LUPITIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27N5O2S
Molecular Weight	413.536
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IKEHSFKMCULMKJ-UHFFFAOYSA-N

InChI=1S/C21H27N5O2S/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)

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

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
The effects of histamine H2 receptor antagonists on androgen action in vivo and dihydrotestosterone binding to the rat prostate androgen receptor in vitro.	1982 Mar 1	6123322
Antinociceptive effects of H1- and H2-antihistaminics in mice.	1993 Sep	7903650
Modulatory role of phosphoinositide 3-kinase in gastric acid secretion.	2007 Sep	17569740

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:39:31 GMT 2023` Edited by `admin` on `Fri Dec 15 18:39:31 GMT 2023`
Record UNII	WF028DWK9N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUPITIDINE

Official Name

English

2-((2-((5-((DIMETHYLAMINO)METHYL)FURFURYL)THIO)ETHYL)AMINO)-5-((6-METHYL-3-PYRIDYL)METHYL)-4-(1H)-PYRIMIDINONE

Systematic Name

English

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

Systematic Name

English

lupitidine [INN]

Common Name

English

CM-10

Code

English

Code System Code Type Description

FDA UNII

WF028DWK9N