Napsagatran

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

MedKoo CAT#: 565208

CAS#: 159668-20-9

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


Price and Availability

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Napsagatran is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


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]


Technical Data

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).

Harmonized System Code:
2934990300


References

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.