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MedKoo Cat#: 565208 | Name: Napsagatran

Description:

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

Napsagatran is an inhibitor of extrinsic and intrinsic thrombin generation which inhibits clot-bound and free (fluid-phase) thrombin.

Chemical Structure

Napsagatran
Napsagatran
CAS#159668-20-9

Theoretical Analysis

MedKoo Cat#: 565208

Name: Napsagatran

CAS#: 159668-20-9

Chemical Formula: C26H36N6O7S

Exact Mass: 576.2366

Molecular Weight: 576.67

Elemental Analysis: C, 54.15; H, 6.29; N, 14.57; O, 19.42; S, 5.56

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 #
No Data
Synonym
Ro 46-6240; Ro-46-6240; Ro 46 6240; Napsagatran
IUPAC/Chemical Name
2-[[(2S)-4-Amino-2-[[(3S)-1-carbamimidoylpiperidin-3-yl]methyl-naphthalen-2-ylsulfonylamino]-4-oxobutanoyl]-cyclopropylamino]acetic acid hydrate
InChi Key
LQROGLFHUNEOES-ZLLYMXMVSA-N
InChi Code
InChI=1S/C26H34N6O6S.H2O/c27-23(33)13-22(25(36)31(16-24(34)35)20-8-9-20)32(15-17-4-3-11-30(14-17)26(28)29)39(37,38)21-10-7-18-5-1-2-6-19(18)12-21;/h1-2,5-7,10,12,17,20,22H,3-4,8-9,11,13-16H2,(H2,27,33)(H3,28,29)(H,34,35);1H2/t17-,22-;/m0./s1
SMILES Code
O=C(N(CC(O)=O)C1CC1)[C@@H](N(C[C@@H]2CN(C(N)=N)CCC2)S(=O)(C3=CC=C4C=CC=CC4=C3)=O)CC(N)=O.[H]O[H]
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 576.67 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: Lundquist P, Lööf J, Fagerholm U, Sjögren I, Johansson J, Briem S, Hoogstraate J, Afzelius L, Andersson TB. Prediction of in vivo rat biliary drug clearance from an in vitro hepatocyte efflux model. Drug Metab Dispos. 2014 Mar;42(3):459-68. doi: 10.1124/dmd.113.054155. Epub 2014 Jan 6. PubMed PMID: 24396143. 2: Poirier A, Funk C, Scherrmann JM, Lavé T. Mechanistic modeling of hepatic transport from cells to whole body: application to napsagatran and fexofenadine. Mol Pharm. 2009 Nov-Dec;6(6):1716-33. doi: 10.1021/mp8002495. PubMed PMID: 19739673. 3: Himber J, Wohlgensinger C, Roux S, Damico LA, Fallon JT, Kirchhofer D, Nemerson Y, Riederer MA. Inhibition of tissue factor limits the growth of venous thrombus in the rabbit. J Thromb Haemost. 2003 May;1(5):889-95. PubMed PMID: 12871353. 4: Aouizerate P, Guizard M. [Management of heparin-induced thrombocytopenia]. Therapie. 2002 Nov-Dec;57(6):577-88. Review. French. PubMed PMID: 12666266. 5: Hauptmann J. Pharmacokinetics of an emerging new class of anticoagulant/antithrombotic drugs. A review of small-molecule thrombin inhibitors. Eur J Clin Pharmacol. 2002 Jan;57(11):751-8. Review. PubMed PMID: 11868795. 6: Kemme MJ, Faaij RA, Schoemaker RC, Kluft C, Meijer P, Cohen AF, Burggraaf J. Disagreement between bedside and laboratory activated partial thromboplastin time and international normalized ratio for various novel anticoagulants. Blood Coagul Fibrinolysis. 2001 Oct;12(7):583-91. PubMed PMID: 11685048. 7: Faaij RA, van Griensven JM, Schoemaker RC, Goggin T, Guenzi A, Kroon JM, Burggraaf J, Cohen AF. The effect of warfarin on the pharmacokinetics and pharmacodynamics of napsagatran in healthy male volunteers. Eur J Clin Pharmacol. 2001 Apr;57(1):25-9. PubMed PMID: 11372586. 8: Bounameaux H, Ehringer H, Gast A, Hulting J, Rasche H, Rapold HJ, Reber G, Tschopp TB. Differential inhibition of thrombin activity and thrombin generation by a synthetic direct thrombin inhibitor (napsagatran, Ro 46-6240) and unfractionated heparin in patients with deep vein thrombosis. ADVENT Investigators. Thromb Haemost. 1999 Apr;81(4):498-501. PubMed PMID: 10235427. 9: Lavé T, Portmann R, Schenker G, Gianni A, Guenzi A, Girometta MA, Schmitt M. Interspecies pharmacokinetic comparisons and allometric scaling of napsagatran, a low molecular weight thrombin inhibitor. J Pharm Pharmacol. 1999 Jan;51(1):85-91. PubMed PMID: 10197423. 10: Sanderson PE. Small, noncovalent serine protease inhibitors. Med Res Rev. 1999 Mar;19(2):179-97. Review. PubMed PMID: 10189177. 11: Himber J, Kirchhofer D, Riederer M, Tschopp TB, Steiner B, Roux SP. Dissociation of antithrombotic effect and bleeding time prolongation in rabbits by inhibiting tissue factor function. Thromb Haemost. 1997 Sep;78(3):1142-9. PubMed PMID: 9308768. 12: Bounameaux H, Ehringer H, Hulting J, Rasche H, Rapold HJ, Zultak M. An exploratory trial of two dosages of a novel synthetic thrombin inhibitor (napsagatran, Ro 46-6240) compared with unfractionated heparin for treatment of proximal deep-vein thrombosis -- results of the European multicenter ADVENT trial. Thromb Haemost. 1997 Sep;78(3):997-1002. PubMed PMID: 9308743. 13: Roux S, Tschopp T, Baumgartner HR. Effects of napsagatran (Ro 46-6240), a new synthetic thrombin inhibitor and of heparin in a canine model of coronary artery thrombosis: comparison with an ex vivo annular perfusion chamber model. J Pharmacol Exp Ther. 1996 Apr;277(1):71-8. PubMed PMID: 8613969.