Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H23ClN6O2 |
Molecular Weight | 450.921 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1CCN(CCN1C(=O)C2=C(C=CC(C)=C2)N3N=CC=N3)C4=NC5=C(O4)C=CC(Cl)=C5
InChI
InChIKey=JYTNQNCOQXFQPK-MRXNPFEDSA-N
InChI=1S/C23H23ClN6O2/c1-15-3-5-20(30-25-8-9-26-30)18(13-15)22(31)29-12-11-28(10-7-16(29)2)23-27-19-14-17(24)4-6-21(19)32-23/h3-6,8-9,13-14,16H,7,10-12H2,1-2H3/t16-/m1/s1
Molecular Formula | C23H23ClN6O2 |
Molecular Weight | 450.921 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/?term=PMC4419247Curator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/204569s001lbl.pdf; http://www.ncbi.nlm.nih.gov/pubmed/?term=24102345
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=PMC4419247
Curator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/204569s001lbl.pdf; http://www.ncbi.nlm.nih.gov/pubmed/?term=24102345
Suvorexant is a selective dual antagonist of orexin receptors OX1R and OX2R. It has been approved for the treatment of insomnia. The mechanism by which suvorexant exerts its therapeutic effect in insomnia is presumed to be through antagonism of orexin receptors. The orexin neuropeptide signaling system is a central promoter of wakefulness. Blocking the binding of wake-promoting neuropeptides orexin A and orexin B to receptors OX1R and OX2R is thought to suppress wake drive.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: O43614 Gene ID: 3062.0 Gene Symbol: HCRTR2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21473737 |
0.55 nM [Ki] | ||
Target ID: O43613 Gene ID: 3061.0 Gene Symbol: HCRTR1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21473737 |
0.35 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | BELSOMRA Approved UseIndicated for the treatment of insomnia characterized by difficulties with sleep onset and/or sleep maintenance. Launch Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.08 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.329 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.425 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.488 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
80 mg 1 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.085 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.356 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.414 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.572 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.574 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.802 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.854 uM Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01043926 |
20 mg single, oral dose: 20 mg route of administration: oral experiment type: single co-administered: |
SUVOREXANT plasma | Homo sapiens population: healthy age: sex: food status: Fasted |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.64 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.48 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
18.1 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
18.32 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
80 mg 1 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
27.62 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.43 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.36 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.03 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.08 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.53 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
12.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
80 mg 1 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
14.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29705869 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUVOREXANT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
12 h |
SUVOREXANT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
SUVOREXANT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 1 times / day steady, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
healthy, 34.3 years(range: 19–45 years) n = 6 Health Status: healthy Age Group: 34.3 years(range: 19–45 years) Sex: M+F Population Size: 6 Sources: |
Other AEs: Somnolence, Fatigue... Other AEs: Somnolence (67%) Sources: Fatigue (83%) Insomnia (17%) Dizziness (33%) Phlebitis (33%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Insomnia | 17% | 100 mg 1 times / day steady, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
healthy, 34.3 years(range: 19–45 years) n = 6 Health Status: healthy Age Group: 34.3 years(range: 19–45 years) Sex: M+F Population Size: 6 Sources: |
Dizziness | 33% | 100 mg 1 times / day steady, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
healthy, 34.3 years(range: 19–45 years) n = 6 Health Status: healthy Age Group: 34.3 years(range: 19–45 years) Sex: M+F Population Size: 6 Sources: |
Phlebitis | 33% | 100 mg 1 times / day steady, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
healthy, 34.3 years(range: 19–45 years) n = 6 Health Status: healthy Age Group: 34.3 years(range: 19–45 years) Sex: M+F Population Size: 6 Sources: |
Somnolence | 67% | 100 mg 1 times / day steady, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
healthy, 34.3 years(range: 19–45 years) n = 6 Health Status: healthy Age Group: 34.3 years(range: 19–45 years) Sex: M+F Population Size: 6 Sources: |
Fatigue | 83% | 100 mg 1 times / day steady, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
healthy, 34.3 years(range: 19–45 years) n = 6 Health Status: healthy Age Group: 34.3 years(range: 19–45 years) Sex: M+F Population Size: 6 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/204569Orig1s007lbl.pdf#page=12 Page: 12.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/204569Orig1s007lbl.pdf#page=12 Page: 12.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/204569Orig1s007lbl.pdf#page=200 Page: 200.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/204569Orig1s007lbl.pdf#page=219 Page: 219.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Discovery of the dual orexin receptor antagonist [(7R)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (MK-4305) for the treatment of insomnia. | 2010 Jul 22 |
|
Promotion of sleep by suvorexant-a novel dual orexin receptor antagonist. | 2011 Mar |
|
The hypocretins/orexins: integrators of multiple physiological functions. | 2014 Jan |
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Dual orexin receptor antagonists - promising agents in the treatment of sleep disorders. | 2014 Jan |
|
Safety and efficacy of suvorexant during 1-year treatment of insomnia with subsequent abrupt treatment discontinuation: a phase 3 randomised, double-blind, placebo-controlled trial. | 2014 May |
|
Suvorexant: a novel therapy for the treatment of insomnia. | 2014 Oct |
|
Suvorexant: a dual orexin receptor antagonist for the treatment of sleep onset and sleep maintenance insomnia. | 2015 Apr |
|
Suvorexant: something new for sleep? | 2015 Feb |
Patents
Sample Use Guides
The recommended dose for BELSOMRA (suvorexant) is 10 mg, taken no more than once per night and within 30 minutes of going to bed, with at least 7 hours remaining before the planned time of awakening. If the 10 mg dose is well-tolerated but not effective, the dose can be increased. The maximum recommended dose of BELSOMRA is 20 mg once daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21473737
Examination of Suvorexant in radioligand binding assays using tissue from transgenic rats expressing the human OX2R found nearly full receptor occupancy (>90%) at plasma exposures of 1.1 μM.
Substance Class |
Chemical
Created
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admin
on
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Fri Dec 15 16:07:42 GMT 2023
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on
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Record UNII |
081L192FO9
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
N05CM19
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DEA NO. |
2223
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NDF-RT |
N0000191000
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SUB180101
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DTXSID90145616
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2890
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CHEMBL1083659
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N0000185503
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PRIMARY | P-Glycoprotein Inhibitors [MoA] | ||
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1547099
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N0000190114
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PRIMARY | Cytochrome P450 3A Inhibitors [MoA] | ||
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081L192FO9
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1030377-33-3
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9435
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N0000190998
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PRIMARY | Orexin Receptor Antagonists [MoA] | ||
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C171858
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XX-119
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4881
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SUVOREXANT
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
In plasma, M10A was the minor metabolite. In feces, M10A was accounted for 9% of dose.
FECAL; PLASMA
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METABOLITE -> PARENT |
M4 was the minor metabolite in plasma, but M4 was the major metabolite in urine and feces, accounting for 4.1% and 17.0% of the dose, respectively.
FECAL; PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MINOR
PLASMA
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METABOLITE -> PARENT |
In plasma, M12 was the minor metabolite. In urine, M12 was accounted for 2.7% of the dose.
PLASMA; URINE
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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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Tmax | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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