Otamixaban

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Otamixaban
DrugBank Accession Number
DB06635
Background

Otamixaban is a novel direct Factor Xa (FXa) inhibitor. It is currently being developed by the French pharmaceutical company Sanofi-Aventis as a treatment for acute coronary syndrome.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 446.4983
Monoisotopic: 446.19540534
Chemical Formula
C25H26N4O4
Synonyms
  • Otamixaban
External IDs
  • FXV-673
  • RPR-130673
  • RPR130673
  • XRP-0673
  • XRP0673

Pharmacology

Indication

Investigated for use/treatment in thrombosis.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCoagulation factor XNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Otamixaban.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Otamixaban.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Otamixaban is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Otamixaban.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Otamixaban.
Albutrepenonacog alfaThe therapeutic efficacy of Albutrepenonacog alfa can be decreased when used in combination with Otamixaban.
AlclofenacThe risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Otamixaban.
AldesleukinThe risk or severity of bleeding can be increased when Otamixaban is combined with Aldesleukin.
AlemtuzumabThe risk or severity of bleeding can be increased when Otamixaban is combined with Alemtuzumab.
AlteplaseThe risk or severity of bleeding can be increased when Alteplase is combined with Otamixaban.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Otamixaban HydrochlorideWL9J31M2HI409081-12-5ROKCPUOLRIBSQQ-BYYQELCVSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Phenylpyridines
Direct Parent
Phenylpyridines
Alternative Parents
Beta amino acids and derivatives / Benzamides / Benzoyl derivatives / Fatty acid esters / Pyridinium derivatives / Methyl esters / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Monocarboxylic acids and derivatives
show 6 more
Substituents
4-phenylpyridine / Amidine / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Beta amino acid or derivatives / Carbonyl group
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
S173RED00L
CAS number
193153-04-7
InChI Key
PFGVNLZDWRZPJW-OPAMFIHVSA-N
InChI
InChI=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
IUPAC Name
4-(4-{[(2R,3R)-3-[(3-carbamimidoylphenyl)methyl]-4-methoxy-4-oxobutan-2-yl]carbamoyl}phenyl)pyridin-1-ium-1-olate
SMILES
COC(=O)[C@H](CC1=CC(=CC=C1)C(N)=N)[C@@H](C)NC(=O)C1=CC=C(C=C1)C1=CC=[N+]([O-])C=C1

References

General References
Not Available
PubChem Compound
5496659
ChemSpider
4593439
BindingDB
50114539
ChEMBL
CHEMBL46618
ZINC
ZINC000001908051
Wikipedia
Otamixaban

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Coronary Syndrome (ACS)1
2CompletedTreatmentAngioplasty, Transluminal, Percutaneous Coronary1
2CompletedTreatmentCoronary Heart Disease (CHD)1
1CompletedBasic ScienceDeteriorating renal function1
1CompletedTreatmentHepatic Impairment1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00202 mg/mLALOGPS
logP2.12ALOGPS
logP1.54ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.94ChemAxon
pKa (Strongest Basic)11.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.73 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity137.62 m3·mol-1ChemAxon
Polarizability48.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5326
Blood Brain Barrier+0.9199
Caco-2 permeable-0.591
P-glycoprotein substrateNon-substrate0.5454
P-glycoprotein inhibitor INon-inhibitor0.9186
P-glycoprotein inhibitor IINon-inhibitor0.7824
Renal organic cation transporterNon-inhibitor0.8502
CYP450 2C9 substrateNon-substrate0.7351
CYP450 2D6 substrateNon-substrate0.8129
CYP450 3A4 substrateNon-substrate0.5141
CYP450 1A2 substrateNon-inhibitor0.7534
CYP450 2C9 inhibitorNon-inhibitor0.6407
CYP450 2D6 inhibitorNon-inhibitor0.8638
CYP450 2C19 inhibitorNon-inhibitor0.6357
CYP450 3A4 inhibitorNon-inhibitor0.9066
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8028
Ames testNon AMES toxic0.5202
CarcinogenicityNon-carcinogens0.8271
BiodegradationNot ready biodegradable0.8529
Rat acute toxicity2.6725 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9975
hERG inhibition (predictor II)Non-inhibitor0.7187
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details
1. Coagulation factor X
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name
F10
Uniprot ID
P00742
Uniprot Name
Coagulation factor X
Molecular Weight
54731.255 Da
References
  1. Ahrens I, Peter K, Bode C: [Factor Xa-inhibition in interventional cardiology]. Hamostaseologie. 2007 Dec;27(5):328-32. [Article]
  2. Paccaly A, Ozoux ML, Chu V, Simcox K, Marks V, Freyburger G, Sibille M, Shukla U: Pharmacodynamic markers in the early clinical assessment of otamixaban, a direct factor Xa inhibitor. Thromb Haemost. 2005 Dec;94(6):1156-63. [Article]

Drug created on March 19, 2008 16:42 / Updated on February 21, 2021 18:52