Ximelagatran | CAS#192939-46-1 | Thrombin Inhibitor

MedKoo Cat#: 318987 | Name: Ximelagatran

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Ximelagatran

CAS#192939-46-1

Theoretical Analysis

MedKoo Cat#: 318987

Name: Ximelagatran

CAS#: 192939-46-1

Chemical Formula: C24H35N5O5

Exact Mass: 473.2638

Molecular Weight: 473.57

Elemental Analysis: C, 60.87; H, 7.45; N, 14.79; O, 16.89

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 550.00	2 Weeks
50mg	USD 950.00	2 Weeks
100mg	USD 1,650.00	2 Weeks

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Related CAS #

192939-46-1

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

More Info

Certificate of Analysis

View CoA: current batch, Lot#S9G03M07

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 473.57 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.

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

1: Dasari SN, Gadde ST, Myneni P, Bodduluri M, Valiveti SC. Effectiveness of Anticoagulants in Reducing Stroke Risk Among Patients With Atrial Fibrillation. Cureus. 2024 Apr 29;16(4):e59298. doi: 10.7759/cureus.59298. PMID: 38813294; PMCID: PMC11134474. 2: Menezes MS, Doria GAA, Valença-Feitosa F, Pereira SN, Silvestre CC, de Oliveira Filho AD, Lobo IMF, Quintans-Júnior LJ. Incidence of drug-related adverse events related to the use of high-alert drugs: A systematic review of randomized controlled trials. Explor Res Clin Soc Pharm. 2024 Apr 8;14:100435. doi: 10.1016/j.rcsop.2024.100435. PMID: 38646469; PMCID: PMC11031819. 3: Chlorogiannis DD, Mavridis T, Adamou A, Kyriakoulis I, Stamatiou I, Botou P, Chen HS, Ntaios G. Argatroban as an Add-On to rtPA in Acute Ischemic Stroke: A Systematic Review and Meta-Analysis. J Clin Med. 2024 Jan 18;13(2):563. doi: 10.3390/jcm13020563. PMID: 38256696; PMCID: PMC10816854. 4: Migliorini F, Maffulli N, Velaj E, Bell A, Kämmer D, Hildebrand F, Hofmann UK, Eschweiler J. Antithrombotic prophylaxis following total hip arthroplasty: a level I Bayesian network meta-analysis. J Orthop Traumatol. 2024 Jan 9;25(1):1. doi: 10.1186/s10195-023-00742-2. PMID: 38194191; PMCID: PMC10776533. 5: Wang X, Ma Y, Hui X, Li M, Li J, Tian J, Wang Q, Yan P, Li J, Xie P, Yang K, Yao L. Oral direct thrombin inhibitors or oral factor Xa inhibitors versus conventional anticoagulants for the treatment of deep vein thrombosis. Cochrane Database Syst Rev. 2023 Apr 14;4(4):CD010956. doi: 10.1002/14651858.CD010956.pub3. PMID: 37058421; PMCID: PMC10105633. 6: Song W, Ma T, Cheng Q, Wen P, Wu J, Hao L, Zhang B, Wang Y, Wang Q, Zhang Y. Global Research Status and Trends in Venous Thromboembolism After Hip or Knee Arthroplasty From 1990 to 2021: A Bibliometric Analysis. Front Med (Lausanne). 2022 Apr 7;9:837163. doi: 10.3389/fmed.2022.837163. PMID: 35462997; PMCID: PMC9021752. 7: Hermann RP, Rockey DC, Suzuki A, Merz M, Tillmann HL. A novel phenotype-based drug-induced liver injury causality assessment tool (DILI-CAT) allows for signal confirmation in early drug development. Aliment Pharmacol Ther. 2022 Apr;55(8):1028-1037. doi: 10.1111/apt.16836. Epub 2022 Mar 9. PMID: 35266155; PMCID: PMC9164935. 8: He T, Han F, Wang J, Hu Y, Zhu J. Efficacy and safety of anticoagulants for postoperative thrombophylaxis in total hip and knee arthroplasty: A PRISMA- compliant Bayesian network meta-analysis. PLoS One. 2021 Jun 17;16(6):e0250096. doi: 10.1371/journal.pone.0250096. PMID: 34138850; PMCID: PMC8211213. 9: Maier V, Slavík L, Ondra P. A synergy of liquid chromatography with high- resolution mass spectrometry and coagulation test for determination of direct oral anticoagulants for clinical and toxicological purposes. Biomed Chromatogr. 2021 Oct;35(10):e5195. doi: 10.1002/bmc.5195. Epub 2021 Jun 21. PMID: 34109658. 10: Matschinske J, Salgado-Albarrán M, Sadegh S, Bongiovanni D, Baumbach J, Blumenthal DB. Individuating Possibly Repurposable Drugs and Drug Targets for COVID-19 Treatment Through Hypothesis-Driven Systems Medicine Using CoVex. Assay Drug Dev Technol. 2020 Nov/Dec;18(8):348-355. doi: 10.1089/adt.2020.1010. Epub 2020 Nov 6. PMID: 33164550; PMCID: PMC7703307. 11: Najidh S, Versteeg HH, Buijs JT. A systematic review on the effects of direct oral anticoagulants on cancer growth and metastasis in animal models. Thromb Res. 2020 Mar;187:18-27. doi: 10.1016/j.thromres.2019.12.022. Epub 2020 Jan 8. PMID: 31945588. 12: Lippi G, Gosselin R, Favaloro EJ. Current and Emerging Direct Oral Anticoagulants: State-of-the-Art. Semin Thromb Hemost. 2019 Jul;45(5):490-501. doi: 10.1055/s-0039-1692703. Epub 2019 Jun 19. PMID: 31216588. 13: Wallentin L. Så blev NOAK den dominerande behandlingen vid förmaksflimmer - Historiskt perspektiv på den kliniska utvecklingen. Lakartidningen. 2018 Dec 4;115:FAS7. Swedish. PMID: 30512138. 14: Groff H, Azboy I, Parvizi J. Differences in Reported Outcomes in Industry- Funded vs Nonfunded Studies Assessing Thromboprophylaxis After Total Joint Arthroplasty. J Arthroplasty. 2018 Nov;33(11):3398-3401. doi: 10.1016/j.arth.2018.06.025. Epub 2018 Jun 28. PMID: 30017220. 15: Kahale LA, Hakoum MB, Tsolakian IG, Matar CF, Terrenato I, Sperati F, Barba M, Yosuico VE, Schünemann H, Akl EA. Anticoagulation for the long-term treatment of venous thromboembolism in people with cancer. Cochrane Database Syst Rev. 2018 Jun 19;6(6):CD006650. doi: 10.1002/14651858.CD006650.pub5. PMID: 29920657; PMCID: PMC6389342. 16: Babai S, Auclert L, Le-Louët H. Safety data and withdrawal of hepatotoxic drugs. Therapie. 2021 Nov-Dec;76(6):715-723. doi: 10.1016/j.therap.2018.02.004. Epub 2018 Feb 21. PMID: 29609830. 17: Cully M. Milestone 9: Ximelagatran sets the stage for NOACs. Nat Rev Cardiol. 2017 Dec 14. doi: 10.1038/nrcardio.2017.179. Epub ahead of print. PMID: 29238051. 18: Gao JH, Chu XC, Wang LL, Ning B, Zhao CX. Effects of different anticoagulant drugs on the prevention of complications in patients after arthroplasty: A network meta-analysis. Medicine (Baltimore). 2017 Oct;96(40):e8059. doi: 10.1097/MD.0000000000008059. PMID: 28984761; PMCID: PMC5737997. 19: Lundgren H, Martinsson K, Cederbrant K, Jirholt J, Mucs D, Madeyski-Bengtson K, Havarinasab S, Hultman P. HLA-DR7 and HLA-DQ2: Transgenic mouse strains tested as a model system for ximelagatran hepatotoxicity. PLoS One. 2017 Sep 21;12(9):e0184744. doi: 10.1371/journal.pone.0184744. PMID: 28934241; PMCID: PMC5608249. 20: Kampouraki E, Kamali F. Dietary implications for patients receiving long- term oral anticoagulation therapy for treatment and prevention of thromboembolic disease. Expert Rev Clin Pharmacol. 2017 Aug;10(8):789-797. doi: 10.1080/17512433.2017.1345622. Epub 2017 Jun 26. PMID: 28635328.