apomorphine indications/contra

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

Drug dosage:

DoseUnitRoute
2 mg SL
20 mg P

Approvals:

DateAgencyCompanyOrphan
April 20, 2004 FDA US WORLDMEDS

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
Fall 124.48 44.09 40 237 58843 3326739
On and off phenomenon 114.19 44.09 15 262 215 3385367
Dyskinesia 105.87 44.09 23 254 7262 3378320
Hallucination, visual 92.92 44.09 19 258 4457 3381125
Soft tissue mass 81.47 44.09 10 267 79 3385503
Illusion 75.17 44.09 11 266 354 3385228
Nasal discomfort 65.44 44.09 11 266 873 3384709
Pelvic fracture 60.07 44.09 11 266 1431 3384151
Oral discomfort 60.06 44.09 11 266 1432 3384150
Hyperhidrosis 57.31 44.09 18 259 23592 3361990
Sensory disturbance 49.67 44.09 11 266 3709 3381873
Nausea 49.51 44.09 26 251 129619 3255963
Formication 49.51 44.09 9 268 1120 3384462
Hallucination 48.89 44.09 14 263 13326 3372256
Skin haemorrhage 47.16 44.09 9 268 1458 3384124
Somnolence 44.17 44.09 16 261 32188 3353394

Pharmacologic Action:

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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:48539 alpha-adrenergic drug
CHEBI has role CHEBI:48278 serotonergic drug
MeSH PA D001337 Autonomic Agents
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)

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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

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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:

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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:

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IDSource
33 IUPHAR_LIGAND_ID
4019618 VUID
N0000147712 NUI
C0003596 UMLSCUI
D02004 KEGG_DRUG
CHEMBL53 ChEMBL_ID
DB00714 DRUGBANK_ID
6005 PUBCHEM_CID
4019618 VANDF
d04991 MMSL
N0000006482 NDFRT
N0000147712 NDFRT
1043 RXNORM
387375001 SNOMEDCT_US
67939000 SNOMEDCT_US
004677 NDDF
CHEBI:48538 CHEBI
CHEMBL1616 ChEMBL_ID
CHEMBL1256708 ChEMBL_ID
F39049Y068 UNII
41372-20-7 SECONDARY_CAS_RN
D001058 MESH_DESCRIPTOR_UI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
APOKYN HUMAN PRESCRIPTION DRUG LABEL 1 27505-004 INJECTION 30 mg SUBCUTANEOUS NDA 21 sections