Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H18N2O3 |
Molecular Weight | 238.2829 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=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)
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 |
|
Pharmacological comparison of R(+), S(-) and racemic secobarbital in mice. | 1970 Mar |
|
Toxic nephropathy after low-dose methoxyflurane anesthesia: drug interaction with secobarbital? | 1976 Feb 21 |
|
Dog liver microsomal P450 enzyme-mediated toluene biotransformation. | 1995 Nov |
|
[Experience in managing refractory status epilepticus caused by viral encephalitis under long-term anesthesia with barbiturate: a case report]. | 1998 May |
|
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection. | 2009 Jun |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
N05CA06
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
||
|
WHO-VATC |
QN05CA06
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
||
|
LIVERTOX |
876
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
||
|
WHO-VATC |
QN51AA02
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
||
|
WHO-VATC |
QN51AA52
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
||
|
DEA NO. |
2315
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
||
|
NCI_THESAURUS |
C67084
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
76-73-3
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
C61937
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
SUB10468MIG
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
5193
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
146
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
2428
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
DB00418
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
SECOBARBITAL
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
29071-21-4
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
SUPERSEDED | |||
|
1P7H87IN75
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
200-982-2
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
3182
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
Secobarbital
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
9624
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | RxNorm | ||
|
7615
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
1611004
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
100000084104
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
m9827
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
1P7H87IN75
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
DTXSID6044145
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
9073
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
D012631
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY | |||
|
CHEMBL447
Created by
admin on Sat Dec 16 16:43:17 GMT 2023 , Edited by admin on Sat Dec 16 16:43:17 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)