Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H26N4O4.ClH |
Molecular Weight | 482.959 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC(=O)[C@H](CC1=CC=CC(=C1)C(N)=N)[C@@H](C)NC(=O)C2=CC=C(C=C2)C3=CC=[N+]([O-])C=C3
InChI
InChIKey=ROKCPUOLRIBSQQ-BYYQELCVSA-N
InChI=1S/C25H26N4O4.ClH/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);1H/t16-,22-;/m1./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17139573Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17979700
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17139573
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17979700
Otamixaban is a synthetically derived parenteral fXa inhibitor currently in late stage clinical development at Sanofi-Aventis for the management of acute coronary syndrome. Otamixaban is a potent (Ki = 0.5 nM), selective, rapid acting, competitive and reversible fXa inhibitor that effectively inhibits both free and prothrombinase-bound fXa. Factor Xa (fXa) is a critical serine protease situated at the confluence of the intrinsic and extrinsic pathways of the blood coagulation cascade. FXa catalyzes the conversion of prothrombin to thrombin via the prothrombinase complex. Its singular role in thrombin generation, coupled with its potentiating effects on clot formation render it an attractive target for therapeutic intervention. In vivo experiments have demonstrated that Otamixaban is highly efficacious in rodent, canine and porcine models of thrombosis. In addition, recent clinical findings indicate that Otamixaban is efficacious, safe and well tolerated in humans and therefore has considerable potential for the treatment of acute coronary syndrome. Following the results of the Treatment of non-ST elevation Acute coronary syndrome with otamixaban, Sanofi has decided to discontinue the investigational programme with otamixaban, due to efficacy lower than expected. Otamixaban did not show superior benefit/risk to the combination of unfractionated heparin.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17979700 |
0.5 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
0.14 mg/kg 1 times / hour multiple, intravenous Studied dose Dose: 0.14 mg/kg, 1 times / hour Route: intravenous Route: multiple Dose: 0.14 mg/kg, 1 times / hour Sources: Page: p.1150 |
unhealthy, ADULT n = 5106 Health Status: unhealthy Condition: myocardial infarction Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 5106 Sources: Page: p.1150 |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (4.7%) Sources: Page: p.1150 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bleeding | 4.7% Disc. AE |
0.14 mg/kg 1 times / hour multiple, intravenous Studied dose Dose: 0.14 mg/kg, 1 times / hour Route: intravenous Route: multiple Dose: 0.14 mg/kg, 1 times / hour Sources: Page: p.1150 |
unhealthy, ADULT n = 5106 Health Status: unhealthy Condition: myocardial infarction Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 5106 Sources: Page: p.1150 |
PubMed
Title | Date | PubMed |
---|---|---|
Anticoagulant and anti-platelet effects are maintained following coadministration of otamixaban, a direct factor Xa inhibitor, with tirofiban in healthy volunteers. | 2005 Apr |
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Novel factor Xa inhibitors for prevention and treatment of thromboembolic diseases. | 2006 Aug |
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Drug evaluation: the directly activated Factor Xa inhibitor otamixaban. | 2006 Dec |
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Pharmacokinetics of otamixaban, a direct factor Xa inhibitor, in healthy male subjects: pharmacokinetic model development for phase 2/3 simulation of exposure. | 2006 Jan |
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Asymmetric synthesis of intermediates for otamixaban and premafloxacin by the chiral ligand-controlled asymmetric conjugate addition of a lithium amide. | 2006 Jun 9 |
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The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development. | 2007 |
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[Factor Xa-inhibition in interventional cardiology]. | 2007 Dec |
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Randomized, double-blind, dose-ranging study of otamixaban, a novel, parenteral, short-acting direct factor Xa inhibitor, in percutaneous coronary intervention: the SEPIA-PCI trial. | 2007 May 22 |
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Gateways to clinical trials. | 2007 Sep |
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[What's new on antithrombotics?]. | 2009 Aug |
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Otamixaban in acute coronary syndromes. | 2009 Sep 5 |
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Otamixaban for the treatment of patients with non-ST-elevation acute coronary syndromes (SEPIA-ACS1 TIMI 42): a randomised, double-blind, active-controlled, phase 2 trial. | 2009 Sep 5 |
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New drugs for the treatment of coronary artery syndromes: otamixaban and ticagrelor. | 2010 Feb |
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Recent research on antithrombotics. News on the treatment of patients with acute coronary syndromes. | 2010 May |
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Post-operative thromboprophylaxis: new oral thrombin and factor X inhibitors and their place in clinical practice. | 2010 May 24 |
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Clinical pharmacology of direct and indirect factor Xa inhibitors. | 2010 Nov 12 |
Patents
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50899073
Created by
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WL9J31M2HI
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409081-12-5
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DTXSID00193901
Created by
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DBSALT002029
Created by
admin on Fri Dec 15 15:38:48 GMT 2023 , Edited by admin on Fri Dec 15 15:38:48 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD