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Burimamide

From Wikipedia, the free encyclopedia
Burimamide
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1-[4-(1H-imidazol-5-yl)butyl]-3-methylthiourea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C9H16N4S/c1-10-9(14)12-5-3-2-4-8-6-11-7-13-8/h6-7H,2-5H2,1H3,(H,11,13)(H2,10,12,14) checkY
    Key: HXRBAVXGYZUSED-UHFFFAOYSA-N checkY
  • InChI=1/C9H16N4S/c1-10-9(14)12-5-3-2-4-8-6-11-7-13-8/h6-7H,2-5H2,1H3,(H,11,13)(H2,10,12,14)
    Key: HXRBAVXGYZUSED-UHFFFAOYAJ
  • CNC(=S)NCCCCc1c[nH]cn1
Properties
C9H16N4S
Molar mass212.32 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Burimamide is anantagonist at theH2 andH3histaminereceptors. At physiological pH, it is largely inactive as an H2 antagonist,[1] but its H3 affinity is 100x higher. It is athiourea derivative.

Burimamide was first developed by scientists at Smith, Kline & French (SK&F; nowGlaxoSmithKline) in their intent to develop a histamine antagonist for the treatment ofpeptic ulcers.[2] The discovery of burimamide ultimately led to the development ofcimetidine (Tagamet).[2]

See also

[edit]

References

[edit]
  1. ^Clayden, Jonathan; Greeves, Nick;Warren, Stuart;Wothers, Peter (2001).Organic Chemistry (1st ed.). Oxford University Press. p. 205.ISBN 978-0-19-850346-0.
  2. ^ab"Tagamet: Discovery of Histamine H2-receptor Antagonists".National Historic Chemical Landmarks. American Chemical Society. Archived fromthe original on December 9, 2012. RetrievedJune 25, 2012.
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
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