| Identification | Back Directory | [Name]
(2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate | [CAS]
115956-12-2 | [Synonyms]
Hsdb 7565
Dolasteron
DOLASETRON
Dolasetronum
Unii-82wi2L7Q6e
dolasetron USP/EP/BP
Dolasetronum [inn-latin]
Octahydro-3-oxo-2,6-Methano-2H-quinolizin-8-yl Ester
3-Oxooctahydro-2H-2,6-methanoquinolizin-8-yl 1H-Indole-3-carboxylate
1H-Indole-3-carboxylic Acid 3-Oxooctahydro-2H-2,6-methanoquinolizin-8-yl Ester
rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate
1H-Indole-3-carboxylicacid, octahydro-3-oxo-2,6-Methano-2H-quinolizin-8-yl ester, stereoisoMer
(2a,6a,8a,9ab)-1H-Indole-3-carboxylic acid, octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester
(2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate
1H-Indole-3-carboxylic acid, octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, (2alpha,6alpha,8alpha,9abeta)- | [Molecular Formula]
C19H20N2O3 | [MDL Number]
MFCD00865542 | [MOL File]
115956-12-2.mol | [Molecular Weight]
325.38 |
| Chemical Properties | Back Directory | [Melting point ]
278 ºC | [Boiling point ]
535.1±50.0 °C(Predicted) | [density ]
1.37±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly) | [form ]
Solid | [pka]
15.36±0.30(Predicted) | [color ]
White | [Water Solubility ]
Soluble | [CAS DataBase Reference]
115956-12-2 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
prevention and treatment of postoperative nausea and vomiting | [Uses]
Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic. | [Brand name]
Anzemet (Sanofi Aventis. | [Description]
Dolasetron is an antagonist of the serotonin (5-HT) receptor subtype 5-HT3 (Ki = 20 nM).1 It is selective for 5-HT3 receptors over 5-HT1A, 5-HT1B, 5-HT2, dopamine D2, α1-, α2-, β-adrenergic, M1-5 muscarinic acetylcholine, and neurokinin-1 (NK1) receptors (IC50s = >10 μM for all).2 Dolasetron inhibits 5-HT-induced membrane currents in NG 108-15 cells (IC50 = 3.8 nM).1 It increases the latency to emesis and reduces the number of vomiting and retching episodes induced by cisplatin (Item No. 13119) in ferrets when administered at doses of 0.5 or 2 mg/kg.2 Formulations containing dolasetron have been used in the prevention of postoperative or chemotherapy-induced nausea. | [Definition]
ChEBI: LSM-5418 is an indolyl carboxylic acid. | [Synthesis]
Ethyl cyclopentenecarboxylate (I), in the presence of a catalytic amount of osmium tetroxide, was oxidized to diol (II) with N-methylmorpholine-N-oxide. It was then split to dialdehyde (III) in the presence of sodium periodate and its aqueous solution was | [storage]
Store at 2-8°C, protect from light | [References]
[1] PETER H. BOEIJINGA . Characterization of the novel 5-HT3 antagonists MDL 73147EF (dolasetron mesilate) and MDL 74156 in NG108-15 neuroblastoma × glioma cells[J]. European journal of pharmacology, 1992, 219 1: Pages 9-13. DOI: 10.1016/0014-2999(92)90573-m
[2] ROBERT C. MILLER. Pharmacological properties of dolasetron, a potent and selective antagonist at 5-HT3 receptors[J]. Drug Development Research, 1993, 28 1: 87-93. DOI: 10.1002/ddr.430280111 |
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