MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 526605 | Name: Efegatran free base

Description:

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

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

Efegatran free base
Efegatran free base
CAS#105806-65-3 (free base)

Theoretical Analysis

MedKoo Cat#: 526605

Name: Efegatran free base

CAS#: 105806-65-3 (free base)

Chemical Formula: C20H30N6O3

Exact Mass: 402.2379

Molecular Weight: 402.50

Elemental Analysis: C, 59.68; H, 7.51; N, 20.88; O, 11.92

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.
Bulk Inquiry
Related CAS #
105806-65-3 (free base) 173006-83-2 (2HCl) 126721-07-1 (sulfate)
Synonym
GYKI-14166; GYKI14166; GYKI 14166; RGH-2958; RGH 2958; RGH2958; LY 294468; LY-294468; LY294468; Efegatran
IUPAC/Chemical Name
(S)-1-(D-phenylalanyl)-N-((S)-5-guanidino-1-oxopentan-2-yl)pyrrolidine-2-carboxamide
InChi Key
InChI=1S/C20H30N6O3/c21-16(12-14-6-2-1-3-7-14)19(29)26-11-5-9-17(26)18(28)25-15(13-27)8-4-10-24-20(22)23/h1-3,6-7,13,15-17H,4-5,8-12,21H2,(H,25,28)(H4,22,23,24)/t15-,16+,17-/m0/s1
InChi Code
InChI=1S/C20H30N6O3/c21-16(12-14-6-2-1-3-7-14)19(29)26-11-5-9-17(26)18(28)25-15(13-27)8-4-10-24-20(22)23/h1-3,6-7,13,15-17H,4-5,8-12,21H2,(H,25,28)(H4,22,23,24)/t15-,16+,17-/m0/s1
SMILES Code
O=C([C@H]1N(C([C@@H](CC2=CC=CC=C2)N)=O)CCC1)N[C@@H](CCCNC(N)=N)C=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, 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
CAS# related to GYKI-14166 83997-16-4 (GYKI-14166 suflate) 77481-39-1 (GYKI-14166 diacetate), 77481-38-0 (GYKI-14166 diHCl), 60503-05-1 (GYKI-14166 free base)

Preparing Stock Solutions

The following data is based on the product molecular weight 402.50 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: 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.