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Revision as of 19:57, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL', 'KEGG').← Previous edit Latest revision as of 13:22, 26 July 2024 edit undo128.240.225.61 (talk) →History: Mycobacterium tuberculosis nomenclature corrected (capital M for genus name, italicised) 
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{{Short description|Pharmaceutical drug}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460016865
| IUPAC_name = (3''S'')-3,6-diamino-''N''-<nowiki>-8--2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide; (3''S'')-3,6-diamino-''N''-<nowiki>-8--2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide | IUPAC_name = (3''S'')-3,6-diamino-''N''-<nowiki>-8--2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide; (3''S'')-3,6-diamino-''N''-<nowiki>-8--2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide
| image = Capreomycin IA.svg | image = Capreomycin IA.svg
Line 5: Line 9:


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Capastat
| Drugs.com = {{drugs.com|monograph|capreomycin-sulfate}} | Drugs.com = {{drugs.com|monograph|capreomycin-sulfate}}
| MedlinePlus = a682860 | MedlinePlus = a682860
| pregnancy_category = | pregnancy_category = C
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration = intramuscular


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =


<!--Identifiers--> <!--Identifiers-->
⚫ | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 11003-38-6 | CAS_number = 11003-38-6
| ATC_prefix = J04 | ATC_prefix = J04
| ATC_suffix = AB30 | ATC_suffix = AB30
| ATC_supplemental = | ATC_supplemental =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | PubChem = 3032400
| DrugBank = DB00314 | DrugBank = DB00314
⚫ | PubChem = 3000502
⚫ | ChemSpiderID = 21106276
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | ChemSpiderID = 2272094
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 232HYX66HC | UNII = 232HYX66HC
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D00135 -->
| KEGG = D07607
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201252 -->
| ChEMBL = 2221250
⚫ | C=25 | H=44 | N=14 | O=8
| NIAID_ChemDB = 007653
| molecular_weight = 668.706 g/mol

⚫ | StdInChI = 1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9-;16-10-/t11-,12?,13?,14+,16+,18?;11-,12+,13?,14?,15-,18?/m10/s1
<!--Chemical data-->
⚫ | StdInChIKey = VCOPTHOUUNAYKQ-TWKMCICTSA-N
⚫ | C=25 | H=44 | N=14 | O=8
| smiles = C1C(=O)N(C(=O)N/C(=C/NC(=O)N)/C(=O)N(C(=O)NC(C(=O)N1)N)2CCN=C(N2)N)CNC(=O)C(CCCN)N.C1CN=C(N12C(=O)NC(C(=O)N(C(=O)N(C(=O)N/C(=C/NC(=O)N)/C(=O)N2)CNC(=O)C(CCCN)N)CO)N)N
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChI = 1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9+;16-10+/t11-,12-,13+,14-,16-,18-;11-,12-,13-,14+,15-,18-/m00/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChIKey = VCOPTHOUUNAYKQ-WBTCAYNUSA-N
}} }}
<!-- Definition and medical uses -->
'''Capreomycin''' is a ] ], commonly grouped with the ]s, which is given in combination with other ] for ]. Adverse effects include ] and 8th cranial ].
'''Capreomycin''' is an ] which is given in combination with other ] for the treatment of ].<ref name=AHFS2016/> Specifically it is a second line treatment used for active ].<ref name=AHFS2016/> It is given by ] or ].<ref name=AHFS2016>{{cite web|title=Capreomycin Sulfate|url=https://www.drugs.com/monograph/capreomycin-sulfate.html|publisher=The American Society of Health-System Pharmacists|accessdate=8 December 2016|url-status=live|archiveurl=https://web.archive.org/web/20161220231143/https://www.drugs.com/monograph/capreomycin-sulfate.html|archivedate=20 December 2016}}</ref>


<!-- Side effects and mechanisms -->
The drug should not be given with ] or other drugs that may damage the 8th nerve.
Common side effects include ], ], poor balance, and pain at the site of injection.<ref name=AHFS2016/> Other side effects include ] resulting in the inability to breathe.<ref name=AHFS2016/> It is not recommended with ] or other medications that may damage the ].<ref name=AHFS2016/> It is not recommended during ] as it may cause kidney or hearing problems in the baby.<ref name=AHFS2016/> Capreomycin is commonly grouped with the ] family of medications.<ref>{{cite book|last1=Navneet|first1=Kumar|title=Textbook of Neurology|date=2015|publisher=PHI Learning Pvt. Ltd.|isbn=9788120342439|page=192|url=https://books.google.com/books?id=gm_W3r91J0YC&pg=PA192|language=en|url-status=live|archiveurl=https://web.archive.org/web/20161220090022/https://books.google.ca/books?id=gm_W3r91J0YC&pg=PA192|archivedate=2016-12-20}}</ref> How it works is unclear.<ref name=AHFS2016/>


<!-- History, society, and culture -->
It is a ].
Capreomycin was discovered from ] in 1960.<ref>{{cite web|last1=Tomlinson|first1=Catherine|title=TB Online – Capreomycin|url=http://www.tbonline.info/posts/2011/8/23/capreomycin/|accessdate=14 September 2014|url-status=live|archiveurl=https://web.archive.org/web/20150113184425/http://www.tbonline.info/posts/2011/8/23/capreomycin/|archivedate=13 January 2015}}</ref> It was removed from the ] in 2019.<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | year = 2019 | title = Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines | publisher = World Health Organization | location = Geneva | author-link = World Health Organization | hdl = 10665/325773 | id = WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref>
Capreomycin is administered intramuscularly and shows bacteriostatic activity. <ref>PMID 16857584</ref>

==Spectrum of susceptibility==
Capreomycin is most commonly used to treat '']'' infections. ''Mycobacterium tuberculosis'' growth has been found to be inhibited at a concentration of 2.5 μg/mL.<ref name="m495">{{cite web | title=Mycobacterium tuberculosis (BACTEC 460 H37Ra) | website=TOKU-E | url=https://antibiotics.toku-e.com/microorganism_detail_7867.html | access-date=2024-06-13}}</ref>

== Side effects ==
{{unreferenced section|date=September 2019}}
High incidence: hematuria, urine output or urinary frequency significantly increased or decreased, loss of appetite or extreme thirst (hypokalemia, renal toxicity).

Less incidence: hearing loss, tinnitus, gait instability, dizziness, dyspnea, lethargy, extreme weakness (neuromuscular blockade, renal toxicity, hypokalemia), nausea or vomiting.

Significant renal toxicity: blood creatinine increase, blood urea nitrogen increase, poor creatinine clearance, proteinuria (need routine blood monitoring of renal functions and urine analysis) during usage of this medication.

Damaging to the 8th cranial nerve . There can be vestibular dysfunction, such as some minor hearing loss after using the medication for 2 to 4 months.

A certain block effect of neuromuscular.

Can cause allergic reactions: rash, drug fever, facial flushing or pale, asthma, palpitations, sense of suppression in the chest, abdominal pain, anaphylactic shock.

== Interactions ==
{{unreferenced section|date=September 2019}}
Combined with an aminoglycoside, it can increase the possibility of ototoxicity, nephrotoxicity and neuromuscular blockage, result in some hearing loss or can continue to deafness. It could be a temporary symptom, but often be permanent. Neuromuscular blockade can lead to skeletal muscle weakness and respiratory depression or paralysis (apnea). Using anti-cholinesterase or calcium salts may release this block.

Combined with amphotericin B, vancomycin, bacitracin, paromomycin, cyclosporine, kanamycin, cisplatin, bumetanide, ], furosemide: Would Increase the possibility of ototoxicity and nephrotoxicity.

Combined with antihistamines, buclizine, cyclizine, meclizine, phenothiazines, thioketones, trimethamine, and capreomycin: can ameliorate the symptoms of tinnitus, dizziness or vertigo and other ototoxic symptoms.

Combined with anti-neuromuscular block drugs: can antagonize the effect of the anti-neuromuscular block drugs on the skeletal muscle (so need to adjust the dose of the drugs for anti-muscle weakness.

Combined with ethyl sulfide isoniazid: may increase the side effects.

Combined with methoxyflurane or polymyxin injection: may increase renal toxicity or neuromuscular blockade effect.

Combined with opioid: The effect of central respiratory inhibition may increase, lead to prolonged respiratory inhibition or respiratory paralysis (apnea).

== History ==

Capreomycin, an antiphlogistic antibiotic which was produced in the United States in 1960, and be applied in clinic in 1968. In 1979, capreomycin was used in the area of antituberculosis by inhibiting the growth of ''Mycobacterium tuberculosis''.{{cn|date=August 2022}}


==References== ==References==
{{Reflist}} {{Reflist}}


==External links==
⚫ {{Antimycobacterials}}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/capreomycin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Capreomycin }}
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⚫ {{Antimycobacterials}}
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