Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H27NO.ClH |
Molecular Weight | 345.906 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=FJQXCDYVZAHXNS-UHFFFAOYSA-N
InChI=1S/C21H27NO.ClH/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19;/h6-15,17H,5,16H2,1-4H3;1H
Molecular Formula | C21H27NO |
Molecular Weight | 309.4452 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf | https://www.drugs.com/pro/diskets.html
Curator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf | https://www.drugs.com/pro/diskets.html
Methadone, sold under the brand names Dolophine among others, is an synthetic opioid that is used as the hydrochloride to treat pain and as maintenance therapy or to help with detoxification in people with opioid dependence. Methadone hydrochloride is a mu-agonist; a synthetic opioid analgesic with multiple actions qualitatively similar to those of morphine. Some data also indicate that methadone acts as an antagonist at the NMDA-receptor. The contribution of NMDA receptor antagonism to methadone’s efficacy is unknown. Most common adverse reactions are: lightheadedness, dizziness, sedation, nausea, vomiting, and sweating. Avoid use mixed agonist/antagonist and partial agonist opioid analgesics with DOLOPHINE because they may reduce analgesic effect of DOLOPHINE or precipitate withdrawal symptoms.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 |
3.51 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | DOLOPHINE HYDROCHLORIDE Approved UseFor the treatment of moderate to severe pain not responsive to non-narcotic analgesics. For detoxification treatment of opioid addiction (heroin or other morphine-like drugs). For maintenance treatment of opioid addiction (heroin or other morphine-like drugs), in conjunction with appropriate social and medical services. Note – Outpatient maintenance and outpatient detoxification treatment may be provided only by Opioid Treatment Programs (OTPs) certified by the Federal Substance Abuse and Mental Health Services Administration (SAMHSA) and registered by the Drug Enforcement Administration (DEA). This does not preclude the maintenance treatment of a patient with concurrent opioid addiction who is hospitalized for conditions other than opioid addiction and who requires temporary maintenance during the critical period of his/her stay, or of a patient whose enrollment has been verified in a program which has been certified for maintenance treatment with methadone. Launch Date-7.0649283E11 |
|||
Palliative | DOLOPHINE HYDROCHLORIDE Approved UseFor the treatment of moderate to severe pain not responsive to non-narcotic analgesics. For detoxification treatment of opioid addiction (heroin or other morphine-like drugs). For maintenance treatment of opioid addiction (heroin or other morphine-like drugs), in conjunction with appropriate social and medical services. Note – Outpatient maintenance and outpatient detoxification treatment may be provided only by Opioid Treatment Programs (OTPs) certified by the Federal Substance Abuse and Mental Health Services Administration (SAMHSA) and registered by the Drug Enforcement Administration (DEA). This does not preclude the maintenance treatment of a patient with concurrent opioid addiction who is hospitalized for conditions other than opioid addiction and who requires temporary maintenance during the critical period of his/her stay, or of a patient whose enrollment has been verified in a program which has been certified for maintenance treatment with methadone. Launch Date-7.0649283E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
548 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8641323/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
METHADONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
494 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15151520/ |
70 mg 1 times / day steady-state, oral dose: 70 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
METHADONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
40.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22621465/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHADONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
54 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8641323/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.54 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8641323/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
METHADONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
8.27 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15151520/ |
70 mg 1 times / day steady-state, oral dose: 70 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
METHADONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1073 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22621465/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHADONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.61 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8641323/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8641323/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
METHADONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15151520/ |
70 mg 1 times / day steady-state, oral dose: 70 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
METHADONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
39.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22621465/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHADONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg 3 times / day multiple, intravenous (starting) Recommended Dose: 10 mg, 3 times / day Route: intravenous Route: multiple Dose: 10 mg, 3 times / day Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal Sources: |
10 mg 3 times / day multiple, intravenous (starting) Recommended Dose: 10 mg, 3 times / day Route: intravenous Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression, Addiction... Other AEs: Respiratory depression (grade 5) Sources: Addiction QT interval prolonged (grade 5) |
20 mg single, oral (starting) Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression, QT interval prolonged... Other AEs: Respiratory depression (grade 5) Sources: QT interval prolonged Arrhythmia (serious) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Withdrawal syndrome neonatal | 10 mg 3 times / day multiple, intravenous (starting) Recommended Dose: 10 mg, 3 times / day Route: intravenous Route: multiple Dose: 10 mg, 3 times / day Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
|
Addiction | 10 mg 3 times / day multiple, intravenous (starting) Recommended Dose: 10 mg, 3 times / day Route: intravenous Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
QT interval prolonged | grade 5 | 10 mg 3 times / day multiple, intravenous (starting) Recommended Dose: 10 mg, 3 times / day Route: intravenous Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Respiratory depression | grade 5 | 10 mg 3 times / day multiple, intravenous (starting) Recommended Dose: 10 mg, 3 times / day Route: intravenous Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
QT interval prolonged | 20 mg single, oral (starting) Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Respiratory depression | grade 5 | 20 mg single, oral (starting) Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Arrhythmia | serious | 20 mg single, oral (starting) Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/20484152/ Page: 8.0 |
major [Inhibition 0.6 uM] | |||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20484152/ Page: 8.0 |
unlikely | |||
yes [Ki 100 uM] | ||||
yes [Ki 2.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | yes (co-administration study) Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively Page: 29.0 |
|||
yes | yes (co-administration study) Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively Page: 29.0 |
|||
yes | yes (co-administration study) Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively Page: 29.0 |
|||
yes | yes (co-administration study) Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively Page: 29.0 |
|||
yes | yes (co-administration study) Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively Page: 29.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Methadone withdrawal syndrome induced by nevirapine]. | 2000 Mar 18 |
|
[Postpartum risk factors in the development of children born to opiate-addicted mothers; comparison between mothers with and without methadone substitution]. | 2000 Sep |
|
Intravenous clonidine use in a neonate experiencing opioid-induced myoclonus. | 2001 Aug |
|
Family history influence on drug abuse severity and treatment outcome. | 2001 Feb 1 |
|
Bile duct dilation with chronic methadone use in asymptomatic patients: ERCP findings in 6 patients. | 2003 Jul |
|
The impact of methadone induction on cardiac conduction in opiate users. | 2003 Jul 15 |
|
Dose-related effects of methadone on QT prolongation in a series of patients with torsade de pointes. | 2003 Jun |
|
Methadone treatment induces attenuation of cerebrovascular deficits associated with the prolonged abuse of cocaine and heroin. | 2003 Mar |
|
Safety of injectable opioid maintenance treatment for heroin dependence. | 2003 Oct 15 |
|
Methadone metabolism by human placenta. | 2004 Aug 1 |
|
Obsessive-compulsive symptoms precipitated by methadone tapering. | 2004 Dec |
|
The effect of quinidine, used as a probe for the involvement of P-glycoprotein, on the intestinal absorption and pharmacodynamics of methadone. | 2004 May |
|
Agonist-like or antagonist-like treatment for cocaine dependence with methadone for heroin dependence: two double-blind randomized clinical trials. | 2004 May |
|
[Preclinical management of accidental methadone intoxication of a 4-year-old girl. Antagonist or intubation?]. | 2004 Oct |
|
QT prolongation and syncope with methadone, doxepin, and a beta-blocker. | 2005 Oct |
|
Methadone treatment of chronic non-malignant pain and opioid dependence--a long-term follow-up. | 2006 Apr |
|
Variables associated with perceived sleep disorders in methadone maintenance treatment (MMT) patients. | 2006 Apr 28 |
Sample Use Guides
Chronic pain: oral initial dose - 2.5 mg every 8 to 12 hours; Intravenous initial dose: 2.5 mg to 10 mg every 8 to 12 hours
Opiate withdrawal: Initial dose - 20 to 30 mg orally; an additional 5 to 10 mg may be given orally after 2 to 4 hours if withdrawal symptoms have not been suppressed or if symptoms reappear.
-Maximum initial dose: 30 mg
-Maximum day 1 dose: 40 mg
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11561100
In the presence of 1 uM methadone, the maximum 86Rb+ efflux stimulated by nicotine (Emax) was markedly reduced, but the EC50 for nicotine was altered only slightly, if at all.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:32:18 UTC 2022
by
admin
on
Fri Dec 16 16:32:18 UTC 2022
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Record UNII |
229809935B
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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 |
C1506
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DEA NO. |
9250
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NCI_THESAURUS |
C67413
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Code System | Code | Type | Description | ||
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CHEMBL651
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PRIMARY | |||
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14184
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PRIMARY | |||
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218337
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70181-39-4
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SUPERSEDED | |||
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DBSALT000346
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PRIMARY | |||
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70172-45-1
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DTXSID2020501
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1095-90-5
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214-140-7
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229809935B
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19600
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229809935B
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SUB03203MIG
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50140
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1398009
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125-56-4
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M7286
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PRIMARY | Merck Index | ||
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C638
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
Cytochrome P450 enzymes, primarily CYP3A4, CYP2B6, and CYP2C19 and to a lesser extent CYP2C9 and CYP2D6, are responsible for conversion of methadone to EDDP and other inactive metabolites, which are excreted mainly in the urine.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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ACTIVE MOIETY |