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

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 potentiates N-methyl-D-aspartate receptors by interacting with an allosteric site distinct from the polyamine binding site.	2010-03	20008958
Pharmacological causes of hyperprolactinemia.	2007-10	18473017
Effects of impromidine- and arpromidine-derived guanidines on recombinant human and guinea pig histamine H1 and H2 receptors.	2007-01	17206612
Probing ligand-specific histamine H1- and H2-receptor conformations with NG-acylated Imidazolylpropylguanidines.	2006-04	16394198
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.	2005-09	15947036
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.	2002-01-29	11812538
Effects of histamine and related compounds on the differentiation of HL-60-Eo cells into eosinophils.	2001-09	11771852
Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.	2001-03	11179434
H3 receptor-mediated inhibition of intestinal acetylcholine release: pharmacological characterization of signal transduction pathways.	2001-02	11219402
Intraluminal acid and gastric mucosal integrity: the importance of blood-borne bicarbonate.	2001-01	11123205
Modulation of the intracellular and H3-histamine receptors and chemically-induced seizures in mice.	1994-06	7976808
Histamine release in the isolated vascularly perfused stomach of the rat: regulation by autoreceptors.	1989-03	2470453
Histamine and hepatic glutathione in the mouse.	1987-05-25	2884542

Patents

Name

Type

Language

impromidine [INN]

Preferred Name

English

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

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