Otamixaban: Difference between revisions

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{{Drugbox
{{Drugbox
| IUPAC_name       = methyl (2''R'',3''R'')-2-(3-carbamimidoylbenzyl)-3- {[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate
| Verifiedfields = changed
| image             = Otamixaban.jpg
| verifiedrevid = 462266309
| image2           = Otamixaban 3D.jpg
| IUPAC_name = Methyl (2''R'',3''R'')-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate
| CAS_number        = 193153-04-7
| image = Otamixaban.svg
| ATC_prefix        =
| image2 = Otamixaban 3D.png
| ATC_suffix        =
| PubChem          = 5496659
| DrugBank          =
| C=25|H=26|N=4|O=4
| molecular_weight  = 446.498 g/mol
| bioavailability  =
| protein_bound    =
| metabolism        =
| elimination_half-life =
| excretion        =
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US      =  <!-- A / B            / C / D / X -->
| pregnancy_category= 
| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA          =  <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK          =  <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US          =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status      =
| routes_of_administration =
}}
{{CMG}}
__NOTOC__


<!--Clinical data-->
| tradename = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration = 


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


'''Otamixaban''' ([[International Nonproprietary Name|INN]]) is an inhibitor of [[Factor X]]a,<ref name="pmid17979700">{{cite journal |author=Guertin KR, Choi YM |title=The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development |journal=Curr. Med. Chem. |volume=14 |issue=23 |pages=2471–81 |year=2007 |pmid=17979700 |doi= |url=http://openurl.ingenta.com/content/nlm?genre=article&issn=0929-8673&volume=14&issue=23&spage=2471&aulast=Guertin}}</ref> currently being developed by the French pharmaceutical company [[Sanofi-Aventis]] as a treatment for [[acute coronary syndrome]].
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 193153-04-7
| ATC_prefix = none
| ATC_suffix =
| PubChem = 5496659
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4593439
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S173RED00L
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 46618


==See also==
<!--Chemical data-->
*[[Apixaban]]
| C=25 | H=26 | N=4 | O=4
*[[Rivaroxaban]]
| molecular_weight = 446.498 g/mol
| smiles = O=C(OC)[C@H](Cc1cc(C(=[N@H])N)ccc1)[C@H](NC(=O)c3ccc(c2cc[n+]([O-])cc2)cc3)C
| InChI = 1/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1
| InChIKey = PFGVNLZDWRZPJW-OPAMFIHVBD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PFGVNLZDWRZPJW-OPAMFIHVSA-N
}}
 
'''Otamixaban''' ([[International Nonproprietary Name|INN]]) is an experimental injectable [[anticoagulant]] [[direct factor Xa inhibitor]],<ref name="pmid17979700">{{cite journal |author=Guertin KR, Choi YM |title=The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development |journal=Curr. Med. Chem. |volume=14 |issue=23 |pages=2471–81 |year=2007 |pmid=17979700 |doi= 10.2174/092986707782023659|url=http://openurl.ingenta.com/content/nlm?genre=article&issn=0929-8673&volume=14&issue=23&spage=2471&aulast=Guertin}}</ref> that was investigated for the treatment for [[acute coronary syndrome]].  In 2013, [[Sanofi]] announced that it had ended [[drug development|development]] of the drug candidate after poor performance in a [[Phase III clinical trial]].<ref>{{cite journal | journal = Chemical & Engineering News | publisher = American Chemical Society | date = June 10, 2013 | volume = 91 | number = 23 | page = 17 | title = AstraZeneca, Sanofi Cut Programs | quote = Sanofi is ending development on two compounds, the anticancer compound iniparib and the anticoagulant otamixaban, both of which flunked Phase III studies.}}</ref><ref>{{cite web|title=Sanofi's Investigational Iniparib, Otamixaban Fail To Meet Goals, Ends Programs|url=http://www.rttnews.com/2129222/sanofi-s-investigational-iniparib-otamixaban-fail-to-meet-goals-ends-programs.aspx|publisher=RTT news|accessdate=11 April 2014}}</ref> 


==References==
==References==
{{reflist|2}}
{{reflist}}


{{Antithrombotics}}
{{Antithrombotics}}


[[Category:Anticoagulants]]
[[Category:Anticoagulants]]


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{{WikiDoc Sources}}
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Revision as of 19:45, 27 July 2014

{{Drugbox | Verifiedfields = changed | verifiedrevid = 462266309 | IUPAC_name = Methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate | image = Otamixaban.svg | image2 = Otamixaban 3D.png

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref =  ☒N | CAS_number = 193153-04-7 | ATC_prefix = none | ATC_suffix = | PubChem = 5496659 | DrugBank_Ref =  ☑Y | DrugBank = | ChemSpiderID_Ref =  ☑Y | ChemSpiderID = 4593439 | UNII_Ref =  ☑Y | UNII = S173RED00L | ChEMBL_Ref =  ☑Y | ChEMBL = 46618

| C=25 | H=26 | N=4 | O=4 | molecular_weight = 446.498 g/mol | smiles = O=C(OC)[C@H](Cc1cc(C(=[N@H])N)ccc1)[C@H](NC(=O)c3ccc(c2cc[n+]([O-])cc2)cc3)C | InChI = 1/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1 | InChIKey = PFGVNLZDWRZPJW-OPAMFIHVBD | StdInChI_Ref =  ☑Y | StdInChI = 1S/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1 | StdInChIKey_Ref =  ☑Y | StdInChIKey = PFGVNLZDWRZPJW-OPAMFIHVSA-N }}

Otamixaban (INN) is an experimental injectable anticoagulant direct factor Xa inhibitor,[1] that was investigated for the treatment for acute coronary syndrome. In 2013, Sanofi announced that it had ended development of the drug candidate after poor performance in a Phase III clinical trial.[2][3]

References

  1. ↑ Guertin KR, Choi YM (2007). "The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development". Curr. Med. Chem. 14 (23): 2471–81. doi:10.2174/092986707782023659. PMID 17979700.
  2. ↑ "AstraZeneca, Sanofi Cut Programs". Chemical & Engineering News. American Chemical Society. 91 (23): 17. June 10, 2013. Sanofi is ending development on two compounds, the anticancer compound iniparib and the anticoagulant otamixaban, both of which flunked Phase III studies.
  3. ↑ "Sanofi's Investigational Iniparib, Otamixaban Fail To Meet Goals, Ends Programs". RTT news. Retrieved 11 April 2014.


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