Lupitidine

Lupitidine (INN; lupitidine hydrochloride (USAN); development code SKF-93479) is a long-acting H2 receptor antagonist[1] developed by Smith, Kline & French and described as an antiulcerogenic that was never marketed.[2] It was shown to inhibit nocturnal gastric acid secretion[3] and, in experiments on rodents, produced diffuse neuroendocrine cell hyperplasia and an increase in multifocal glandular hyperplasia due to hypergastrinemia resulting from the pharmacological suppression of gastric acid secretion.[4]

Lupitidine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 2-[2-[[5-(2-Aminopropan-2-yl)furan-2-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1H-pyrimidin-6-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H27N5O2S
Molar mass413.54 g·mol−1
3D model (JSmol)
SMILES
  • CC1=NC=C(C=C1)CC2=CN=C(NC2=O)NCCSCC3=CC=C(O3)C(C)(C)N
InChI
  • InChI=1S/C21H27N5O2S/c1-14-4-5-15(11-24-14)10-16-12-25-20(26-19(16)27)23-8-9-29-13-17-6-7-18(28-17)21(2,3)22/h4-7,11-12H,8-10,13,22H2,1-3H3,(H2,23,25,26,27)
  • Key:CZTPLYMKHNEVHO-UHFFFAOYSA-N

References
  1. Franzén L, Ghassemifar R, Malcherek P (July 1991). "Experimental mast cell activation improves connective tissue repair in the perforated rat mesentery". Agents and Actions. 33 (3–4): 371–7. doi:10.1007/bf01986588. PMID 1683107. S2CID 23827166.
  2. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 745–. ISBN 978-1-4757-2085-3.
  3. Dammann HG, Müller P, Simon B (January 1982). "Inhibition of nocturnal acid secretion by H2-receptor-antagonist SKF 93479". Lancet. 1 (8265): 224. doi:10.1016/S0140-6736(82)90788-7. PMID 6119582. S2CID 5525326.
  4. Betton GR, Dormer CS, Wells T, Pert P, Price CA, Buckley P (1 February 1988). "Gastric ECL-cell hyperplasia and carcinoids in rodents following chronic administration of H2-antagonists SK&F 93479 and oxmetidine and omeprazole". Toxicologic Pathology. 16 (2): 288–98. doi:10.1177/019262338801600222. PMID 2903544.
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