BEMESETRON

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H17Cl2NO2
Molecular Weight	314.207
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C3=CC(Cl)=CC(Cl)=C3

InChI

InChIKey=MNJNPLVXBISNSX-WDNDVIMCSA-N

InChI=1S/C15H17Cl2NO2/c1-18-12-2-3-13(18)8-14(7-12)20-15(19)9-4-10(16)6-11(17)5-9/h4-6,12-14H,2-3,7-8H2,1H3/t12-,13+,14+

HIDE SMILES / InChI

Molecular Formula	C15H17Cl2NO2
Molecular Weight	314.207
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452114 | https://www.ncbi.nlm.nih.gov/pubmed/17948891

Bemesetron, also known as MDL 72222, is a potent and highly selective antagonist of neuronal 5-hydroxytryptamine receptors, 5HT3. Bemesetron possesses antiemetic efficacy in comparison with a high-dose metoclopramide regimen (HDM) for chemotherapy-induced nausea and vomiting. But this application is not clinically used. Drug is used as scientific tool for the study 5HT3 receptor properties in the actions of drugs of abuse.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3114804	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nausea and vomiting 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452114	Palliative		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Conditional involvement of striatal serotonin3 receptors in the control of in vivo dopamine outflow in the rat striatum.	2003 Feb	12603267
Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats.	2003 Feb	12451437
Effects of ginsenoside Rg2 on the 5-HT3A receptor-mediated ion current in Xenopus oocytes.	2003 Feb 28	12661769
Roles for CCK1 and 5-HT3 receptors in the effects of CCK on presympathetic vasomotor neuronal discharge in the rat.	2003 May	12770947
Antinociceptive effect of shakuyakukanzoto, a Kampo medicine, in diabetic mice.	2005 Dec	16314688
Effects of repeated daily treatments with a 5-HT3 receptor antagonist on dopamine neurotransmission and functional activity of 5-HT3 receptors within the nucleus accumbens of Wistar rats.	2006 Jun	16828150
A dual role of 5-hydroxytryptamine receptor 3 in serotonin induced ion transport in rat distal colon.	2008 Apr 14	18313044
GABA(A) receptors mediate the attenuating effects of a 5-HT(3) receptor antagonist on methamphetamine-induced behavioral sensitization in mice.	2010 Apr	19953653

Patents

Sample Use Guides

In Vivo Use Guide

MDL 72,222 (Bemesetron) was given in 20 mg intravenous doses 30 minutes before chemotherapy, as well as 2, 6, and 12 hours after chemotherapy infusion

Route of Administration: Intravenous

In Vitro Use Guide

The properties of MDL 72222 (bemesetron) with potent and selective blocking actions at certain excitatory 5-hydroxytryptamine (5-HT) receptors on mammalian peripheral neurones, are described. On the rabbit isolated heart, MDL 72222 was a potent antagonist of responses mediated through the receptors for 5-HT present on the terminal sympathetic fibres. The threshold for antagonism was approximately 0.1 nM and the negative logarithm of the molar concentration of MDL 72222 which reduced the chronotropic response of the isolated rabbit heart to twice an ED50 of 5-HT to that of the ED50 was 9.27. MDL 72222 was also highly selective since responses to the nicotine receptor agonist, dimethylphenylpiperazinum iodine (DMPP), were inhibited only at concentrations more than 1000 times those necessary to inhibit 5-HT.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:51:08 UTC 2023` Edited by `admin` on `Sat Dec 16 17:51:08 UTC 2023`
Record UNII	O98T3677PA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BEMESETRON

Official Name

English

MDL-72,222

Code

English

MDL 72,222

Code

English

1αH,5αH-Tropan-3α-yl 3,5-dichlorobenzoate

Common Name

English

BEMESETRON [USAN]

Common Name

English

8-METHYL-8-AZABICYCLO(3.2.1)OCTAN-3-YL 3,5-DICHLOROBENZOATE

Systematic Name

English

bemesetron [INN]

Common Name

English

3-Tropanyl-3,5-dichlorobenzoate

Common Name

English

MDL-72222

Code

English

BENZOIC ACID, 3,5-DICHLORO-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C94726