Amoxapine

Amoxapine
Clinical data
Pronunciation	A-mox-a-peen
Trade names	Asendin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682202
License data	US FDA: Amoxapine;
Routes of; administration	Oral
ATC code	N06AA17 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	>60%
Protein binding	90%
Metabolism	Hepatic (cytochrome P450 system)
Elimination half-life	8–10 hours (30 hours for chief active metabolite)
Excretion	Renal (60%), feces (18%)
Identifiers
	IUPAC name 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine;
CAS Number	14028-44-5 ;
PubChem CID	2170;
IUPHAR/BPS	201;
DrugBank	DB00543 ;
ChemSpider	2085 ;
UNII	R63VQ857OT;
KEGG	D00228 ;
ChEBI	CHEBI:2675 ;
ChEMBL	ChEMBL1113 ;
CompTox Dashboard (EPA)	DTXSID7022598 ;
ECHA InfoCard	100.034.411
Chemical and physical data
Formula	C17H16ClN3O
Molar mass	313.79 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4;
	InChI InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2 ; Key:QWGDMFLQWFTERH-UHFFFAOYSA-N ;
	(verify)

Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1980, approximately 10 to 20 years after most of the other TCAs were introduced in the United States.^[6]

^ "Amoxapine: Indications, Side Effects, Warnings -Drugs.com". Drugs.com. 6 November 2013. Retrieved 26 November 2013.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ ^a ^b ^c "Asendin, (amoxapine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 26 November 2013.
^ ^a ^b Kinney JL, Evans RL (September–October 1982). "Evaluation of amoxapine". Clinical Pharmacy. 1 (5): 417–424. PMID 6764165.
^ National Center for Drugs and Biologics (U.S.) (1984). Approved Prescription Drug Products with Therapeutic Equivalence Evaluations (5th, Cumulative Supplement 3 ed.). Rockville, MD: U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration. p. IV-9.

[Drugs-1] "Amoxapine: Indications, Side Effects, Warnings -Drugs.com". Drugs.com. 6 November 2013. Retrieved 26 November 2013.

[FDA-AllBoxedWarnings-2] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[3] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[MSR-4] "Asendin, (amoxapine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 26 November 2013.

[pmid6764165-5] Kinney JL, Evans RL (September–October 1982). "Evaluation of amoxapine". Clinical Pharmacy. 1 (5): 417–424. PMID 6764165.

[6] National Center for Drugs and Biologics (U.S.) (1984). Approved Prescription Drug Products with Therapeutic Equivalence Evaluations (5th, Cumulative Supplement 3 ed.). Rockville, MD: U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration. p. IV-9.

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Clinical data


Pronunciation	A-mox-a-peen^[1]
Trade names	Asendin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682202
License data	US FDA: Amoxapine
Routes of administration	Oral
ATC code	N06AA17 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C1 (Other controlled substances)^[3] US: WARNING^[2]Rx-only
Pharmacokinetic data
Bioavailability	>60%^[4]
Protein binding	90%^[5]
Metabolism	Hepatic (cytochrome P450 system)^[4]
Elimination half-life	8–10 hours (30 hours for chief active metabolite)^[5]
Excretion	Renal (60%), feces (18%)^[4]
Identifiers
IUPAC name 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine
CAS Number	14028-44-5^Y
PubChem CID	2170
IUPHAR/BPS	201
DrugBank	DB00543^Y
ChemSpider	2085^Y
UNII	R63VQ857OT
KEGG	D00228^Y
ChEBI	CHEBI:2675^Y
ChEMBL	ChEMBL1113^Y
CompTox Dashboard (EPA)	DTXSID7022598
ECHA InfoCard	100.034.411
Chemical and physical data
Formula	C₁₇H₁₆ClN₃O
Molar mass	313.79 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
InChI InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2^Y Key:QWGDMFLQWFTERH-UHFFFAOYSA-N^Y
(verify)