lupitidine

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid =

| IUPAC_name = 2-[2-[[5-(2-Aminopropan-2-yl)furan-2-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1H-pyrimidin-6-one

| image = Lupitidine.svg

| width = 260

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number = 83903-06-4

| ATC_prefix = None

| PubChem = 51671

| DrugBank =

| ChemSpiderID = 3577726

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = WF028DWK9N

| KEGG = D04794

| synonyms =

| C=21 | H=27 | N=5 | O=2 | S=1

| SMILES = CC1=NC=C(C=C1)CC2=CN=C(NC2=O)NCCSCC3=CC=C(O3)C(C)(C)N

| StdInChI = 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)

| StdInChIKey = CZTPLYMKHNEVHO-UHFFFAOYSA-N

}}

Lupitidine (INN; lupitidine hydrochloride (USAN); development code SKF-93479) is a long-acting H₂ receptor antagonist{{cite journal | vauthors = Franzén L, Ghassemifar R, Malcherek P | title = Experimental mast cell activation improves connective tissue repair in the perforated rat mesentery | journal = Agents and Actions | volume = 33 | issue = 3–4 | pages = 371–7 | date = July 1991 | pmid = 1683107 | doi = 10.1007/bf01986588 | s2cid = 23827166 }} developed by Smith, Kline & French and described as an antiulcerogenic that was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA745 |date=14 November 2014 |publisher=Springer |isbn=978-1-4757-2085-3 |pages=745– }} It was shown to inhibit nocturnal gastric acid secretion{{cite journal | vauthors = Dammann HG, Müller P, Simon B | title = Inhibition of nocturnal acid secretion by H2-receptor-antagonist SKF 93479 | journal = Lancet | volume = 1 | issue = 8265 | pages = 224 | date = January 1982 | pmid = 6119582 | doi = 10.1016/S0140-6736(82)90788-7 | s2cid = 5525326 }} 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.{{cite journal | vauthors = Betton GR, Dormer CS, Wells T, Pert P, Price CA, Buckley P | title = Gastric ECL-cell hyperplasia and carcinoids in rodents following chronic administration of H2-antagonists SK&F 93479 and oxmetidine and omeprazole | journal = Toxicologic Pathology | volume = 16 | issue = 2 | pages = 288–98 | date = 1 February 1988 | pmid = 2903544 | doi = 10.1177/019262338801600222 | doi-access = free }}