Ifetroban

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

MedKoo CAT#: 525269

CAS#: 143443-90-7

Description: Ifetroban is a potent and selective TxA2/PGH2 receptor antagonist.


Chemical Structure

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Ifetroban
CAS# 143443-90-7

Theoretical Analysis

MedKoo Cat#: 525269
Name: Ifetroban
CAS#: 143443-90-7
Chemical Formula: C25H32N2O5
Exact Mass: 440.23112
Molecular Weight: 440.53
Elemental Analysis: C, 68.16; H, 7.32; N, 6.36; O, 18.16

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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Synonym: Ifetroban; BMS 180291-02; BMS-180291; BMS180291; Ifetroban [USAN:INN].

IUPAC/Chemical Name: o-((1S,2R,3S,4R)-3-(4-(Pentylcarbamoyl)-2-oxazolyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)hydrocinnamic acid

InChi Key: BBPRUNPUJIUXSE-DXXSNHLCSA-N

InChi Code: InChI=1S/C25H32N2O5/c1-2-3-6-13-26-24(30)19-15-31-25(27-19)23-18(20-10-11-21(23)32-20)14-17-8-5-4-7-16(17)9-12-22(28)29/h4-5,7-8,15,18,20-21,23H,2-3,6,9-14H2,1H3,(H,26,30)(H,28,29)/t18?,20-,21?,23?/m0/s1

SMILES Code: O=C(O)CCC1=CC=CC=C1CC2[C@](O3)([H])CCC3C2C4=NC(C(NCCCCC)=O)=CO4

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: >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

Preparing Stock Solutions

The following data is based on the product molecular weight 440.53 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.

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

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1: Pestel S, Nath A, Jungermann K, Schieferdecker HL. Inhibition of prostaglandin D2 clearance in rat hepatocytes by the thromboxane receptor antagonists daltroban and ifetroban and the thromboxane synthase inhibitor furegrelate. Biochem Pharmacol. 2003 Aug 15;66(4):643-52. PubMed PMID: 12906929.

2: Rosenfeld L, Grover GJ, Stier CT Jr. Ifetroban sodium: an effective TxA2/PGH2 receptor antagonist. Cardiovasc Drug Rev. 2001 Summer;19(2):97-115. Review. PubMed PMID: 11484065.

3: Dockens RC, Santone KS, Mitroka JG, Morrison RA, Jemal M, Greene DS, Barbhaiya RH. Disposition of radiolabeled ifetroban in rats, dogs, monkeys, and humans. Drug Metab Dispos. 2000 Aug;28(8):973-80. PubMed PMID: 10901709.

4: Katz SD, Radin M, Graves T, Hauck C, Block A, LeJemtel TH. Effect of aspirin and ifetroban on skeletal muscle blood flow in patients with congestive heart failure treated with Enalapril. Ifetroban Study Group. J Am Coll Cardiol. 1999 Jul;34(1):170-6. PubMed PMID: 10400007.

5: Johnson RA, Belmonte A, Fan NY, Lavesa M, Nasjletti A, Stier CT Jr. Effect of ifetroban, a thromboxane A2 receptor antagonist, in stroke-prone spontaneously hypertensive rats. Clin Exp Hypertens. 1996 Feb;18(2):171-88. PubMed PMID: 8868999.

6: Gomoll AW, Schumacher WA, Ogletree ML. Dose-related cardioprotection by ifetroban in relation to inhibition of thrombosis and ex vivo platelet function. Pharmacology. 1995 Feb;50(2):92-110. PubMed PMID: 7716179.

7: Gomoll AW, Ogletree ML. Failure of aspirin to interfere with the cardioprotective effects of ifetroban. Eur J Pharmacol. 1994 Dec 27;271(2-3):471-9. PubMed PMID: 7705447.

8: Gomoll AW, Grover GJ, Ogletree ML. Myocardial salvage efficacy of the thromboxane receptor antagonist ifetroban in ferrets and dogs. J Cardiovasc Pharmacol. 1994 Dec;24(6):960-8. PubMed PMID: 7898080.

9: Lodge NJ. Direct vasoconstrictor effects of sandimmune (cyclosporine A) are mediated by its vehicle cremophor EL: inhibition by the thromboxane A2/prostaglandin endoperoxide receptor antagonist ifetroban. J Pharmacol Exp Ther. 1994 Nov;271(2):730-4. PubMed PMID: 7965789.