3-[(3R)-3-(4-fluorobenzenesulfonamido)-2,3,4,9-tetrahydro-1H-carbazol-9-yl]propanoic acid

• ChemBase ID: 154383
• Molecular Formular: C21H21FN2O4S
• Molecular Mass: 416.4658432
• Monoisotopic Mass: 416.12060638
• SMILES: c1ccc2c(c1)c1c(n2CCC(=O)O)CC[C@H](C1)NS(=O)(=O)c1ccc(cc1)F
• Canonical SMILES: OC(=O)CCn1c2CC[C@H](Cc2c2c1cccc2)NS(=O)(=O)c1ccc(cc1)F
• InChI: 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
• InChIKey: LDXDSHIEDAPSSA-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3R)-3-(4-fluorobenzenesulfonamido)-2,3,4,9-tetrahydro-1H-carbazol-9-yl]propanoic acid
• IUPAC Traditional name: ramatroban
• Synonyms: (3R)-3-[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazole-9-propanoic Acid; BAY-u 3405; Baynas; Ramatroban; BAY u3405; Ramatroban; (+)-(3R)-3-[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazole-9-propanoic acid

Database IDs

• CAS Number: 116649-85-5
• MDL Number: MFCD00887606
• PubChem SID: 162248522
• PubChem CID: 123879

CALCULATED PROPERTIES

• Acid pKa: 4.3877997
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.1616697
• LogD (pH = 7.4): 0.4054446
• Log P: 3.3045409
• Molar Refractivity: 107.0761 cm^3
• Polarizability: 42.739445 Å^3
• Polar Surface Area: 88.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥40 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H21FN2O4S

DETAILS

Sigma Aldrich - R0531

Biochem/physiol Actions
Ramatroban is used for the treatment of allergic rhinitis as an antagonist of the thromboxane receptor. It is also 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.

Toronto Research Chemicals - R109000

A thromboxane receptor antagonist for use in the treatment of coronary artery disease.

REFERENCES

• Rahman, M., et al.: Int. Immunopharmacol., 6, 1736 (2006)
• Sato, T., et al.: J. Med. Chem., 51, 7705 (2006)
• Sandham, D., et al.: Bioorg. Med. Chem. Lett., 19, 4794 (2006)