Amoxapine

Title: Amoxapine
CAS Registry Number: 14028-44-5
CAS Name: 2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine
Manufacturers' Codes: CL-67772
Trademarks: Asendin (Lederle); Asendis (Wyeth); Defanyl (Lederle); Demolox (Am. Cyanamid); Moxadil (Lederle)
Molecular Formula: C17H16ClN3O
Molecular Weight: 313.78
Percent Composition: C 65.07%, H 5.14%, Cl 11.30%, N 13.39%, O 5.10%
Literature References: Prepn: J. Schmutz et al., Helv. Chim. Acta 50, 245 (1967); eidem, Chim. Ther. 2, 424 (1967); C. F. Howell et al., FR 1508536; eidem, US 3663696 (1968, 1972 both to Am. Cyanamid). Analysis of amoxapine and its metabolites by GLC: T. B. Cooper, R. G. Kelly, J. Pharm. Sci. 68, 216 (1979). X-ray crystallography: D. B. Cosulich, F. M. Lovell, Acta Crystallogr. B33, 1147 (1977). Pharmacology: E. N. Greenblatt et al., Arch. Int. Pharmacodyn. Ther. 233, 107 (1978). Clinical study: R. Takahashi et al., J. Int. Med. Res. 7, 7 (1979). Review: T. A. Ban, Psychopharmacol. Bull. 15, 22-25 (1979); E. N. Greenblatt et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 1-18. Review of pharmacology and therapeutic efficacy: S. G. Jue et al., Drugs 24, 1-23 (1982).
Properties: Crystals from benzene/petr ether, mp 175-176°. LD50 in mice (mg/kg): 122 i.p.; 112 orally (Howell, 1972).
Melting point: mp 175-176°
Toxicity data: LD50 in mice (mg/kg): 122 i.p.; 112 orally (Howell, 1972)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.
Amoxicillin AMPA Ampelopsin Amperozide Amphecloral

Amoxapine
Amoxapine2DACS.svg
Amoxapine3Dan.gif
Systematic (IUPAC) name
2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine
Clinical data
Trade names Asendin, Asendis, Defanyl, Demolox
AHFS/Drugs.com monograph
MedlinePlus a682202
Licence data US FDA:link
Pregnancy cat. C (US)
Legal status Prescription Only (S4) (AU) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability >60%[1]
Protein binding 90%[2]
Metabolism Hepatic (cytochrome P450 system)[1]
Half-life 8–10 hours (30 hours for chief active metabolite)[2]
Excretion Renal (60%), faeces (18%)[1]
Identifiers
CAS number 14028-44-5 YesY
ATC code N06AA17
PubChem CID 2170
IUPHAR ligand 201
DrugBank DB00543
ChemSpider 2085 YesY
UNII R63VQ857OT YesY
KEGG D00228 YesY
ChEBI CHEBI:2675 YesY
ChEMBL CHEMBL1113 YesY
Chemical data
Formula C17H16ClN3O 
Mol. mass 313.781 g/mol
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Amoxapine (pronounced: a-mox-a-peen.[3] Notable brand names include: Asendin, Asendis, Defanyl, Demolox. See here for more brand name information) is a tetracyclic antidepressant of the dibenzoxazepine family, though it is often classified as a secondary amine tricyclic antidepressant. It is the N-demethylated metabolite of Loxapine. It first received marketing approval in the US in 1992 (approximately thirty to forty years after most of the other tricyclic antidepressants were introduced in the US).[3]