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Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O3
Molecular Weight 232.2353
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOBARBITAL

SMILES

CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2

InChI

InChIKey=DDBREPKUVSBGFI-UHFFFAOYSA-N
InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)

HIDE SMILES / InChI

Molecular Formula C12H12N2O3
Molecular Weight 232.2353
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Phenobarbital is a barbiturate derivative used to treat insomnia and anxiety, seizures, hyperbilirubinemia in neonates and cholestasis. Phenobarbital promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Enhancement of GABAergic inhibition: a mechanism of action of benzodiazepines, phenobarbital, valproate and L-cycloserine in the cat spinal cord.
1982
General anaesthetic actions on ligand-gated ion channels.
1999 Aug 15
On the mechanism of alleviation by phenobarbital of the malfunction of an epilepsy-linked GABA(A) receptor.
2006 Sep 26
Patents

Sample Use Guides

In Vivo Use Guide
Phenobarbital is administered orally or by IM or slow IV injection. For treatment of anxiety, phenobarbital is administered orally 6 mg/kg daily or 180 mg/m2 daily, in 3 equally divided doses. For treatment of seizure disorders, the drug is administered orally 15–50 mg 2 or 3 times daily. Alternatively, 3–5 mg/kg or 125 mg/m2 daily; IV or IM 4–6 mg/kg daily for 7–10 days to reach therapeutic blood concentrations; alternatively, 10–15 mg/kg daily.
Route of Administration: oral; intramuscular; intravenous
In Vitro Use Guide
Potentiation of the GABAA by phenobarbital was evaluated in HEK293 cells expressing recombinant rat GABAA receptors. Currents were recorded using the cell-flow technique and corrected for receptor desensitization. Co-application of phenobarbital with 300uM GABA lead to 20-30 amplification of chloride currents with EC50 of 100-200 uM
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:45:43 UTC 2019
Edited
by admin
on Tue Oct 22 00:45:43 UTC 2019
Record UNII
YQE403BP4D
Record Status Validated (UNII)
Record Version
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Name Type Language
PHENOBARBITAL
EP   HSDB   INN   MART.   MI   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
PHENOBARBITALUM
HPUS   WHO-IP LATIN  
Common Name English
TEDRAL SUSPENSION
Common Name English
PHENOBARBITAL [INN]
Common Name English
THEOPHED
Common Name English
GARDEPANYL
Common Name English
PHENOBARBITAL [WHO-DD]
Common Name English
PHENOBARBITAL [USP]
Common Name English
LUMINAL
Brand Name English
PHENOBARBITAL [JAN]
Common Name English
5-ETHYL-5-PHENYLBARBITURIC ACID
Systematic Name English
5-ETHYL-5-PHENYLPYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE
Systematic Name English
PHENOBARBITAL [VANDF]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-PHENYL-
Systematic Name English
PHENOBARBITAL [EP]
Common Name English
NSC-9848
Code English
PHENOBARBITAL [WHO-IP]
Common Name English
PHENOBARBITAL CIV [USP-RS]
Common Name English
PRIMATENE
Common Name English
VERSOMNAL
Common Name English
PHENOBARBITAL [MART.]
Common Name English
NSC-128143-
Code English
GARDENAL
Brand Name English
PHENOBARBITAL CIV
USP-RS  
Common Name English
PHENOBARBITONE
Common Name English
PHENOBARBITALUM [HPUS]
Common Name English
PHENOBARBITAL [IARC]
Common Name English
PHENOBARBITAL [MI]
Common Name English
TRIPHENATOL
Common Name English
PHENOBARBITALUM [WHO-IP LATIN]
Common Name English
TEDRIGEN
Common Name English
NSC-128143
Code English
SEDOPHEN
Common Name English
TEDRAL
Common Name English
PHENOBARBITAL [HSDB]
Common Name English
Classification Tree Code System Code
WHO-VATC QN03AA02
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
CFR 21 CFR 1308.22
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
NCI_THESAURUS C264
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
WHO-ATC N03AA02
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
EPA PESTICIDE CODE 600122
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
FDA ORPHAN DRUG 601717
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
LIVERTOX 770
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
NCI_THESAURUS C67084
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
IARC Phenobarbital
DEA NO. 2285
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
CFR 21 CFR 862.3660
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
Code System Code Type Description
IUPHAR
2804
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
NCI_THESAURUS
C739
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
WIKIPEDIA
PHENOBARBITAL
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-007-0
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHENOBARBITAL
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless. Solubility: Soluble in about 1100 parts of water, in about 10 parts of ethanol (~750 g/l) TS and in about 15 parts of ether R. Category: Hypnotic; sedative; anticonvulsant. Storage: Phenobarbital should be kept in a well-closed container. Additional information: Phenobarbital may exhibit polymorphism. Definition: Phenobarbital contains not less than 98.0% and not more than 101.0% of C12H12N2O3, calculated with reference tothe dried substance.
EPA CompTox
50-06-6
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
MERCK INDEX
M8622
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY Merck Index
LactMed
50-06-6
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
MESH
D010634
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
HSDB
50-06-6
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
ChEMBL
CHEMBL40
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
DRUG BANK
DB01174
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
PUBCHEM
4763
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
EVMPD
SUB09770MIG
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
CAS
50-06-6
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
RXCUI
8134
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY RxNorm
INN
414
Created by admin on Tue Oct 22 00:45:43 UTC 2019 , Edited by admin on Tue Oct 22 00:45:43 UTC 2019
PRIMARY
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ACTIVE MOIETY
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PHARMACOKINETIC
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