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Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O3
Molecular Weight 232.2357
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOBARBITAL

SMILES

CCC1(c2ccccc2)C(=NC(=O)N=C1O)O

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 232.2357
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01174

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LUMINAL

Approved Use

Short-term treatment of insomnia. However, generally not used orally as a hypnotic because several hours are required to achieve maximal effectsa and barbiturates have decreased effectiveness for sleep induction and maintenance after 2 weeks.
Primary
LUMINAL

Approved Use

Relief of anxiety, tension, and apprehension. However, barbiturates used infrequently for routine sedation, since there are few clinical situations in which oral barbiturates provide a safety or efficacy advantage over nonbarbiturate sedatives/hypnotics.
Primary
LUMINAL

Approved Use

Management of tonic-clonic seizures and partial seizures; used alone (particularly in infants and young children) or, more commonly, in combination with phenytoin or other anticonvulsants.
Preventing
LUMINAL

Approved Use

Prevention of febrile seizures in infants and young children.
Primary
LUMINAL

Approved Use

Second-line agent in the termination of status epilepticus; may be useful to prevent seizure recurrence after seizures are initially terminated with other anticonvulsants (e.g., diazepam, phenytoin) or for termination of status epilepticus that does not respond to initial therapy with other anticonvulsants. Usefulness of parenteral phenobarbital in terminating acute seizure episodes is limited by its slow onset of action
Preventing
LUMINAL

Approved Use

Prophylactic management of epilepsy.
Primary
LUMINAL

Approved Use

Prevention and treatment of hyperbilirubinemia in neonates
Primary
LUMINAL

Approved Use

Has been used to reduce bilirubin concentrations in patients with congenital nonhemolytic unconjugated hyperbilirubinemia or chronic intrahepatic cholestasis. Has been used in the management of hyperlipemia associated with intrahepatic and extrahepatic cholestasis
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

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: Other
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 Fri Jun 25 21:15:51 UTC 2021
Edited
by admin
on Fri Jun 25 21:15:51 UTC 2021
Record UNII
YQE403BP4D
Record Status Validated (UNII)
Record Version
  • Download
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
PHENOBARBITAL [EP MONOGRAPH]
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
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
PRIMIDONE IMPURITY B [EP]
Common Name 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 Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
FDA ORPHAN DRUG 703819
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
CFR 21 CFR 1308.22
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
WHO-ATC N03AA02
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
EPA PESTICIDE CODE 600122
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
FDA ORPHAN DRUG 725519
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
FDA ORPHAN DRUG 601717
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
LIVERTOX 770
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
NCI_THESAURUS C67084
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
IARC Phenobarbital
DEA NO. 2285
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
CFR 21 CFR 862.3660
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
Code System Code Type Description
IUPHAR
2804
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
DRUG CENTRAL
2134
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
NCI_THESAURUS
C739
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
WIKIPEDIA
PHENOBARBITAL
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-007-0
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHENOBARBITAL
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
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.
USP_CATALOG
1524001
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY USP-RS
LACTMED
Phenobarbital
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
EPA CompTox
50-06-6
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
MERCK INDEX
M8622
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY Merck Index
MESH
D010634
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
HSDB
3157
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL40
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
FDA UNII
YQE403BP4D
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
DRUG BANK
DB01174
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
PUBCHEM
4763
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
EVMPD
SUB09770MIG
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
CAS
50-06-6
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
RXCUI
8134
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY RxNorm
INN
414
Created by admin on Fri Jun 25 21:15:52 UTC 2021 , Edited by admin on Fri Jun 25 21:15:52 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
METABOLIC ENZYME -> INDUCER
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INDUCER
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
LABELED -> NON-LABELED
BINDER->LIGAND
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
METABOLIC ENZYME -> INDUCER
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Elimimation
PHARMACOKINETIC
Elimination
PHARMACOKINETIC