Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H18N2O3 |
Molecular Weight | 238.2834 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC(C)C1(CC=C)C(=NC(=O)N=C1O)O
InChI
InChIKey=KQPKPCNLIDLUMF-UHFFFAOYSA-N
InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
Molecular Formula | C12H18N2O3 |
Molecular Weight | 238.2834 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.drugs.com/cdi/secobarbital.htmlCurator's Comment:: description was created based on several sources, including:
http://www.rxlist.com/seconal-sodium-drug.htm
http://www.wikidoc.org/index.php/Secobarbital_sodium
https://www.glowm.com/resources/glowm/cd/pages/drugs/s004.html
Sources: https://www.drugs.com/cdi/secobarbital.html
Curator's Comment:: description was created based on several sources, including:
http://www.rxlist.com/seconal-sodium-drug.htm
http://www.wikidoc.org/index.php/Secobarbital_sodium
https://www.glowm.com/resources/glowm/cd/pages/drugs/s004.html
Secobarbital sodium, a barbiturate, is FDA approved for the treatment of insomnia and for pre-anesthetic use. This drug binds at a distinct site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. Adverse reactions are drowsiness, lethargy, hangover, paradoxical excitement in elderly patients, somnolence. Rifampin may decrease secobarbital levels by increasing metabolism.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SECONAL SODIUM Approved UseA.Hypnotic, for the short-term treatment of insomnia, since it appears to lose its effectiveness for sleep induction and sleep maintenance after 2 weeks (see Clinical Pharmacology). B.Preanesthetic Launch Date4.33987191E11 |
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Preventing | SECONAL SODIUM Approved UseA.Hypnotic, for the short-term treatment of insomnia, since it appears to lose its effectiveness for sleep induction and sleep maintenance after 2 weeks (see Clinical Pharmacology). B.Preanesthetic Launch Date4.16102416E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175723/ |
5 mg/kg single, rectal dose: 5 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
SECOBARBITAL plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175723/ |
5 mg/kg single, rectal dose: 5 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
SECOBARBITAL plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175723/ |
5 mg/kg single, rectal dose: 5 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
SECOBARBITAL plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
16.5 mg single, intraarterial (mean) Recommended Dose: 16.5 mg Route: intraarterial Route: single Dose: 16.5 mg Sources: |
unhealthy, adult n = 43 Health Status: unhealthy Condition: neurological disorders Age Group: adult Sex: unknown Population Size: 43 Sources: |
Other AEs: Scintillating scotoma, Epileptic fit... Other AEs: Scintillating scotoma (1 patient) Sources: Epileptic fit (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Epileptic fit | 1 patient | 16.5 mg single, intraarterial (mean) Recommended Dose: 16.5 mg Route: intraarterial Route: single Dose: 16.5 mg Sources: |
unhealthy, adult n = 43 Health Status: unhealthy Condition: neurological disorders Age Group: adult Sex: unknown Population Size: 43 Sources: |
Scintillating scotoma | 1 patient | 16.5 mg single, intraarterial (mean) Recommended Dose: 16.5 mg Route: intraarterial Route: single Dose: 16.5 mg Sources: |
unhealthy, adult n = 43 Health Status: unhealthy Condition: neurological disorders Age Group: adult Sex: unknown Population Size: 43 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/10064569/ |
yes | |||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17558303/ Page: 3.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
A hypotensive episode caused by amitriptyline? | 1969 Oct 4 |
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[Experience in managing refractory status epilepticus caused by viral encephalitis under long-term anesthesia with barbiturate: a case report]. | 1998 May |
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Induction of CYP1A2 by phenobarbital in the livers of aryl hydrocarbon-responsive and -nonresponsive mice. | 1999 Mar |
Patents
Sample Use Guides
As a hypnotic, 100 mg at bedtime. Preoperatively, 200 to 300 mg 1 to 2 hours before surgery.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5034548
Early studies revealed that 0.2 mM secobarbital caused
a maximum decrease in cytochrome P450, requiring NADPH or an NADPH-generating system.
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Jun 26 09:28:24 UTC 2021
by
admin
on
Sat Jun 26 09:28:24 UTC 2021
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Record UNII |
1P7H87IN75
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N05CA06
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WHO-VATC |
QN05CA06
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LIVERTOX |
876
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WHO-VATC |
QN51AA02
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WHO-VATC |
QN51AA52
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DEA NO. |
2315
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NCI_THESAURUS |
C67084
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Code System | Code | Type | Description | ||
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76-73-3
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1611004
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PRIMARY | USP-RS | ||
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C61937
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PRIMARY | |||
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SUB10468MIG
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5193
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146
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2428
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DB00418
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SECOBARBITAL
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29071-21-4
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SUPERSEDED | |||
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200-982-2
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PRIMARY | |||
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3182
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Secobarbital
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9624
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7615
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M9827
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1P7H87IN75
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76-73-3
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D012631
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PRIMARY | |||
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CHEMBL447
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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LABELED -> NON-LABELED | |||
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LABELED -> NON-LABELED |
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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