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

MedKoo CAT#: 526086

CAS#: 116649-85-5

Description: Ramatroban is a thromboxane receptor antagonist. Ramatroban is also a DP2 receptor antagonist. It is indicated for the treatment of coronary artery disease. Ramatroban has also been used for the treatment of asthma.


Price and Availability

Size
Price

10mg
USD 350
Size
Price

20mg
USD 650
Size
Price

50mg
USD 1150

Ramatroban, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526086
Name: Ramatroban
CAS#: 116649-85-5
Chemical Formula: C21H21FN2O4S
Exact Mass: 416.1206
Molecular Weight: 416.47
Elemental Analysis: C, 60.56; H, 5.08; F, 4.56; N, 6.73; O, 15.37; S, 7.70


Synonym: Ramatroban; Bay u 3406; Bay u-3405; BAY u3405; EN 137774.

IUPAC/Chemical Name: (+)-(3R)-3-(p-Fluorobenzenesulfonamido)-1,2,3,4-tetrahydrocarbazole-9-propionic acid

InChi Key: LDXDSHIEDAPSSA-OAHLLOKOSA-N

InChi Code: InChI=1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1

SMILES Code: O=C(O)CCN1C2=C(C3=C1C=CC=C3)C[C@H](NS(=O)(C4=CC=C(F)C=C4)=O)CC2


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: Chakraborty R, Bhullar RP, Dakshinamurti S, Hwa J, Chelikani P. Inverse agonism of SQ 29,548 and Ramatroban on Thromboxane A2 receptor. PLoS One. 2014 Jan 23;9(1):e85937. doi: 10.1371/journal.pone.0085937. eCollection 2014. PubMed PMID: 24465800; PubMed Central PMCID: PMC3900440.

2: Busto E, Gotor-Fernández V, Gotor V. Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases. J Org Chem. 2012 May 18;77(10):4842-8. doi: 10.1021/jo300552v. Epub 2012 May 1. PubMed PMID: 22515546.

3: Suzuki Y, Inoue T, Yamamoto A, Sugimoto Y. Prophylactic effects of the histamine H1 receptor antagonist epinastine and the dual thromboxane A2 receptor and chemoattractant receptor-homologous molecule expressed on Th2 cells antagonist ramatroban on allergic rhinitis model in mice. Biol Pharm Bull. 2011;34(4):507-10. PubMed PMID: 21467637.

4: Wada T, Uemaetomari I, Murashita H, Tobita T, Tsuji S, Tabuchi K, Okubo H, Hara A. Successful treatment of eosinophilic otitis media using ramatroban: report of two cases. Auris Nasus Larynx. 2006 Dec;33(4):455-60. Epub 2006 Aug 8. PubMed PMID: 16899348.

5: Sugimoto H, Shichijo M, Okano M, Bacon KB. CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses. Eur J Pharmacol. 2005 Nov 7;524(1-3):30-7. Epub 2005 Oct 27. PubMed PMID: 16256979.

6: Robarge MJ, Bom DC, Tumey LN, Varga N, Gleason E, Silver D, Song J, Murphy SM, Ekema G, Doucette C, Hanniford D, Palmer M, Pawlowski G, Danzig J, Loftus M, Hunady K, Sherf BA, Mays RW, Stricker-Krongrad A, Brunden KR, Harrington JJ, Bennani YL. Isosteric ramatroban analogs: selective and potent CRTH-2 antagonists. Bioorg Med Chem Lett. 2005 Mar 15;15(6):1749-53. PubMed PMID: 15745833.

7: Ulven T, Kostenis E. Minor structural modifications convert the dual TP/CRTH2 antagonist ramatroban into a highly selective and potent CRTH2 antagonist. J Med Chem. 2005 Feb 24;48(4):897-900. PubMed PMID: 15715457.

8: Moriwaki T, Yasui H, Yamamoto A. Pharmacokinetic analysis of ramatroban using a recirculatory model with enterohepatic circulation by measuring portal and systemic blood concentration difference in Sprague-Dawley and Eisai hyperbilirubinemic rats. Pharm Res. 2004 Jun;21(6):1055-64. PubMed PMID: 15212172.

9: Ishizuka T, Matsui T, Okamoto Y, Ohta A, Shichijo M. Ramatroban (BAY u 3405): a novel dual antagonist of TXA2 receptor and CRTh2, a newly identified prostaglandin D2 receptor. Cardiovasc Drug Rev. 2004 Summer;22(2):71-90. Review. PubMed PMID: 15179446.

10: Kariyazono H, Nakamura K, Arima J, Ayukawa O, Onimaru S, Masuda H, Iguro Y, Majima HJ, Sakata R, Yamada K. Evaluation of anti-platelet aggregatory effects of aspirin, cilostazol and ramatroban on platelet-rich plasma and whole blood. Blood Coagul Fibrinolysis. 2004 Mar;15(2):157-67. PubMed PMID: 15091003.

11: Kitamura N, Hukuda R, Majima T, Horie T, Sugihara T. [The 3 effective cases of cough variant asthma with ramatroban]. Arerugi. 2003 Nov;52(11):1089-92. Japanese. PubMed PMID: 14685041.

12: Ishizuka T, Matsui T, Kurita A. Ramatroban, a TP receptor antagonist, improves vascular responses to acetylcholine in hypercholesterolemic rabbits in vivo. Eur J Pharmacol. 2003 May 2;468(1):27-35. PubMed PMID: 12729840.

13: Ishizuka T, Matsumura K, Matsui T, Takase B, Kurita A. Ramatroban, a thromboxane A2 receptor antagonist, prevents macrophage accumulation and neointimal formation after balloon arterial injury in cholesterol-fed rabbits. J Cardiovasc Pharmacol. 2003 Apr;41(4):571-8. PubMed PMID: 12658058.

14: Sugimoto H, Shichijo M, Iino T, Manabe Y, Watanabe A, Shimazaki M, Gantner F, Bacon KB. An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro. J Pharmacol Exp Ther. 2003 Apr;305(1):347-52. PubMed PMID: 12649388.

15: Motobayashi Y, Imagawa W, Saida K. [Ramatroban (Baynas): a review of its pharmacological and clinical profile]. Nihon Yakurigaku Zasshi. 2001 Dec;118(6):397-402. Review. Japanese. PubMed PMID: 11778458.

16: Terada N, Yamakoshi T, Hasegawa M, Tanikawa H, Maesako K, Ishikawa K, Konno A. The effect of ramatroban (BAY u 3405), a thromboxane A2 receptor antagonist, on nasal cavity volume and minimum cross-sectional area and nasal mucosal hemodynamics after nasal mucosal allergen challenge in patients with perennial allergic rhinitis. Acta Otolaryngol Suppl. 1998;537:32-7. PubMed PMID: 9870646.

17: Steinke W, Ahr HJ, Hirayama M. Pharmacokinetics and metabolism of the new thromboxane A2 receptor antagonist ramatroban in animals. 2nd communication: distribution to organs and tissues in male, female and pregnant rats, and characteristics of protein binding in plasma. Arzneimittelforschung. 1997 Aug;47(8):939-48. PubMed PMID: 9296280.

18: Boberg M, Ahr HJ, Beckermann B, Bühner K, Siefert HM, Steinke W, Wünsche C, Hirayama M. Pharmacokinetics and metabolism of the new thromboxane A2 receptor antagonist ramatroban in animals. 1st communication: absorption, concentrations in plasma, metabolism, and excretion after single administration to rats and dogs. Arzneimittelforschung. 1997 Aug;47(8):928-38. PubMed PMID: 9296279.