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burimamide
Sign in to saveBurimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist, but its H3 affinity is 100x higher. It is a thiourea derivative.
Chemical data
- Formula
- C9H16N4S
- Molecular weight
- 212.32 g/mol
- IUPAC name
- 1-[4-(1H-imidazol-5-yl)butyl]-3-methylthiourea
- SMILES
- CNC(=S)NCCCCC1=CN=CN1
- InChIKey
- HXRBAVXGYZUSED-UHFFFAOYSA-N
- XLogP
- 0.4
- Polar surface area
- 84.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
298 papers- Burimamide, metiamide, cimetidine..Lancet (London, England) · 1975
- A third life for burimamide. Discovery and characterization of a novel class of non-opioid analgesics derived from histamine antagonists.Annals of the New York Academy of Sciences · 2000
- A Quantitative study of histamine H2-receptor bockade by burimamide in isolated artica.Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.) · 1975
- Histamine H2-receptor antagonists.Acta hepato-gastroenterologica · 1976
- New analogs of burimamide as potent and selective histamine H3 receptor antagonists: the effect of chain length variation of the alkyl spacer and modifications of the N-thiourea substituent.Journal of medicinal chemistry · 1995
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 212.11
Show 5 more facts
- subject has role
- H2 antagonists
- chemical formula
- C₉H₁₆N₄S
- canonical SMILES
- CNC(=S)NCCCCC1=CN=CN1
- isomeric SMILES
- C/N=C(\S)/NCCCCC1=CNC=N1
- Commons category
- Burimamide
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Burimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist, but its H3 affinity is 100x higher. It is a thiourea derivative.
Burimamide was first developed by scientists at Smith, Kline & French (SK&F; now GlaxoSmithKline) in their intent to develop a histamine antagonist for the treatment of peptic ulcers. The discovery of burimamide ultimately led to the development of cimetidine (Tagamet).
Excerpted from Wikipedia’s “burimamide” article, available under the CC BY-SA 4.0 licence.