Lupitidine

Lupitidine

Systematic (IUPAC) name
2-[2-[[5-(2-Aminopropan-2-yl)furan-2-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1H-pyrimidin-6-one
Identifiers
CAS Number	83903-06-4
ATC code	None
PubChem	CID 51670
ChemSpider	3577726
UNII	WF028DWK9N
KEGG	D04794
Chemical data
Formula	C21H27N5O2S
Molar mass	413.54 g/mol
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

Lupitidine (INN) (code name SKF-93479), or lupitidine hydrochloride (USAN), 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]

Synthesis

Lupitidine synthesis:^[5] also:^[6]

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. PMID 1683107.
2. J. Elks (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, H.G.; Muller, P.; Simon, B. (January 1982). "Inhibition of Nocturnal Acid Secretion by H₂-Receptor-Antagonist SKF 93479". The Lancet 319 (8265): 224. doi:10.1016/S0140-6736(82)90788-7.
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): 288–298. doi:10.1177/019262338801600222. PMID 2903544.
5. Lam, B. L.; Pridgen, L. N.; 1982, U.S. Patent 4,352,933
6. Laird, T., Chern. Ind. (London), 1986, 134 (synth)