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Details

Stereochemistry ACHIRAL
Molecular Formula C12H11N2O3.Na
Molecular Weight 254.2171
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOBARBITAL SODIUM

SMILES

[Na+].CCC1(C(=O)NC(=O)[N-]C1=O)C2=CC=CC=C2

InChI

InChIKey=WRLGYAWRGXKSKG-UHFFFAOYSA-M
InChI=1S/C12H12N2O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

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
General anaesthetic actions on ligand-gated ion channels.
1999 Aug 15
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
Name Type Language
PHENOBARBITAL SODIUM
EP   INN   JAN   MART.   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
PHENOBARBITAL SODIUM SALT
MI  
Common Name English
GARDENAL SODIUM
Common Name English
PHENOBARBITAL SODIUM [MART.]
Common Name English
Phenobarbital sodium [WHO-DD]
Common Name English
PHENOBARBITAL SODIUM [USP MONOGRAPH]
Common Name English
LUMINAL SODIUM
Brand Name English
PHENOBARBITAL SODIUM SALT [MI]
Common Name English
phenobarbital sodium [INN]
Common Name English
PHENOBARBITAL SODIUM [WHO-IP]
Common Name English
PHENOBARBITAL SODIUM [JAN]
Common Name English
SODIUM PHENOBARBITAL
Common Name English
SEZABY
Brand Name English
PHENOBARBITAL SODIUM [VANDF]
Common Name English
PHENOBARBITAL SODIUM [EP MONOGRAPH]
Common Name English
Sodium 5-ethyl-5-phenylbarbiturate
Systematic Name English
PHENOBARBITALUM NATRICUM [WHO-IP LATIN]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-PHENYL-, MONOSODIUM SALT
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 768420
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
FDA ORPHAN DRUG 725419
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
FDA ORPHAN DRUG 725819
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
NCI_THESAURUS C264
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
FDA ORPHAN DRUG 633118
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT001491
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL40
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
DAILYMED
SW9M9BB5K3
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
PUBCHEM
12598276
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
SMS_ID
100000091098
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID0021123
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
INN
4172
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-322-3
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
FDA UNII
SW9M9BB5K3
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
RXCUI
82077
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C76956
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
EVMPD
SUB09771MIG
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHENOBARBITAL SODIUM
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY Description: White, crystalline granules or a white, crystalline powder; odourless. Solubility: Freely soluble in water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Hypnotic; sedative; anticonvulsant. Storage: Phenobarbital sodium should be kept in a tightly closed container, protected from light. Additional information: Phenobarbital sodium is hygroscopic. Even in the absence of light, Phenobarbital sodium is graduallydegraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Phenobarbital sodium contains not less than 98.0% and not more than 101.0% of C12H11N2NaO3, calculated withreference to the dried substance.
MERCK INDEX
m8622
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY Merck Index
CAS
57-30-7
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY
CHEBI
8070
Created by admin on Fri Dec 15 14:59:52 GMT 2023 , Edited by admin on Fri Dec 15 14:59:52 GMT 2023
PRIMARY