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 mass 212.32 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Burimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist,[1] 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.[2] The discovery of burimamide ultimately led to the development of cimetidine (Tagamet).[2]

See also

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References

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  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. ^ a b "Tagamet: Discovery of Histamine H2-receptor Antagonists". National Historic Chemical Landmarks. American Chemical Society. Retrieved June 25, 2012.{{cite web}}: CS1 maint: deprecated archival service (link)
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📚 Artikel Terkait di Wikipedia

H2 receptor antagonist

inverse agonists rather than receptor antagonists (with the exception of burimamide), due to the constitutive activity of these receptors. The prototypical

Cimetidine

refined and eventually led to the development of burimamide, the first H2 receptor antagonist. Burimamide, a specific competitive antagonist at the H2 receptor

Cetirizine

Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine

Metiamide

histamine H2 receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful

Famotidine

Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine

Fexofenadine

Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine

Cyclobenzaprine

Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine

Hydroxyzine

Histamine HTMT Impromidine L-Histidine UR-AK49 Antagonists Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine