U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BEMESETRON

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

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

Curator's Comment: Known to be CNS non-penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats.
2003 Feb
Effects of ginsenoside Rg2 on the 5-HT3A receptor-mediated ion current in Xenopus oocytes.
2003 Feb 28
Evaluation of the anti-emetic potential of anti-migraine drugs to prevent resiniferatoxin-induced emesis in Suncus murinus (house musk shrew).
2005 Jan 31
Mechanisms of analgesic action of neurotropin on chronic pain in adjuvant-induced arthritic rat: roles of descending noradrenergic and serotonergic systems.
2005 Mar
Effects of quipazine and m-chlorophenylbiguanide (m-CPBG) on temporal differentiation: evidence for the involvement of 5-HT2A but not 5-HT3 receptors in interval timing behaviour.
2005 Sep
Involvement of 5-HT receptors in the development and expression of methamphetamine-induced behavioral sensitization: 5-HT receptor channel and binding study.
2006 Nov
Long-term depression in the superior cervical ganglion of the rat.
2008 Oct 9
Effects of triterpenoids from Poria cocos Wolf on the serotonin type 3A receptor-mediated ion current in Xenopus oocytes.
2009 Aug 1
Effects of serotonin on acid secretion in isolated rat stomach: the role of 5-HT3 receptors.
2009 Nov 30
The chemical basis of pharmacology.
2010 Dec 7
Patents

Patents

Sample Use Guides

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 GMT 2023
Edited
by admin
on Sat Dec 16 17:51:08 GMT 2023
Record UNII
O98T3677PA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEMESETRON
INN   USAN  
INN   USAN  
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
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
Code System Code Type Description
MESH
C042253
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
WIKIPEDIA
Bemesetron
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID8042632
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
CAS
40796-97-2
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
USAN
BB-8
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107804
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
SMS_ID
100000086139
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
EVMPD
SUB05692MIG
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
INN
6682
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
NCI_THESAURUS
C80766
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
FDA UNII
O98T3677PA
Created by admin on Sat Dec 16 17:51:08 GMT 2023 , Edited by admin on Sat Dec 16 17:51:08 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDING
IC50
Related Record Type Details
ACTIVE MOIETY