Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H25NO2.C7H6O2 |
Molecular Weight | 385.4965 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC=CC=C1.CN(C)CC(C2=CC=C(O)C=C2)C3(O)CCCCC3
InChI
InChIKey=DGJCDBBBNQGOIR-UHFFFAOYSA-N
InChI=1S/C16H25NO2.C7H6O2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16;8-7(9)6-4-2-1-3-5-6/h6-9,15,18-19H,3-5,10-12H2,1-2H3;1-5H,(H,8,9)
Molecular Formula | C7H6O2 |
Molecular Weight | 122.1213 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C16H25NO2 |
Molecular Weight | 263.3752 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16675639 | http://adisinsight.springer.com/drugs/800000550
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16675639 | http://adisinsight.springer.com/drugs/800000550
Desvenlafaxine is a dual serotonin and norepinephrine reuptake inhibitor in vitro and in vivo that demonstrates good brain-to-plasma ratios.
Desvenlafaxine has demonstrated antidepressant effects in preclinical studies. Pfizer is developing an oral, extended-release formulation of desvenlafaxine for the treatment of major depressive disorder. Desvenlafaxine has been registered and is available on the market for the treatment of major depressive disorder in adults.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16675639 |
40.2 nM [Ki] | ||
Target ID: CHEMBL222 |
558.4 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PRISTIQ Approved UsePRISTIQ (DESVENLAFAXINE SUCCINATE), a selective serotonin and norepinephrine reuptake inhibitor, is indicated for the treatment of major depressive disorder. Launch Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
39.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19142106/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESVENLAFAXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
591 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19142106/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESVENLAFAXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19142106/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESVENLAFAXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19142106/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESVENLAFAXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
750 mg single, oral MTD Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: Page: 28 |
healthy, 23.95 n = 11 Health Status: healthy Age Group: 23.95 Sex: M Population Size: 11 Sources: Page: 28 |
Other AEs: Vomiting... Other AEs: Vomiting (27%) Sources: Page: 28 |
900 mg single, oral Highest studied dose Dose: 900 mg Route: oral Route: single Dose: 900 mg Sources: Page: 28 |
healthy, 27.5 ± 9.0 n = 6 Health Status: healthy Age Group: 27.5 ± 9.0 Sex: M Population Size: 6 Sources: Page: 28 |
DLT: Vomiting... Other AEs: Nausea... Dose limiting toxicities: Vomiting (67%) Other AEs:Nausea (severe, 33%) Sources: Page: 28 |
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 28 |
healthy, 32.9 ± 4.7 n = 9 Health Status: healthy Age Group: 32.9 ± 4.7 Sex: M Population Size: 9 Sources: Page: 28 |
DLT: Orthostatic hypotension... Dose limiting toxicities: Orthostatic hypotension (67%) Sources: Page: 28 |
3500 mg single, oral Overdose Dose: 3500 mg Route: oral Route: single Dose: 3500 mg Sources: Page: p.6 |
healthy, 33 n = 1 Health Status: healthy Age Group: 33 Sex: F Population Size: 1 Sources: Page: p.6 |
Disc. AE: Serotonin syndrome... AEs leading to discontinuation/dose reduction: Serotonin syndrome Sources: Page: p.6 |
450 mg 1 times / day multiple, oral MTD Dose: 450 mg, 1 times / day Route: oral Route: multiple Dose: 450 mg, 1 times / day Sources: Page: 28 |
healthy, 34.9 ± 7.4 n = 9 Health Status: healthy Age Group: 34.9 ± 7.4 Sex: M Population Size: 9 Sources: Page: 28 |
Other AEs: Nausea... |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Disc. AE: Suicidal ideation, Serotonin syndrome... AEs leading to discontinuation/dose reduction: Suicidal ideation Sources: Page: p.1Serotonin syndrome Neuroleptic malignant syndrome Blood pressure increased Bleeding Glaucoma Mania Hypomania Cardiovascular disease, unspecified Unspecified cerebrovascular disease Elevated cholesterol Elevated triglycerides Seizure Hyponatremia |
100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Other AEs: Lightheadedness, Sickness/nausea... Other AEs: Lightheadedness (below serious, 11 patient) Sources: Sickness/nausea (below serious, 11 patient) Drowsiness (below serious, 7 patients) Insomnia (below serious, 5 patients) Decreased appetite (below serious, 6 patients) Indigestion (below serious, 4 patients) Soft stools (below serious, 5 patients) Dry mouth (below serious, 3 patients) |
100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Other AEs: Sleep decreased, Daytime sleepiness... Other AEs: Sleep decreased (below serious, 10 patients) Sources: Daytime sleepiness (below serious, 9 patients) Headache (below serious, 9 patients) Nausea (below serious, 9 patients) Dry mouth (below serious, 7 patients) Agitation (below serious, 5 patients) Dizziness (below serious, 5 patients) Sweating (below serious, 5 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Vomiting | 27% | 750 mg single, oral MTD Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: Page: 28 |
healthy, 23.95 n = 11 Health Status: healthy Age Group: 23.95 Sex: M Population Size: 11 Sources: Page: 28 |
Vomiting | 67% DLT |
900 mg single, oral Highest studied dose Dose: 900 mg Route: oral Route: single Dose: 900 mg Sources: Page: 28 |
healthy, 27.5 ± 9.0 n = 6 Health Status: healthy Age Group: 27.5 ± 9.0 Sex: M Population Size: 6 Sources: Page: 28 |
Nausea | severe, 33% | 900 mg single, oral Highest studied dose Dose: 900 mg Route: oral Route: single Dose: 900 mg Sources: Page: 28 |
healthy, 27.5 ± 9.0 n = 6 Health Status: healthy Age Group: 27.5 ± 9.0 Sex: M Population Size: 6 Sources: Page: 28 |
Orthostatic hypotension | 67% DLT |
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 28 |
healthy, 32.9 ± 4.7 n = 9 Health Status: healthy Age Group: 32.9 ± 4.7 Sex: M Population Size: 9 Sources: Page: 28 |
Serotonin syndrome | Disc. AE | 3500 mg single, oral Overdose Dose: 3500 mg Route: oral Route: single Dose: 3500 mg Sources: Page: p.6 |
healthy, 33 n = 1 Health Status: healthy Age Group: 33 Sex: F Population Size: 1 Sources: Page: p.6 |
Nausea | 67% | 450 mg 1 times / day multiple, oral MTD Dose: 450 mg, 1 times / day Route: oral Route: multiple Dose: 450 mg, 1 times / day Sources: Page: 28 |
healthy, 34.9 ± 7.4 n = 9 Health Status: healthy Age Group: 34.9 ± 7.4 Sex: M Population Size: 9 Sources: Page: 28 |
Bleeding | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Blood pressure increased | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Cardiovascular disease, unspecified | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Elevated cholesterol | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Elevated triglycerides | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Glaucoma | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Hypomania | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Hyponatremia | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Mania | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Neuroleptic malignant syndrome | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Seizure | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Serotonin syndrome | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Suicidal ideation | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Unspecified cerebrovascular disease | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Major depressive disorder Sources: Page: p.1 |
Lightheadedness | below serious, 11 patient | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Sickness/nausea | below serious, 11 patient | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Dry mouth | below serious, 3 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Indigestion | below serious, 4 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Insomnia | below serious, 5 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Soft stools | below serious, 5 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Decreased appetite | below serious, 6 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Drowsiness | below serious, 7 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Social Anxiety Disorder Population Size: 30 Sources: |
Sleep decreased | below serious, 10 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Agitation | below serious, 5 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Dizziness | below serious, 5 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Sweating | below serious, 5 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Dry mouth | below serious, 7 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Daytime sleepiness | below serious, 9 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Headache | below serious, 9 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Nausea | below serious, 9 patients | 100 mg 1 times / day steady, oral (max) Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Chronic Depression Population Size: 30 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 57.0 |
no | |||
Page: 57.0 |
no | |||
Page: 57.0 |
no | |||
Page: 57.0 |
no | |||
Page: 57.0 |
no | |||
Page: 62.0 |
no | |||
Page: 57.0 |
no | |||
Page: 29.0 |
no | |||
Page: 4, 41 |
weak | likely (co-administration study) Comment: "coadministration with desipramine showed desipramine increased Cmax 25% and AUC 17% and ""clinical significance of changes in desipramine Cmax is not clear""; desvenlaxafine is not an inhibitor of the CYP P450 isozymes except a possible inhibiton of CYP1A2" Page: 4, 41 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 62.0 |
minor | yes (co-administration study) Comment: ketoconazole increased Cmax by 1.08-fold and AUC by 1.43-fold Page: 62.0 |
||
Page: 29.0 |
no | |||
Page: 8, 33 |
yes | |||
Page: 34.0 |
yes | |||
Page: 34.0 |
yes | |||
Page: 34.0 |
yes | |||
Page: 34.0 |
yes | |||
Page: 34.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[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 |
|
Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. | 2008 Dec |
|
Desvenlafaxine succinate monohydrate. | 2008 May |
|
Desvenlafaxine and venlafaxine exert minimal in vitro inhibition of human cytochrome P450 and P-glycoprotein activities. | 2009 |
|
Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers. | 2009 Feb |
|
Desvenlafaxine, a serotonin-norepinephrine uptake inhibitor for major depressive disorder, neuropathic pain and the vasomotor symptoms associated with menopause. | 2009 Jan |
|
Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. | 2010 |
|
Short-term efficacy and safety of desvenlafaxine in a randomized, placebo-controlled study of perimenopausal and postmenopausal women with major depressive disorder. | 2010 Aug |
|
Assessment of infant dose through milk in a lactating woman taking amisulpride and desvenlafaxine for treatment-resistant depression. | 2010 Dec |
|
Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. | 2010 Jan |
|
Desvenlafaxine in the treatment of major depressive disorder. | 2011 Dec |
|
Influence of CYP2D6 genotype on the disposition of the enantiomers of venlafaxine and its major metabolites in postmortem femoral blood. | 2012 Jan 10 |
|
Syndrome of inappropriate antidiuretic hormone secretion associated with desvenlafaxine. | 2014 Apr |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:55:18 GMT 2023
by
admin
on
Sat Dec 16 08:55:18 GMT 2023
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Record UNII |
ZG9HEJ3BBR
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Record Status |
Validated (UNII)
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Record Version |
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300000027151
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1147940-37-1
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25265778
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ACTIVE MOIETY |