Apafant

Apafant
Identifiers
	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;
CAS Number	105219-56-5;
PubChem CID	65889;
IUPHAR/BPS	1859;
ChemSpider	59298;
UNII	J613NI05SV;
KEGG	D01652;
ChEBI	CHEBI:92490;
ChEMBL	ChEMBL280164;
CompTox Dashboard (EPA)	DTXSID5048974 ;
ECHA InfoCard	100.220.442
Chemical and physical data
Formula	C22H22ClN5O2S
Molar mass	455.96 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=NN=C2N1C3=C(C=C(S3)CCC(=O)N4CCOCC4)C(=NC2)C5=CC=CC=C5Cl;
	InChI InChI=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; Key: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.^[1]^[2]^[3]^[4]

References

^ Casals-Stenzel J (December 1991). "Thieno-triazolo-1,4-diazepines as antagonists of platelet-activating factor: present status". Lipids. 26 (12): 1157–1161. doi:10.1007/BF02536522. PMID 1668111. S2CID 4053407.
^ Brecht HM, Adamus WS, Heuer HO, Birke FW, Kempe ER (January 1991). "Pharmacodynamics, pharmacokinetics and safety profile of the new platelet-activating factor antagonist apafant in man". Arzneimittel-Forschung. 41 (1): 51–59. PMID 1646613.
^ Ikegami K, Hata H, Fuchigami J, Tanaka K, Kohjimoto Y, Uchida S, Tasaka K (June 1997). "Apafant (a PAF receptor antagonist) suppresses the early and late airway responses in guinea pigs: a comparison with antiasthmatic drugs". European Journal of Pharmacology. 328 (1): 75–81. doi:10.1016/s0014-2999(97)83031-2. PMID 9203572.
^ Kato M, Imoto K, Miyake H, Oda T, Miyaji S, Nakamura M (August 2004). "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 of Pharmacological Sciences. 95 (4): 435–442. doi:10.1254/jphs.fp0040265. PMID 15286429. S2CID 34872524.

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[1] Casals-Stenzel J (December 1991). "Thieno-triazolo-1,4-diazepines as antagonists of platelet-activating factor: present status". Lipids. 26 (12): 1157–1161. doi:10.1007/BF02536522. PMID 1668111. S2CID 4053407.

[2] Brecht HM, Adamus WS, Heuer HO, Birke FW, Kempe ER (January 1991). "Pharmacodynamics, pharmacokinetics and safety profile of the new platelet-activating factor antagonist apafant in man". Arzneimittel-Forschung. 41 (1): 51–59. PMID 1646613.

[3] Ikegami K, Hata H, Fuchigami J, Tanaka K, Kohjimoto Y, Uchida S, Tasaka K (June 1997). "Apafant (a PAF receptor antagonist) suppresses the early and late airway responses in guinea pigs: a comparison with antiasthmatic drugs". European Journal of Pharmacology. 328 (1): 75–81. doi:10.1016/s0014-2999(97)83031-2. PMID 9203572.

[4] Kato M, Imoto K, Miyake H, Oda T, Miyaji S, Nakamura M (August 2004). "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 of Pharmacological Sciences. 95 (4): 435–442. doi:10.1254/jphs.fp0040265. PMID 15286429. S2CID 34872524.

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v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite of Rilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (not GABA_A receptor ligands)