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 82.42 33.96 19 1261 3352 46681430
Dyskinesia 80.12 33.96 30 1250 28895 46655887
Injection site necrosis 63.19 33.96 13 1267 1349 46683433
Hyperkinesia 59.49 33.96 13 1267 1799 46682983
On and off phenomenon 58.27 33.96 13 1267 1978 46682804
Freezing phenomenon 50.74 33.96 11 1269 1466 46683316
Hallucination 40.62 33.96 22 1258 49929 46634853
Blood pressure decreased 40.53 33.96 23 1257 57136 46627646
Somnolence 38.93 33.96 33 1247 156488 46528294
Nausea 36.46 33.96 66 1214 687388 45997394

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
Hallucination, visual 84.27 32.98 35 2212 16078 29934153
Dyskinesia 83.41 32.98 38 2209 21796 29928435
Hallucination 81.99 32.98 49 2198 49010 29901221
On and off phenomenon 70.79 32.98 20 2227 2871 29947360
Injection site necrosis 66.06 32.98 13 2234 385 29949846
Yawning 61.70 32.98 13 2234 544 29949687
Somnolence 58.10 32.98 52 2195 96711 29853520
Fall 57.17 32.98 69 2178 181803 29768428
Oesophageal achalasia 51.01 32.98 10 2237 290 29949941
Oral discomfort 50.64 32.98 15 2232 2541 29947690
Injection site nodule 49.26 32.98 13 2234 1445 29948786
Illusion 46.86 32.98 11 2236 757 29949474
Nodule 45.16 32.98 16 2231 4772 29945459
Soft tissue mass 45.11 32.98 9 2238 286 29949945
Impulse-control disorder 45.04 32.98 12 2235 1383 29948848
Hypersexuality 44.28 32.98 12 2235 1475 29948756
Haemolytic anaemia 43.21 32.98 19 2228 9991 29940240
Blood pressure decreased 40.04 32.98 31 2216 47044 29903187
Dopamine dysregulation syndrome 39.89 32.98 9 2238 519 29949712
Psychotic disorder 37.18 32.98 22 2225 21493 29928738
Nasal discomfort 37.12 32.98 10 2237 1201 29949030
Hyperhidrosis 34.26 32.98 33 2214 67057 29883174
Dizziness 34.21 32.98 56 2191 194853 29755378

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 MoA N0000000117 Dopamine Agonists
FDA EPC N0000175580 Dopaminergic Agonist
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
CHEBI has role CHEBI:48278 serotonergic drugs
CHEBI has role CHEBI:48407 antiparkinson agent
CHEBI has role CHEBI:48539 alpha-adrenergic drugs
CHEBI has role CHEBI:51065 agonista dopaminergico
CHEBI has role CHEBI:66956 antidyskinetic drugs
CHEBI has role CHEBI:149552 emetics

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
10MG KYNMOBI SUNOVION PHARMS INC N210875 May 21, 2020 RX FILM SUBLINGUAL May 21, 2023 NEW PRODUCT
15MG KYNMOBI SUNOVION PHARMS INC N210875 May 21, 2020 RX FILM SUBLINGUAL May 21, 2023 NEW PRODUCT
20MG KYNMOBI SUNOVION PHARMS INC N210875 May 21, 2020 RX FILM SUBLINGUAL May 21, 2023 NEW PRODUCT
25MG KYNMOBI SUNOVION PHARMS INC N210875 May 21, 2020 RX FILM SUBLINGUAL May 21, 2023 NEW PRODUCT
30MG KYNMOBI SUNOVION PHARMS INC N210875 May 21, 2020 RX FILM SUBLINGUAL May 21, 2023 NEW PRODUCT

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
N21FAR7B4S UNII
4019618 VUID
N0000147712 NUI
D02004 KEGG_DRUG
41372-20-7 SECONDARY_CAS_RN
C0003596 UMLSCUI
CHEBI:48538 CHEBI
OR9 PDB_CHEM_ID
CHEMBL53 ChEMBL_ID
CHEMBL1616 ChEMBL_ID
CHEMBL1256708 ChEMBL_ID
6005 PUBCHEM_CID
DB00714 DRUGBANK_ID
D001058 MESH_DESCRIPTOR_UI
33 IUPHAR_LIGAND_ID
1043 RXNORM
17790 MMSL
71829 MMSL
d04991 MMSL
001665 NDDF
004677 NDDF
387375001 SNOMEDCT_US
67939000 SNOMEDCT_US
725667002 SNOMEDCT_US
74950007 SNOMEDCT_US
4017524 VANDF
4019618 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
APOKYN HUMAN PRESCRIPTION DRUG LABEL 1 27505-004 INJECTION 30 mg SUBCUTANEOUS NDA 33 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-010 FILM, SOLUBLE 10 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-015 FILM, SOLUBLE 15 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-020 FILM, SOLUBLE 20 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-025 FILM, SOLUBLE 25 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-030 FILM, SOLUBLE 30 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-110 FILM, SOLUBLE 10 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-115 FILM, SOLUBLE 15 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-120 FILM, SOLUBLE 20 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-125 FILM, SOLUBLE 25 mg SUBLINGUAL NDA 30 sections
KYNMOBI HUMAN PRESCRIPTION DRUG LABEL 1 63402-130 FILM, SOLUBLE 30 mg SUBLINGUAL NDA 30 sections