Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H17N2O3.Na |
Molecular Weight | 260.2647 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCC(C)C1(CC=C)C(=O)NC(=O)[N-]C1=O
InChI
InChIKey=AXXJTNXVUHVOJW-UHFFFAOYSA-M
InChI=1S/C12H18N2O3.Na/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);/q;+1/p-1
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 Date1983 |
|||
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 Date1983 |
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 |
---|---|---|
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 |
|
Volkmann's ischemic contracture after intra-arterial injection of secobarbital. | 1970 Apr 20 |
|
Pharmacological comparison of R(+), S(-) and racemic secobarbital in mice. | 1970 Mar |
|
Seven cases of somnambulism induced by drugs. | 1979 Jul |
|
Reflex sympathetic dystrophy associated with antiepileptic drugs. | 1994 Mar-Apr |
|
Dog liver microsomal P450 enzyme-mediated toluene biotransformation. | 1995 Nov |
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.
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DEA NO. |
2315
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CFR |
21 CFR 522.900
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NCI_THESAURUS |
C67084
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51165-35-6
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XBP604F6UM
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C66530
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14148199
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m9827
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91110
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309-43-3
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ACTIVE MOIETY
SUBSTANCE RECORD