astemizole

{{short description|Antihistamine drug}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 457285684

| IUPAC_name = 1-[(4-fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidyl]benzoimidazol-2-amine

| image = Astemizole.svg

| width = 250

| tradename =

| Drugs.com = {{drugs.com|MTM|astemizole}}

| MedlinePlus = a600034

| pregnancy_category = C (USA)

| legal_status = Withdrawn

| routes_of_administration = Oral

| bioavailability =

| protein_bound = ~96%

| metabolism = Hepatic (CYP3A4){{cite journal | vauthors = Matsumoto S, Yamazoe Y | title = Involvement of multiple human cytochromes P450 in the liver microsomal metabolism of astemizole and a comparison with terfenadine | journal = British Journal of Clinical Pharmacology | volume = 51 | issue = 2 | pages = 133–142 | date = February 2001 | pmid = 11259984 | pmc = 2014443 | doi = 10.1111/j.1365-2125.2001.01292.x }}

| elimination_half-life = 24 hours

| excretion = Fecal

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 68844-77-9

| ATC_prefix = R06

| ATC_suffix = AX11

| PubChem = 2247

| IUPHAR_ligand = 2603

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00637

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2160

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

| UNII = 7HU6337315

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00234

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 2896

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 296419

| C=28 | H=31 | F=1 | N=4 | O=1

| smiles = Fc1ccc(cc1)Cn2c5ccccc5nc2NC4CCN(CCc3ccc(OC)cc3)CC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C28H31FN4O/c1-34-25-12-8-21(9-13-25)14-17-32-18-15-24(16-19-32)30-28-31-26-4-2-3-5-27(26)33(28)20-22-6-10-23(29)11-7-22/h2-13,24H,14-20H2,1H3,(H,30,31)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GXDALQBWZGODGZ-UHFFFAOYSA-N

}}

Astemizole (marketed under the brand name Hismanal, developmental code R43512) was a second-generation antihistamine drug that has a long duration of action. Astemizole was discovered by Janssen Pharmaceutica in 1977. It was withdrawn from the market globally in 1999 because of rare but potentially fatal side effects (QTc interval prolongation and related arrhythmias due to hERG channel blockade).{{cite journal | vauthors = Zhou Z, Vorperian VR, Gong Q, Zhang S, January CT | title = Block of HERG potassium channels by the antihistamine astemizole and its metabolites desmethylastemizole and norastemizole | journal = Journal of Cardiovascular Electrophysiology | volume = 10 | issue = 6 | pages = 836–843 | date = June 1999 | pmid = 10376921 | doi = 10.1111/j.1540-8167.1999.tb00264.x | s2cid = 25655101 }}{{cite journal | vauthors = Charles O, Onakpoya I, Benipal S, Woods H, Bali A, Aronson JK, Heneghan C, Persaud N | display-authors = 6 | title = Withdrawn medicines included in the essential medicines lists of 136 countries | journal = PLOS ONE | volume = 14 | issue = 12 | pages = e0225429 | date = 2019 | pmid = 31791048 | pmc = 6887519 | doi = 10.1371/journal.pone.0225429 | doi-access = free | bibcode = 2019PLoSO..1425429C }}