Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H17NO2.ClH |
Molecular Weight | 303.783 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12CC3=C(C(O)=C(O)C=C3)C4=C1C(CCN2C)=CC=C4
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 | C17H17NO2 |
Molecular Weight | 267.3224 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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 Date1.08241918E12 |
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: Page: Table 2 |
unhealthy, 30 - 90 years n = 5 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 5 Sources: Page: Table 2 |
|
1.5 mg single, respiratory Recommended Dose: 1.5 mg Route: respiratory Route: single Dose: 1.5 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 32 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 32 Sources: Page: Table 2 |
Other AEs: Somnolence, Dysgeusia... Other AEs: Somnolence (1 patient) Sources: Page: Table 2Dysgeusia (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: Page: Table 2 |
unhealthy, 30 - 90 years n = 18 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 18 Sources: Page: Table 2 |
|
3 mg single, respiratory Recommended Dose: 3 mg Route: respiratory Route: single Dose: 3 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 12 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 12 Sources: Page: Table 2 |
Other AEs: Somnolence, Yawning... Other AEs: Somnolence (1 patient) Sources: Page: Table 2Yawning (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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
Disc. AE: Cognitive impairment, Skin reaction... AEs leading to discontinuation/dose reduction: Cognitive impairment (16 patients) Sources: Page: Fig. 1Skin 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 (mean) Highest studied dose Dose: 4 mg, 1 times / day Route: subcutaneous Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, 65.21 years n = 546 Health Status: unhealthy Condition: Parkinson's disease Age Group: 65.21 years Sex: M+F Population Size: 546 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 (max) Recommended Dose: 10 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10 mg, 1 times / day Co-administed with:: trimethobenzamide Sources: Page: 4 |
unhealthy, adult n = 522 Health Status: unhealthy Condition: Parkinson's disease Age Group: adult Sex: unknown Population Size: 522 Sources: Page: 4 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (3%) Sources: Page: 4Vomiting (2%) |
10 mg 1 times / day steady, subcutaneous (max) Recommended Dose: 10 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10 mg, 1 times / day Sources: Page: 5 |
unhealthy, adult n = 522 Health Status: unhealthy Condition: Parkinson's disease Age Group: adult Sex: unknown Population Size: 522 Sources: Page: 5 |
Disc. AE: Hallucination... AEs leading to discontinuation/dose reduction: Hallucination (1%) Sources: Page: 5 |
35 mg 1 times / day steady, sublingual (max) Recommended Dose: 35 mg, 1 times / day Route: sublingual Route: steady Dose: 35 mg, 1 times / day Sources: |
unhealthy, mean 62.9 years n = 54 Health Status: unhealthy Condition: Parkinson's disease Age Group: mean 62.9 years Sex: M+F Population Size: 54 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: Page: Table 2 |
unhealthy, 30 - 90 years n = 32 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 32 Sources: Page: Table 2 |
Dysgeusia | 1 patient | 1.5 mg single, respiratory Recommended Dose: 1.5 mg Route: respiratory Route: single Dose: 1.5 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 32 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 32 Sources: Page: Table 2 |
Orthostatic hypotension | 1 patient | 1.5 mg single, respiratory Recommended Dose: 1.5 mg Route: respiratory Route: single Dose: 1.5 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 32 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 32 Sources: Page: Table 2 |
Somnolence | 1 patient | 1.5 mg single, respiratory Recommended Dose: 1.5 mg Route: respiratory Route: single Dose: 1.5 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 32 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 32 Sources: Page: Table 2 |
Flushing | 1 patient | 3 mg single, respiratory Recommended Dose: 3 mg Route: respiratory Route: single Dose: 3 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 12 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 12 Sources: Page: Table 2 |
Somnolence | 1 patient | 3 mg single, respiratory Recommended Dose: 3 mg Route: respiratory Route: single Dose: 3 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 12 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 12 Sources: Page: Table 2 |
Yawning | 1 patient | 3 mg single, respiratory Recommended Dose: 3 mg Route: respiratory Route: single Dose: 3 mg Sources: Page: Table 2 |
unhealthy, 30 - 90 years n = 12 Health Status: unhealthy Condition: Parkinson's disease Age Group: 30 - 90 years Sex: unknown Population Size: 12 Sources: Page: Table 2 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
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: Page: Fig. 1 |
unhealthy, 44 - 87 years n = 114 Health Status: unhealthy Condition: Parkinson's disease Age Group: 44 - 87 years Sex: M+F Population Size: 114 Sources: Page: Fig. 1 |
Nausea and vomiting | 187 patients Disc. AE |
4 mg 1 times / day multiple, subcutaneous (mean) Highest studied dose Dose: 4 mg, 1 times / day Route: subcutaneous Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, 65.21 years n = 546 Health Status: unhealthy Condition: Parkinson's disease Age Group: 65.21 years Sex: M+F Population Size: 546 Sources: |
Vomiting | 2% Disc. AE |
10 mg 1 times / day steady, subcutaneous (max) Recommended Dose: 10 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10 mg, 1 times / day Co-administed with:: trimethobenzamide Sources: Page: 4 |
unhealthy, adult n = 522 Health Status: unhealthy Condition: Parkinson's disease Age Group: adult Sex: unknown Population Size: 522 Sources: Page: 4 |
Nausea | 3% Disc. AE |
10 mg 1 times / day steady, subcutaneous (max) Recommended Dose: 10 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10 mg, 1 times / day Co-administed with:: trimethobenzamide Sources: Page: 4 |
unhealthy, adult n = 522 Health Status: unhealthy Condition: Parkinson's disease Age Group: adult Sex: unknown Population Size: 522 Sources: Page: 4 |
Hallucination | 1% Disc. AE |
10 mg 1 times / day steady, subcutaneous (max) Recommended Dose: 10 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10 mg, 1 times / day Sources: Page: 5 |
unhealthy, adult n = 522 Health Status: unhealthy Condition: Parkinson's disease Age Group: adult Sex: unknown Population Size: 522 Sources: Page: 5 |
Respiratory tract signs and symptoms | 9 patients Disc. AE |
35 mg 1 times / day steady, sublingual (max) Recommended Dose: 35 mg, 1 times / day Route: sublingual Route: steady Dose: 35 mg, 1 times / day Sources: |
unhealthy, mean 62.9 years n = 54 Health Status: unhealthy Condition: Parkinson's disease Age Group: mean 62.9 years Sex: M+F Population Size: 54 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 |
---|---|---|
Inhibition by ginsenosides Rb1 and Rg1 of cocaine-induced hyperactivity, conditioned place preference, and postsynaptic dopamine receptor supersensitivity in mice. | 1999 Jul |
|
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 |
|
Test conditions influence the response to a drug challenge in rodents. | 2000 Mar |
|
Apomorphine: an update of clinical trial results. | 2000 Oct |
|
Dopamine agonists. | 2001 |
|
Intrapallidal dopamine restores motor deficits induced by 6-hydroxydopamine in the rat. | 2001 |
|
No functional effects of embryonic neuronal grafts on motor deficits in a 3-nitropropionic acid rat model of advanced striatonigral degeneration (multiple system atrophy). | 2001 |
|
Effects of systemic injections of dopaminergic agents on the habituation of rats submitted to an open field test. | 2001 |
|
Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage. | 2001 Apr 13 |
|
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism. | 2001 Apr 27 |
|
Generation and pharmacological analysis of M2 and M4 muscarinic receptor knockout mice. | 2001 Apr 27 |
|
Orphanin FQ/nociceptin attenuates motor stimulation and changes in nucleus accumbens extracellular dopamine induced by cocaine in rats. | 2001 Feb |
|
[Motor impairment, in patients with severe Parkinson's disease, associated with dopaminergic hyperstimulation (entacapone)]. | 2001 Feb |
|
Stimulatory role of dopamine on fibroblast growth factor-2 expression in rat striatum. | 2001 Feb |
|
Increased growth hormone response to apomorphine in Parkinson disease compared with multiple system atrophy. | 2001 Feb |
|
Intravenous apomorphine therapy in Parkinson's disease: clinical and pharmacokinetic observations. | 2001 Feb |
|
The role of neurochemical mechanisms of ventromedial hypothalamus in various models of anxiety in rats. | 2001 Jan |
|
Neurotoxic regimen of methamphetamine produces evidence of behavioral sensitization in the rat. | 2001 Jan |
|
Dopamine attenuates prefrontal cortical suppression of sensory inputs to the basolateral amygdala of rats. | 2001 Jun 1 |
|
Reproductive experience modulates dopamine-related behavioral responses. | 2001 Mar |
|
Increased sensitivity of dopamine systems following reproductive experience in rats. | 2001 Mar |
|
Psychopathological correlates of reduced dopamine receptor sensitivity in depression, schizophrenia, and opiate and alcohol dependence. | 2001 Mar |
|
Consensus statement on the role of acute dopaminergic challenge in Parkinson's disease. | 2001 Mar |
|
Apomorphine-induced aggressive behaviour in para-chlorophenylalanine-treated male rats: implications to brain. | 2001 Mar |
|
Cannabinoid CB(1) receptor agonists produce cerebellar dysfunction in mice. | 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
Fri Dec 16 16:17:09 UTC 2022
by
admin
on
Fri Dec 16 16:17:09 UTC 2022
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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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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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SUB127079
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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 |
Related Record | Type | Details | ||
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ACTIVE MOIETY |