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amoxapine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| psychoactive | 191 | 14028-44-5 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.15 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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 |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 2.079 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 1.127 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 34.674 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 9.376 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 8.900 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 16.410 | % | High | 1 |
| herg | hERG pIC50 | 5.430 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 1.714 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 5.957 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 11.020 | % | High | 1 |
| kinase-safety-class | ACVR2B,AXL,BRAF,CAMK2D,CDK5,EIF2AK3,ERBB2,GRK2,ITK,MAPK10,MET,NTRK2,PDK2,PDK4,PRKDC | 15 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 2.780 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 27.227 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 9.380 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 9.016 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 17.820 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 62.087 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 32.720 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 11.480 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 494.311 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Sept. 22, 1980 | FDA | LEDERLE |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Poisoning | 65.92 | 46.13 | 16 | 565 | 15201 | 90612665 |
| Intentional overdose | 58.19 | 46.13 | 22 | 559 | 93812 | 90534054 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Poisoning | 85.39 | 43.59 | 21 | 376 | 14678 | 42606260 |
| Asphyxia | 43.73 | 43.59 | 11 | 386 | 8315 | 42612623 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Poisoning | 146.50 | 35.94 | 37 | 975 | 29068 | 110559219 |
| Drug abuse | 71.57 | 35.94 | 34 | 978 | 177377 | 110410910 |
| Asphyxia | 66.11 | 35.94 | 17 | 995 | 14198 | 110574089 |
| Intentional overdose | 52.15 | 35.94 | 25 | 987 | 132476 | 110455811 |
| Altered state of consciousness | 46.22 | 35.94 | 18 | 994 | 57608 | 110530679 |
| Suicide attempt | 39.10 | 35.94 | 19 | 993 | 103375 | 110484912 |
| Toxicity to various agents | 36.29 | 35.94 | 32 | 980 | 480523 | 110107764 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | N06AA17 | NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Non-selective monoamine reuptake 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 |
| CHEBI has role | CHEBI:176497 | geroprotector |
| MeSH PA | D000928 | Antidepressive Agents |
| MeSH PA | D000929 | Antidepressive Agents, Tricyclic |
| MeSH PA | D011619 | Psychotropic Drugs |
| MeSH PA | D014179 | Neurotransmitter Uptake Inhibitors |
| MeSH PA | D015259 | Dopamine Agents |
| MeSH PA | D017367 | Selective Serotonin Reuptake Inhibitors |
| MeSH PA | D018377 | Neurotransmitter Agents |
| MeSH PA | D018490 | Serotonin Agents |
| MeSH PA | D018492 | Dopamine Antagonists |
| MeSH PA | D018663 | Adrenergic Agents |
| MeSH PA | D018759 | Adrenergic Uptake Inhibitors |
| MeSH PA | D049990 | Membrane Transport Modulators |
| FDA EPC | N0000175752 | Tricyclic Antidepressant |
Related Drugs by ATC class:
N06AA Non-selective monoamine reuptake inhibitors 20 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 level | Dissociation constant | Type (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:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 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 |
| 4017919 | VANDF |
| 001506 | NDDF |
| 29840005 | SNOMEDCT_US |
| 373754002 | SNOMEDCT_US |
| R63VQ857OT | INXIGHT DRUGS |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 | 0591-5715 | 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 | 54868-2438 | TABLET | 50 mg | ORAL | ANDA | 22 sections |
| Amoxapine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 62135-700 | TABLET | 25 mg | ORAL | ANDA | 13 sections |
| Amoxapine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 62135-701 | TABLET | 50 mg | ORAL | ANDA | 13 sections |
| Amoxapine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 62135-702 | TABLET | 100 mg | ORAL | ANDA | 13 sections |
| Amoxapine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 62135-703 | TABLET | 150 mg | ORAL | ANDA | 13 sections |