PUMOSETRAG HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H17N3O2S.ClH
Molecular Weight	339.84
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.O=C(N[C@H]1CN2CCC1CC2)C3=CNC4=C(SC=C4)C3=O

InChI

InChIKey=XGVADZZDFADEOO-YDALLXLXSA-N

InChI=1S/C15H17N3O2S.ClH/c19-13-10(7-16-11-3-6-21-14(11)13)15(20)17-12-8-18-4-1-9(12)2-5-18;/h3,6-7,9,12H,1-2,4-5,8H2,(H,16,19)(H,17,20);1H/t12-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C15H17N3O2S
Molecular Weight	303.379
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24001105 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/9d825897e9782df267d7e97eed9cc5b8.html | https://www.ncbi.nlm.nih.gov/pubmed/17520871

Pumosetrag is a novel, orally active and selective 5-HT 3 agonist. It is a partial agonist in rats and guinea-pig and a full agonist in the mouse, suggesting important species differences in 5-HT3 receptor structure. Pumosetrag had been in phase II clinical trials for the treatment of gastroesophageal reflux disease and irritable bowel syndrome. No serious adverse events were reported. Diarrhea was not more common on the drug and only one subject experienced pruritus. All researches on this drug candidate are discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 3a (5-HT3a) receptor 46 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14616171	Agonist 2678	0.8 nM [Ki]
cholinergic receptor, muscarinic 1 4 Target ID: 483776.0 Gene Symbol: CHRM1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14616171	Binding Agent 1064	7.7 µM [Ki]
cholinergic receptor, muscarinic 2 7 Target ID: 403858.0 Gene Symbol: CHRM2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14616171	Binding Agent 1064	3.3 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Gastroesophageal reflux disease 59 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24001105 https://www.pharmacodia.com/yaodu/html/v1/chemicals/9d825897e9782df267d7e97eed9cc5b8.html	Primary	Phase II 1132	Unknown Approved Use Unknown
Irritable bowel syndrome 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17520871 https://www.pharmacodia.com/yaodu/html/v1/chemicals/9d825897e9782df267d7e97eed9cc5b8.html	Primary	Phase II 1132	Unknown Approved Use Unknown
Constipation 112 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16336295	Primary	Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 CYP2C19 1478 CYP1A2 1524

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21146988/	inconclusive [IC50 >10 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21146988/	inconclusive [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21146988/	inconclusive [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21146988/	inconclusive [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21146988/	inconclusive [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21146988/	yes [IC50 9.3 uM]

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BBOH	https://www.1pchem.com/search?query=1P00BBOH
Chem Scene	CS-7917	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7917
Hangzhou APIChem Technology	AC-24754
MedChem Express	HY-19650	https://www.medchemexpress.com/search.html?q=HY-19650&ft=&fa=&fp=
MolPort	MolPort-005-943-185	https://www.molport.com/shop/molecule-link/MolPort-005-943-185
Molnova	M13042	https://www.molnova.com/en/serch-list.html?keywords=M13042
MuseChem	M038844	https://www.musechem.com/product/M038844.html
MuseChem	M139542	https://www.musechem.com/product/M139542.html
eMolecules	295312153	https://orderbb.emolecules.com/search/#?query=295312153
eMolecules	50423856	https://orderbb.emolecules.com/search/#?query=50423856

PubMed

Title	Date	PubMed
Effect of a novel 5-HT3 receptor agonist MKC-733 on upper gastrointestinal motility in humans.	2003 Nov 15	14616171
Effect of MKC-733, a 5-HT receptor partial agonist, on bowel motility and symptoms in subjects with constipation: an exploratory study.	2005 Dec	16336295
Drug evaluation: Pumosetrag for the treatment of irritable bowel syndrome and gastroesophageal reflux disease.	2007 May	17520871
Effects of the novel 5-HT3 agonist MKC-733 on the rat, mouse and guinea pig digestive tract.	2008	17952012
Inotropic effects of prokinetic agents with 5-HT(4) receptor agonist actions on human isolated myocardial trabeculae.	2012 Apr 9	22326501

Patents

Sample Use Guides

In Vivo Use Guide

0.2, 0.5, or 0.8 mg

Route of Administration: Oral

In Vitro Use Guide

In the presence of methysergide (1 mol/l) and GR125487 (0.1 mol/l), MKC-733 appeared to have little to no contractile effect in the jejunum (E max = 11.85 %), ileum (E max = 9.65 %) and distal colon of the rat (E max = 14.30 %).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:14:35 GMT 2023` Edited by `admin` on `Sat Dec 16 05:14:35 GMT 2023`
Record UNII	UVW44TKU66
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PUMOSETRAG HYDROCHLORIDE

Common Name

English

DDP-773

Code

English

MKC-773

Code

English

THIENO(3,2-B)PYRIDINE-6-CARBOXAMIDE, N-(3R)-1-AZABICYCLO(2.2.2)OCT-3-YL-4,7-DIHYDRO-7-OXO-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

194093-42-0