MedKoo Cat#: 465003 | Name: Melagatran

Description:

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

Melagatran is a thrombin inhibitor. Melagatran prevents tissue factor expression in human platelet-monocyte heterotypic complexes. Melagatran reduces advanced atherosclerotic lesion size and may promote plaque stability in apolipoprotein E-deficient mice.

Chemical Structure

Melagatran
Melagatran
CAS#159776-70-2 (free base)

Theoretical Analysis

MedKoo Cat#: 465003

Name: Melagatran

CAS#: 159776-70-2 (free base)

Chemical Formula: C22H31N5O4

Exact Mass: 429.2376

Molecular Weight: 429.52

Elemental Analysis: C, 61.52; H, 7.28; N, 16.31; O, 14.90

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
159776-70-2 (free base) 179418-09-8 (HCl) 318245-80-6 (hydrate)
Synonym
Melagatran;
IUPAC/Chemical Name
((R)-2-((S)-2-((4-carbamimidoylbenzyl)carbamoyl)azetidin-1-yl)-1-cyclohexyl-2-oxoethyl)glycine
InChi Key
DKWNMCUOEDMMIN-PKOBYXMFSA-N
InChi Code
InChI=1S/C22H31N5O4/c23-20(24)16-8-6-14(7-9-16)12-26-21(30)17-10-11-27(17)22(31)19(25-13-18(28)29)15-4-2-1-3-5-15/h6-9,15,17,19,25H,1-5,10-13H2,(H3,23,24)(H,26,30)(H,28,29)/t17-,19+/m0/s1
SMILES Code
O=C(N(CC1)[C@@H]1C(NCC2=CC=C(C(N)=N)C=C2)=O)[C@@H](C3CCCCC3)NCC(O)=O
Appearance
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
Shelf Life
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 429.52 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
1: Belliard A, Mauco G, Bonnet ML, Hauet T, Macchi L. Melagatran prevents tissue factor expression in human platelet-monocyte heterotypic complexes. Cell Mol Biol (Noisy-le-grand). 2008 Dec 31;54 Suppl:OL1077-82. PubMed PMID: 19149969. 2: Hellstern P, Stürzebecher U, Wuchold B, Haubelt H, Seyfert UT, Bauer M, Vogt A, Stürzebecher J. Preservation of in vitro function of platelets stored in the presence of a synthetic dual inhibitor of factor Xa and thrombin. J Thromb Haemost. 2007 Oct;5(10):2119-26. Epub 2007 Jul 31. PubMed PMID: 17666019. 3: Nitescu N, Grimberg E, Ricksten SE, Marcussen N, Guron G. Thrombin inhibition with melagatran does not attenuate renal ischaemia-reperfusion injury in rats. Nephrol Dial Transplant. 2007 Aug;22(8):2149-55. Epub 2007 Apr 3. PubMed PMID: 17405786. 4: Cullberg M, Eriksson UG, Wåhlander K, Eriksson H, Schulman S, Karlsson MO. Pharmacokinetics of ximelagatran and relationship to clinical response in acute deep vein thrombosis. Clin Pharmacol Ther. 2005 Apr;77(4):279-90. PubMed PMID: 15903126. 5: Fenyvesi T, Jörg I, Weiss C, Harenberg J. Effects of vitamin K antagonist phenprocoumon on activated partial thromboplastin time measurement of direct thrombin inhibitors. Blood Coagul Fibrinolysis. 2004 Oct;15(7):605-11. PubMed PMID: 15389129. 6: Hemdahl AL, Falk E, Thorén P, Hansson GK. Thrombin inhibitor reduces myocardial infarction in apoE-/- x LDLR-/- mice. Am J Physiol Heart Circ Physiol. 2004 Aug;287(2):H872-7. Epub 2004 Mar 18. PubMed PMID: 15031124. 7: Wåhlander K, Lapidus L, Olsson CG, Thuresson A, Eriksson UG, Larson G, Eriksson H. Pharmacokinetics, pharmacodynamics and clinical effects of the oral direct thrombin inhibitor ximelagatran in acute treatment of patients with pulmonary embolism and deep vein thrombosis. Thromb Res. 2002 Aug 15;107(3-4):93-9. PubMed PMID: 12431473. 8: Fenyvesi T, Joerg I, Harenberg J. Influence of lepirudin, argatroban, and melagatran on prothrombin time and additional effect of oral anticoagulation. Clin Chem. 2002 Oct;48(10):1791-4. PubMed PMID: 12324500. 9: Fenyvesi T, Jörg I, Harenberg J. Monitoring of anticoagulant effects of direct thrombin inhibitors. Semin Thromb Hemost. 2002 Aug;28(4):361-8. PubMed PMID: 12244483.