LUPITIDINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27N5O2S.3ClH
Molecular Weight	522.919
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.Cl.CN(C)CC1=CC=C(CSCCNC2=NC=C(CC3=CN=C(C)C=C3)C(=O)N2)O1

InChI

InChIKey=YMVSCUJJVSENIP-UHFFFAOYSA-N

InChI=1S/C21H27N5O2S.3ClH/c1-15-4-5-16(11-23-15)10-17-12-24-21(25-20(17)27)22-8-9-29-14-19-7-6-18(28-19)13-26(2)3;;;/h4-7,11-12H,8-10,13-14H2,1-3H3,(H2,22,24,25,27);3*1H

HIDE SMILES / InChI

Molecular Formula	C21H27N5O2S
Molecular Weight	413.536
Charge	0
Count

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

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/6123322 | https://www.ncbi.nlm.nih.gov/pubmed/6144180 | https://www.ncbi.nlm.nih.gov/pubmed/2824935

Lupitidine (SKF 93479) is a histamine H2 receptor antagonist. Lupitidine is a potent inhibitor of gastric acid secretion with a long duration of action. It lacks an antiandrogenic effect. It enhances pituitary thyroid stimulating hormone drive by increasing thyroid hormone clearance. It exerts an antinociceptive effect in rodents.

Approval Year

PubMed

Title	Date	PubMed
Modulatory role of phosphoinositide 3-kinase in gastric acid secretion.	2007-09	17569740
Antinociceptive effects of H1- and H2-antihistaminics in mice.	1993-09	7903650
The perchlorate discharge test for examining thyroid function in rats.	1987-11	2824935
Repeated pentagastrin-stimulated gastric acid secretory tests carried out in the evaluation of the pharmacodynamics of a new histamine H2-receptor antagonist, SK&F 93479.	1984-03	6144180
The effects of histamine H2 receptor antagonists on androgen action in vivo and dihydrotestosterone binding to the rat prostate androgen receptor in vitro.	1982-03-01	6123322

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:04:32 GMT 2025` Edited by `admin` on `Mon Mar 31 19:04:32 GMT 2025`
Record UNII	XKU5YY749W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUPITIDINE HYDROCHLORIDE

Official Name

English

SK&F 93479

Preferred Name

English

2-[[2-[[5-[(Dimethylamino)methyl]furfuryl]thio]ethyl]amino]-5-[(6-methyl-3-pyridyl)methyl]-4-(1H)-pyrimidinone trihydrochloride

Systematic Name

English

LUPITIDINE HYDROCHLORIDE [USAN]

Common Name

English

SK&F-93479

Code

English

4(1H)-PYRIMIDINONE, 2-((2-(((5-((DIMETHYLAMINO)METHYL)-2-FURANYL)METHYL)THIO)ETHYL)AMINO)-5-((6-METHYL-3-PYRIDINYL)METHYL)-, TRIHYDROCHLORIDE

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL69178