amoxapine indications/contra

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.
  • Molecular weight: 313.79
  • Formula: C17H16ClN3O
  • CLOGP: 3.41
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 36.86
  • ALOGS: -3.26
  • ROTB: 0

Drug dosage:

DoseUnitRoute
0.15 g O

Approvals:

DateAgencyCompanyOrphan
Sept. 22, 1980 FDA LEDERLE

FDA Adverse Event Reporting System

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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
Overdose 85.39 44.53 23 128 33955 3351753
Toxicity to various agents 73.54 44.53 22 129 47032 3338676
Neuroleptic malignant syndrome 60.61 44.53 12 139 4429 3381279
Completed suicide 54.65 44.53 16 135 31098 3354610
Intentional overdose 50.80 44.53 13 138 15212 3370496

Pharmacologic Action:

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SourceCodeDescription
ATC N06AA17 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
FDA EPC N0000175752 Tricyclic Antidepressant
MeSH PA D018663 Adrenergic Agents
MeSH PA D018759 Adrenergic Uptake Inhibitors
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35640 adrenergic uptake inhibitor
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:50949 serotonin uptake inhibitor
MeSH PA D000928 Antidepressive Agents
MeSH PA D018687 Antidepressive Agents, Second-Generation
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 D018490 Serotonin Agents
MeSH PA D017367 Serotonin Uptake Inhibitors

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007 DOID:2848
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
Kidney disease contraindication 90708001 DOID:2527
Tardive dyskinesia contraindication 102449007
Seizure disorder contraindication 128613002 DOID:1826
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
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

Acid dissociation constants calculated using MoKa v3.0.0

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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:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent serotonin transporter Transporter INHIBITOR IC50 7.47 DRUG MATRIX CHEMBL
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Ki 7.89 DRUG MATRIX CHEMBL
D(3) dopamine receptor GPCR Ki 7.73 PDSP
D(2) dopamine receptor GPCR Ki 7.80 PDSP
5-hydroxytryptamine receptor 6 GPCR Ki 7.57 IUPHAR
D(1A) dopamine receptor GPCR Ki 6.71 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.31 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 8.18 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 6.59 DRUG MATRIX
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
Cytochrome P450 2D6 Enzyme IC50 5 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.84 DRUG MATRIX
5-hydroxytryptamine receptor 3A Ion channel Ki 6.57 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 6.66 CHEMBL
D(4) dopamine receptor GPCR ANTAGONIST Ki 7.47 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.75 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 6.30 CHEMBL
Sodium-dependent dopamine transporter Transporter Kd 5.37 WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel WOMBAT-PK
Sodium- and chloride-dependent glycine transporter 2 Transporter IC50 4.04 WOMBAT-PK
Multidrug resistance protein 1 Transporter WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.40 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 7.22 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 8.70 IUPHAR
Alpha-1A adrenergic receptor GPCR IC50 6.45 CHEMBL
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 9 IUPHAR

External reference:

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IDSource
DB00543 DRUGBANK_ID
201 IUPHAR_LIGAND_ID
4017919 VUID
N0000146270 NUI
C0002644 UMLSCUI
D00228 KEGG_DRUG
4017919 VANDF
4385 MMSL
722 RXNORM
29840005 SNOMEDCT_US
373754002 SNOMEDCT_US
4186 MMSL
d00874 MMSL
N0000005838 NDFRT
N0000146270 NDFRT
001506 NDDF
CHEMBL1113 ChEMBL_ID
2170 PUBCHEM_CID
R63VQ857OT UNII
3049 INN_ID
D000657 MESH_DESCRIPTOR_UI
CHEBI:2675 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5713 TABLET 25 mg ORAL ANDA 13 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5714 TABLET 50 mg ORAL ANDA 13 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5715 TABLET 100 mg ORAL ANDA 13 sections
Amoxapine HUMAN PRESCRIPTION DRUG LABEL 1 0591-5716 TABLET 150 mg ORAL ANDA 13 sections
AMOXAPINE HUMAN PRESCRIPTION DRUG LABEL 1 54868-2438 TABLET 50 mg ORAL ANDA 13 sections