Vapiprost

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

MedKoo CAT#: 584415

CAS#: 85505-64-2

Description: Vapiprost is a thromboxane receptor antagonist and prostaglandin receptor antagonist.


Price and Availability

Size
Price

Size
Price

Size
Price

Vapiprost is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 584415
Name: Vapiprost
CAS#: 85505-64-2
Chemical Formula: C30H39NO4
Exact Mass: 477.2879
Molecular Weight: 477.645
Elemental Analysis: C, 75.44; H, 8.23; N, 2.93; O, 13.40


Synonym: Vapiprost; GR 32191; GR32191; GR-32191

IUPAC/Chemical Name: 4-Heptenoic acid, 7-(5-((1,1'-biphenyl)-4-ylmethoxy)-3-hydroxy-2-(1-piperidinyl)cyclopentyl)-, (1R-(1alpha(Z),2beta,3beta,5alpha))-

InChi Key: GQGRDYWMOPRROR-XUSMOFMBSA-N

InChi Code: InChI=1S/C30H39NO4/c32-27-21-28(35-22-23-15-17-25(18-16-23)24-11-5-3-6-12-24)26(13-7-1-2-8-14-29(33)34)30(27)31-19-9-4-10-20-31/h1-3,5-6,11-12,15-18,26-28,30,32H,4,7-10,13-14,19-22H2,(H,33,34)/b2-1-/t26-,27-,28-,30+/m0/s1

SMILES Code: O=C(O)CC/C=C\CC[C@@H]1[C@@H](N2CCCCC2)[C@@H](O)C[C@@H]1OCC3=CC=C(C4=CC=CC=C4)C=C3


Technical Data

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).

Harmonized System Code:
293490


References

1: Uematsu T, Nagashima S, Mizuno A, Hirano K, Nakashima M. Pharmacokinetic and pharmacodynamic profiles of vapiprost, a selective, long-lasting thromboxane receptor antagonist, after single and multiple oral administration to healthy volunteers. J Clin Pharmacol. 1991 Sep;31(9):815-22. PubMed PMID: 1839540.

2: Nishiyama H, Umemura K, Saniabadi AR, Takiguchi Y, Uematsu T, Nakashima M. Enhancement of thrombolytic efficacy of tissue-type plasminogen activator by adjuvants in the guinea pig thrombosis model. Eur J Pharmacol. 1994 Oct 24;264(2):191-8. PubMed PMID: 7851482.

3: Kan KK, Jones RL, Ngan MP, Rudd JA. Action of prostanoids on the emetic reflex of Suncus murinus (the house musk shrew). Eur J Pharmacol. 2003 Sep 23;477(3):247-51. PubMed PMID: 14522363.

4: Matsuzaki T, Noguchi K, Nakasone J, Uezu K, Higuchi M, Sakanashi M. Effects of the new thromboxane A2 antagonist vapiprost on isolated canine blood vessels. Arzneimittelforschung. 1992 Nov;42(11):1318-22. PubMed PMID: 1492844.

5: Idris-Khodja N, Auger C, Koch E, Schini-Kerth VB. Crataegus special extract WS(®)1442 prevents aging-related endothelial dysfunction. Phytomedicine. 2012 Jun 15;19(8-9):699-706. doi: 10.1016/j.phymed.2012.04.005. Epub 2012 May 22. PubMed PMID: 22621780.

6: Carter PR, McElhatten RM, Zhang S, Wright WS, Harris NR. Thromboxane-prostanoid receptor expression and antagonism in dextran-sodium sulfate-induced colitis. Inflamm Res. 2011 Jan;60(1):87-92. doi: 10.1007/s00011-010-0240-2. Epub 2010 Aug 8. PubMed PMID: 20694740.

7: Sakanashi M, Matsuzaki T, Noguchi K, Nakasone J, Itomine T, Uza M, Toyama F, Higuchi M. Inhibitory effect of vapiprost on contractile responses of isolated dog renal arteries to thromboxane A2 analogue, U46619. Gen Pharmacol. 1994 Jul;25(4):617-22. PubMed PMID: 7958719.

8: Exner HJ, Schlicker E. Prostanoid receptors of the EP3 subtype mediate the inhibitory effect of prostaglandin E2 on noradrenaline release in the mouse brain cortex. Naunyn Schmiedebergs Arch Pharmacol. 1995 Jan;351(1):46-52. PubMed PMID: 7715741.

9: Umemura K, Asai Y, Uematsu T, Nakashima M. Role of thromboxane A2 in a microcirculation disorder of the rat inner ear. Eur Arch Otorhinolaryngol. 1993;250(6):342-4. PubMed PMID: 8260145.

10: Umemura K, Kawai H, Ishihara H, Nakashima M. Inhibitory effect of clopidogrel, vapiprost and argatroban on the middle cerebral artery thrombosis in the rat. Jpn J Pharmacol. 1995 Mar;67(3):253-8. PubMed PMID: 7630043.

11: Tsui SS, Kirshbom PM, Davies MJ, Jacobs MT, Kern FH, Gaynor JW, Greeley WJ, Ungerleider RM. Thromboxane A2-receptor blockade improves cerebral protection for deep hypothermic circulatory arrest. Eur J Cardiothorac Surg. 1997 Aug;12(2):228-35. PubMed PMID: 9288512.

12: Ohashi K, Aso R. Influence of age on the pharmacokinetics of vapiprost, a thromboxane A2 receptor antagonist, and platelet aggregation: comparison of pharmacokinetics by routine approach and population pharmacokinetics. Int J Clin Pharmacol Res. 2001;21(2):85-94. PubMed PMID: 11824652.

13: White BP, Sullivan AT, Lumley P. Prevention of intra-coronary thrombosis in the anaesthetised dog: the importance of thromboxane A2 and thrombin. Thromb Haemost. 1994 Mar;71(3):366-74. PubMed PMID: 8029802.

14: Hirata Y, Umemura K, Uematsu T, Nakashima M. An experimental myocardial infarction model in the rat and its properties. Jpn J Pharmacol. 1995 Jan;67(1):51-7. PubMed PMID: 7745845.

15: Lundell A, Bergqvist D, Leide S, Lindblad B, Ljungberg J. The effect of a thromboxane receptor antagonist on acute ePTFE arterial graft thrombogenicity--an experimental study in sheep. Eur J Vasc Surg. 1991 Jun;5(3):321-6. PubMed PMID: 1830856.

16: Takiguchi Y, Hirata Y, Wada K, Nakashima M. Arterial thrombosis model with photochemical reaction in guinea-pig and its property. Thromb Res. 1992 Aug 15;67(4):435-45. PubMed PMID: 1412222.

17: Takiguchi Y, Wada K, Nakashima M. Comparison of the inhibitory effects of the TXA2 receptor antagonist, vapiprost, and other antiplatelet drugs on arterial thrombosis in rats: possible role of TXA2. Thromb Haemost. 1992 Oct 5;68(4):460-3. PubMed PMID: 1448780.

18: Matsuno H, Uematsu T, Umemura K, Takiguchi Y, Wada K, Nakashima M. Effects of vapiprost, a novel thromboxane receptor antagonist, on thrombus formation and vascular patency after thrombolysis by tissue-type plasminogen activator. Br J Pharmacol. 1992 Jul;106(3):533-8. PubMed PMID: 1387025; PubMed Central PMCID: PMC1907568.

19: Takiguchi Y, Asai F, Wada K, Nakashima M. Comparison of antithrombotic effects of GPIIb-IIIa receptor antagonist and TXA2 receptor antagonist in the guinea-pig thrombosis model: possible role of TXA2 in reocclusion after thrombolysis. Thromb Haemost. 1995 Apr;73(4):683-8. PubMed PMID: 7495079.

20: Kawano KI, Hokamura K, Kondo K, Ikeda Y, Suzuki Y, Umemura K. Thromboxane A(2) synthase inhibitor enhanced antithrombotic efficacy of GPIIb-IIIa receptor antagonist without increasing bleeding. Eur J Pharmacol. 2001 Apr 13;417(3):217-22. PubMed PMID: 11334853.