metiamide

Also known as NSC 307755, SK&F 92058, Metiamida, Metiamidum, Methiamide

Metiamide is a histamine H2 receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful anti-ulcer drug cimetidine (Tagamet).

In the Vinony graph

Vinony's link graph records 332 inbound references to metiamide, and connects out to nitrogen, electron and International Standard Book Number.

It sits within the topics Chembox image size set, H2 receptor antagonists and Imidazoles.

Vinony links it to 6 Wikipedia language editions.

Chemical data

Formula: C9H16N4S2
Molecular weight: 244.4 g/mol
IUPAC name: 1-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]thiourea
SMILES: CC1=C(N=CN1)CSCCNC(=S)NC
InChIKey: FPBPLBWLMYGIQR-UHFFFAOYSA-N
XLogP: 0.5
Polar surface area: 110 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Research

931 papers

Burimamide, metiamide, cimetidine..Lancet (London, England) · 1975
Histamine H2-receptor antagonists.Advances in internal medicine · 1978
Metiamide: an antagonist of histamine-stimulated gastric acid secretion.Annals of surgery · 1975
Metiamide: more than an H2-receptor antagonist.The American journal of digestive diseases · 1978
Histamine H2-receptor antagonists.Acta hepato-gastroenterologica · 1976

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 244.082

Show 5 more facts

chemical formula: C₉H₁₆N₄S₂
isomeric SMILES: C/N=C(\S)/NCCSCC=1NC=NC1C
subject has role: H2 antagonists
canonical SMILES: CC1=C(N=CN1)CSCCNC(=S)NC
Commons category: Metiamide

Sources (3)

via Wikidata · CC0

~3 min read

Encyclopedic overview

4 sections

Contents

Development of metiamide from burimamide
Modification of metiamide to cimetidine
Synthesis
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443226059 | Name = Metiamide | PIN = N-Methyl-''N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)thiourea | OtherNames = 1-Methyl-3-(2-{[(5-methyl-1H''-imidazol-4-yl)methyl]thio}ethyl)thiourea | ImageFile = Metiamide.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageName = Metiamide

| Section1 =

Excerpted from Wikipedia’s “metiamide” article, available under the CC BY-SA 4.0 licence.