IMPROMIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H23N7S
Molecular Weight	321.444
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CSCCNC(=N)NCCCC2=CNC=N2)N=CN1

InChI

InChIKey=MURRAGMMNAYLNA-UHFFFAOYSA-N

InChI=1S/C14H23N7S/c1-11-13(21-10-19-11)8-22-6-5-18-14(15)17-4-2-3-12-7-16-9-20-12/h7,9-10H,2-6,8H2,1H3,(H,16,20)(H,19,21)(H3,15,17,18)

HIDE SMILES / InChI

Molecular Formula	C14H23N7S
Molecular Weight	321.444
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/17206612 | https://www.ncbi.nlm.nih.gov/pubmed/8520976 | https://www.ncbi.nlm.nih.gov/pubmed/8565080 | https://www.ncbi.nlm.nih.gov/pubmed/6235604

Impromidine is a highly potent and specific histamine H2 receptor agonist used diagnostically as a gastric secretion indicator. The value of impromidine as an effective acid-secretory stimulant is limited by its tendency to cause cardiovascular side-effects, that mediated by H2-receptors in the cardiovascular system.

Originator

Approval Year

PubMed

Title	Date	PubMed
Histamine and hepatic glutathione in the mouse.	1987 May 25	2884542
Histamine release in the isolated vascularly perfused stomach of the rat: regulation by autoreceptors.	1989 Mar	2470453
Modulation of the intracellular and H3-histamine receptors and chemically-induced seizures in mice.	1994 Jun	7976808
H3 receptor-mediated inhibition of intestinal acetylcholine release: pharmacological characterization of signal transduction pathways.	2001 Feb	11219402
Intraluminal acid and gastric mucosal integrity: the importance of blood-borne bicarbonate.	2001 Jan	11123205
Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.	2001 Mar	11179434
Effects of histamine and related compounds on the differentiation of HL-60-Eo cells into eosinophils.	2001 Sep	11771852
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.	2002 Jan-Feb	11812538
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.	2005 Sep	15947036
Probing ligand-specific histamine H1- and H2-receptor conformations with NG-acylated Imidazolylpropylguanidines.	2006 Apr	16394198
Effects of impromidine- and arpromidine-derived guanidines on recombinant human and guinea pig histamine H1 and H2 receptors.	2007 Jan	17206612
Pharmacological causes of hyperprolactinemia.	2007 Oct	18473017
Histamine potentiates N-methyl-D-aspartate receptors by interacting with an allosteric site distinct from the polyamine binding site.	2010 Mar	20008958

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:52:37 GMT 2023` Edited by `admin` on `Sat Dec 16 15:52:37 GMT 2023`
Record UNII	931L4X5WMM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMPROMIDINE

Official Name

English

GUANIDINE, N-(3-(1H-IMIDAZOL-4-YL)PROPYL)-N'-(2-(((5-METHYL-1H-IMIDAZOL-4-YL)METHYL)THIO)ETHYL)-

Systematic Name

English

impromidine [INN]

Common Name

English

1-(3-IMIDAZOL-4-YLPROPYL)-3-(2-(((5-METHYLIMIDAZOL-4-YL)METHYL)THIO)ETHYL)GUANIDINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29702