Ximelagatran
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MedKoo CAT#: 318987

CAS#: 192939-46-1

Description: Ximelagatran (Exanta or Exarta, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin[1] that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, this drug was discontinued due to hepatotoxicity (liver damage). Ximelagatran, a direct thrombin inhibitor,[3] was the first member of this class that can be taken orally. It acts solely by inhibiting the actions of thrombin. It is taken orally twice daily, and rapidly absorbed by the small intestine. Ximelagatran is a prodrug, being converted in vivo to the active agent melagatran.


Chemical Structure

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Ximelagatran
CAS# 192939-46-1

Theoretical Analysis

MedKoo Cat#: 318987
Name: Ximelagatran
CAS#: 192939-46-1
Chemical Formula: C24H35N5O5
Exact Mass: 473.26382
Molecular Weight: 473.574
Elemental Analysis: C, 60.87; H, 7.45; N, 14.79; O, 16.89

Price and Availability

Size Price Availability Quantity
5.0mg USD 450.0 2 Weeks
25.0mg USD 1450.0 2 Weeks
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Synonym: H 376-95; H 376/95; H 37695; H-37695; H37695; Ximelagatran; Exanta; Exarta

IUPAC/Chemical Name: N-[(1R)-1-cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]-glycine, ethyl ester

InChi Key: PMOVWDINZOACJB-ILZRESODSA-N

InChi Code: InChI=1S/C24H35N5O5/c1-2-34-21(30)16-25-22(19-6-4-3-5-7-19)24(32)29-13-12-20(29)23(31)26-14-17-8-10-18(11-9-17)15-27-28-33/h8-11,15,19-20,22,25,28,33H,2-7,12-14,16H2,1H3,(H,26,31)/b27-15+/t20-,22+/m0/s1

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

Appearance: White to beige solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 473.574 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Keisu M, Andersson TB. Drug-induced liver injury in humans: the case of ximelagatran. Handb Exp Pharmacol. 2010;(196):407-18. doi: 10.1007/978-3-642-00663-0_13. Review. PubMed PMID: 20020269.

2: Lazo-Langner A, Rodger MA, Wells PS. Lessons from ximelagatran: issues for future studies evaluating new oral direct thrombin inhibitors for venous thromboembolism prophylaxis in orthopedic surgery. Clin Appl Thromb Hemost. 2009 May-Jun;15(3):316-26. doi: 10.1177/1076029608326166. Review. PubMed PMID: 19028773.

3: Testa L, Bhindi R, Agostoni P, Abbate A, Zoccai GG, van Gaal WJ. The direct thrombin inhibitor ximelagatran/melagatran: a systematic review on clinical applications and an evidence based assessment of risk benefit profile. Expert Opin Drug Saf. 2007 Jul;6(4):397-406. Review. PubMed PMID: 17688383.

4: Koscielny J, Kiesewetter H, Jörg I, Harenberg J. Ximelagatran for treatment and prophylaxis of recurrent events in deep vein thrombosis. Clin Appl Thromb Hemost. 2007 Jul;13(3):299-307. Review. PubMed PMID: 17636192.

5: Nagata K. [Ximelagatran]. Nihon Rinsho. 2006 Oct 28;64 Suppl 7:630-6. Review. Japanese. PubMed PMID: 17461216.

6: Selçuk H, Selçuk MT, Maden O. [Antithrombotic therapy in atrial fibrillation with ximelagatran: can it be an alternative to warfarin?]. Anadolu Kardiyol Derg. 2007 Mar;7(1):54-8. Review. Turkish. PubMed PMID: 17347079.

7: Yoshida WB, El Dib RP, Yoshida Rde A, Maffei FH. Ximelagatran versus warfarin for prophylaxis of venous thromboembolism in major orthopedic surgery: systematic review of randomized controlled trials. Sao Paulo Med J. 2006 Nov 7;124(6):355-61. Review. PubMed PMID: 17322960.

8: Ho SJ, Brighton TA. Ximelagatran: direct thrombin inhibitor. Vasc Health Risk Manag. 2006;2(1):49-58. Review. PubMed PMID: 17319469; PubMed Central PMCID: PMC1993972.

9: Boudes PF. The challenges of new drugs benefits and risks analysis: lessons from the ximelagatran FDA Cardiovascular Advisory Committee. Contemp Clin Trials. 2006 Oct;27(5):432-40. Review. PubMed PMID: 16769255.

10: Mousa SA, Abdel-Razeq HN. Ximelagatran, the new oral anticoagulant: would warfarin survive the challenge? Cardiovasc Drug Rev. 2005 Winter;23(4):331-44. Review. PubMed PMID: 16614732.

11: Rewiuk K, Franczuk P, Grodzicki T. [New antithrombotic drugs: fondaparinux, idraparinux, ximelagatran]. Przegl Lek. 2005;62(8):799-803. Review. Polish. PubMed PMID: 16521501.

12: Choudhury A, Goyal D, Lip GY. Ximelagatran. Drugs Today (Barc). 2006 Jan;42(1):3-19. Review. PubMed PMID: 16511607.

13: Kwok L, Molckovsky D, Boucher M. Ximelagatran: a new type of oral anticoagulant. Int J Technol Assess Health Care. 2005 Fall;21(4):480-6. Review. PubMed PMID: 16262971.

14: Cohen AT, Hirst C, Sherrill B, Holmes P, Fidan D. Meta-analysis of trials comparing ximelagatran with low molecular weight heparin for prevention of venous thromboembolism after major orthopaedic surgery. Br J Surg. 2005 Nov;92(11):1335-44. Review. PubMed PMID: 16237737.

15: Lip GY, Edwards SJ. Stroke prevention with aspirin, warfarin and ximelagatran in patients with non-valvular atrial fibrillation: a systematic review and meta-analysis. Thromb Res. 2006;118(3):321-33. Epub 2005 Sep 29. Review. PubMed PMID: 16198396.

16: Schulman S, Lip GY. Ximelagatran in the clinic: practical management of patients. Semin Vasc Med. 2005 Aug;5(3):301-7. Review. PubMed PMID: 16123918.

17: Colwell C, Mouret P. Ximelagatran for the prevention of venous thromboembolism following elective hip or knee replacement surgery. Semin Vasc Med. 2005 Aug;5(3):266-75. Review. PubMed PMID: 16123914.

18: Carlsson SC, Schulman S. A step change in oral anticoagulation: lack of coagulation monitoring with ximelagatran. Semin Vasc Med. 2005 Aug;5(3):259-65. Review. PubMed PMID: 16123913.

19: Wolzt M, Sarich TS, Eriksson UG. Low potential for interactions between melagatran/ximelagatran and other drugs, food, or alcohol. Semin Vasc Med. 2005 Aug;5(3):254-8. Review. PubMed PMID: 16123912.

20: Wolzt M, Sarich TS, Eriksson UG. Pharmacokinetics and pharmacodynamics of ximelagatran. Semin Vasc Med. 2005 Aug;5(3):245-53. Review. PubMed PMID: 16123911.