| Revision as of 10:24, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 465835023 of page Telavancin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number'). |
Latest revision as of 17:57, 11 November 2024 edit Cbare (talk | contribs)103 editsm Add DrugBank accession |
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{{Short description|Pharmaceutical drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 415119592 |
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| verifiedrevid = 477861289 |
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| image = Telavancin.png |
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| image = Telavancin.png |
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| width = 200px |
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| width = 200px |
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| IUPAC_name = (1''S'',2''R'',18''R'',19''R'',22''S'',25''R'',28''R'',40''S'')-22-(2-Amino-2-oxoethyl)-5,15-dichloro-48-<nowiki/>{amino}-2,3,6-trideoxy-3-methyl-α-<small>L</small>-lyxo-hexopyranosyl)-β-<small>D</small>-glucopyranosyl]oxy}-2,18,32,35,37-pentahydroxy-19--20,23,26,42,44-pentaoxo-36-<nowiki/>{methyl}-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclopentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = C |
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| pregnancy_US = C |
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| licence_EU = yes |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = N/A |
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| bioavailability = N/A |
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| protein_bound = 90%, mostly to ] |
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| metabolism = |
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| elimination_half-life = 9 hours |
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| elimination_half-life = 9 hours |
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| excretion = 76% in urine, <1% in feces |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = <!-- blanked - oldvalue: 372151-71-8 --> |
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| CAS_number = 372151-71-8 |
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| ATC_prefix = J01 |
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| ATC_prefix = J01 |
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| ATC_suffix = XA03 |
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| ATC_suffix = XA03 |
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| DrugBank = DB06402 |
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| PubChem = 3081362 |
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| PubChem = 3081362 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 71229 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2338980 |
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| ChemSpiderID = 2338980 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = XK134822Z0 |
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| UNII = XK134822Z0 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 607993 --> |
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| ChEMBL = 507870 |
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<!--Chemical data--> |
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| C=80 | H=106 | Cl=2 | N=11 | O=27 | P=1 |
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| C=80 | H=106 | Cl=2 | N=11 | O=27 | P=1 |
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| smiles = CCCCCCCCCCNCCN1(C(O(1O)C)O2(((O2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)((C(=O)N(C(=O)N5C(=O)N7C8=CC(=C(C=C8)O)C9=C(C(=C(C=C9(NC(=O)((C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)CNCP(=O)(O)O)O)CC(=O)N)NC(=O)(CC(C)C)NC)O)Cl)CO)O)O)C |
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| molecular_weight = 1755.63 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C80H106Cl2N11O27P/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114)/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-/m0/s1 |
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| StdInChI = 1S/C80H106Cl2N11O27P/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114)/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-/m0/s1 |
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| StdInChIKey = ONUMZHGUFYIKPM-MXNFEBESSA-N |
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| StdInChIKey = ONUMZHGUFYIKPM-MXNFEBESSA-N |
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}} |
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}} |
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'''Telavancin''' (trade name '''Vibativ''' by Cumberland Pharmaceuticals) is a ] ] for use in ] or other ] infections. Telavancin is a semi-synthetic derivative of ].<ref>Astellas, Inc. ''VIBATIV prescribing information'', 9/2009.</ref><ref name=HIG2005/> |
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The FDA approved the drug in September 2009 for ]s (cSSSI),<ref name=TA-FDA/> and in June 2013 for ] and ventilator-associated bacterial pneumonia caused by ].<ref>{{cite web |url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm358209.htm |title=FDA approves Vibativ for hospitalized patients with bacterial pneumonia |website=] |access-date=2013-08-19 |url-status=live |archive-url=https://web.archive.org/web/20130831000445/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm358209.htm |archive-date=2013-08-31 }}</ref> |
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==History== |
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On 19 October 2007, the ] ] (FDA) issued an ] for telavancin. Its developer, ], submitted a complete response to the letter, and the FDA has assigned a ] (PDUFA) target date of 21 July 2008.<ref>{{Cite web |url=https://www.drugs.com/nda/telavancin_080306.html |title=Drugs.com, FDA Accepts for Review Response to Approvable Letter for Telavancin |access-date=2008-03-08 |url-status=live |archive-url=https://web.archive.org/web/20080309092012/http://www.drugs.com/nda/telavancin_080306.html |archive-date=2008-03-09 }}</ref> |
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On 19 November 2008, an FDA antiinfective drug advisory committee concluded that they would recommend telavancin be approved by the FDA. |
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The FDA approved the drug on 11 September 2009 for complicated skin and skin structure infections (]).<ref name=TA-FDA>{{cite press release |
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|title = Theravance and Astellas Announce FDA Approval of Vibativ (telavancin) for the Treatment of Complicated Skin and Skin Structure Infections |
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|publisher = Theravance, Inc. and Astellas Pharma US, Inc. |
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|date = 2009-09-11 |
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|url = https://www.drugs.com/newdrugs/theravance-astellas-announce-fda-approval-vibativ-telavancin-complicated-skin-skin-structure-1629.html |
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|access-date = 16 September 2009 |
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|url-status = live |
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|archive-url = https://web.archive.org/web/20090922174003/http://www.drugs.com/newdrugs/theravance-astellas-announce-fda-approval-vibativ-telavancin-complicated-skin-skin-structure-1629.html |
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|archive-date = 22 September 2009 |
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}}</ref> |
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Theravance has also submitted telavancin to the FDA in a second indication, ], sometimes referred to as hospital-acquired pneumonia, or HAP. On 30 November 2012, an FDA advisory panel endorsed approval of a once-daily formulation of telavancin for nosocomial pneumonia when other alternatives are not suitable. However, telavancin did not win the advisory committee's recommendation as first-line therapy for this indication. The committee indicated that the trial data did not prove "substantial evidence" of telavancin's safety and efficacy in hospital-acquired pneumonia, including ventilator-associated pneumonia caused by Gram-positive organisms ''Staphylococcus aureus'' and ''Streptococcus pneumoniae''.<ref>{{cite web | vauthors = Leuty R | url = http://www.bizjournals.com/sanfrancisco/blog/biotech/2012/11/theravance-vibativ-pneumonia.html | title = FDA advisory group gives mixed review of Theravance pneumonia treatment. | date = 30 November 2012 | archive-url = https://web.archive.org/web/20121204080539/http://www.bizjournals.com/sanfrancisco/blog/biotech/2012/11/theravance-vibativ-pneumonia.html | archive-date=2012-12-04 | work = American City Business Journals/San Francisco/BiotechSF blog }}</ref> On 21 June 2013 FDA gave approval for telavancin to treat patients with hospital-acquired pneumonia, but indicated it should be used only when alternative treatments are not suitable. FDA staff had indicated telavancin has a "substantially higher risk for death" for patients with kidney problems or diabetes compared to vancomycin.<ref>{{cite web | vauthors = Leuty R | url = http://www.bizjournals.com/sanfrancisco/blog/biotech/2013/06/theravance-mrsa-vibativ-pneumonia.html |title = Theravance gets FDA OK for antibiotic against pneumonia, with limits. | archive-url = https://web.archive.org/web/20130623223752/http://www.bizjournals.com/sanfrancisco/blog/biotech/2013/06/theravance-mrsa-vibativ-pneumonia.html | archive-date=2013-06-23 | work = San Francisco Business Times | date = 21 June 2013 }}</ref> |
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On March 11 2013, Clinigen Group plc and Theravance, Inc. announced that they have entered into an exclusive commercialization agreement in the European Union (EU) and certain other countries located in Europe for VIBATIV® (telavancin) for the treatment of nosocomial pneumonia (hospital-acquired), including ventilator-associated pneumonia, known or suspected to be caused by methicillin resistant Staphylococcus aureus (MRSA) when other alternatives are not suitable.<ref>{{Cite web |url=http://www.vibativ.eu/category/news | work = www.vibativ.eu | title = Clinigen and Theravance Announce Exclusive Commercialization Agreement in the EU for VIBATIV® (telavancin) |access-date=2014-12-09 |url-status=live |archive-url=https://web.archive.org/web/20140913014534/http://www.vibativ.eu/category/news/ |archive-date=2014-09-13 }}</ref> |
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==Mechanism of action== |
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Like vancomycin, telavancin inhibits bacterial ] synthesis by binding to the <small>D</small>-]-<small>D</small>-Ala terminus of the peptidoglycan in the growing cell wall (see ]). In addition, it disrupts bacterial ] by ].<ref name=HIG2005>{{cite journal | vauthors = Higgins DL, Chang R, Debabov DV, Leung J, Wu T, Krause KM, Sandvik E, Hubbard JM, Kaniga K, Schmidt DE, Gao Q, Cass RT, Karr DE, Benton BM, Humphrey PP | display-authors = 6 | title = Telavancin, a multifunctional lipoglycopeptide, disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus | journal = Antimicrobial Agents and Chemotherapy | volume = 49 | issue = 3 | pages = 1127–1134 | date = March 2005 | pmid = 15728913 | pmc = 549257 | doi = 10.1128/AAC.49.3.1127-1134.2005 }}</ref><ref>{{Cite journal | vauthors = Spreitzer H | date = 2 February 2009 | title = Neue Wirkstoffe - Telavancin | journal = Österreichische Apothekerzeitung | issue = 3/2009 | language = de }}</ref> |
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==Adverse effects== |
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Common but harmless adverse effects include nausea, vomiting, constipation, and headache.<ref name="Drugs.com">Telavancin hydrochloride {{drugs.com|monograph|telavancin-hydrochloride}}</ref> |
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Telavancin has a higher rate of kidney failure than ] in two clinical trials.<ref>{{cite journal | vauthors = Saravolatz LD, Stein GE, Johnson LB | title = Telavancin: a novel lipoglycopeptide | journal = Clinical Infectious Diseases | volume = 49 | issue = 12 | pages = 1908–1914 | date = December 2009 | pmid = 19911938 | doi = 10.1086/648438 | doi-access = free }}</ref> It showed ] effects in animal studies.<ref name="Drugs.com" /> |
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== Interactions == |
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Telavancin inhibits the liver enzymes ] and ]. No data regarding the clinical relevance are available.<ref name="Drugs.com" /> |
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== References == |
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{{Reflist}} |
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{{Other antibacterials}} |
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] |
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] |
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] |