apomorphine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
228 58-00-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • apomorphine
  • (-)-Apomorphine
  • apomorphin
  • L-Apomorphine
  • apomorphine hydrochloride
  • apomorphine hydrochloride hydrate
  • apomorphine hydrochloride hemihydrate
  • apomorphine HCl
  • apomorphine chloride
A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.
  • Molecular weight: 267.33
  • Formula: C17H17NO2
  • CLOGP: 2.49
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 43.70
  • ALOGS: -2.72
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 mg SL
20 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.30 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.32 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 10 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.05 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.68 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 20, 2004 FDA US WORLDMEDS

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
Injection site nodule 105.05 44.45 18 270 1169 2356628
Injection site necrosis 77.76 44.45 12 276 399 2357398
Dyskinesia 74.55 44.45 17 271 4772 2353025
Fall 56.12 44.45 23 265 47076 2310721
Haemolytic anaemia 53.59 44.45 11 277 1870 2355927
Somnolence 47.82 44.45 17 271 23468 2334329

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
Fall 125.74 42.45 46 405 27168 1719162
Dyskinesia 101.15 42.45 25 426 3794 1742536
Hallucination 91.02 42.45 27 424 8143 1738187
Hallucination, visual 89.32 42.45 21 430 2571 1743759
On and off phenomenon 85.11 42.45 14 437 261 1746069
Injection site necrosis 81.62 42.45 13 438 196 1746134
Injection site nodule 68.84 42.45 13 438 546 1745784
Soft tissue mass 66.39 42.45 9 442 39 1746291
Nausea 61.98 42.45 34 417 51162 1695168
Somnolence 61.17 42.45 24 427 16715 1729615
Hyperhidrosis 60.44 42.45 22 429 12466 1733864
Illusion 60.27 42.45 10 441 196 1746134
Haemolytic anaemia 58.40 42.45 14 437 1848 1744482
Nasal discomfort 57.17 42.45 10 441 271 1746059
Pelvic fracture 56.48 42.45 10 441 291 1746039
Oral discomfort 51.03 42.45 10 441 510 1745820
Psychotic disorder 48.77 42.45 15 436 5041 1741289
Tremor 48.49 42.45 19 432 13112 1733218
Drug ineffective 44.97 42.45 30 421 63771 1682559
Skin mass 43.73 42.45 9 442 588 1745742

Pharmacologic Action:

SourceCodeDescription
ATC G04BE07 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs used in erectile dysfunction
ATC N04BC07 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Dopamine agonists
FDA EPC N0000175580 Dopaminergic Agonist
CHEBI has role CHEBI:66956 antidyskinesia agent
CHEBI has role CHEBI:48407 antiparkinson drug
CHEBI has role CHEBI:51065 dopamine agonist
CHEBI has role CHEBI:149552 emetic
CHEBI has role CHEBI:48539 alpha-adrenergic drug
CHEBI has role CHEBI:48278 serotonergic drug
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018491 Dopamine Agonists
MeSH PA D004639 Emetics
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Parkinson's disease indication 49049000 DOID:14330
Priapism contraindication 6273006 DOID:9286
Alcoholism contraindication 7200002
Dyskinesia contraindication 9748009
Acute vomiting contraindication 23971007
Alcohol intoxication contraindication 25702006
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Hypokalemia contraindication 43339004
Acute nephropathy contraindication 58574008
Cerebrovascular disease contraindication 62914000 DOID:6713
Psychotic disorder contraindication 69322001
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Drowsy contraindication 271782001
Disorder of coronary artery contraindication 414024009
Congenital long QT syndrome contraindication 442917000
Progressive Angina Pectoris contraindication
Severe Nausea contraindication
Predisposition to Nausea and Vomiting contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.88 acidic
pKa2 12.98 acidic
pKa3 8.36 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
D(2) dopamine receptor GPCR AGONIST Ki 9.21 CHEMBL CHEMBL
D(1B) dopamine receptor GPCR AGONIST Ki 7.80 IUPHAR
Alpha-2C adrenergic receptor GPCR ANTAGONIST Ki 7.40 IUPHAR
Alpha-2B adrenergic receptor GPCR ANTAGONIST Ki 7.20 IUPHAR
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 7 IUPHAR
Alpha-2A adrenergic receptor GPCR AGONIST Ki 6.90 IUPHAR
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 6.90 IUPHAR
5-hydroxytryptamine receptor 2B GPCR ANTAGONIST Ki 6.90 IUPHAR
D(3) dopamine receptor GPCR AGONIST Ki 8.59 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.68 CHEMBL
D(1A) dopamine receptor GPCR Ki 8.34 CHEMBL
D(4) dopamine receptor GPCR AGONIST Ki 8.05 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.53 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.17 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 5.91 PDSP
Alpha-1A adrenergic receptor GPCR Ki 5.70 PDSP
5-hydroxytryptamine receptor 1B GPCR Ki 5.53 PDSP
Transient receptor potential cation channel subfamily A member 1 Ion channel ACTIVATOR EC50 5.10 IUPHAR
Mannose-6-phosphate isomerase Enzyme IC50 4.84 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 7.19 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 7 CHEMBL
Dopamine receptor GPCR IC50 9 CHEMBL
Adrenergic receptor alpha-2 GPCR IC50 7.20 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.53 CHEMBL
D(1A) dopamine receptor GPCR Ki 7.28 CHEMBL
D(2) dopamine receptor GPCR Ki 8.74 CHEMBL
Dopamine receptor GPCR IC50 9 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 6.73 CHEMBL
D(4) dopamine receptor GPCR EC50 8.82 CHEMBL
Adrenergic receptor alpha-1 GPCR IC50 5.11 CHEMBL
D(2) dopamine receptor GPCR Ki 6.70 CHEMBL
D(3) dopamine receptor GPCR Ki 7.44 CHEMBL
Serotonin (5-HT) receptor GPCR IC50 5.35 CHEMBL
Opioid receptor GPCR IC50 6.52 CHEMBL
Cytoplasmic zinc-finger protein Unclassified EC50 4.77 CHEMBL
Zinc finger protein mex-5 Cytosolic other EC50 5.35 CHEMBL

External reference:

IDSource
D001058 MESH_DESCRIPTOR_UI
4019618 VUID
N0000147712 NUI
C0003596 UMLSCUI
D02004 KEGG_DRUG
67939000 SNOMEDCT_US
4019618 VANDF
d04991 MMSL
1043 RXNORM
387375001 SNOMEDCT_US
004677 NDDF
CHEBI:48538 CHEBI
CHEMBL53 ChEMBL_ID
DB00714 DRUGBANK_ID
CHEMBL1616 ChEMBL_ID
F39049Y068 UNII
41372-20-7 SECONDARY_CAS_RN
5RL PDB_CHEM_ID
33 IUPHAR_LIGAND_ID
6005 PUBCHEM_CID
CHEMBL1256708 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
APOKYN HUMAN PRESCRIPTION DRUG LABEL 1 27505-004 INJECTION 30 mg SUBCUTANEOUS NDA 21 sections
Viatrexx-Arthros HUMAN PRESCRIPTION DRUG LABEL 4 73069-035 INJECTION 31 [kp_C] INTRAVENOUS unapproved drug other 11 sections
Viatrexx-Ithurts HUMAN PRESCRIPTION DRUG LABEL 1 73069-270 INJECTION 201 [kp_C] INTRAVENOUS unapproved drug other 11 sections
Viatrexx-Ouch HUMAN PRESCRIPTION DRUG LABEL 1 73069-402 INJECTION 31 [kp_C] INTRAVENOUS unapproved drug other 11 sections
Viatrexx-Prolo HUMAN PRESCRIPTION DRUG LABEL 12 73069-443 INJECTION 31 [kp_C] INTRAVENOUS unapproved drug other 11 sections