OTAMIXABAN HYDROCHLORIDE

Investigational

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C25H26N4O4
Molecular Weight	446.4983
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
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
Coagulation factor X 21 Target ID: CHEMBL244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17979700	Inhibitor 8504		0.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute coronary syndrome 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19717186	Primary		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
252 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	100 μg/kg/h 1 times / day other, intravenous dose: 100 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
458 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	125 μg/kg/h 1 times / day other, intravenous dose: 125 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
635 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	150 μg/kg/h 1 times / day other, intravenous dose: 150 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
85 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	50 μg/kg/h 1 times / day other, intravenous dose: 50 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
6476 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	100 μg/kg/h 1 times / day other, intravenous dose: 100 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12007 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	125 μg/kg/h 1 times / day other, intravenous dose: 125 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
15674 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	150 μg/kg/h 1 times / day other, intravenous dose: 150 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2437 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17178269	50 μg/kg/h 1 times / day other, intravenous dose: 50 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:	OTAMIXABAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

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: https://pubmed.ncbi.nlm.nih.gov/23995608	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23995608	Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (4.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/23995608

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: https://pubmed.ncbi.nlm.nih.gov/23995608	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23995608

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00AC1T	https://www.1pchem.com/search?query=1P00AC1T
AK Scientific	3954AH	https://aksci.com/item_detail.php?cat=3954AH
AstaTech	C11731	http://astatechinc.com/CPSResult.php?CRNO=C11731
BLD Pharm	BD630502	http://www.bldpharm.com/search/Search.html?keyword=BD630502
Chem Scene	CS-M0942	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-M0942
eMolecules	275178643	https://orderbb.emolecules.com/search/#?query=275178643
eMolecules	300616481	https://orderbb.emolecules.com/search/#?query=300616481
eMolecules	42854482	https://orderbb.emolecules.com/search/#?query=42854482
eMolecules	50283164	https://orderbb.emolecules.com/search/#?query=50283164
KeyOrganics	AS-75017	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75017
MedChem Express	HY-70035	https://www.medchemexpress.com/search.html?q=HY-70035&ft=&fa=&fp=
Molnova	M13026	https://www.molnova.com/en/serch-list.html?keywords=M13026
MolPort	MolPort-006-170-155	https://www.molport.com/shop/molecule-link/MolPort-006-170-155
MolPort	MolPort-046-703-217	https://www.molport.com/shop/molecule-link/MolPort-046-703-217
MuseChem	I002471	https://www.musechem.com/product/I002471.html
ShangHai Biochempartner	BCP000758	http://www.biochempartner.com/search_BCP000758
Toronto Research Chemicals	O712500	https://www.trc-canada.com/product-detail/?CatNum=O712500

PubMed

Title	Date	PubMed
Clinical pharmacology of direct and indirect factor Xa inhibitors.	2010-11-12	20964458
Post-operative thromboprophylaxis: new oral thrombin and factor X inhibitors and their place in clinical practice.	2010-05-24	20948848
Recent research on antithrombotics. News on the treatment of patients with acute coronary syndromes.	2010-05	20866007
New drugs for the treatment of coronary artery syndromes: otamixaban and ticagrelor.	2010-02	20088750
Otamixaban in acute coronary syndromes.	2009-09-05	19717186
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.	2009-09-05	19717184
[What's new on antithrombotics?].	2009-08	18950743
[Factor Xa-inhibition in interventional cardiology].	2007-12	18060241
Gateways to clinical trials.	2007-09	17982511
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.	2007-05-22	17502577
The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development.	2007	17979700
Direct and rapid inhibition of factor Xa by otamixaban: a pharmacokinetic and pharmacodynamic investigation in patients with coronary artery disease.	2006-12	17178269
Drug evaluation: the directly activated Factor Xa inhibitor otamixaban.	2006-12	17139573
Novel factor Xa inhibitors for prevention and treatment of thromboembolic diseases.	2006-08	16859389
Asymmetric synthesis of intermediates for otamixaban and premafloxacin by the chiral ligand-controlled asymmetric conjugate addition of a lithium amide.	2006-06-09	16749814
Anticoagulant and anti-platelet effects are maintained following coadministration of otamixaban, a direct factor Xa inhibitor, and acetylsalicylic acid.	2006-02	16493482
Pharmacokinetic/pharmacodynamic relationships for otamixaban, a direct factor Xa inhibitor, in healthy subjects.	2006-01	16397283
Pharmacokinetics of otamixaban, a direct factor Xa inhibitor, in healthy male subjects: pharmacokinetic model development for phase 2/3 simulation of exposure.	2006-01	16397282
Pharmacodynamic markers in the early clinical assessment of otamixaban, a direct factor Xa inhibitor.	2005-12	16411387
Anticoagulant and anti-platelet effects are maintained following coadministration of otamixaban, a direct factor Xa inhibitor, with tirofiban in healthy volunteers.	2005-04	15841331
Small molecule coagulation cascade inhibitors in the clinic.	2005	16375748

Patents

Sample Use Guides

In Vivo Use Guide

0.080 mg/kg bolus followed by continuous 0.100 mg/kg/h infusion

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:05 GMT 2025`
Record UNII	WL9J31M2HI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OTAMIXABAN HYDROCHLORIDE

Common Name

English

RPR-130673 HCL

Preferred Name

English

Otamixaban Hydrochloride [WHO-DD]

Common Name

English

METHYL (2R,3R)-2-(3-AMIDINOBENZYL)-3-((4-(1-OXIDO-4-PYRIDINYL)BENZOYL)AMINO)BUTANOATE HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

PUBCHEM

50899073