Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H15NO2S |
Molecular Weight | 273.35 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C[S@@+]([O-])C(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=YFGHCGITMMYXAQ-LJQANCHMSA-N
InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)/t19-/m1/s1
Molecular Formula | C15H15NO2S |
Molecular Weight | 273.35 |
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/nda/98/020717A_Provigil_prntlbl.pdf
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/020717A_Provigil_prntlbl.pdf
Modafinil is a stimulant drug marketed as a 'wakefulness promoting agent' and is one of the stimulants used in the treatment of narcolepsy. Narcolepsy is caused by dysfunction of a family of wakefulness-promoting and sleep-suppressing peptides, the orexins, whose neurons are activated by modafinil. The prexin neuron activation is associated with psychoactivation and euphoria. Modafinil is not indicated for complaints of lack of energy or fatigue; but it appears to be very helpful for some patients. Also, it has been used in the treatment of hypersomnia, a disorder in which patients lack the capacity for meaningful sleep and may require ten or more hours per day. Recent studies have have found that modafinil may help recovering cocaine addicts fight their addiction. The exact mechanism of action is unclear, although in vitro studies have shown it to inhibit the reuptake of dopamine by binding to the dopamine reuptake pump, and lead to an increase in extracellular dopamine. Modafinil activates glutamatergic circuits while inhibiting GABA. Modafinil is thought to have less potential for abuse than other stimulants due to the absence of any significant euphoric or pleasurable effects. It is possible that modafinil acts by a synergistic combination of mechanisms including direct inhibition of dopamine reuptake, indirect inhibition of noradrenalin reuptake in the VLPO and orexin activation. Modafinil has partial alpha 1B-adrenergic agonist effects by directly stimulating the receptors. Modafinil is indicated for the improvement of wakefulness in patients with excessive daytime sleepiness (EDS) associated with narcolepsy.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26338061 |
51.79 µM [IC50] | ||
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26338061 |
51.79 µM [IC50] | ||
Target ID: CHEMBL238 Sources: http://www.drugbank.ca/drugs/DB00745 |
13.0 µM [Ki] | ||
Target ID: CHEMBL238 |
4.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PROVIGIL Approved UseProvigil is indicated to improve wakefulness in adult patients with excessive sleepiness associated with narcolepsy, obstructive sleep apnea (OSA), or shift work disorder (SWD). Launch Date9.1437118E11 |
|||
Primary | PROVIGIL Approved UseProvigil is indicated to improve wakefulness in adult patients with excessive sleepiness associated with narcolepsy, obstructive sleep apnea (OSA), or shift work disorder (SWD). Launch Date9.1437118E11 |
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Primary | NUVIGIL Approved UseNUVIGIL is indicated to improve wakefulness in patients with excessive sleepiness associated with obstructive sleep apnea, narcolepsy and shift work disorder. In OSA, NUVIGIL is indicated as an adjunct to standard treatment(s) for the underlying obstruction. If continuous positive airway pressure (CPAP) is the treatment of choice for a patient, a maximal effort to treat with CPAP for an adequate period of time should be made prior to initiating NUVIGIL. If NUVIGIL is used adjunctively with CPAP, the encouragement of and periodic assessment of CPAP compliance is necessary. In all cases, careful attention to the diagnosis and treatment of the underlying sleep disorder(s) is of utmost importance. Prescribers should be aware that some patients may have more than one sleep disorder contributing to their excessive sleepiness. The effectiveness of NUVIGIL in long-term use (greater than 12 weeks) has not been systematically evaluated in placebo-controlled trials. The physician who elects to prescribe NUVIGIL for an extended time in patients should periodically re-evaluate long-term usefulness for the individual patient. Launch Date1.18186561E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
13.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
4.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
105.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
136.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
150.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
189.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
23.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
56.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
142.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
146 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
40.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
43.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
75.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARMODAFINIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: idiopathic hypersomnia Age Group: 21 years Sex: F Population Size: 1 Sources: |
Disc. AE: Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Stevens-Johnson syndrome (1 patient) Sources: |
400 mg single, oral Highest studied dose |
healthy, 21–40 years n = 6 Health Status: healthy Age Group: 21–40 years Sex: M Population Size: 6 Sources: |
|
400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
healthy, 21–40 years n = 4 Health Status: healthy Age Group: 21–40 years Sex: M Population Size: 4 Sources: |
Disc. AE: Adverse event... AEs leading to discontinuation/dose reduction: Adverse event Sources: |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (1%) Sources: |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: Page: p.6 |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: Page: p.6 |
Disc. AE: Rash, Angioneurotic edema... AEs leading to discontinuation/dose reduction: Rash (2%) Sources: Page: p.6Angioneurotic edema (1%) Hyperhidrosis (1%) Rash papular (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Stevens-Johnson syndrome | 1 patient Disc. AE |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: idiopathic hypersomnia Age Group: 21 years Sex: F Population Size: 1 Sources: |
Adverse event | Disc. AE | 400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
healthy, 21–40 years n = 4 Health Status: healthy Age Group: 21–40 years Sex: M Population Size: 4 Sources: |
Headache | 1% Disc. AE |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: |
Angioneurotic edema | 1% Disc. AE |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: Page: p.6 |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: Page: p.6 |
Hyperhidrosis | 1% Disc. AE |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: Page: p.6 |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: Page: p.6 |
Rash papular | 1% Disc. AE |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: Page: p.6 |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: Page: p.6 |
Rash | 2% Disc. AE |
150 mg 1 times / day steady, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: Page: p.6 |
unhealthy n = 645 Health Status: unhealthy Population Size: 645 Sources: Page: p.6 |
PubMed
Title | Date | PubMed |
---|---|---|
Benefits and risks of pharmacotherapy for narcolepsy. | 2002 |
|
Sexual dimorphism of the catechol-O-methyltransferase gene in narcolepsy is associated with response to modafinil. | 2002 |
|
Steady-state pharmacokinetics and tolerability of modafinil administered alone or in combination with dextroamphetamine in healthy volunteers. | 2002 Apr |
|
Effects of modafinil on heat thermoregulatory responses in humans at rest. | 2002 Aug |
|
Drugs under investigation for attention-deficit hyperactivity disorder. | 2002 Aug |
|
Modafinil in treatment of fatigue in multiple sclerosis. Results of an open-label study. | 2002 Aug |
|
Discriminative-stimulus effects of modafinil in cocaine-trained humans. | 2002 Aug 1 |
|
Modafinil for the treatment of daytime sleepiness in Parkinson's disease: a double-blind, randomized, crossover, placebo-controlled polygraphic trial. | 2002 Dec |
|
Role of brain alpha 1B-adrenoceptors in modafinil-induced behavioral activity. | 2002 Dec 15 |
|
Modafinil reduces excessive somnolence and enhances mood in patients with myotonic dystrophy. | 2002 Dec 24 |
|
Psychopharmacology of wakefulness: pathways and neurotransmitters. | 2002 Jul |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
Modafinil in the treatment of depression with severe comorbid medical illness. | 2002 Jul-Aug |
|
Attention deficit disorder in adults. | 2002 Jun |
|
Gateways to Clinical Trials. June 2002. | 2002 Jun |
|
Study of the addictive potential of modafinil in naive and cocaine-experienced rats. | 2002 Jun |
|
Secondary narcolepsy in children with brain tumors. | 2002 Jun 15 |
|
The central nucleus of the amygdala and the wake-promoting effects of modafinil. | 2002 Jun 21 |
|
Use of modafinil in spastic cerebral palsy. | 2002 Mar |
|
Acute behavioral and physiological effects of modafinil in drug abusers. | 2002 Mar |
|
Treatment of excessive daytime sleepiness in patients with Parkinson's disease with modafinil. | 2002 Mar-Apr |
|
Modafinil monotherapy in depression. | 2002 May |
|
Effect of modafinil on core temperature during sustained wakefulness and exercise in a warm environment. | 2002 Nov |
|
Modafinil for social phobia and amphetamine dependence. | 2002 Nov |
|
Circadian rhythm of rectal temperature during sleep deprivation with modafinil. | 2002 Oct |
|
Adjunctive modafinil in ALS. | 2002 Spring |
|
Clinical applications of modafinil in stimulant abusers: low abuse potential. | 2002 Summer |
|
Temporal pattern of hippocampal high-frequency oscillations during sleep after stimulant-evoked waking. | 2003 |
|
Narcolepsy in the older adult: epidemiology, diagnosis and management. | 2003 |
|
Fatigue in multiple sclerosis: definition, pathophysiology and treatment. | 2003 |
|
[Therapy of day time fatigue in patients with multiple sclerosis]. | 2003 |
|
Three case reports of modafinil use in treating sedation induced by antipsychotic medications. | 2003 Apr |
|
Non-stimulant treatment of attention-deficit/hyperactivity disorder. | 2003 Apr |
|
Chiral analysis of d- and l-modafinil in human serum: application to human pharmacokinetic studies. | 2003 Apr |
|
An open-label trial of modafinil augmentation in patients with partial response to antidepressant therapy. | 2003 Apr |
|
[Modafinil: pharmacology and therapeutic perspectives]. | 2003 Jan |
|
Cognitive enhancing effects of modafinil in healthy volunteers. | 2003 Jan |
|
Con: modafinil has no role in management of sleep apnea. | 2003 Jan 15 |
|
Pro: modafinil has a role in management of sleep apnea. | 2003 Jan 15 |
|
Modafinil treatment of opioid-induced sedation. | 2003 Jun |
|
Reduction in excess daytime sleepiness by modafinil in patients with myotonic dystrophy. | 2003 Jun |
|
Modafinil--medical considerations for use in sustained operations. | 2003 Jun |
|
Modafinil for treatment of cognitive side effects of antiepileptic drugs in a patient with seizures and stroke. | 2003 Jun |
|
Initiating treatment with modafinil for control of excessive daytime sleepiness in patients switching from methylphenidate: an open-label safety study assessing three strategies. | 2003 Jun |
|
Randomized trial of modafinil for treating subjective daytime sleepiness in patients with Parkinson's disease. | 2003 Mar |
|
Distinctive effects of modafinil and d-amphetamine on the homeostatic and circadian modulation of the human waking EEG. | 2003 Mar |
|
Modafinil maintains waking in the fruit fly drosophila melanogaster. | 2003 Mar 15 |
|
Modafinil increases histamine release in the anterior hypothalamus of rats. | 2003 Mar 20 |
|
Modafinil and cocaine: a double-blind, placebo-controlled drug interaction study. | 2003 May 1 |
Patents
Sample Use Guides
The recommended dosage of NUVIGIL (armodafinil) for each indication is as follows: obstructive sleep apnea or Narcolepsy: 150 mg to 250 mg once a day in the morning. Shift work disorder: 150 mg once a day, taken approximately one hour prior to start of the work shift.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:04:10 UTC 2023
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admin
on
Wed Jul 05 23:04:10 UTC 2023
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Record UNII |
V63XWA605I
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Validated (UNII)
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N06BA13
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NCI_THESAURUS |
C47795
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LIVERTOX |
NBK548274
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DB06413
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Armodafinil
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641465
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C65241
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751850
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CHEMBL1201192
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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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