Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H17NO2 |
Molecular Weight | 267.3224 |
Optical Activity | ( - ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC2=C3[C@H]1CC4=CC=C(O)C(O)=C4C3=CC=C2
InChI
InChIKey=VMWNQDUVQKEIOC-CYBMUJFWSA-N
InChI=1S/C17H17NO2/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/t13-/m1/s1
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 |
|
Inhibition by ginsenosides Rb1 and Rg1 of cocaine-induced hyperactivity, conditioned place preference, and postsynaptic dopamine receptor supersensitivity in mice. | 1999 Jul |
|
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 |
|
5-HT1A receptor agonists buspirone and gepirone attenuate apomorphine-induced aggressive behaviour in adult male Wistar rats. | 2000 Dec |
|
Involvement of GABAergic neurotransmission in the neurobiology of the apomorphine-induced aggressive behavior paradigm, a model of psychotic behavior in rats. | 2000 Oct |
|
The Posturo-Locomotion-Manual Test. A simple method for the characterization of neurological movement disturbances. | 2001 |
|
A risk-benefit assessment of sildenafil in the treatment of erectile dysfunction. | 2001 |
|
Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study. | 2001 |
|
Acute trazodone and quipazine treatment attenuates apomorphine-induced aggressive behaviour in male rats without major impact on emotional behaviour or monoamine content post mortem. | 2001 Apr |
|
The effects of apomorphine and haloperidol on memory consolidation in the day-old chick. | 2001 Apr |
|
Generation and pharmacological analysis of M2 and M4 muscarinic receptor knockout mice. | 2001 Apr 27 |
|
Microencapsulated bovine chromaffin cell xenografts into hemiparkinsonian rats: a drug-induced rotational behavior and histological changes analysis. | 2001 Feb |
|
Apomorphine in the treatment of Parkinson's disease. | 2001 Feb |
|
Dopamine increases glial cell line-derived neurotrophic factor in human fetal astrocytes. | 2001 Feb |
|
Increased growth hormone response to apomorphine in Parkinson disease compared with multiple system atrophy. | 2001 Feb |
|
Ethanol acts synergistically with a D2 dopamine agonist to cause translocation of protein kinase C. | 2001 Jan |
|
Toxic effects of apomorphine on rat cultured neurons and glial C6 cells, and protection with antioxidants. | 2001 Jan 1 |
|
The localization of dopamine D2 receptor mRNA in the human placenta and the anti-angiogenic effect of apomorphine in the chorioallantoic membrane. | 2001 Jan 19 |
|
Intranigral transplantation of solid tissue ventral mesencephalon or striatal grafts induces behavioral recovery in 6-OHDA-lesioned rats. | 2001 Jan 26 |
|
Clinical and electrophysiological effects of apomorphine in Parkinson's disease patients are not paralleled by amino acid release changes: a microdialysis study. | 2001 Jan-Mar |
|
Corticosterone selectively attenuates 8-OH-DPAT-mediated hypothermia in mice. | 2001 Mar |
|
Reproductive experience modulates dopamine-related behavioral responses. | 2001 Mar |
|
Neural modulation of visuomotor functions underlying prey-catching behaviour in anurans: perception, attention, motor performance, learning. | 2001 Mar |
|
Apomorphine-induced aggressive behaviour in para-chlorophenylalanine-treated male rats: implications to brain. | 2001 Mar |
|
Pharmacology of erectile function and dysfunction. | 2001 May |
|
The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist. | 2001 May |
|
Control of serotonergic neurons in rat brain by dopaminergic receptors outside the dorsal raphe nucleus. | 2001 May |
|
Interaction between D2 dopaminergic and glutamatergic excitatory influences on lower urinary tract function in normal and cerebral-infarcted rats. | 2001 May |
|
Intrasubthalamic injection of 6-hydroxydopamine induces changes in the firing rate and pattern of subthalamic nucleus neurons in the rat. | 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 17:54:46 GMT 2025
by
admin
on
Mon Mar 31 17:54:46 GMT 2025
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Record UNII |
N21FAR7B4S
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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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WHO-ATC |
G04BE07
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WHO-VATC |
QG04BE07
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NDF-RT |
N0000175580
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NCI_THESAURUS |
C38149
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LIVERTOX |
NBK548143
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EU-Orphan Drug |
EU/3/01/072
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FDA ORPHAN DRUG |
89295
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WHO-ATC |
N04BC07
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NDF-RT |
N0000000117
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FDA ORPHAN DRUG |
107997
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WHO-VATC |
QN04BC07
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DB00714
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D001058
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6005
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DTXSID8022614
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SUB12923MIG
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CHEMBL53
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33
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200-360-0
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m2003
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C61639
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N21FAR7B4S
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Apomorphine
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3289
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48538
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228
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1043
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100000090486
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N21FAR7B4S
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APOMORPHINE
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Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> AGONIST |
Emax 82% Transfected CHO cells
EC50
|
||
|
TARGET -> AGONIST |
Emax 45% Emax 82% Transfected CHO cells
EC50
|
||
|
SALT/SOLVATE -> PARENT |
|
||
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METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> INDUCER |
MAXIMUM FOLD INCREASE
|
||
|
BINDER->LIGAND |
BINDING
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
OFF-TARGET->INHIBITOR |
BINDING
IC50
|
||
|
TARGET -> AGONIST |
D2S Primary receptor interaction.. Emax 79%
EC50
|
||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
EXCRETED UNCHANGED |
INTRAVENOUS ADMINISTRATION
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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SUBCUTANEOUS ADMINISTRATION |
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CSF/PLASMA RATIO | PHARMACOKINETIC |
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Tmax PHARMACOKINETIC PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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