dolasetron Chemical Properties

Melting point:

278 ºC

Boiling point:

535.1±50.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)

pka

15.36±0.30(Predicted)

form 

Solid

color 

White

Water Solubility 

Soluble

CAS DataBase Reference

115956-12-2

Safety Information

Hazardous Substances Data

115956-12-2(Hazardous Substances Data)

dolasetron Usage And Synthesis

Description

Dolasetron is an antagonist of the serotonin (5-HT) receptor subtype 5-HT₃ (K_i = 20 nM). It is selective for 5-HT₃ receptors over 5-HT_1A, 5-HT_1B, 5-HT₂, dopamine D₂, α₁-, α₂-, β-adrenergic, M_1-5 muscarinic acetylcholine, and neurokinin-1 (NK₁) receptors (IC₅₀s = >10 μM for all). Dolasetron inhibits 5-HT-induced membrane currents in NG 108-15 cells (IC₅₀ = 3.8 nM). It increases the latency to emesis and reduces the number of vomiting and retching episodes induced by cisplatin in ferrets when administered at doses of 0.5 or 2 mg/kg. Formulations containing dolasetron have been used in the prevention of postoperative or chemotherapy-induced nausea.

Chemical Properties

White Solid

Uses

prevention and treatment of postoperative nausea and vomiting

Uses

Dolasetron is a bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist.It is used as antiemetic.

Uses

Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.

Definition

ChEBI: LSM-5418 is an indolyl carboxylic acid.

brand name

Anzemet (Sanofi Aventis.

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 converted to bicyclization (IV) at pH 4 by Robinson-Schoepf reaction. (IV) was then reduced to alcohol (V) with sodium borohydride and reacted with dihydropyran to form tetrahydrofuran ether (VI) to protect the hydroxyl group formed. This is then converted to the tricyclic compound (VII), which is then acylated to give dolasetron by reacting with an acyl chloride (VIII) in the presence of silver tetrafluoroborate.

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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