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MedKoo Cat#: 461622 | Name: Terutroban
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Description:

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

Terutroban is a selective antagonist of the thromboxane/prostaglandin endoperoxide receptor.

Chemical Structure

Terutroban
CAS#165538-40-9

Theoretical Analysis

MedKoo Cat#: 461622

Name: Terutroban

CAS#: 165538-40-9

Chemical Formula: C20H22ClNO4S

Exact Mass: 407.0958

Molecular Weight: 407.90

Elemental Analysis: C, 58.89; H, 5.44; Cl, 8.69; N, 3.43; O, 15.69; S, 7.86

Price and Availability

Size Price Availability Quantity
10mg USD 270.00
50mg USD 640.00
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Related CAS #
No Data
Synonym
Terutroban; S 18886; S-18886; S18886;
IUPAC/Chemical Name
(R)-3-(6-((4-chlorophenyl)sulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoic acid
InChi Key
HWEOXFSBSQIWSY-MRXNPFEDSA-N
InChi Code
InChI=1S/C20H22ClNO4S/c1-13-2-3-14-12-16(6-9-19(14)18(13)10-11-20(23)24)22-27(25,26)17-7-4-15(21)5-8-17/h2-5,7-8,16,22H,6,9-12H2,1H3,(H,23,24)/t16-/m1/s1
SMILES Code
O=C(O)CCC1=C2CC[C@@H](NS(=O)(C3=CC=C(Cl)C=C3)=O)CC2=CC=C1C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 407.90 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
1: Ahmed W, Mainkar PS, Pabbaraja S, Chandrasekhar S. Total synthesis of a thromboxane receptor antagonist, terutroban. Org Biomol Chem. 2015 Mar 14;13(10):2951-7. doi: 10.1039/c4ob02302a. PubMed PMID: 25611989. 2: Rosado E, Rodríguez-Vilarrupla A, Gracia-Sancho J, Tripathi D, García-Calderó H, Bosch J, García-Pagán JC. Terutroban, a TP-receptor antagonist, reduces portal pressure in cirrhotic rats. Hepatology. 2013 Oct;58(4):1424-35. doi: 10.1002/hep.26520. Epub 2013 Aug 7. PubMed PMID: 23703868. 3: De La Cruz JP, Jebrouni N, López-Villodres JA, Muñoz-Marín J, Guerrero A, González-Correa JA. Effects of terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, on retinal vascularity in diabetic rats. Diabetes Metab Res Rev. 2012 Feb;28(2):132-8. PubMed PMID: 22423383. 4: Bousser MG, Amarenco P, Chamorro A, Fisher M, Ford I, Fox KM, Hennerici MG, Mattle HP, Rothwell PM, de Cordoüe A, Fratacci MD; PERFORM Study Investigators. Terutroban versus aspirin in patients with cerebral ischaemic events (PERFORM): a randomised, double-blind, parallel-group trial. Lancet. 2011 Jun 11;377(9782):2013-22. doi: 10.1016/S0140-6736(11)60600-4. Epub 2011 May 25. Erratum in: Lancet. 2011 Jul 30;378(9789):402. PubMed PMID: 21616527. 5: Lee M, Ovbiagele B. Vascular events after stroke: terutroban fails to PERFORM. Lancet. 2011 Jun 11;377(9782):1980-2. doi: 10.1016/S0140-6736(11)60708-3. Epub 2011 May 25. PubMed PMID: 21616526. 6: Gelosa P, Sevin G, Pignieri A, Budelli S, Castiglioni L, Blanc-Guillemaud V, Lerond L, Tremoli E, Sironi L. Terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, prevents hypertensive vascular hypertrophy and fibrosis. Am J Physiol Heart Circ Physiol. 2011 Mar;300(3):H762-8. doi: 10.1152/ajpheart.00880.2010. Epub 2010 Dec 10. PubMed PMID: 21148758. 7: Fiessinger JN, Bounameaux H, Cairols MA, Clement DL, Coccheri S, Fletcher JP, Hoffmann U, Turpie AG; TAIPAD investigators. Thromboxane Antagonism with terutroban in Peripheral Arterial Disease: the TAIPAD study. J Thromb Haemost. 2010 Nov;8(11):2369-76. doi: 10.1111/j.1538-7836.2010.04020.x. PubMed PMID: 20723034. 8: Lesault PF, Boyer L, Pelle G, Covali-Noroc A, Rideau D, Akakpo S, Teiger E, Dubois-Randé JL, Adnot S. Daily administration of the TP receptor antagonist terutroban improved endothelial function in high-cardiovascular-risk patients with atherosclerosis. Br J Clin Pharmacol. 2011 Jun;71(6):844-51. doi: 10.1111/j.1365-2125.2010.03858.x. PubMed PMID: 21564160; PubMed Central PMCID: PMC3099371. 9: Gelosa P, Ballerio R, Banfi C, Nobili E, Gianella A, Pignieri A, Brioschi M, Guerrini U, Castiglioni L, Blanc-Guillemaud V, Lerond L, Tremoli E, Sironi L. Terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, increases survival in stroke-prone rats by preventing systemic inflammation and endothelial dysfunction: comparison with aspirin and rosuvastatin. J Pharmacol Exp Ther. 2010 Jul;334(1):199-205. doi: 10.1124/jpet.110.165787. Epub 2010 Mar 23. PubMed PMID: 20332187. 10: Bots ML, Ford I, Lloyd SM, Laurent S, Touboul PJ, Hennerici MG; Prevention of Cerebrovascular and Cardiovascular Events of Ischemic Origin With Terutroban in Patients With a History of Ischemic Stroke or Transient Ischemic Attack Vascular Ultrasound Study Investigators. Thromboxane prostaglandin receptor antagonist and carotid atherosclerosis progression in patients with cerebrovascular disease of ischemic origin: a randomized controlled trial. Stroke. 2014 Aug;45(8):2348-53. doi: 10.1161/STROKEAHA.114.004775. Epub 2014 Jun 24. PubMed PMID: 25070960. 11: Bal Dit Sollier C, Crassard I, Simoneau G, Bergmann JF, Bousser MG, Drouet L. Effect of the thromboxane prostaglandin receptor antagonist terutroban on arterial thrombogenesis after repeated administration in patients treated for the prevention of ischemic stroke. Cerebrovasc Dis. 2009;28(5):505-13. doi: 10.1159/000236915. Epub 2009 Sep 12. PubMed PMID: 19752552. 12: Fox K, Bousser MG, Amarenco P, Chamorro A, Fisher M, Ford I, Hennerici MG, Mattle HP, Rothwell PM; PERFORM Study Investigators. Heart rate is a prognostic risk factor for myocardial infarction: a post hoc analysis in the PERFORM (Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack) study population. Int J Cardiol. 2013 Oct 9;168(4):3500-5. doi: 10.1016/j.ijcard.2013.04.206. Epub 2013 May 22. PubMed PMID: 23706327. 13: Verbeuren TJ. [Terutroban and endothelial TP receptors in atherogenesis]. Med Sci (Paris). 2006 Apr;22(4):437-43. Review. French. PubMed PMID: 16597416. 14: Hennerici MG, Bots ML, Ford I, Laurent S, Touboul PJ. Rationale, design and population baseline characteristics of the PERFORM vascular project: an ancillary study of the Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack (PERFORM) trial. Cardiovasc Drugs Ther. 2010 Apr;24(2):175-80. doi: 10.1007/s10557-010-6231-2. PubMed PMID: 20490906; PubMed Central PMCID: PMC2887499. 15: Mearns BM. Antiplatelet therapy: terutroban does not out-PERFORM aspirin in secondary prevention. Nat Rev Cardiol. 2011 Jun 21;8(8):423. doi: 10.1038/nrcardio.2011.93. PubMed PMID: 21691313. 16: Bousser MG, Amarenco P, Chamorro A, Fisher M, Ford I, Fox K, Hennerici M, Mattle HP, Rothwell PM; PERFORM Study Investigators. The Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack (PERFORM) study: baseline characteristics of the population. Cerebrovasc Dis. 2009;27(6):608-13. doi: 10.1159/000216835. Epub 2009 Apr 30. PubMed PMID: 19407444. 17: Bousser MG, Amarenco P, Chamorro A, Fisher M, Ford I, Fox K, Hennerici MG, Mattle HP, Rothwell PM; PERFORM Study Investigators. Rationale and design of a randomized, double-blind, parallel-group study of terutroban 30 mg/day versus aspirin 100 mg/day in stroke patients: the prevention of cerebrovascular and cardiovascular events of ischemic origin with terutroban in patients with a history of ischemic stroke or transient ischemic attack (PERFORM) study. Cerebrovasc Dis. 2009;27(5):509-18. doi: 10.1159/000212671. Epub 2009 Apr 16. Erratum in: Cerebrovasc Dis. ;43(3-4):206. PubMed PMID: 19372653. 18: Sebeková K, Eifert T, Klassen A, Heidland A, Amann K. Renal effects of S18886 (Terutroban), a TP receptor antagonist, in an experimental model of type 2 diabetes. Diabetes. 2007 Apr;56(4):968-74. Epub 2007 Jan 31. PubMed PMID: 17267764. 19: Xie W, Zheng F, Zhong B, Song X. Long-Term Antiplatelet Mono- and Dual Therapies After Ischemic Stroke or Transient Ischemic Attack: Network Meta-Analysis. J Am Heart Assoc. 2015 Aug 24;4(8):e002259. doi: 10.1161/JAHA.115.002259. Review. PubMed PMID: 26304937; PubMed Central PMCID: PMC4599476. 20: Hennerici MG; PERFORM Study Investigators. Rationale and design of the Prevention of Cerebrovascular and Cardiovascular Events of Ischemic Origin with Terutroban in Patients with a History of Ischemic Stroke or Transient Ischemic Attack (PERFORM) Study. Cerebrovasc Dis. 2009;27 Suppl 3:28-32. doi: 10.1159/000209263. Epub 2009 May 14. Review. PubMed PMID: 19439938.

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