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MedKoo Cat#: 526086 | Name: Ramatroban
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Description:

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

Ramatroban is a thromboxane receptor antagonist and a DP2 receptor antagonist. Ramatroban is indicated for the treatment of coronary artery disease. Ramatroban has also been used for the treatment of asthma. Four consecutive outpatients with COVID-19 pneumonia treated with ramatroban exhibited rapid relief of dyspnea and hypoxemia within 12-36 h and complete resolution over 5 days, thereby avoiding hospitalization.

Chemical Structure

Ramatroban
Ramatroban
CAS#116649-85-5

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

Price and Availability

Size Price Availability Quantity
10mg USD 350.00
20mg USD 650.00
50mg USD 1,150.00
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Related CAS #
No Data
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
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, DMF, and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO, DMF, and ethanol
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ramatroban is an antagonist of the DP2 receptor with IC50 values of 100-170 nM. It is more potent at the DP2 receptor than the TP receptor by 4-5 fold. It is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.
In vitro activity:
The results from this study suggest that Ramatroban is an inverse agonists for thromboxane A2 receptor, which has important therapeutic applications in the treatment of thromboxane A2 receptor mediated pathophysiological conditions. Reference: PLoS One. 2014 Jan 23;9(1):e85937. https://pubmed.ncbi.nlm.nih.gov/24465800/
In vivo activity:
Four patients with COVID-19 pneumonia treated with ramatroban exhibited rapid relief of dyspnea and hypoxemia within 12-36 h and complete resolution over 5 days. These results indicate that ramatroban is an antivasospastic, broncho-relaxant, antithrombotic, and immunomodulatory agent. Reference: Front Pharmacol. 2022 Jul 22;13:904020. https://pubmed.ncbi.nlm.nih.gov/35935851/
Solvent mg/mL mM
Solubility
DMSO 30.0 72.03
DMF 30.0 72.03
Ethanol 50.0 120.06
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 416.47 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
Formulation protocol:
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. PMID: 24465800; PMCID: PMC3900440. 2. 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. doi: 10.1124/jpet.102.046748. PMID: 12649388. 3. Ogletree ML, Chander Chiang K, Kulshrestha R, Agarwal A, Agarwal A, Gupta A. Treatment of COVID-19 Pneumonia and Acute Respiratory Distress With Ramatroban, a Thromboxane A2 and Prostaglandin D2 Receptor Antagonist: A Four-Patient Case Series Report. Front Pharmacol. 2022 Jul 22;13:904020. doi: 10.3389/fphar.2022.904020. PMID: 35935851; PMCID: PMC9355466. 4. Gupta A, Kalantar-Zadeh K, Reddy ST. Ramatroban as a Novel Immunotherapy for COVID-19. J Mol Genet Med. 2020;14(3):10.37421/jmgm.2020.14.457. doi: 10.37421/jmgm.2020.14.457. Epub 2020 Jul 30. PMID: 32952595; PMCID: PMC7500620.
In vitro protocol:
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. PMID: 24465800; PMCID: PMC3900440. 2. 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. doi: 10.1124/jpet.102.046748. PMID: 12649388.
In vivo protocol:
1. Ogletree ML, Chander Chiang K, Kulshrestha R, Agarwal A, Agarwal A, Gupta A. Treatment of COVID-19 Pneumonia and Acute Respiratory Distress With Ramatroban, a Thromboxane A2 and Prostaglandin D2 Receptor Antagonist: A Four-Patient Case Series Report. Front Pharmacol. 2022 Jul 22;13:904020. doi: 10.3389/fphar.2022.904020. PMID: 35935851; PMCID: PMC9355466. 2. Gupta A, Kalantar-Zadeh K, Reddy ST. Ramatroban as a Novel Immunotherapy for COVID-19. J Mol Genet Med. 2020;14(3):10.37421/jmgm.2020.14.457. doi: 10.37421/jmgm.2020.14.457. Epub 2020 Jul 30. PMID: 32952595; PMCID: PMC7500620.
1: Samarelli F, Graziano G, Gambacorta N, Graps EA, Leonetti F, Nicolotti O, Altomare CD. Small Molecules for the Treatment of Long-COVID-Related Vascular Damage and Abnormal Blood Clotting: A Patent-Based Appraisal. Viruses. 2024 Mar 14;16(3):450. doi: 10.3390/v16030450. PMID: 38543815; PMCID: PMC10976273. 2: Chiang KC, Gupta A, Sundd P, Krishnamurti L. Thrombo-Inflammation in COVID-19 and Sickle Cell Disease: Two Faces of the Same Coin. Biomedicines. 2023 Jan 25;11(2):338. doi: 10.3390/biomedicines11020338. PMID: 36830874; PMCID: PMC9953430. 3: Al-Kuraishy HM, Al-Gareeb AI, Saad HM, Batiha GE. The effect of ramatroban on cytokine and thrombotic storms in Covid-19. Inflammopharmacology. 2023 Feb;31(1):543-545. doi: 10.1007/s10787-022-01114-8. Epub 2022 Dec 20. PMID: 36538271; PMCID: PMC9763788. 4: Ogletree ML, Chander Chiang K, Kulshrestha R, Agarwal A, Agarwal A, Gupta A. Treatment of COVID-19 Pneumonia and Acute Respiratory Distress With Ramatroban, a Thromboxane A2 and Prostaglandin D2 Receptor Antagonist: A Four-Patient Case Series Report. Front Pharmacol. 2022 Jul 22;13:904020. doi: 10.3389/fphar.2022.904020. PMID: 35935851; PMCID: PMC9355466. 5: Thangaraju P, Narasimhan G, Ramamurthy VA, Gurunthalingam MP, Yella SST, Venkatesan S, Thangaraju E. Molecular Docking Analysis of Adhatoda vasica with Thromboxane A2 Receptor (TXA2R) (6IIU) and Antiviral Molecules for Possible Dengue Complications. Infect Disord Drug Targets. 2023;23(1):e180722206836. doi: 10.2174/1871526522666220718101544. PMID: 35850647. 6: Krawinski P, Caffrey M. Thromboxane A2 G Protein-Coupled Receptor Production and Crystallization for Structure Studies. Methods Mol Biol. 2022;2507:241-271. doi: 10.1007/978-1-0716-2368-8_13. PMID: 35773586. 7: Chiang KC, Rizk JG, Nelson DJ, Krishnamurti L, Subbian S, Imig JD, Khan I, Reddy ST, Gupta A. Ramatroban for chemoprophylaxis and treatment of COVID-19: David takes on Goliath. Expert Opin Ther Targets. 2022 Jan;26(1):13-28. doi: 10.1080/14728222.2022.2031975. Epub 2022 Feb 22. PMID: 35068281; PMCID: PMC10119876. 8: Chiang KC, Imig JD, Kalantar-Zadeh K, Gupta A. Kidney in the net of acute and long-haul coronavirus disease 2019: a potential role for lipid mediators in causing renal injury and fibrosis. Curr Opin Nephrol Hypertens. 2022 Jan 1;31(1):36-46. doi: 10.1097/MNH.0000000000000750. PMID: 34846312. 9: Ozen G, Aljesri K, Abdelazeem H, Norel X, Turkyılmaz G, Turkyılmaz S, Topal G. Comparative study on the effect of aspirin, TP receptor antagonist and TxA2 synthase inhibitor on the vascular tone of human saphenous vein and internal mammary artery. Life Sci. 2021 Dec 1;286:120073. doi: 10.1016/j.lfs.2021.120073. Epub 2021 Oct 21. PMID: 34688694. 10: Chiang KC, Raghavan R, Gupta A. SARS-CoV-2 vaccination induced cerebral venous sinus thrombosis: Do megakaryocytes, platelets and lipid mediators make up the orchestra? Free Neuropathol. 2021 Jul 7;2:2-18. doi: 10.17879/freeneuropathology-2021-3395. PMID: 37284614; PMCID: PMC10209909. 11: Huang LA, Huang KX, Tu J, Kandeel F, Li J. Ramatroban-Based Analogues Containing Fluorine Group as Potential 18F-Labeled Positron Emission Tomography (PET) G-Protein Coupled Receptor 44 (GPR44) Tracers. Molecules. 2021 Mar 6;26(5):1433. doi: 10.3390/molecules26051433. PMID: 33800801; PMCID: PMC7961607. 12: Lau WL, Zuckerman JE, Gupta A, Kalantar-Zadeh K. The COVID-Kidney Controversy: Can SARS-CoV-2 Cause Direct Renal Infection? Nephron. 2021;145(3):275-279. doi: 10.1159/000513789. Epub 2021 Feb 18. PMID: 33601392; PMCID: PMC8018211. 13: Pang J, Qi X, Luo Y, Li X, Shu T, Li B, Song M, Liu Y, Wei D, Chen J, Wang J, Wang C. Multi-omics study of silicosis reveals the potential therapeutic targets PGD2 and TXA2. Theranostics. 2021 Jan 1;11(5):2381-2394. doi: 10.7150/thno.47627. PMID: 33500731; PMCID: PMC7797695. 14: Gupta A, Kalantar-Zadeh K, Reddy ST. Ramatroban as a Novel Immunotherapy for COVID-19. J Mol Genet Med. 2020;14(3):10.37421/jmgm.2020.14.457. doi: 10.37421/jmgm.2020.14.457. Epub 2020 Jul 30. PMID: 32952595; PMCID: PMC7500620. 15: Gupta A, Chander Chiang K. Prostaglandin D2 as a mediator of lymphopenia and a therapeutic target in COVID-19 disease. Med Hypotheses. 2020 Oct;143:110122. doi: 10.1016/j.mehy.2020.110122. Epub 2020 Jul 21. PMID: 32759007; PMCID: PMC7373045. 16: Rizk JG, Kalantar-Zadeh K, Mehra MR, Lavie CJ, Rizk Y, Forthal DN. Pharmaco- Immunomodulatory Therapy in COVID-19. Drugs. 2020 Sep;80(13):1267-1292. doi: 10.1007/s40265-020-01367-z. PMID: 32696108; PMCID: PMC7372203. 17: Issahaku AR, Agoni C, Kumi RO, Olotu FA, Soliman MES. Lipid-Embedded Molecular Dynamics Simulation Model for Exploring the Reverse Prostaglandin D2 Agonism of CT-133 towards CRTH2 in the Treatment of Type-2 Inflammation Dependent Diseases. Chem Biodivers. 2020 Mar;17(3):e1900548. doi: 10.1002/cbdv.201900548. Epub 2020 Feb 20. PMID: 32034875. 18: Tojima I, Matsumoto K, Kikuoka H, Hara S, Yamamoto S, Shimizu S, Kouzaki H, Shimizu T. Evidence for the induction of Th2 inflammation by group 2 innate lymphoid cells in response to prostaglandin D2 and cysteinyl leukotrienes in allergic rhinitis. Allergy. 2019 Dec;74(12):2417-2426. doi: 10.1111/all.13974. Epub 2019 Aug 12. PMID: 31267527. 19: Fan H, Chen S, Yuan X, Han S, Zhang H, Xia W, Xu Y, Zhao Q, Wu B. Structural basis for ligand recognition of the human thromboxane A2 receptor. Nat Chem Biol. 2019 Jan;15(1):27-33. doi: 10.1038/s41589-018-0170-9. Epub 2018 Dec 3. PMID: 30510189. 20: Kupczyk M, Kuna P. Targeting the PGD2/CRTH2/DP1 Signaling Pathway in Asthma and Allergic Disease: Current Status and Future Perspectives. Drugs. 2017 Aug;77(12):1281-1294. doi: 10.1007/s40265-017-0777-2. PMID: 28612233; PMCID: PMC5529497.