Otamixaban

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

Identification

Name
Otamixaban
Accession Number
DB06635
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
FXV-673 / RPR-130673 / RPR130673 / XRP-0673 / XRP0673
Product Ingredients
IngredientUNIICASInChI Key
Otamixaban HydrochlorideWL9J31M2HI409081-12-5ROKCPUOLRIBSQQ-BYYQELCVSA-N
Categories
UNII
S173RED00L
CAS number
193153-04-7
Weight
Average: 446.4983
Monoisotopic: 446.19540534
Chemical Formula
C25H26N4O4
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

Pharmacology

Indication

Investigated for use/treatment in thrombosis.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCoagulation factor XNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcemetacinThe risk or severity of bleeding can be increased when Otamixaban is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Otamixaban is combined with Acetylsalicylic acid.
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with Otamixaban.
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Otamixaban.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Otamixaban.
AmitriptylinoxideThe serum concentration of Amitriptylinoxide can be increased when it is combined with Otamixaban.
AnagrelideThe risk or severity of bleeding can be increased when Otamixaban is combined with Anagrelide.
Antihemophilic factor, human recombinantThe therapeutic efficacy of Antihemophilic factor, human recombinant can be decreased when used in combination with Otamixaban.
ApixabanApixaban may increase the anticoagulant activities of Otamixaban.
ArgatrobanThe risk or severity of bleeding can be increased when Argatroban is combined with Otamixaban.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5496659
ChemSpider
4593439
BindingDB
50114539
ChEMBL
CHEMBL46618
Wikipedia
Otamixaban

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceImpaired Renal Function1
2CompletedTreatmentAngioplasty, Transluminal, Percutaneous Coronary1
2CompletedTreatmentCoronary Heart Disease (CHD)1
3CompletedTreatmentAcute Coronary Syndromes (ACS)1

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

Taxonomy

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 / Beta amino acid or derivatives / Benzamide / Benzoic acid or derivatives / Benzoyl / Fatty acid ester / Monocyclic benzene moiety / Fatty acyl / Benzenoid / Pyridinium
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Coagulation factor X
Kind
Protein
Organism
Human
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. [PubMed:18060241]
  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. [PubMed:16411387]

Drug created on March 19, 2008 10:42 / Updated on October 01, 2018 16:46