Apafant

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 3-(4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-yl)-1-(4-morpholinyl)-1-propanone

| image = Apafant_structure.png

| width = 220

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number = 105219-56-5

| PubChem = 65889

| ChemSpiderID = 59298

| ChEMBL = 280164

| ChEBI = 92490

| KEGG = D01652

| UNII = J613NI05SV

| IUPHAR_ligand = 1859

| C=22 | H=22 | Cl=1 | N=5 | O=2 | S=1

| smiles = CC1=NN=C2N1C3=C(C=C(S3)CCC(=O)N4CCOCC4)C(=NC2)C5=CC=CC=C5Cl

| StdInChI = 1S/C22H22ClN5O2S/c1-14-25-26-19-13-24-21(16-4-2-3-5-18(16)23)17-12-15(31-22(17)28(14)19)6-7-20(29)27-8-10-30-11-9-27/h2-5,12H,6-11,13H2,1H3

| StdInChIKey = JGPJQFOROWSRRS-UHFFFAOYSA-N

}}

Apafant (WEB-2086, LSM-2613) is a drug which acts as a potent and selective inhibitor of the phospholipid mediator platelet-activating factor (PAF). It was developed by structural modification of the thienotriazolodiazepine sedative drug brotizolam and demonstrated that PAF inhibitory actions could be separated from activity at the benzodiazepine receptor. Apafant was investigated for several applications involving inflammatory responses such as asthma and conjunctivitis but was never adopted for medical use, however it continues to be used in pharmacology research.{{cite journal | vauthors = Casals-Stenzel J | title = Thieno-triazolo-1,4-diazepines as antagonists of platelet-activating factor: present status | journal = Lipids | volume = 26 | issue = 12 | pages = 1157–1161 | date = December 1991 | pmid = 1668111 | doi = 10.1007/BF02536522 | s2cid = 4053407 }}{{cite journal | vauthors = Brecht HM, Adamus WS, Heuer HO, Birke FW, Kempe ER | title = Pharmacodynamics, pharmacokinetics and safety profile of the new platelet-activating factor antagonist apafant in man | journal = Arzneimittel-Forschung | volume = 41 | issue = 1 | pages = 51–59 | date = January 1991 | pmid = 1646613 }}{{cite journal | vauthors = Ikegami K, Hata H, Fuchigami J, Tanaka K, Kohjimoto Y, Uchida S, Tasaka K | title = Apafant (a PAF receptor antagonist) suppresses the early and late airway responses in guinea pigs: a comparison with antiasthmatic drugs | journal = European Journal of Pharmacology | volume = 328 | issue = 1 | pages = 75–81 | date = June 1997 | pmid = 9203572 | doi = 10.1016/s0014-2999(97)83031-2 }}{{cite journal | vauthors = Kato M, Imoto K, Miyake H, Oda T, Miyaji S, Nakamura M | title = Apafant, a potent platelet-activating factor antagonist, blocks eosinophil activation and is effective in the chronic phase of experimental allergic conjunctivitis in guinea pigs | journal = Journal of Pharmacological Sciences | volume = 95 | issue = 4 | pages = 435–442 | date = August 2004 | pmid = 15286429 | doi = 10.1254/jphs.fp0040265 | s2cid = 34872524 | doi-access = free }}