CAS 192939-46-1

Ximelagatran

Description:

Ximelagatran is an anticoagulant medication that was developed as an alternative to traditional anticoagulants like warfarin. It is a direct thrombin inhibitor, which means it works by directly inhibiting the activity of thrombin, an enzyme crucial for blood clot formation. Ximelagatran is characterized by its oral bioavailability, which allows for convenient administration without the need for routine monitoring of coagulation parameters, unlike warfarin. The substance is a prodrug, meaning it is metabolized in the body to its active form, which exerts the anticoagulant effect. Its pharmacokinetic profile includes rapid absorption and a relatively short half-life, necessitating twice-daily dosing. However, despite its advantages, ximelagatran was associated with liver toxicity in some patients, leading to its withdrawal from the market. The compound's chemical structure includes a unique combination of functional groups that contribute to its pharmacological activity. Overall, ximelagatran represents an important step in the development of anticoagulant therapies, although its clinical use has been limited due to safety concerns.

Formula: C₂₄H₃₅N₅O₅

InChI: InChI=1S/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

InChI key: InChIKey=ZXIBCJHYVWYIKI-PZJWPPBQSA-N

SMILES: C([C@H](NCC(OCC)=O)C1CCCCC1)(=O)N2[C@H](C(NCC3=CC=C(C(NO)=N)C=C3)=O)CC2

Synonyms:

• Exanta/Ximelegatran
• Glycine, N-[(1R)-1-cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]-, ethyl ester
• H 376/95
• N-[(1R)-1-Cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]glycine Ethyl Ester
• Ximelagatran
• Ximelegatran
• ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate
• Exanta

Ximelagatran

CAS: 192939-46-1

Ximelagatran

Formula: C₂₄H₃₅N₅O₅

Purity: 99.5%

Molecular weight: 473.57

Ref: 54-BUP14228

Ethyl ((R)-1-cyclohexyl-2-((S)-2-((4-(N-hydroxycarbamimidoyl)benzyl)carbamoyl)azetidin-1-yl)-2-oxoethyl)glycinate

CAS: 192939-46-1

Formula: C₂₄H₃₅N₅O₅

Purity: 97%

Color and Shape: Solid

Molecular weight: 473.5652

Ref: IN-DA00ADU3

Ximelagatran

Controlled Product

CAS: 192939-46-1

Stability Hygroscopic
Applications An orally active direct thrombin inhibitor; prodrug of Melagatran. Antithrombotic.
References Owens, P.K., et al.: J. Pharm. Biomed. Anal., 27, 587 (2002), Kalus, J.S., et al.: Expert Opin. Invest. Drugs, 13, 465 (2004), Boos, C.J., et al.: Eur. J. Int. Med., 16, 267 (2005), Cullberg, M., et al.: Clin. Pharmacol. Ther., 77, 279 (2005),

Formula: C₂₄H₃₅N₅O₅

Color and Shape: Neat

Molecular weight: 473.57

Ref: TR-X745000

Ximelagatran

CAS: 192939-46-1

Ximelagatran, oral direct thrombin inhibitor, transforms to active melagatran in body.

Formula: C₂₄H₃₅N₅O₅

Purity: 95.48% - 99.60%

Color and Shape: Solid

Molecular weight: 473.5652

Ref: TM-T17265

Ethyl ((R)-1-cyclohexyl-2-((S)-2-((4-(N-hydroxycarbamimidoyl)benzyl)carbamoyl)azetidin-1-yl)-2-oxoethyl)glycinate

CAS: 192939-46-1

Ethyl ((R)-1-cyclohexyl-2-((S)-2-((4-(N-hydroxycarbamimidoyl)benzyl)carbamoyl)azetidin-1-yl)-2-oxoethyl)glycinate

Formula: C₂₄H₃₅N₅O₅

Purity: 97%

Molecular weight: 473.57

Ref: IN-DG129936

Ximelagatran-d11

Controlled Product

CAS: 192939-46-1

Stability Hygroscopic
Applications An orally active direct thrombin inhibitor; prodrug of Melagatran. Antithrombotic.
References Owens, P.K., et al.: J. Pharm. Biomed. Anal., 27, 587 (2002), Kalus, J.S., et al.: Expert Opin. Invest. Drugs, 13, 465 (2004), Boos, C.J., et al.: Eur. J. Int. Med., 16, 267 (2005), Cullberg, M., et al.: Clin. Pharmacol. Ther., 77, 279 (2005),

Formula: C₂₄H₂₄D₁₁N₅O₅

Color and Shape: Neat

Molecular weight: 484.63

Ref: TR-X745002

Ximelagatran

CAS: 192939-46-1

Ximelagatran is a coumarin derivative that inhibits the enzyme thrombin by binding to its active site. It has been shown to be an effective anticoagulant for the prevention of deep vein thrombosis and pulmonary embolism. Ximelagatran is converted in vivo to its active form, melagatran, which has been shown to have inhibitory properties on human coagulation factor VIIa. Ximelagatran also has a long half-life and does not require regular dosing.

Formula: C₂₄H₃₅N₅O₅

Purity: Min. 95%

Molecular weight: 473.57 g/mol

Ref: 3D-FX28738