Ramatroban
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Grundinformationen
- CAS
116649-85-5- Standard-SMILES
O=C(O)CCn1c2c(c3ccccc31)C[C@H](NS(=O)(=O)c1ccc(F)cc1)CC2- InChIKey
LDXDSHIEDAPSSA-OAHLLOKOSA-N- Summenformel
- C21H21FN2O4S
- Durchschnittliche Molmasse
- 416,474 g/mol
- Monoisotopische Masse
- 416,12060637
Namen und Bezeichner
- Bevorzugter Name
- Ramatroban
- IUPAC
- 3-{(3R)-3-[(4-Fluorobenzene-1-sulfonyl)amino]-1,2,3,4-tetrahydro-9H-carbazol-9-yl}propanoic acid
- Englischer Name
- Ramatroban
- Summenformel
- C21H21FN2O4S
- Molmasse
- 416.47
Namen und Synonyme
BaynasCS-1350BAY-U3405RAMATROBANRaMantrobanRay ma music classBAY U3405BAY-U3405RaMatroban(BAY-u3405)Ramatroban for researchRamatroban, 10 mM in DMSO
Datenbank-Bezeichner
- CAS
116649-85-5- PubChem CID
- 123879
- DTXSID
DTXSID1046685- ChEMBL
CHEMBL361812- ChEBI
CHEBI:32087- UNII
- P1ALI72U6C
- EC Number
- 631-428-1
- Nikkaji
- J388.276D
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 134 · 134-135°
- Siedepunkt
- 654.7 · 654.7±65.0 °C(Predicted)
- Dichte
- 1.43 · 1.43±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 40 mg/mL · DMSO: ≥40mg/mL
- Aggregatzustand
- solid
- pka
- 4.6 · 4.60±0.10(Predicted)
- Farbe
- white
- 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
- SMILES
- N1(CCC(O)=O)C2=C(C=CC=C2)C2=C1CC[C@@H](NS(C1=CC=C(F)C=C1)(=O)=O)C2
- CAS Datenbank
- 116649 · 116649-85-5(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 1
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36/37/39-45
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Anwendungen
BeschreibungRamatroban, originally developed for the treatment of cardiovascular pathologies as thromboembolism, was finally introduced in Japan for the treatment of allergic rhinitis. It is a (3R)-enantiomer that can be synthesized in 5 steps from 3-oxo-1,2,3,4- tetrahydrocarbazole by stereoselective reductive amination, using S-phenethylamine as the chiral source, followed by hydrogenolysis, sulfonylation and finally 2-step Ncarboxyethylation. Ramatroban is a potent antagonist of prostaglandin receptors (PGD2, PGH2) and thromboxane receptors (TxA2); accordingly, it blocks the contractions induced by thromboxane or TxA2-mimetics in animal and human airway smooth muscle. It also prevents, when administered i.v., p.o. or by aerosol, bronchoconstriction induced by PGD2 or antigen. In animal models of nasal allergy, ramatroban inhibits antigen-induced neutrophil infiltration into nasal mucosa and also inhibits nasal symptoms. In several species including humans, it is well-absorbed, extensively protein-bound (>95%) and eliminated mainly as a glucuro-conjugate; in man, its terminal half-life is 2 to 3 hours.
VerwendenA thromboxane receptor antagonist for use in the treatment of coronary artery disease.
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