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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17NO2.ClH
Molecular Weight 303.783
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APOMORPHINE HYDROCHLORIDE ANHYDROUS

SMILES

Cl.CN1CCC2=C3[C@H]1CC4=CC=C(O)C(O)=C4C3=CC=C2

InChI

InChIKey=SKYZYDSNJIOXRL-BTQNPOSSSA-N
InChI=1S/C17H17NO2.ClH/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12;/h2-6,13,19-20H,7-9H2,1H3;1H/t13-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H17NO2
Molecular Weight 267.3224
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Apomorphine (brand names: Apokyn, Ixense, Spontane, Uprima) is indicated for the acute, intermittent treatment of hypomobility, “off” episodes (“end-of-dose wearing off” and unpredictable “on/off” episodes) in patients with advanced Parkinson’s disease. Apomorphine has been studied as an adjunct to other medications. It is a non-ergoline dopamine agonist with high in vitro binding affinity for the dopamine D4 receptor, and moderate affinity for the dopamine D2, D3, and D5, and adrenergic α1D, α2B, α2C receptors. The precise mechanism of action as a treatment for Parkinson’s disease is unknown, although it is believed to be due to stimulation of post-synaptic dopamine D2-type receptors within the caudate-putamen in the brain.

CNS Activity

Curator's Comment: Apomorphine quickly passes the nasal and intestinal mucosa as well as the blood-brain barrier (depending on the administration route)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
APOKYN

Approved Use

APOKYN (apomorphine hydrochloride injection) is indicated for the acute, intermittent treatment of hypomobility, off episodes (end-of-dose wearing off and unpredictable on/off episodes) in patients with advanced Parkinson's disease. APOKYN has been studied as an adjunct to other medications [see Clinical Studies (14)

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
47.5 pmol/mL
30 μg/kg bw single, subcutaneous
dose: 30 μg/kg bw
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
APOMORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
41.7 pmol × h/mL
30 μg/kg bw single, subcutaneous
dose: 30 μg/kg bw
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
APOMORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
33.6 min
30 μg/kg bw single, subcutaneous
dose: 30 μg/kg bw
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
APOMORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 mg single, respiratory
Highest studied dose
Dose: 4 mg
Route: respiratory
Route: single
Dose: 4 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
1.5 mg single, respiratory
Recommended
Dose: 1.5 mg
Route: respiratory
Route: single
Dose: 1.5 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Other AEs: Somnolence, Dysgeusia...
Other AEs:
Somnolence (1 patient)
Dysgeusia (1 patient)
Dizziness (1 patient)
Orthostatic hypotension (1 patient)
Sources:
2.3 mg single, respiratory
Recommended
Dose: 2.3 mg
Route: respiratory
Route: single
Dose: 2.3 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
3 mg single, respiratory
Recommended
Dose: 3 mg
Route: respiratory
Route: single
Dose: 3 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Other AEs: Somnolence, Yawning...
Other AEs:
Somnolence (1 patient)
Yawning (1 patient)
Flushing (1 patient)
Sources:
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Disc. AE: Cognitive impairment, Skin reaction...
AEs leading to
discontinuation/dose reduction:
Cognitive impairment (16 patients)
Skin reaction (14 patients)
Posture abnormal (12 patients)
Psychosis (11 patient)
Anxiety/depression (11 patient)
Hypotension (3 patients)
Gastrointestinal disorder (NOS) (1 patient)
Cardiovascular disorder (1 patient)
Weight loss (1 patient)
Excessive daytime sleepiness (1 patient)
Sources:
4 mg 1 times / day multiple, subcutaneous
Highest studied dose
Dose: 4 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 65.21 years
Health Status: unhealthy
Age Group: 65.21 years
Sex: M+F
Sources:
Disc. AE: Nausea and vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea and vomiting (187 patients)
Sources:
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Hallucination...
AEs leading to
discontinuation/dose reduction:
Hallucination (1%)
Sources:
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (3%)
Vomiting (2%)
Sources:
35 mg 1 times / day steady, sublingual
Recommended
Dose: 35 mg, 1 times / day
Route: sublingual
Route: steady
Dose: 35 mg, 1 times / day
Sources:
unhealthy, mean 62.9 years
Health Status: unhealthy
Age Group: mean 62.9 years
Sex: M+F
Sources:
Disc. AE: Respiratory tract signs and symptoms...
AEs leading to
discontinuation/dose reduction:
Respiratory tract signs and symptoms (9 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dizziness 1 patient
1.5 mg single, respiratory
Recommended
Dose: 1.5 mg
Route: respiratory
Route: single
Dose: 1.5 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Dysgeusia 1 patient
1.5 mg single, respiratory
Recommended
Dose: 1.5 mg
Route: respiratory
Route: single
Dose: 1.5 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Orthostatic hypotension 1 patient
1.5 mg single, respiratory
Recommended
Dose: 1.5 mg
Route: respiratory
Route: single
Dose: 1.5 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Somnolence 1 patient
1.5 mg single, respiratory
Recommended
Dose: 1.5 mg
Route: respiratory
Route: single
Dose: 1.5 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Flushing 1 patient
3 mg single, respiratory
Recommended
Dose: 3 mg
Route: respiratory
Route: single
Dose: 3 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Somnolence 1 patient
3 mg single, respiratory
Recommended
Dose: 3 mg
Route: respiratory
Route: single
Dose: 3 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Yawning 1 patient
3 mg single, respiratory
Recommended
Dose: 3 mg
Route: respiratory
Route: single
Dose: 3 mg
Sources:
unhealthy, 30 - 90 years
Health Status: unhealthy
Age Group: 30 - 90 years
Sex: unknown
Sources:
Cardiovascular disorder 1 patient
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Excessive daytime sleepiness 1 patient
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Gastrointestinal disorder (NOS) 1 patient
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Weight loss 1 patient
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Anxiety/depression 11 patient
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Psychosis 11 patient
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Posture abnormal 12 patients
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Skin reaction 14 patients
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Cognitive impairment 16 patients
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Hypotension 3 patients
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 44 - 87 years
Health Status: unhealthy
Age Group: 44 - 87 years
Sex: M+F
Sources:
Nausea and vomiting 187 patients
Disc. AE
4 mg 1 times / day multiple, subcutaneous
Highest studied dose
Dose: 4 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 65.21 years
Health Status: unhealthy
Age Group: 65.21 years
Sex: M+F
Sources:
Hallucination 1%
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Vomiting 2%
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea 3%
Disc. AE
10 mg 1 times / day steady, subcutaneous
Recommended
Dose: 10 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Respiratory tract signs and symptoms 9 patients
Disc. AE
35 mg 1 times / day steady, sublingual
Recommended
Dose: 35 mg, 1 times / day
Route: sublingual
Route: steady
Dose: 35 mg, 1 times / day
Sources:
unhealthy, mean 62.9 years
Health Status: unhealthy
Age Group: mean 62.9 years
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
weak [Inhibition 50 uM]
weak [Inhibition 50 uM]
weak [Inhibition 50 uM]
weak [Inhibition 50 uM]
yes [IC50 50 uM]
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs.
1976 Aug
Modulatory role of 5-HT3 receptors in mediation of apomorphine-induced aggressive behaviour in male rats.
1999 Dec
Inhibition by ginsenosides Rb1 and Rg1 of cocaine-induced hyperactivity, conditioned place preference, and postsynaptic dopamine receptor supersensitivity in mice.
1999 Jul
Modification of naloxone-induced withdrawal signs by dextromethorphan in morphine-dependent mice.
1999 Jul 14
Drug-induced motor complications in dopa-responsive dystonia: implications for the pathogenesis of dyskinesias and motor fluctuations.
1999 Jul-Aug
Worsening of levodopa-induced dyskinesias by motor and mental tasks.
1999 Mar
Test conditions influence the response to a drug challenge in rodents.
2000 Mar
Compulsive checking behavior of quinpirole-sensitized rats as an animal model of Obsessive-Compulsive Disorder(OCD): form and control.
2001
Intrapallidal dopamine restores motor deficits induced by 6-hydroxydopamine in the rat.
2001
A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure.
2001 Apr
Attenuation of paraquat-induced dopaminergic toxicity on the substantia nigra by (-)-deprenyl in vivo.
2001 Apr 1
Microdialysis in Parkinsonian patient basal ganglia: acute apomorphine-induced clinical and electrophysiological effects not paralleled by changes in the release of neuroactive amino acids.
2001 Feb
The role of neurochemical mechanisms of ventromedial hypothalamus in various models of anxiety in rats.
2001 Jan
Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity.
2001 Jan
Regulation by the medial amygdala of copulation and medial preoptic dopamine release.
2001 Jan 1
Intranigral transplantation of solid tissue ventral mesencephalon or striatal grafts induces behavioral recovery in 6-OHDA-lesioned rats.
2001 Jan 26
Autoregulation of dopamine synthesis in subregions of the rat nucleus accumbens.
2001 Jan 5
Erectile dysfunction.
2001 Jun
Forced limb-use effects on the behavioral and neurochemical effects of 6-hydroxydopamine.
2001 Jun 15
Reproductive experience modulates dopamine-related behavioral responses.
2001 Mar
Increased sensitivity of dopamine systems following reproductive experience in rats.
2001 Mar
Differential effects of 7-OH-DPAT on the development of behavioral sensitization to apomorphine and cocaine.
2001 Mar
Oral drug therapy for erectile dysfunction.
2001 May
Pharmacology of erectile function and dysfunction.
2001 May
Central dopaminergic function in anorexia and bulimia nervosa: a psychoneuroendocrine approach.
2001 May
Patents

Sample Use Guides

The recommended starting dose of is 0.2 mL (2 mg). Titrate on the basis of effectiveness and tolerance, up to a maximum recommended dose of 0.6 mL (6 mg)
Route of Administration: Other
In Vitro Use Guide
Apomorphine at concentrations of higher than 2 x 10(-5) M dramatically reduced the growth-stimulatory effect of retinal pigment epithelium (RPE) cells on the scleral chondrocytes, whereas the inhibitory effect of apomorphine on the proliferation of scleral chondrocytes without RPE cells was very little
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:39 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:39 GMT 2025
Record UNII
9K13MD7A0D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APOMORPHINE HYDROCHLORIDE ANHYDROUS
Common Name English
APOKINON
Preferred Name English
BRITAJECT
Brand Name English
NSC-11442
Code English
APOMORPHINE HYDROCHLORIDE [MI]
Common Name English
6A.BETA.-APORPHINE-10,11-DIOL HYDROCHLORIDE
Common Name English
ANHYDROUS APOMORPHINE HYDROCHLORIDE
Common Name English
(6AR)-5,6,6A,7-TETRAHYDRO-6-METHYL-4H-DIBENZO(DE,G)QUINOLINE-10,11-DIOL HYDROCHLORIDE
Common Name English
4H-DIBENZO(DE,G)QUINOLINE-10,11-DIOL, 5,6,6A,7-TETRAHYDRO-6-METHYL-, HYDROCHLORIDE, (R)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
NCI_THESAURUS C443
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
NCI_THESAURUS C67439
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
Code System Code Type Description
FDA UNII
9K13MD7A0D
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
SMS_ID
100000153194
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
MERCK INDEX
m2003
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
206-243-0
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID5040598
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
EVMPD
SUB127079
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
PUBCHEM
9410
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
NSC
11442
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
CAS
314-19-2
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
NCI_THESAURUS
C80572
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
DRUG BANK
DB12276
Created by admin on Mon Mar 31 17:47:39 GMT 2025 , Edited by admin on Mon Mar 31 17:47:39 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY