amoxapine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
psychoactive 191 14028-44-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amoxapine
  • amoxan
  • moxadil
  • desmethylloxapine
The N-demethylated derivative of the antipsychotic agent LOXAPINE that works by blocking the reuptake of norepinephrine, serotonin, or both; it also blocks dopamine receptors. Amoxapine is used for the treatment of depression.
  • Molecular weight: 313.79
  • Formula: C17H16ClN3O
  • CLOGP: 3.11
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 36.86
  • ALOGS: -3.26
  • ROTB: 0
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.15 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 31.87 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 36 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Sept. 22, 1980 FDA LEDERLE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Intentional overdose 52.77 44.99 21 542 74131 63414328
Poisoning 52.75 44.99 14 549 13686 63474773

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Poisoning 67.11 43.64 17 339 12209 34944366

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Poisoning 113.44 36.62 31 920 25241 79718196
Asphyxia 60.12 36.62 16 935 11704 79731733
Drug abuse 49.05 36.62 28 923 162663 79580774
Intentional overdose 45.25 36.62 23 928 105937 79637500
Altered state of consciousness 39.39 36.62 16 935 43806 79699631

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N06AA17 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
CHEBI has role CHEBI:35469 antidepressants
CHEBI has role CHEBI:35640 adrenergic uptake inhibitors
CHEBI has role CHEBI:48561 dopaminergic antagonists
CHEBI has role CHEBI:50949 SSRI
CHEBI has role CHEBI:176497 geroprotectors
MeSH PA D018663 Adrenergic Agents
MeSH PA D018759 Adrenergic Uptake Inhibitors
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D017367 Selective Serotonin Reuptake Inhibitors
MeSH PA D018490 Serotonin Agents
FDA EPC N0000175752 Tricyclic Antidepressant

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007
Ocular hypertension contraindication 4210003 DOID:9282
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Bipolar disorder contraindication 13746004 DOID:3312
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Hyperthyroidism contraindication 34486009 DOID:7998
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Schizophrenia contraindication 58214004 DOID:5419
Kidney disease contraindication 90708001 DOID:557
Tardive dyskinesia contraindication 102449007
Seizure disorder contraindication 128613002
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Angle-closure glaucoma contraindication 392291006 DOID:13550
Myocardial infarction in recovery phase contraindication 418044006




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.51 Basic
pKa2 3.9 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Ki 7.89 DRUG MATRIX CHEMBL
Sodium-dependent serotonin transporter Transporter INHIBITOR IC50 7.47 DRUG MATRIX CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.31 DRUG MATRIX
Multidrug resistance protein 1 Transporter WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.66 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.75 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 8.18 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 8.70 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.30 IUPHAR
5-hydroxytryptamine receptor 7 GPCR Ki 6.30 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 6.59 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 7.73 PDSP
Histamine H1 receptor GPCR Ki 7.96 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.54 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 6.03 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.42 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.62 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 6.21 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.34 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Kd 5.37 WOMBAT-PK
Cytochrome P450 2D6 Enzyme IC50 5 DRUG MATRIX
D(4) dopamine receptor GPCR ANTAGONIST Ki 7.47 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 6.84 DRUG MATRIX
5-hydroxytryptamine receptor 3A Ion channel Ki 6.57 DRUG MATRIX
Voltage-dependent N-type calcium channel subunit alpha-1B Ion channel IC50 4.57 CHEMBL
Sodium- and chloride-dependent glycine transporter 2 Transporter IC50 4.04 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 6.71 DRUG MATRIX
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel WOMBAT-PK
D(2) dopamine receptor GPCR Ki 7.80 PDSP
Alpha-1B adrenergic receptor GPCR Ki 7.22 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 6.45 CHEMBL
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 9 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.40 IUPHAR
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 8.70 IUPHAR
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 8.20 IUPHAR

External reference:

IDSource
4017919 VUID
N0000146270 NUI
D00228 KEGG_DRUG
722 RXNORM
C0002644 UMLSCUI
CHEBI:2675 CHEBI
CHEMBL1113 ChEMBL_ID
DB00543 DRUGBANK_ID
D000657 MESH_DESCRIPTOR_UI
2170 PUBCHEM_CID
201 IUPHAR_LIGAND_ID
3049 INN_ID
R63VQ857OT UNII
4186 MMSL
4385 MMSL
d00874 MMSL
29840005 SNOMEDCT_US
373754002 SNOMEDCT_US
4017919 VANDF
001506 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5713 TABLET 25 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5713 TABLET 25 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5714 TABLET 50 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5714 TABLET 50 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5715 TABLET 100 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5715 TABLET 100 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5716 TABLET 150 mg ORAL ANDA 22 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5716 TABLET 150 mg ORAL ANDA 22 sections
AMOXAPINE HUMAN PRESCRIPTION DRUG LABEL 1 54868-2438 TABLET 50 mg ORAL ANDA 22 sections