Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H15NO2S |
Molecular Weight | 273.35 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 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-UHFFFAOYSA-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)
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 |
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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 |
---|---|---|
Off-label uses of modafinil. | 2001 Aug |
|
An enantioselective assay for (+/-)-modafinil. | 2001 Aug |
|
Methylphenidate and narcolepsy: new indication. When modafinil fails. | 2001 Feb |
|
Sleep disorders. | 2001 Feb |
|
Effects of modafinil in children with attention-deficit/hyperactivity disorder: an open-label study. | 2001 Feb |
|
Successful treatment of excessive daytime sleepiness in Parkinson's disease with modafinil. | 2001 Jul |
|
Modafinil and pramipexole-associated somnolence. | 2001 Jul |
|
Comparison in symptoms between aged and younger patients with narcolepsy. | 2001 Jun |
|
Practice parameters for the treatment of narcolepsy: an update for 2000. | 2001 Jun 15 |
|
Dopaminergic role in stimulant-induced wakefulness. | 2001 Mar 1 |
|
Modafinil augmentation of mirtazapine in a failure-to-thrive geriatric inpatient. | 2002 |
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Steady-state pharmacokinetics and tolerability of modafinil administered alone or in combination with dextroamphetamine in healthy volunteers. | 2002 Apr |
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Discriminative-stimulus effects of modafinil in cocaine-trained humans. | 2002 Aug 1 |
|
The SK-N-MC cell line expresses an orexin binding site different from recombinant orexin 1-type receptor. | 2002 Feb |
|
Narcolepsy and psychopathology: is there an association? | 2002 Jul |
|
Attention deficit disorder in adults. | 2002 Jun |
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Gateways to Clinical Trials. June 2002. | 2002 Jun |
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Secondary narcolepsy in children with brain tumors. | 2002 Jun 15 |
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Modafinil affects mood, but not cognitive function, in healthy young volunteers. | 2003 Apr |
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Modafinil in children with attention-deficit hyperactivity disorder. | 2003 Aug |
|
By the way, doctor. What can you tell me about the new drug Provigil? I've read that it helps people stay awake without feeling jittery. For those of us who work a lot of overtime, it sounds like a dream come true. | 2003 Jan |
|
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 |
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Dosing regimen effects of modafinil for improving daytime wakefulness in patients with narcolepsy. | 2003 Sep-Oct |
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Anti-narcoleptic agent modafinil and its sulfone: a novel facile synthesis and potential anti-epileptic activity. | 2004 Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Modafinil for excessive sleepiness associated with chronic shift work sleep disorder: effects on patient functioning and health-related quality of life. | 2007 |
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Chest tightness and palpitations associated with modafinil and consumption of free glutamate. | 2008 Apr |
|
A double-blind, placebo-controlled trial of modafinil (200 mg/day) for methamphetamine dependence. | 2009 Feb |
|
Open-label pilot study of modafinil for methamphetamine dependence. | 2009 Oct |
|
Effects of modafinil on the sleep EEG depend on Val158Met genotype of COMT. | 2010 Aug |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
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 23:03:11 UTC 2023
by
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on
Wed Jul 05 23:03:11 UTC 2023
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Record UNII |
R3UK8X3U3D
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47795
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NDF-RT |
N0000175651
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FDA ORPHAN DRUG |
73793
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NDF-RT |
N0000175729
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DEA NO. |
1680
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WHO-ATC |
N06BA07
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FDA ORPHAN DRUG |
536716
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NDF-RT |
N0000175769
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WHO-VATC |
QN06BA07
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LIVERTOX |
NBK548274
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6055
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DB00745
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759110
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M7584
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Modafinil
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1445404
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751178
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C048833
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DTXSID0023329
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C26661
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7555
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68693-11-8
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1826
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GG-74
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CHEMBL1373
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30125
Created by
admin on Wed Jul 05 23:03:12 UTC 2023 , Edited by admin on Wed Jul 05 23:03:12 UTC 2023
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PRIMARY | RxNorm | ||
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SUB09026MIG
Created by
admin on Wed Jul 05 23:03:11 UTC 2023 , Edited by admin on Wed Jul 05 23:03:11 UTC 2023
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MODAFINIL
Created by
admin on Wed Jul 05 23:03:12 UTC 2023 , Edited by admin on Wed Jul 05 23:03:12 UTC 2023
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31859
Created by
admin on Wed Jul 05 23:03:11 UTC 2023 , Edited by admin on Wed Jul 05 23:03:11 UTC 2023
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R3UK8X3U3D
Created by
admin on Wed Jul 05 23:03:11 UTC 2023 , Edited by admin on Wed Jul 05 23:03:11 UTC 2023
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PRIMARY |
Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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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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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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