistance are in cluster I, in a 81bp hotspot core region called RRDR for "rifampcin resistance determining region".<ref>{{Cite web | vauthors = Pierre-Audiger C, Gicquel B |title=The Contribution of Molecular Biology in Diagnosing Tuberculosis and Detecting Antibiotic Resistance |url=http://www.moleculartb.org/gb/pdf/doc/Revue.pdf |website=Molecular TB |url-status=live |archive-url=https://web.archive.org/web/20170116201943/http://www.moleculartb.org/gb/pdf/doc/Revue.pdf |archive-date=2017-01-16 }}</ref> A change in amino acid 531 from ] to ] arising from a change in the DNA sequence of TCG to TTG is the most common mutation.<ref name=pmid25118103/> Tuberculosis resistance has also occurred due to mutations in the ] region of ''rpoB'' and cluster III.<ref name=pmid25118103/>

An alternative mechanism of resistance is through Arr-catalyzed ] of rifampicin. With the assistance of the enzyme Arr produced by the pathogen&nbsp;''],'' ADP-ribose is added to rifampicin at one of its ansa chain hydroxy groups, thereby inactivating the drug.<ref name=pmid18349144>{{cite journal | vauthors = Baysarowich J, Koteva K, Hughes DW, Ejim L, Griffiths E, Zhang K, Junop M, Wright GD | display-authors = 6 | title = Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 105 | issue = 12 | pages = 4886–4891 | date = March 2008 | pmid = 18349144 | pmc = 2290778 | doi = 10.1073/pnas.0711939105 | doi-access = free | bibcode = 2008PNAS..105.4886B }}</ref>

=== Resistance in tuberculosis ===
Mycobacterial resistance to rifampicin may occur alone or along with resistance to other first-line antitubercular drugs. Early detection of such multidrug or extensively drug-resistant tuberculosis is critical in improving patient outcomes by instituting appropriate second-line treatments, and in decreasing transmission of drug-resistant TB.<ref>{{cite book|title=Policy Framework for Implementing New Tuberculosis Diagnostics|date=2011|publisher=World Health Organization|location=Geneva|url=https://www.who.int/tb/laboratory/whopolicyframework_rev_june2011.pdf|access-date=21 March 2016|url-status=live|archive-url=https://web.archive.org/web/20161009124243/http://www.who.int/tb/laboratory/whopolicyframework_rev_june2011.pdf|archive-date=9 October 2016}}</ref> Traditional methods of detecting resistance involve mycobacterial culture and drug susceptibility testing, results of which could take up to 6 weeks. Xpert MTB/RIF assay is an automated test that can detect rifampicin resistance, and also diagnose tuberculosis. A ] updated in 2014 and 2021 concluded that for rifampicin resistance detection, Xpert MTB/RIF was accurate, that is (95%) sensitive and (98%) specific.<ref>{{cite journal | vauthors = Zifodya JS, Kreniske JS, Schiller I, Kohli M, Dendukuri N, Schumacher SG, Ochodo EA, Haraka F, Zwerling AA, Pai M, Steingart KR, Horne DJ | display-authors = 6 | title = Xpert Ultra versus Xpert MTB/RIF for pulmonary tuberculosis and rifampicin resistance in adults with presumptive pulmonary tuberculosis | journal = The Cochrane Database of Systematic Reviews | volume = 2 | pages = CD009593 | date = February 2021 | issue = 5 | pmid = 33616229 | doi = 10.1002/14651858.CD009593.pub5 | s2cid = 231987831 }}</ref>

===Pharmacokinetics===
Orally administered rifampicin results in peak plasma concentrations in about 2–4 hours. ] (another antituberculosis drug) significantly reduces absorption of rifampicin,<ref>G Curci, A Ninni, A.D'Aleccio (1969) Atti Tavola Rotonda Rifampicina, Taormina, page 19. Edizioni Rassegna Medica, Lepetit, Milano</ref> and peak concentrations may be lower. If these two drugs must be used concurrently, they must be given separately, with an interval of 8 to 12 hours between administrations.{{cn|date=December 2022}}

Rifampicin is easily absorbed from the ] (GI) tract; its ] functional group is quickly ] in ], and it is catalyzed by a high pH and substrate-specific ]. After about 6 hours, almost all of the drug is deacetylated. Even in this deacetylated form, rifampicin is still a potent antibiotic; however, it can no longer be reabsorbed by the intestines and is eliminated from the body. Only about 7% of the administered drug is excreted unchanged in urine, though urinary elimination accounts for only about 30% of the drug excretion. About 60% to 65% is excreted through feces.{{cn|date=August 2022}}

The ] of rifampicin ranges from 1.5 to 5.0 hours, though hepatic impairment significantly increases it. Food consumption inhibits its absorption from the GI tract, and the drug is more quickly eliminated. When rifampicin is taken with a meal, its peak blood concentration falls by 36%. Antacids do not affect its absorption.<ref name=pmid9925057>{{cite journal | vauthors = Peloquin CA, Namdar R, Singleton MD, Nix DE | title = Pharmacokinetics of rifampin under fasting conditions, with food, and with antacids | journal = Chest | volume = 115 | issue = 1 | pages = 12–18 | date = January 1999 | pmid = 9925057 | doi = 10.1378/chest.115.1.12 }}</ref> The decrease in rifampicin absorption with food is sometimes enough to noticeably affect urine color, which can be used as a marker for whether or not a dose of the drug has been effectively absorbed.{{cn|date=August 2022}}

Distribution of the drug is high throughout the body, and reaches effective concentrations in many organs and body fluids, including the ]. Since the substance itself is red, this high distribution is the reason for the orange-red color of the saliva, tears, sweat, urine, and feces. About 60% to 90% of the drug is bound to plasma proteins.<ref name="Hardman">{{cite book | vauthors = Hardman JG, Limbrid LE, Gilman AG | author-link2 = Lee E. Limbird | chapter = Rifampin | title = The Pharmacological Basis of Therapeutics. | edition = 10th | location = United States of America | publisher = The McGraw-Hill Companies | date = 2001 | pages = 1277–1279 }}</ref>
<!-- if you can understand this, please rewrite rifampicin is considered as liver microsomal enzyme inducer lead to "high metabolic rate"-->

== Use in biotechnology ==
Rifampicin inhibits bacterial RNA polymerase, and is commonly used to inhibit the synthesis of host bacterial proteins during recombinant protein expression in bacteria. RNA encoding for the recombinant gene is usually transcribed from DNA by a viral ], which is not affected by rifampicin.{{cn|date=December 2022}}

== History ==
In 1957, a soil sample from a pine forest on the French Riviera was brought for analysis to the Lepetit Pharmaceuticals research lab in ], Italy. There, a research group headed by Piero Sensi<ref>{{cite web|url=http://archiviostorico.corriere.it/2013/agosto/10/chimico_che_salvo_molte_vite_co_0_20130810_63918b4e-017d-11e3-ae0c-005a4b618eb7.shtml|title=Il chimico che salvò molte vite|work=corriere.it|url-status=live|archive-url=https://web.archive.org/web/20140109161358/http://archiviostorico.corriere.it/2013/agosto/10/chimico_che_salvo_molte_vite_co_0_20130810_63918b4e-017d-11e3-ae0c-005a4b618eb7.shtml|archive-date=2014-01-09}}</ref> and Maria Teresa Timbal discovered a new bacterium. This new species produced a new class of molecules with antibiotic activity. Because Sensi, Timbal and the researchers were particularly fond of the French crime story '']'' (about a jewel heist and rival gangs),<ref name=pmid28850992>{{cite journal | vauthors = Aronson J | title = That's show business | journal = BMJ | volume = 319 | issue = 7215 | pages = 972 | date = October 1999 | pmid = 10514162 | pmc = 1116803 | doi = 10.1136/bmj.319.7215.972 }}</ref> they decided to call these compounds ''rifamycins''. After two years of attempts to obtain more stable semisynthetic products, a new molecule with high efficacy and good tolerability was produced in 1965 and was named rifampicin.<ref name=Sensi1983/>

Rifampicin was first sold in Italy in 1968 and was approved by the FDA in 1971.<ref name=Sensi1983/>

== Society and culture ==
===Cancer-causing impurities===
{{Anchor|impurities}}
{{See also|Ranitidine#impurities}}

In August 2020, the U.S. ] (FDA) became aware of nitrosamine impurities in certain samples of rifampin.<ref name="FDA 20200826">{{cite web | title=FDA works to mitigate shortages of rifampin and rifapentine | website=U.S. ] (FDA) | date=26 August 2020 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-works-mitigate-shortages-rifampin-and-rifapentine-after-manufacturers-find-nitrosamine | access-date=28 August 2020}} {{PD-notice}}</ref> The FDA and manufacturers are investigating the origin of these impurities in rifampin, and the agency is developing testing methods for regulators and industry to detect the {{Not a typo|1-methyl-4-nitrosopiperazine}} (MNP).<ref name="FDA 20200826" /> MNP belongs to the nitrosamine class of compounds, some of which are classified as probable or possible human carcinogens (substances that could cause cancer), based on laboratory tests such as rodent carcinogenicity studies.<ref name="FDA 20200826" /> Although there are no data available to directly evaluate the carcinogenic potential of MNP, information available on closely related nitrosamine compounds was used to calculate lifetime exposure limits for MNP.<ref name="FDA 20200826" />

As of January 2021, the FDA continues to investigate the presence of {{Not a typo|1-methyl-4-nitrosopiperazine}} (MNP) in rifampin or {{Not a typo|1-cyclopentyl-4-nitrosopiperazine}} (CPNP) in rifapentine approved for sale in the US.<ref>{{cite web | title=Laboratory analysis of rifampin/rifapentine products | website=U.S. ] (FDA) | date=28 January 2021 | url=https://www.fda.gov/drugs/drug-safety-and-availability/laboratory-analysis-rifampinrifapentine-products | access-date=28 January 2021}} {{PD-notice}}</ref>

=== Names ===
Rifampicin is the ] and ], while rifampin is the ]. Rifampicin may be abbreviated R, RMP, RA, RF, or RIF (US).{{cn|date=December 2022}}

Rifampicin is also known as rifaldazine,<ref>{{cite journal | vauthors = Moncalvo F, Moreo G | title = | journal = Giornale Italiano delle Malattie del Torace | volume = 20 | issue = 3 | pages = 120–131 | year = 1966 | pmid = 5974175 }}</ref><ref>{{cite web | title = Rifampicin | url = http://www.inchem.org/documents/pims/pharm/rifam.htm#SectionTitle:1.3%20Synonyms | work =Chemical Safety Information from Intergovernmental Organizations |publisher=International Programme on Chemical Safety |access-date=14 November 2014|url-status=live|archive-url=https://web.archive.org/web/20171031032819/http://www.inchem.org/documents/pims/pharm/rifam.htm#SectionTitle:1.3%20Synonyms|archive-date=31 October 2017}}</ref> rofact, and rifampin in the United States, also as rifamycin SV.<ref name="US Patent 3963705">{{cite patent |country= US |number= 3963705 |status= granted |title= Process for the preparation of rifampicin |pubdate= |gdate= 13 November 1979 |fdate= |pridate= |inventor= Bruzzese T |assign1= Holco Investment Inc. }}</ref>

Its chemical name is {{Not a typo|5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8--2,7-(epoxypentadecatrienimino)-naphthofuran-1,11(2H)-dione 21-acetate}}.{{cn|date=December 2022}}

Rifampicin is available under many brand names worldwide.<ref>{{cite web | url = https://www.drugs.com/international/rifampicin.html | work = Drugs.com International | title = Rifampicin }}</ref>

== References ==
{{reflist}}

== External links ==
* {{cite web | title=Nitrosamine impurities in medications: Guidance | website=Health Canada | date=4 April 2022 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/compliance-enforcement/information-health-product/drugs/nitrosamine-impurities/medications-guidance.html }}

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