Terbogrel | CAS#149979-74-8 | A2 receptor antagonist

MedKoo Cat#: 328088 | Name: Terbogrel

Description:

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

Terbogrel, also known as BIBV-308; BIBV-308-SE; BIBV-308SE, is a thromboxane A2 receptor antagonist potentially for the treatment of pulmonary arterial hypertension. Terbogrel concentration-dependently inhibited collagen (0.6 microg/ml)- and U46619 (11alpha,9alpha-epoxymethano-15(S)-hydroxy-prosta-5Z,+ ++13E-dienoic acid) (1 microM)-induced aggregation and thromboxane synthesis of washed human platelets. In this system, terbogrel exhibited an equipotent (IC50 of about 10 nM) activity as thromboxane A2 synthase inhibitor and thromboxane A2 receptor antagonist. Terbogrel appears to be a compound with an equipotent molar potency as thromboxane A2 synthase inhibitor and receptor antagonist.

Chemical Structure

Terbogrel

CAS#149979-74-8

Theoretical Analysis

MedKoo Cat#: 328088

Name: Terbogrel

CAS#: 149979-74-8

Chemical Formula: C23H27N5O2

Exact Mass: 405.2165

Molecular Weight: 405.50

Elemental Analysis: C, 68.13; H, 6.71; N, 17.27; O, 7.89

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 #

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Synonym

Terbogrel; BIBV-308; BIBV-308-SE; BIBV-308SE; BIBV308; BIBV308-SE; BIBV308SE.

IUPAC/Chemical Name

(5E)-6-(m-(3-tert-Butyl-2-cyanoguanidino)phenyl)-6-(3-pyridyl)-5-hexenoic acid

InChi Key

XUTLOCQNGLJNSA-RGVLZGJSSA-N

InChi Code

InChI=1S/C23H27N5O2/c1-23(2,3)28-22(26-16-24)27-19-10-6-8-17(14-19)20(11-4-5-12-21(29)30)18-9-7-13-25-15-18/h6-11,13-15H,4-5,12H2,1-3H3,(H,29,30)(H2,26,27,28)/b20-11+

SMILES Code

O=C(O)CCC/C=C(C1=CC=CC(N/C(NC(C)(C)C)=N\C#N)=C1)/C2=CC=CN=C2

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 405.50 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.

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: Zhang HD, Zhang R, Jiang X, Sun K, Wu DC, Jing ZC. Effects of oral treatments on clinical outcomes in pulmonary arterial hypertension: A systematic review and meta-analysis. Am Heart J. 2015 Jul;170(1):96-103, 103.e1-14. doi: 10.1016/j.ahj.2015.04.003. Review. PubMed PMID: 26093869. 2: More AS, Kim HM, Khang G, Hildebrandt T, Bernlöhr C, Doods H, Vanhoutte PM, Wu D. Des-Arg9-bradykinin causes kinin B1 receptor mediated endothelium-independent contractions in endotoxin-treated porcine coronary arteries. Pharmacol Res. 2014 Dec;90:18-24. doi: 10.1016/j.phrs.2014.09.001. PubMed PMID: 25258294. 3: More AS, Kim HM, Zhao R, Khang G, Hildebrandt T, Bernlöhr C, Doods H, Lee D, Lee SH, Vanhoutte PM, Wu D. COX-2 mediated induction of endothelium-independent contraction to bradykinin in endotoxin-treated porcine coronary artery. J Cardiovasc Pharmacol. 2014 Sep;64(3):209-17. doi: 10.1097/FJC.0000000000000105. PubMed PMID: 25192543. 4: Ivandic BT, Giannitsis E, Schlick P, Staritz P, Katus HA, Hohlfeld T. Determination of aspirin responsiveness by use of whole blood platelet aggregometry. Clin Chem. 2007 Apr;53(4):614-9. PubMed PMID: 17332149. 5: Fike CD, Zhang Y, Kaplowitz MR. Thromboxane inhibition reduces an early stage of chronic hypoxia-induced pulmonary hypertension in piglets. J Appl Physiol (1985). 2005 Aug;99(2):670-6. PubMed PMID: 15802364. 6: Lowson SM. Alternatives to nitric oxide. Br Med Bull. 2004 Nov 5;70:119-31. Review. PubMed PMID: 15531733. 7: Guth BD, Narjes H, Schubert HD, Tanswell P, Riedel A, Nehmiz G. Pharmacokinetics and pharmacodynamics of terbogrel, a combined thromboxane A2 receptor and synthase inhibitor, in healthy subjects. Br J Clin Pharmacol. 2004 Jul;58(1):40-51. PubMed PMID: 15206991; PubMed Central PMCID: PMC1884538. 8: Zimmermann N, Wenk A, Kim U, Kienzle P, Weber AA, Gams E, Schrör K, Hohlfeld T. Functional and biochemical evaluation of platelet aspirin resistance after coronary artery bypass surgery. Circulation. 2003 Aug 5;108(5):542-7. PubMed PMID: 12874188. 9: Galiè N, Manes A, Branzi A. Emerging medical therapies for pulmonary arterial hypertension. Prog Cardiovasc Dis. 2002 Nov-Dec;45(3):213-24. Review. PubMed PMID: 12525997. 10: Galiè N, Manes A, Branzi A. The new clinical trials on pharmacological treatment in pulmonary arterial hypertension. Eur Respir J. 2002 Oct;20(4):1037-49. Review. PubMed PMID: 12412701. 11: Langleben D, Christman BW, Barst RJ, Dias VC, Galiè N, Higenbottam TW, Kneussl M, Korducki L, Naeije R, Riedel A, Simonneau G, Hirsch AM, Rich S, Robbins IM, Oudiz R, McGoon MD, Badesch DB, Levy RD, Mehta S, Seeger W, Solèr M. Effects of the thromboxane synthetase inhibitor and receptor antagonist terbogrel in patients with primary pulmonary hypertension. Am Heart J. 2002 May;143(5):E4. PubMed PMID: 12040360. 12: Michaux C, Rolin S, Dogné JM, Durant F, Masereel B, Delarge J, Wouters J. Structure determination and comparison of BM567, a sulfonylurea, with terbogrel, two compounds with dual action, thromboxane receptor antagonism and thromboxane synthase inhibition. Bioorg Med Chem Lett. 2001 Apr 23;11(8):1019-22. PubMed PMID: 11327579. 13: Michaux C, Norberg B, Dogné JM, Durant F, Masereel B, Delarge J, Wouters J. Terbogrel, a dual-acting agent for thromboxane receptor antagonism and thromboxane synthase inhibition. Acta Crystallogr C. 2000 Oct;56 ( Pt 10):1265-6. PubMed PMID: 11025320. 14: Soyka R, Guth BD, Weisenberger HM, Luger P, Müller TH. Guanidine derivatives as combined thromboxane A2 receptor antagonists and synthase inhibitors. J Med Chem. 1999 Apr 8;42(7):1235-49. PubMed PMID: 10197967. 15: Muck S, Weber AA, Schrör K. Effects of terbogrel on platelet function and prostaglandin endoperoxide transfer. Eur J Pharmacol. 1998 Feb 26;344(1):45-8. PubMed PMID: 9570446.