Efegatran HCl

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

MedKoo CAT#: 597828

CAS#: 173006-83-2 (2HCl)

Description: Efegatran, also known as GYKI-14166, RGH-2958 and LY294468, a thrombin inhibitor which is being developed by IVAX for the potential treatment of thromboembolic disorders.


Chemical Structure

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Efegatran HCl
CAS# 173006-83-2 (2HCl)

Theoretical Analysis

MedKoo Cat#: 597828
Name: Efegatran HCl
CAS#: 173006-83-2 (2HCl)
Chemical Formula: C21H34Cl2N6O3
Exact Mass: 416.25
Molecular Weight: 489.442
Elemental Analysis: C, 51.53; H, 7.00; Cl, 14.49; N, 17.17; O, 9.81

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 105806-65-3 (free base)   173006-83-2 (2HCl)   126721-07-1 (sulfate)    

Synonym: Efegatran HCl; Efegatran dihydrochloride; GYKI-14166; GYKI14166; GYKI 14166; RGH-2958; RGH 2958; RGH2958; LY 294468; LY-294468; LY294468; Efegatran

IUPAC/Chemical Name: (S)-N-((S)-5-guanidino-1-oxopentan-2-yl)-1-(methyl-D-phenylalanyl)pyrrolidine-2-carboxamide dihydrochloride

InChi Key: NRMUVRCVXCYWNB-VWRRVXQQSA-N

InChi Code: InChI=1S/C21H32N6O3.2ClH/c1-24-17(13-15-7-3-2-4-8-15)20(30)27-12-6-10-18(27)19(29)26-16(14-28)9-5-11-25-21(22)23;;/h2-4,7-8,14,16-18,24H,5-6,9-13H2,1H3,(H,26,29)(H4,22,23,25);2*1H/t16-,17+,18-;;/m0../s1

SMILES Code: O=C([C@H]1N(C([C@@H](CC2=CC=CC=C2)NC)=O)CCC1)N[C@@H](CCCNC(N)=N)C=O.[H]Cl.[H]Cl

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 489.44 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tarzami ST, Wang G, Li W, Green L, Singh JP. Thrombin and PAR-1 stimulate differentiation of bone marrow-derived endothelial progenitor cells. J Thromb Haemost. 2006 Mar;4(3):656-63. PubMed PMID: 16460448.

2: Turer AT, Mahaffey KW, Gallup D, Weaver WD, Christenson RH, Every NR, Ohman EM. Enzyme estimates of infarct size correlate with functional and clinical outcomes in the setting of ST-segment elevation myocardial infarction. Curr Control Trials Cardiovasc Med. 2005 Aug 23;6:12. PubMed PMID: 16115321; PubMed Central PMCID: PMC1236947.

3: Lijnen HR. Efegatran. Institute for drug research/IVAX. IDrugs. 2001 Jun;4(6):691-4. PubMed PMID: 16001314.

4: Tobu M, Iqbal O, Hoppensteadt D, Neville B, Messmore HL, Fareed J. Anti-Xa and anti-IIa drugs alter international normalized ratio measurements: potential problems in the monitoring of oral anticoagulants. Clin Appl Thromb Hemost. 2004 Oct;10(4):301-9. PubMed PMID: 15497016.

5: Tobu M, Iqbal O, Messmore HL, Ma Q, Hoppensteadt DA, Fareed J. Influence of different anticoagulant agents on fibrinopeptide a generation. Clin Appl Thromb Hemost. 2003 Oct;9(4):273-92. PubMed PMID: 14653437.

6: Adams TE, Everse SJ, Mann KG. Predicting the pharmacology of thrombin inhibitors. J Thromb Haemost. 2003 May;1(5):1024-7. PubMed PMID: 12871372.

7: Bajusz S. Josef Rudinger Memorial Lecture 2002. Peptide related drug research. J Pept Sci. 2003 Jun;9(6):321-32. Review. PubMed PMID: 12846479.

8: Aouizerate P, Guizard M. [Management of heparin-induced thrombocytopenia]. Therapie. 2002 Nov-Dec;57(6):577-88. Review. French. PubMed PMID: 12666266.

9: Szabó G, Barabás E, Kedves R, Csomor K, Kuszmann J. Effect of some new thioglycosides on endotoxin-induced disseminated intravascular coagulation in rabbits. Thromb Res. 2002 Sep 15;107(6):357-63. PubMed PMID: 12565724.

10: 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.

11: Direct Thrombin Inhibitor Trialists' Collaborative Group. Direct thrombin inhibitors in acute coronary syndromes: principal results of a meta-analysis based on individual patients' data. Lancet. 2002 Jan 26;359(9303):294-302. PubMed PMID: 11830196.

12: PRIME Investigators. Multicenter, dose-ranging study of efegatran sulfate versus heparin with thrombolysis for acute myocardial infarction: The Promotion of Reperfusion in Myocardial Infarction Evolution (PRIME) trial. Am Heart J. 2002 Jan;143(1):95-105. PubMed PMID: 11773918.

13: Bajusz S. [Research on synthetic peptides of biological interest]. Acta Pharm Hung. 2001;71(1):13-24. Hungarian. PubMed PMID: 11769093.

14: Van Aken H, Bode C, Darius H, Diehm C, Encke A, Gulba DC, Haas S, Hacke W, Puhl W, Quante M, Riess H, Scharf R, Schellong S, Schrör T, Schulte KL, Tebbe U. Anticoagulation: the present and future. Clin Appl Thromb Hemost. 2001 Jul;7(3):195-204. Review. PubMed PMID: 11441979.

15: Fareed J, Hoppensteadt DA, Leya F, Lewis B, Callas D, Wolf H, Bick RL. Thrombogenesis in myocardial infarction and related syndromes: the role of molecular markers in diagnosis and management. Clin Appl Thromb Hemost. 1999 Apr;5(2):78-91. Review. PubMed PMID: 10725987.

16: Fung AY, Lorch G, Cambier PA, Hansen D, Titus BG, Martin JS, Lee JJ, Every NR, Hallstrom AP, Stock-Novack D, Scherer J, Weaver WD. Efegatran sulfate as an adjunct to streptokinase versus heparin as an adjunct to tissue plasminogen activator in patients with acute myocardial infarction. ESCALAT Investigators. Am Heart J. 1999 Oct;138(4 Pt 1):696-704. PubMed PMID: 10502216.

17: Klootwijk P, Lenderink T, Meij S, Boersma H, Melkert R, Umans VA, Stibbe J, Müller EJ, Poortermans KJ, Deckers JW, Simoons ML. Anticoagulant properties, clinical efficacy and safety of efegatran, a direct thrombin inhibitor, in patients with unstable angina. Eur Heart J. 1999 Aug;20(15):1101-11. PubMed PMID: 10413640.

18: Oberhoff M, Karsch KR. Synthetic direct thrombin inhibitors in unstable angina - more questions than answers. Eur Heart J. 1999 Aug;20(15):1058-60. PubMed PMID: 10413631.

19: Nilsson T, Sjöling-Ericksson A, Deinum J. The mechanism of binding of low-molecular-weight active site inhibitors to human alpha-thrombin. J Enzyme Inhib. 1998 Feb;13(1):11-29. PubMed PMID: 9879511.

20: Harmat NJ, Di Bugno C, Criscuoli M, Giorgi R, Lippi A, Martinelli A, Monti S, Subissi A. 1,2-disubstituted cyclohexane derived tripeptide aldehydes as novel selective thrombin inhibitors. Bioorg Med Chem Lett. 1998 May 19;8(10):1249-54. PubMed PMID: 9871744.