WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 584941
CAS#: 163250-90-6
Description: Orbofiban is an orally active GPIIb/IIIa antagonist that has antiplatelet and antithrombotic effects.
MedKoo Cat#: 584941
Name: Orbofiban
CAS#: 163250-90-6
Chemical Formula: C17H23N5O4
Exact Mass: 361.175
Molecular Weight: 361.402
Elemental Analysis: C, 56.50; H, 6.42; N, 19.38; O, 17.71
This product is not in stock, which may be available by custom synthesis.
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Synonym: Orbofiban
IUPAC/Chemical Name: beta-Alanine, N-((((3S)-1-(4-(aminoiminomethyl)phenyl)-2-oxo-3- pyrrolidinyl)amino)carbonyl)-, ethyl ester
InChi Key: VJDOPFARMOLELX-ZDUSSCGKSA-N
InChi Code: InChI=1S/C17H23N5O4/c1-2-26-14(23)7-9-20-17(25)21-13-8-10-22(16(13)24)12-5-3-11(4-6-12)15(18)19/h3-6,13H,2,7-10H2,1H3,(H3,18,19)(H2,20,21,25)/t13-/m0/s1
SMILES Code: O=C(OCC)CCNC(N[C@@H]1C(N(C2=CC=C(C(N)=N)C=C2)CC1)=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
The following data is based on the product molecular weight 361.402 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.
| 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: Cannon CP, McCabe CH, Wilcox RG, Langer A, Caspi A, Berink P, Lopez-Sendon J, Toman J, Charlesworth A, Anders RJ, Alexander JC, Skene A, Braunwald E. Oral glycoprotein IIb/IIIa inhibition with orbofiban in patients with unstable coronary syndromes (OPUS-TIMI 16) trial. Circulation. 2000 Jul 11;102(2):149-56. PubMed PMID: 10889124.
2: Ogawa T, Sugidachi A, Naganuma H, Asai F. Antiplatelet and antithrombotic effects of orbofiban, a new orally active GPIIb/IIIa antagonist, in guinea pigs. Thromb Res. 2000 Mar 1;97(5):307-15. PubMed PMID: 10709906.
3: Racanelli AL, Gibbs SK, Zondlo SC, Seiffert DA, Friedman SM, Feuerstein GZ. Differential effect of the GPIIb/IIIa antagonist orbofiban on human platelet aggregate formation in vitro. Thromb Res. 2003 May 1;110(2-3):99-105. PubMed PMID: 12893024.
4: Mousa SA, Abulencia JP, McCarty OJ, Turner NA, Konstantopoulos K. Comparative efficacy between the glycoprotein IIb/IIIa antagonists roxifiban and orbofiban in inhibiting platelet responses in flow models of thrombosis. J Cardiovasc Pharmacol. 2002 Apr;39(4):552-60. PubMed PMID: 11904529.
5: Anders R, Kleiman J, Nicholson N, Wazowicz B, Burns D. Xemilofiban/orbofiban: insight into drug development. Cardiovasc Drug Rev. 2001 Summer;19(2):116-32. Review. PubMed PMID: 11484066.
6: Holmes MB, Sobel BE, Cannon CP, Schneider DJ. Increased platelet reactivity in patients given orbofiban after an acute coronary syndrome: an OPUS-TIMI 16 substudy. Orbofiban in Patients with Unstable coronary syndromes. Thrombolysis In Myocardial Infarction. Am J Cardiol. 2000 Feb 15;85(4):491-3, A10. PubMed PMID: 10728957.
7: Smith EE, Cannon CP, Murphy S, Feske SK, Schwamm LH. Risk factors for stroke after acute coronary syndromes in the Orbofiban in Patients with Unstable Coronary Syndromes--Thrombolysis In Myocardial Infarction (OPUS-TIMI) 16 study. Am Heart J. 2006 Feb;151(2):338-44. PubMed PMID: 16442896.
8: Mager DE, Shirey JD, Cox D, Fitzgerald DJ, Abernethy DR. Mapping the dose-effect relationship of orbofiban from sparse data with an artificial neural network. J Pharm Sci. 2005 Nov;94(11):2475-86. PubMed PMID: 16200613.
9: Cotter G, Cannon CP, McCabe CH, Michowitz Y, Kaluski E, Charlesworth A, Milo O, Bentley J, Blatt A, Krakover R, Zimlichman R, Reisin L, Marmor A, Lewis B, Vered Z, Caspi A, Braunwald E; OPUS-TIMI 16 Investigators. Prior peripheral arterial disease and cerebrovascular disease are independent predictors of adverse outcome in patients with acute coronary syndromes: are we doing enough? Results from the Orbofiban in Patients with Unstable Coronary Syndromes-Thrombolysis In Myocardial Infarction (OPUS-TIMI) 16 study. Am Heart J. 2003 Apr;145(4):622-7. PubMed PMID: 12679757.
10: Nicholson NS, Abood NA, Panzer-Knodle SG, Frederick LG, Page JD, Salyers AK, Suleymanov OD, Szalony JA, Taite BB, Anders RJ. Orbofiban: an orally active GPIIb/IIIa platelet receptor antagonist. Med Res Rev. 2001 May;21(3):211-26. PubMed PMID: 11301411.
11: Maree AO, Vangjeli C, Jneid H, Ryan J, Cox D, Cannon CP, Shields DC, Fitzgerald DJ. G-protein beta3 subunit polymorphism and bleeding in the orbofiban in patients with unstable coronary syndromes-thrombolysis in myocardial infarction 16 trial. J Thromb Haemost. 2010 May;8(5):934-41. doi: 10.1111/j.1538-7836.2010.03775.x. Epub 2010 Jan 22. PubMed PMID: 20096003.
12: Atar S, Cannon CP, Murphy SA, Rosanio S, Uretsky BF, Birnbaum Y. Statins are associated with lower risk of gastrointestinal bleeding in patients with unstable coronary syndromes: analysis of the Orbofiban in Patients with Unstable coronary Syndromes-Thrombolysis In Myocardial Infarction 16 (OPUS-TIMI 16) trial. Am Heart J. 2006 May;151(5):976.e1-6. PubMed PMID: 16644315.
13: Scirica BM, Cannon CP, Cooper R, Aster RH, Brassard J, McCabe CH, Charlesworth A, Skene AM, Braunwald E. Drug-induced thrombocytopenia and thrombosis: evidence from patients receiving an oral glycoprotein IIb/IIIa inhibitor in the Orbofiban in Patients with Unstable coronary Syndromes- (OPUS-TIMI 16) trial. J Thromb Thrombolysis. 2006 Oct;22(2):95-102. PubMed PMID: 17008974.
14: Cox D, Smith R, Quinn M, Theroux P, Crean P, Fitzgerald DJ. Evidence of platelet activation during treatment with a GPIIb/IIIa antagonist in patients presenting with acute coronary syndromes. J Am Coll Cardiol. 2000 Nov 1;36(5):1514-9. PubMed PMID: 11079651.
15: Serrano CV Jr, Nicolau JC, Venturinelli M, Baracioli LM, Anders RJ, Cannon CP, Ramires JA. Role of oral blockade of platelet glycoprotein IIb/IIIa on neutrophil activation in patients with acute coronary syndromes. Cardiovasc Drugs Ther. 2003 Mar;17(2):129-32. PubMed PMID: 12975594.
16: Brassard JA, Curtis BR, Cooper RA, Ferguson J, Komocsar W, Ehardt M, Kupfer S, Maurath C, Swabb E, Cannon CP, Aster RH. Acute thrombocytopenia in patients treated with the oral glycoprotein IIb/IIIa inhibitors xemilofiban and orbofiban: evidence for an immune etiology. Thromb Haemost. 2002 Dec;88(6):892-7. PubMed PMID: 12529735.
17: O'Connor FF, Shields DC, Fitzgerald A, Cannon CP, Braunwald E, Fitzgerald DJ. Genetic variation in glycoprotein IIb/IIIa (GPIIb/IIIa) as a determinant of the responses to an oral GPIIb/IIIa antagonist in patients with unstable coronary syndromes. Blood. 2001 Dec 1;98(12):3256-60. PubMed PMID: 11719362.
18: Adderley SR, Fitzgerald DJ. Glycoprotein IIb/IIIa antagonists induce apoptosis in rat cardiomyocytes by caspase-3 activation. J Biol Chem. 2000 Feb 25;275(8):5760-6. PubMed PMID: 10681563.
19: Hantgan RR, Stahle MC, Connor JH, Connor RF, Mousa SA. AlphaIIbbeta3 priming and clustering by orally active and intravenous integrin antagonists. J Thromb Haemost. 2007 Mar;5(3):542-50. Epub 2006 Dec 13. PubMed PMID: 17166246.
20: Smith CS, Cannon CP, McCabe CH, Murphy SA, Bentley J, Braunwald E. Early initiation of lipid-lowering therapy for acute coronary syndromes improves compliance with guideline recommendations: observations from the Orbofiban in Patients with Unstable Coronary Syndromes (OPUS-TIMI 16) trial. Am Heart J. 2005 Mar;149(3):444-50. PubMed PMID: 15864232.
