METIAMIDE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H16N4S2
Molecular Weight	244.38
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=S)NCCSCC1=C(C)NC=N1

InChI

InChIKey=FPBPLBWLMYGIQR-UHFFFAOYSA-N

InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)

HIDE SMILES / InChI

Molecular Formula	C9H16N4S2
Molecular Weight	244.38
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/7806839 | https://www.ncbi.nlm.nih.gov/pubmed/53035 | https://www.ncbi.nlm.nih.gov/pubmed/234981

Metiamide is an antagonist of histamine H2-receptors synthesized at Smith Kline & French Laboratories. It potently inhibited gastric acid secretion. Metiamide demonstrated promising clinical effects in patients with duodenal ulcers but questionable safety.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4401751 \| https://www.ncbi.nlm.nih.gov/pubmed/7806839	Antagonist 2849
Benzodiazepine receptors; peripheral & central 9 Target ID: CHEMBL2096683 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6133770	Binding Agent 1076
4-trimethylaminobutyraldehyde dehydrogenase 1 Target ID: P49189 Gene ID: 223.0 Gene Symbol: ALDH9A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9271349	Inhibitor 8504	122.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Duodenal ulcer 49 Sources: https://www.ncbi.nlm.nih.gov/pubmed/66567 https://www.ncbi.nlm.nih.gov/pubmed/326638	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Constitutive activity and ligand selectivity of human, guinea pig, rat, and canine histamine H2 receptors.	2007-06	17332265
Degranulation of mast cells located in median eminence in response to compound 48/80 evokes adrenocortical secretion via histamine and CRF in dogs.	2004-10	15231494
Interactions among three classes of mediators explain antigen-induced bronchoconstriction in the isolated perfused and ventilated guinea pig lung.	2003-10	12954791
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.	1997-11	9384502
Side effects of cimetidine.	1979-05	375397
A comparison of the cardiovascular effects of centrally administered clonidine and adrenaline in the anaesthetized rat.	1979-01	32359
Clonidine-induced hypotension: further evidence for a central interaction with histamine H2 receptor antagonists in the rat.	1978-04-01	26032
[Treatment of peptic ulcer in the Zollinger-Ellison syndrome with histamine H2-receptor antagonists (author's transl)].	1977-11-25	21785
Some aspects of medical management of gastrointestinal disease. I.	1975-01-25	234288

Patents

Sample Use Guides

In Vivo Use Guide

Patients with duodenal ulcers were stimulated by a steak meal, and acid secretion was measured by in vivo intragastric titration. Metiamide in a 400-mg dose produced no side effects and almost completely abolished food-stimulated acid secretion. A dose-response curve revealed that a 50-mg dose of metiamide was required to suppress food-stimulated acid secretion by 50%.

Route of Administration: Oral

In Vitro Use Guide

A study characterized the kinetics of and determined the mediators involved in antigen-induced contraction of pulmonary arteries (PA) and lung parenchyma isolated from actively sensitized guinea pigs. Ovalbumin (10(-2) mg/ml) induced contractions of PA rings, which reached maximum amplitude by 2 min and decayed to 50% of maximum by 4-6 min. Pyrilamine (10(-6) M) delayed the onset of contraction and decreased the peak of the response by > 50%. Metiamide (10(-4) M) partially reversed this effect.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:10:10 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:10 GMT 2025`
Record UNII	3K7670861M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METIAMIDE

Official Name

English

NSC-307755

Preferred Name

English

METIAMIDE [USAN]

Common Name

English

SK&F-92058

Code

English

SK&F 92058

Code

English

metiamide [INN]

Common Name

English

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

Systematic Name

English

1-Methyl-3-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]-2-thiourea

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29702