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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=10511920
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2331075 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27561098 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | APOKYN Approved UseAPOKYN (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 Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
47.5 pmol/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2774511/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
41.7 pmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2774511/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2774511/ |
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
Dose | Population | Adverse 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) Sources: Dysgeusia (1 patient) Dizziness (1 patient) Orthostatic hypotension (1 patient) |
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) Sources: Yawning (1 patient) Flushing (1 patient) |
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) Sources: 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) |
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%) Sources: Vomiting (2%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/210875Orig1s000ClinPharmR.pdf#page=28 Page: 28.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/210875Orig1s000ClinPharmR.pdf#page=28 Page: 28.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/210875Orig1s000ClinPharmR.pdf#page=28 Page: 28.0 |
yes | |||
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/210875Orig1s000ClinPharmR.pdf#page=15 Page: 15.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9377797
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
Edited
Mon Mar 31 17:47:39 GMT 2025
by
admin
on
Mon Mar 31 17:47:39 GMT 2025
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Record UNII |
9K13MD7A0D
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66884
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NCI_THESAURUS |
C443
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NCI_THESAURUS |
C67413
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NCI_THESAURUS |
C67439
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m2003
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206-243-0
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DTXSID5040598
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11442
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314-19-2
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C80572
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DB12276
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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SOLVATE->ANHYDROUS |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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