192939-46-1

Basic information

• Product Name: EXANTA
• Synonyms: N-[(1R)-1-Cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]glycine Ethyl Ester;Glycine, N-[(1R)-1-cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyaMino)iMinoMethyl]phenyl]Methyl]aMino]carbonyl]-1-azetidinyl]-2-oxoethyl]-, ethyl ester;Exanta (XiMelagatran);Ethyl 2-[[(1R)-1-Cyclohexyl-2-[(2S)-2-[[4-(N'-Hydroxycarbamimidoyl)Phenyl]Methylcarbamoyl]Azetidin-1-Yl]-2-Oxoethyl]Amino]Acetate Ximelagatran;Ethyl 2-[[(1R)-1-Cyclohexyl-2-[(2S)-2-[[4-(N'-Hydroxycarbamimidoyl)Phenyl]Methylcarbamoyl]Azetidin-1-Yl]-2-Oxoethyl]Amino]Acetate Ethyl 2-[[(1R)-1-Cyclohexyl-2-[(2S)-2-[[4-(N'-Hydroxycarbamimidoyl)Phenyl]Methylcarbamoyl]Azetidin-1-Yl]-2-Oxo-Ethyl;EXANTA;XIMELEGATRAN;EXANTA/XIMELEGATRAN
• CAS NO: 192939-46-1
• Molecular Formula: C24H35N5O5
• Molecular Weight: 473.57
• Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 192939-46-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 65-68?C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.35g/cm³
• Refractive Index: 1.635
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• PKA: 6.87±0.69(Predicted)
• CAS DataBase Reference: EXANTA(CAS DataBase Reference)
• NIST Chemistry Reference: EXANTA(192939-46-1)
• EPA Substance Registry System: EXANTA(192939-46-1)

Safety Data

• Hazardous Substances Data: 192939-46-1(Hazardous Substances Data)

Usage

Description

EXANTA, also known as Ximelagatran, is an ester prodrug of melagatran, a potent, direct, and reversible thrombin inhibitor. It is an orally active direct thrombin inhibitor with improved bioavailability, making it a preferable alternative to traditional antithrombotic therapies. Ximelagatran is converted to melagatran by reduction and hydrolysis at the liver and other tissues, where it reversibly binds to the arginine side pocket of both free and clot-bound thrombin, ultimately blocking the conversion of fibrinogen to fibrin, the final step of the coagulation process.

Uses

Used in Pharmaceutical Industry:
EXANTA is used as an anticoagulant for the prevention of venous thromboembolic events (VTE) in elective hip or knee replacement surgery. It is also used for stroke prevention in patients with nonvalvular atrial fibrillation and therapy in vein thrombosis.
Used in Antithrombotic Applications:
EXANTA is used as an orally active direct thrombin inhibitor for antithrombotic purposes, providing an alternative to low molecular weight heparin (LMWH) or warfarin. It offers the convenience of oral therapy, does not require frequent laboratory monitoring and dosage adjustment, and has been shown to be non-inferior to warfarin in clinical studies for stroke prevention.
Used in Research and Development:
EXANTA serves as a prodrug for melagatran, which is a potent, direct, and reversible thrombin inhibitor. It is used in research and development for the creation of novel drug delivery systems to enhance its applications and efficacy against various thromboembolic disorders.

Originator

AstraZeneca (Germany)

Biochem/physiol Actions

Ximelagatran is orally active, selective and potent direct thrombin inhibitor. Ximelagatran is a prodrug of thrombin inhibitor melagatran.

InChI:InChI=1/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1