Lotrafiban | CAS#171049-14-2 | nonpeptide antagonist

MedKoo Cat#: 599261 | Name: Lotrafiban

Description:

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

Lotrafiban is a selective, nonpeptide antagonist of the human platelet fibrinogen receptor (glycoprotein IIb/IIIa) for treatment of coronary or cerebral atherosclerotic disease.

Chemical Structure

Lotrafiban

CAS#171049-14-2

Theoretical Analysis

MedKoo Cat#: 599261

Name: Lotrafiban

CAS#: 171049-14-2

Chemical Formula: C23H32N4O4

Exact Mass: 428.2424

Molecular Weight: 428.53

Elemental Analysis: C, 64.46; H, 7.53; N, 13.07; O, 14.93

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

Lotrafiban; SB 214857; SB-214857; SB214857;

IUPAC/Chemical Name

(S)-2-(7-([4,4'-bipiperidine]-1-carbonyl)-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-2-yl)acetic acid

InChi Key

PYZOVVQJTLOHDG-FQEVSTJZSA-N

InChi Code

InChI=1S/C23H32N4O4/c1-26-14-18-12-17(2-3-19(18)25-20(23(26)31)13-21(28)29)22(30)27-10-6-16(7-11-27)15-4-8-24-9-5-15/h2-3,12,15-16,20,24-25H,4-11,13-14H2,1H3,(H,28,29)/t20-/m0/s1

SMILES Code

O=C(O)C[C@@H]1NC2=CC=C(C(N3CCC(C4CCNCC4)CC3)=O)C=C2CN(C)C1=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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 428.53 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

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PubMed PMID: 12769654. 4: Harrington RA, Armstrong PW, Graffagnino C, Van De Werf F, Kereiakes DJ, Sigmon KN, Card T, Joseph DM, Samuels R, Granett J, Chan R, Califf RM, Topol EJ. Dose-finding, safety, and tolerability study of an oral platelet glycoprotein IIb/IIIa inhibitor, lotrafiban, in patients with coronary or cerebral atherosclerotic disease. Circulation. 2000 Aug 15;102(7):728-35. PubMed PMID: 10942739. 5: Mould D, Chapelsky M, Aluri J, Swagzdis J, Samuels R, Granett J. A population pharmacokinetic-pharmacodynamic and logistic regression analysis of lotrafiban in patients. Clin Pharmacol Ther. 2001 Apr;69(4):210-22. PubMed PMID: 11309549. 6: SoRelle R. SmithKline Beecham halts tests of lotrafiban, an oral glycoprotein IIb/IIIa inhibitor. Circulation. 2001 Jan 2;103(1):E9001-2. 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Activation of caspase-3/caspase-3-like activity in rat cardiomyocytes by an RGD peptide, but not the GPIIb/IIIa antagonist lotrafiban. Thromb Res. 2001 Jul 15;103(2):143-8. PubMed PMID: 11457472. 11: Jones ML, Harper MT, Aitken EW, Williams CM, Poole AW. RGD-ligand mimetic antagonists of integrin alphaIIbbeta3 paradoxically enhance GPVI-induced human platelet activation. J Thromb Haemost. 2010 Mar;8(3):567-76. doi: 10.1111/j.1538-7836.2009.03719.x. Epub 2009 Dec 11. Erratum in: J Thromb Haemost. 2010 Nov;8(11):2588. PubMed PMID: 20002543. 12: Billheimer JT, He B, Spitz SM, Stern AM, Seiffert D. Effects of glycoprotein IIb/IIIa antagonists on platelet activation: development of a transfer method to mimic peak to trough receptor occupancy. Thromb Res. 2002 Sep 15;107(6):303-17. PubMed PMID: 12565717. 13: Jarvis GE, Atkinson BT, Frampton J, Watson SP. Thrombin-induced conversion of fibrinogen to fibrin results in rapid platelet trapping which is not dependent on platelet activation or GPIb. Br J Pharmacol. 2003 Feb;138(4):574-83. PubMed PMID: 12598411; PubMed Central PMCID: PMC1573703. 14: Salam AM. Is there a role for oral blockade of platelet glycoprotein IIb/IIIa receptors in coronary and cerebrovascular disease? Expert Opin Investig Drugs. 2003 Oct;12(10):1709-12. PubMed PMID: 14519089. 15: Wang X, Dorsam RT, Lauver A, Wang H, Barbera FA, Gibbs S, Varon D, Savion N, Friedman SM, Feuerstein GZ. Comparative analysis of various platelet glycoprotein IIb/IIIa antagonists on shear-induced platelet activation and adhesion. J Pharmacol Exp Ther. 2002 Dec;303(3):1114-20. PubMed PMID: 12438534. 16: Atkinson BT, Jarvis GE, Watson SP. Activation of GPVI by collagen is regulated by alpha2beta1 and secondary mediators. J Thromb Haemost. 2003 Jun;1(6):1278-87. PubMed PMID: 12871331. 17: McCarty OJ, Calaminus SD, Berndt MC, Machesky LM, Watson SP. von Willebrand factor mediates platelet spreading through glycoprotein Ib and alpha(IIb)beta3 in the presence of botrocetin and ristocetin, respectively. J Thromb Haemost. 2006 Jun;4(6):1367-78. PubMed PMID: 16706984. 18: Lapchak PA, Araujo DM. Therapeutic potential of platelet glycoprotein IIb/IIIa receptor antagonists in the management of ischemic stroke. Am J Cardiovasc Drugs. 2003;3(2):87-94. Review. PubMed PMID: 14727935. 19: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Nov;25(9):747-71. PubMed PMID: 14685303. 20: Seyfarth HJ, Koksch M. Fibrinogen receptor antagonists induce conformational changes of the human platelet glycoprotein IIb. Cytometry B Clin Cytom. 2004 Nov;62(1):14-24. PubMed PMID: 15476209.