Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H26F3N3OS |
Molecular Weight | 437.522 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCN1CCN(CCCN2C3=C(SC4=C2C=C(C=C4)C(F)(F)F)C=CC=C3)CC1
InChI
InChIKey=PLDUPXSUYLZYBN-UHFFFAOYSA-N
InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2
Molecular Formula | C22H26F3N3OS |
Molecular Weight | 437.522 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00623Curator's Comment: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00623
Curator's Comment: Description was created based on several sources, including
Fluphenazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Fluphenazine has not been shown effective in the management of behaviorial complications in patients with mental retardation. Fluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800002142
Curator's Comment: Introduced in 1959
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9755905 |
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Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB00623 |
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Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11561066 |
1.412 µM [EC50] | ||
Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2879204 |
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Target ID: CHEMBL2056 Sources: http://www.drugbank.ca/drugs/DB00623 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FLUPHENAZINE DECANOATE Approved UseFluphenazine Decanoate Injection is a longacting parenteral antipsychotic drug intended for use in the management of patients requiring prolonged parenteral neuroleptic therapy (e.g., chronic schizophrenics). Launch Date5.5313282E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
12 mg single, oral dose: 12 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
261 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
2.5 mg 3 times / 3 days multiple, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.52 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2313572 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.92 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2313572 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
12 mg single, oral dose: 12 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
2.5 mg 3 times / 3 days multiple, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2313572 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.6% |
FLUPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Disc. AE: Akathisia, Dyskinesia... AEs leading to discontinuation/dose reduction: Akathisia (3.3%) Sources: Page: p.315Dyskinesia (3.3%) Hypertonia (3.3%) Stupor (3.3%) |
250 mg 1 times / week multiple, intramuscular Highest studied dose Dose: 250 mg, 1 times / week Route: intramuscular Route: multiple Dose: 250 mg, 1 times / week Sources: Page: p.1438 |
unhealthy, 44 n = 25 Health Status: unhealthy Condition: Schizophrenia Age Group: 44 Sex: M+F Population Size: 25 Sources: Page: p.1438 |
|
100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Disc. AE: Tardive dyskinesia, Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Tardive dyskinesia Sources: Neuroleptic malignant syndrome Fall |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Akathisia | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Dyskinesia | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Hypertonia | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Stupor | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Fall | Disc. AE | 100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Neuroleptic malignant syndrome | Disc. AE | 100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Tardive dyskinesia | Disc. AE | 100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate [Ki 40.2 uM] | ||||
Page: 5.0 |
weak [IC50 398.1 uM] | |||
Page: 5.0 |
weak [IC50 441.2 uM] | |||
yes [Ki 9.4 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/23395964/ Page: 7.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Dystonic reactions to phenothiazine derivatives. | 1966 Oct |
|
Treatment of resistant schizophrenics with extreme high dosage fluphenazine hydrochloride. | 1970 Sep-Oct |
|
Maintenance treatment of schizophrenia with long-acting fluphenazine. | 1974 Aug |
|
Phenothiazine-induced decompensation. | 1974 Jan |
|
The effect of 5-hydroxytrytamine synthesis inhibitors on neuroleptic-induced catalepsy in rats. | 1975 |
|
Dystonic reaction to high dose propranolol. | 1977 Oct 29 |
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High vs standard dosage fluphenazine HCL in acute schizophrenia. | 1978 Nov |
|
The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats. | 1978 Sep-Oct |
|
Sleep disturbance associated with fluphenazine HCl: a case report. | 1979 Jul |
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Benztropine prophylaxis of dystonic reactions. | 1979 Mar 28 |
|
Delirium associated with combined fluphenazine-clonidine therapy. | 1979 May |
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Neuroleptic-induced acute dyskinesias in rhesus monkeys. | 1981 |
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Intrauterine effect of phenothiazines. | 1981 Apr 18 |
|
Neuroleptic-induced seizures. An in vitro technique for assessing relative risk. | 1982 Feb |
|
Occurrence of neuroleptic malignant syndrome in a narcoleptic patient. | 1983 Jun |
|
Neuroleptic malignant syndrome. | 1984 Jan 7 |
|
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. | 1984 Sep |
|
[Catatonia due to fluphenazine]. | 1986 Apr 1 |
|
Drug-induced dystonia in young and elderly patients. | 1988 Jul |
|
Manic syndrome associated with zidovudine treatment. | 1988 Jun 17 |
|
Prolonged fever without extrapyramidal symptoms during neuroleptic treatment. | 1989 Jun |
|
Propranolol withdrawal in psychosis. | 1990 Apr |
|
Fluphenazine dose, clinical response, and extrapyramidal symptoms during acute treatment. | 1990 Aug |
|
Affective disorder following use of phenylpropanolamine. | 1990 Mar |
|
Blockade of both D-1 and D-2 dopamine receptors may induce catalepsy in mice. | 1991 |
|
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1. | 1991 Apr 18 |
|
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. | 1994 Mar |
|
Some behavioral effects of CNQX AND NBQX, AMPA receptor antagonists. | 1995 Jul-Aug |
|
Fluphenazine plasma levels, dosage, efficacy, and side effects. | 1995 May |
|
Some central effects of GYKI 52466, a non-competitive AMPA receptor antagonist. | 1995 Nov-Dec |
|
Roxindole, a potential antidepressant. I. Effect on the dopamine system. | 1996 |
|
Tardive dyskinesia induced by risperidone? | 1996 Jun |
|
Case report of withdrawal syndrome after olanzapine discontinuation. | 2000 Aug |
|
Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans. | 2000 Sep |
|
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. | 2003 Mar |
|
Analysis of phenothiazine and its derivatives using LC/electrochemistry/MS and LC/electrochemistry/fluorescence. | 2003 Sep 15 |
|
Limbic and motor circuitry underlying footshock-induced reinstatement of cocaine-seeking behavior. | 2004 Feb 18 |
|
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs. | 2005 May |
|
Amphetamine improves cognitive function in medicated individuals with schizophrenia and in healthy volunteers. | 2005 Sep 1 |
|
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations]. | 2006 Jun |
|
Dopamine antagonist alters serum cortisol and prolactin secretion in lactating Holstein cows. | 2006 Jun |
|
Hybrid approach for the design of highly affine and selective dopamine D(3) receptor ligands using privileged scaffolds of biogenic amine GPCR ligands. | 2007 Dec 1 |
|
Neuroleptic-induced dysphagia: case report and literature review. | 2007 Jan |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs. | 2007 Jul 17 |
|
Chronic treatment with fluphenazine alters parameters of oxidative stress in liver and kidney of rats. | 2009 Jul |
|
An insight into the sialotranscriptome of the brown dog tick, Rhipicephalus sanguineus. | 2010 Jul 22 |
|
[A case of drug-induced syndrome of inappropriate secretion of antidiuretic hormone]. | 2010 Jul-Aug |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Antitubercular pharmacodynamics of phenothiazines. | 2013 Apr |
Patents
Sample Use Guides
For most patients, a dose of 12.5 to 25 mg (0.5 to 1 mL) may be given to initiate therapy.
Route of Administration:
Intramuscular
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8302284
30uM Fluphenazine inhibited the high-threshold Ca2 channel current in rat sympathetic neurons (blocking by 66%).
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:59:29 UTC 2023
by
admin
on
Wed Jul 05 23:59:29 UTC 2023
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Record UNII |
S79426A41Z
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007544
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WHO-ATC |
N05AB02
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WHO-VATC |
QN05AB02
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NDF-RT |
N0000007544
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NCI_THESAURUS |
C29710
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LIVERTOX |
NBK548610
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NDF-RT |
N0000175746
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NDF-RT |
N0000007544
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WHO-ESSENTIAL MEDICINES LIST |
24.1
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Code System | Code | Type | Description | ||
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CHEMBL726
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PRIMARY | |||
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69-23-8
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PRIMARY | |||
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Fluphenazine
Created by
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PRIMARY | |||
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3372
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PRIMARY | |||
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4496
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PRIMARY | RxNorm | ||
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1212
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PRIMARY | |||
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CHEMBL1200951
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PRIMARY | |||
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S79426A41Z
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DTXSID2023068
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DB00623
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204
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M5490
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100000080739
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946
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62323
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S79426A41Z
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PRIMARY | |||
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C47536
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3334
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5123
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SUB07730MIG
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200-702-9
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D005476
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FLUPHENAZINE
Created by
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |