Idraparinux

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

Identification

Generic Name
Idraparinux
DrugBank Accession Number
DB06406
Background

Idraparinux, a synthetic pentasaccharide is an antithrombin-dependent inhibitor of activated factor X. It was developed for the treatment and prevention of thromboembolic events. However, clinical trials have revealed that idraparinux had lead to bleeding. As a result, Sanofi stopped the development of the drug.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 1529.3
Monoisotopic: 1528.056116659
Chemical Formula
C38H64O49S7
Synonyms
Not Available
External IDs
  • SanOrg 34006
  • SR 34006
  • SR-34006
  • SR34006

Pharmacology

Indication

Investigated for use/treatment in thrombosis, venous thromboembolism, strokes, heart disease, and atrial fibrillation.

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Idraparinux sodium is a novel long-acting synthetic highly potent synthetic and specific indirect inhibitor of coagulation factor Xa, injectable subcutaneously.

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
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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 Idraparinux.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Idraparinux.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Idraparinux is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Idraparinux.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Idraparinux.
Albutrepenonacog alfaThe therapeutic efficacy of Albutrepenonacog alfa can be decreased when used in combination with Idraparinux.
AlclofenacThe risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Idraparinux.
AldesleukinThe risk or severity of bleeding can be increased when Idraparinux is combined with Aldesleukin.
AlemtuzumabThe risk or severity of bleeding can be increased when Idraparinux is combined with Alemtuzumab.
AlteplaseThe risk or severity of bleeding can be increased when Alteplase is combined with Idraparinux.
Interactions
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Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Idraparinux sodiumH84IXP29FN149920-56-9MVPQUSQUURLQKF-MCPDASDXSA-E

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
6ADD3H8MFZ
CAS number
162610-17-5
InChI Key
AJBMORBNKXNZSF-COSHMZDQSA-N
InChI
InChI=1S/C38H64O49S7/c1-64-15-12(9-72-88(43,44)45)76-35(27(68-5)18(15)65-2)80-21-19(66-3)28(69-6)37(82-25(21)32(39)40)79-17-14(11-74-90(49,50)51)77-38(31(87-94(61,62)63)24(17)85-92(55,56)57)81-22-20(67-4)29(70-7)36(83-26(22)33(41)42)78-16-13(10-73-89(46,47)48)75-34(71-8)30(86-93(58,59)60)23(16)84-91(52,53)54/h12-31,34-38H,9-11H2,1-8H3,(H,39,40)(H,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54)(H,55,56,57)(H,58,59,60)(H,61,62,63)/t12-,13-,14-,15-,16-,17-,18+,19+,20+,21+,22+,23+,24+,25+,26-,27-,28-,29-,30-,31-,34+,35-,36-,37-,38-/m1/s1
IUPAC Name
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4S,5R,6R)-6-{[(2R,3S,4S,5R,6R)-2-carboxy-4,5-dimethoxy-6-{[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(sulfooxy)-2-[(sulfooxy)methyl]oxan-3-yl]oxy}oxan-3-yl]oxy}-4,5-bis(sulfooxy)-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-4,5-dimethoxy-3-{[(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-[(sulfooxy)methyl]oxan-2-yl]oxy}oxane-2-carboxylic acid
SMILES
[H][C@]1(O[C@H]2[C@H](OC)[C@@H](OC)[C@]([H])(O[C@@H]3[C@@H](COS(O)(=O)=O)O[C@]([H])(O[C@H]4[C@H](OC)[C@@H](OC)[C@]([H])(O[C@@H]5[C@@H](COS(O)(=O)=O)O[C@H](OC)[C@H](OS(O)(=O)=O)[C@H]5OS(O)(=O)=O)O[C@H]4C(O)=O)[C@H](OS(O)(=O)=O)[C@H]3OS(O)(=O)=O)O[C@@H]2C(O)=O)O[C@H](COS(O)(=O)=O)[C@@H](OC)[C@H](OC)[C@H]1OC

References

General References
Not Available
ChemSpider
2340657
Wikipedia
Idraparinux

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedNot AvailableDeep Vein Thrombosis / Pulmonary Embolism1
3CompletedTreatmentAtrial Fibrillation1
3CompletedTreatmentDeep Vein Thrombosis2
3CompletedTreatmentPulmonary Embolism1
3CompletedTreatmentSystemic Embolism / Thrombotic events1
3TerminatedPreventionAtrial Fibrillation1

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 Solubility2.55 mg/mLALOGPS
logP-1.4ALOGPS
logP-3.8ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)-3.1ChemAxon
Physiological Charge-9ChemAxon
Hydrogen Acceptor Count42ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area676.71 Å2ChemAxon
Rotatable Bond Count35ChemAxon
Refractivity273.26 m3·mol-1ChemAxon
Polarizability128.26 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2
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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

Drug created on March 19, 2008 16:29 / Updated on May 10, 2021 12:42