Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H18ClNO |
Molecular Weight | 239.741 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1
InChI
InChIKey=SNPPWIUOZRMYNY-UHFFFAOYSA-N
InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3
Molecular Formula | C13H18ClNO |
Molecular Weight | 239.741 |
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.drugbank.ca/drugs/DB01156 | http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm103318.htm
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB01156 | http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm103318.htm
Bupropion, an antidepressant of the aminoketone class and a non-nicotine aid to smoking cessation, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine, serotonin, and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behavior tasks, and, at high doses, induction of mild stereotyped behavior. Bupropion is marketed as Wellbutrin, Zyban, and generics. Bupropion is indicated for the treatment of major depressive disorder (MDD). WELLBUTRIN, WELLBUTRIN SR, and
WELLBUTRIN XL are not approved for smoking cessation treatment, but bupropion under the name ZYBAN is approved for this use.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
550.0 nM [IC50] | |||
443.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | WELLBUTRIN Approved UseINDICATIONS & USAGE Major Depressive Disorder:Bupropion hydrochloride extended-release tablets (XL) are indicated for the treatment of major depressive disorder. The efficacy of bupropion in the treatment of a major depressive episode was established in two 4-week controlled trials of inpatients and in one 6-week controlled trial of outpatients whose diagnoses corresponded most closely to the Major Depression category of the APA Diagnostic and Statistical Manual (DSM) (seeCLINICAL TRIALS). A major depressive episode (DSM-IV) implies the presence of 1) depressed mood or 2) loss of interest or pleasure; in addition, at least 5 of the following symptoms have been present during the same 2-week period and represent a change from previous functioning: depressed mood, markedly diminished interest or pleasure in usual activities, significant change in weight and/or appetite, insomnia or hypersomnia, psychomotor agitation or retardation, increased fatigue, feelings of guilt or worthlessness, slowed thinking or impaired concentration, a suicide attempt, or suicidal ideation. The efficacy of bupropion in maintaining an antidepressant response for up to 44 weeks following 8 weeks of acute treatment was demonstrated in a placebo-controlled trial with the sustained-release formulation of bupropion (seeCLINICAL TRIALS). Nevertheless, the physician who elects to use bupropion hydrochloride extended-release tablets (XL) for extended periods should periodically reevaluate the long-term usefulness of the drug for the individual patient. Seasonal Affective Disorder:Bupropion hydrochloride extended-release tablets (XL) are indicated for the prevention of seasonal major depressive episodes in patients with a diagnosis of seasonal affective disorder. The efficacy of bupropion hydrochloride extended-release tablets (XL) for the prevention of seasonal major depressive episodes was established in 3 controlled trials of adult outpatients with a history of major depressive disorder with an autumn-winter seasonal pattern as defined by Diagnostic and Statistical Manual of Mental Disorders, 4th edition (DSM-IV) criteria (seeCLINICAL TRIALS). Seasonal affective disorder is characterized by recurrent major depressive episodes, most commonly occurring during the autumn and/or winter months. Episodes may last up to 6 months in duration, typically beginning in the autumn and remitting in the springtime. Although patients with seasonal affective disorder may have depressive episodes during other times of the year, the diagnosis of seasonal affective disorder requires that the number of seasonal episodes substantially outnumber the number of non-seasonal episodes during the individual's lifetime. Launch Date5.04748802E11 |
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Primary | ZYBAN Approved UseZyban is indicated as an aid to smoking cessation treatment. Launch Date5.04748802E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
134 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
93 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
136 ng/mL |
150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
91 ng/mL |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
688 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
469 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28685396 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
21 h |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16% |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUPROPION HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy, adult n = 214 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 214 Sources: |
Other AEs: Seizures... Other AEs: Seizures (2.8%) Sources: |
600 mg 1 times / day multiple, oral (max) Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 2400 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 2400 Sources: |
Disc. AE: Neuropsychiatric symptoms, Gastrointestinal disturbance... Other AEs: Neuropsychiatric symptoms... AEs leading to discontinuation/dose reduction: Neuropsychiatric symptoms (3%) Other AEs:Gastrointestinal disturbance (2.1%) Neurological disorder NOS (1.7%) Skin and subcutaneous tissue disorders (1.4%) Neuropsychiatric symptoms Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Seizures | 2.8% | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy, adult n = 214 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 214 Sources: |
Neuropsychiatric symptoms | 600 mg 1 times / day multiple, oral (max) Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 2400 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 2400 Sources: |
|
Skin and subcutaneous tissue disorders | 1.4% Disc. AE |
600 mg 1 times / day multiple, oral (max) Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 2400 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 2400 Sources: |
Neurological disorder NOS | 1.7% Disc. AE |
600 mg 1 times / day multiple, oral (max) Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 2400 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 2400 Sources: |
Gastrointestinal disturbance | 2.1% Disc. AE |
600 mg 1 times / day multiple, oral (max) Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 2400 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 2400 Sources: |
Neuropsychiatric symptoms | 3% Disc. AE |
600 mg 1 times / day multiple, oral (max) Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 2400 Health Status: unhealthy Condition: depression Age Group: adult Sex: unknown Population Size: 2400 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021515_Wellbutrin_biopharmr.PDF Page: 30.0 |
inconclusive | |||
Page: 15.0 |
yes [IC50 9.3 uM] | |||
Page: 90.0 |
yes | yes (co-administration study) Comment: from FDA label https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021515s040lbl.pdf: coadministration with desipramine increased the Cmax of desipramine by 2-fold, and AUC by 5-fold Page: 90.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021515_Wellbutrin_biopharmr.PDF Page: 30.0 |
inconclusive | |||
Page: 4, 43 |
likely | |||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
Page: 10.0 |
yes | yes (co-administration study) Comment: from FDA label https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021515s040lbl.pdf: coadministration with ticlopidine increased buproprion Cmax 38% and AUC by 85% Page: 10.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 46.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Algorithm for the treatment of chronic depression. | 2001 |
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Health-related quality-of-life measure enhances acute treatment response prediction in depressed inpatients. | 2001 Apr |
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Bupropion sustained release for bereavement: results of an open trial. | 2001 Apr |
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Modification of norepinephrine and serotonin, but not dopamine, neuron firing by sustained bupropion treatment. | 2001 Apr |
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Bupropion overdose: a potential problem with the new 'miracle' anti-smoking drug. | 2001 Apr |
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[Pharmacologic therapy for smoking cessation]. | 2001 Apr |
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Bupropion overdose in an adolescent. | 2001 Apr |
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[Bupropion: a new hope for smokers willing to quit]. | 2001 Apr |
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Does pretreatment anxiety predict response to either bupropion SR or sertraline? | 2001 Apr |
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Effects of sustained-release bupropion and supportive group therapy on cigarette consumption in patients with schizophrenia. | 2001 Apr |
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Effects of bupropion SR on anterior paralimbic function during waking and REM sleep in depression: preliminary findings using. | 2001 Apr 10 |
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Bupropion hydrochloride: the development of a chiral separation using an ovomucoid column. | 2001 Apr 13 |
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[Zyban in smoking cessation]. | 2001 Feb 10 |
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[Zyban and medical ethics]. | 2001 Feb 28 |
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[Zyban in smoking cessation--where is medical ethics?]. | 2001 Feb 28 |
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Treating nicotine dependence. | 2001 Jan-Feb |
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Response in relation to baseline anxiety levels in major depressive disorder treated with bupropion sustained release or sertraline. | 2001 Jul |
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Effects of cocaine prior to and during bupropion maintenance in cocaine-abusing volunteers. | 2001 Jul 1 |
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The Stanley Foundation Bipolar Network. I. Rationale and methods. | 2001 Jun |
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Depression and anxiety disorders. | 2001 Jun |
|
Bupropion-induced erythema multiforme. | 2001 Jun |
|
Variations in treatment benefits influence smoking cessation: results of a randomised controlled trial. | 2001 Jun |
|
Bupropion sustained-release for the treatment of dysthymic disorder: an open-label study. | 2001 Jun |
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Erythema multiforme associated with bupropion use. | 2001 Jun 25 |
|
A practical guide to tobacco cessation in dental offices. | 2001 Mar |
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Tobacco-use cessation programs and policies at the University of Manitoba's faculty of dentistry. | 2001 Mar |
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Substitution of an SSRI with bupropion sustained release following SSRI-induced sexual dysfunction. | 2001 Mar |
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Bupropion sustained release in adolescents with comorbid attention-deficit/hyperactivity disorder and depression. | 2001 Mar |
|
Smoking cessation in the hospitalized patient using the transtheoretical model of behavior change. | 2001 Mar-Apr |
|
Type II error and antidepressants. | 2001 May |
|
Late-term smoking cessation despite initial failure: an evaluation of bupropion sustained release, nicotine patch, combination therapy, and placebo. | 2001 May |
|
Ondansetron rather than metoclopramide for bupropion-induced nausea. | 2001 May |
|
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man. | 2001 May |
|
Smoking cessation. The key to treating older smokers? Don't quit helping. | 2001 May |
|
The use of bupropion in the treatment of restlessness after a traumatic brain injury. | 2001 May |
|
Use of bupropion SR in a pharmacist-managed outpatient smoking-cessation program. | 2001 May |
|
Bupropion for smoking cessation : predictors of successful outcome. | 2001 May |
|
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines. | 2001 May |
|
Sustained-release bupropion for selective serotonin reuptake inhibitor-induced sexual dysfunction: a randomized, double-blind, placebo-controlled, parallel-group study. | 2001 May |
|
Identification and treatment of depression in a cohort of patients maintained on chronic peritoneal dialysis. | 2001 May |
|
Seizures after buproprion overdose. | 2001 May 19 |
|
Smoking cessation in patients with chronic obstructive pulmonary disease: a double-blind, placebo-controlled, randomised trial. | 2001 May 19 |
|
Place of bupropion in smoking-cessation therapy. | 2001 May 19 |
|
[Nicotine-free pill. Easy smoking cessation]. | 2001 May 3 |
|
Newly available treatments for nicotine addiction. Smokers wanting help with stopping now have effective treatment options. | 2001 May 5 |
|
Bupropion and serum sickness-like reaction. | 2001 May 7 |
|
Bupropion sustained release (SR) for the treatment of hypoactive sexual desire disorder (HSDD) in nondepressed women. | 2001 May-Jun |
|
Pharmacologic treatments for the nicotine dependent smoker. | 2001 May-Jun |
|
Pharmacological aids for smoking cessation. | 2001 Spring |
|
Pharmacokinetic interactions between cyclosporine and bupropion or methylphenidate. | 2001 Summer |
Sample Use Guides
The usual adult dose is 300 mg/day, given 3 times daily. Dosing
should begin at 200 mg/day, given as 100 mg twice daily. Based on clinical response, this dose may
be increased to 300 mg/day, given as 100 mg 3 times daily, no sooner than 3 days after beginning therapy.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17477919
Bupropion (10 uM) significantly decreased nicotine-evoked [(3)H]dopamine release by approximately 50% in rat striatal synaptosomes and slices.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sun Dec 18 19:16:03 UTC 2022
by
admin
on
Sun Dec 18 19:16:03 UTC 2022
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Record UNII |
01ZG3TPX31
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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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WHO-ATC |
N06AX12
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LIVERTOX |
NBK559444
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NDF-RT |
N0000009282
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NDF-RT |
N0000000114
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WHO-VATC |
QN06AX12
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WHO-ATC |
A08AA62
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NDF-RT |
N0000009456
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NDF-RT |
N0000000102
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NCI_THESAURUS |
C265
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NDF-RT |
N0000180855
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3219
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3562
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M2773
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DB01156
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C62012
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BUPROPION
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Bupropion
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42347
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DTXSID7022706
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34841-39-9
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758686
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01ZG3TPX31
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D016642
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34911-55-2
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CHEMBL894
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7135
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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EXCRETED UNCHANGED |
FECAL; URINE
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> INHIBITOR |
Strong Inhibitors(2)
5-fold increase in AUC
or > 80% decrease in CL
MAJOR
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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FASTED STATE |
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Tmax | PHARMACOKINETIC |
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SINGLE DOSE |
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