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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H12N2O3.C10H21N
Molecular Weight 387.5166
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BARBEXACLONE

SMILES

CCC1(c2ccccc2)C(=NC(=O)N=C1O)O.C[C@@]([H])(CC1CCCCC1)NC

InChI

InChIKey=MJCBWPMBFCUHBP-NPULLEENSA-N
InChI=1S/C12H12N2O3.C10H21N/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16;1-9(11-2)8-10-6-4-3-5-7-10/h3-7H,2H2,1H3,(H2,13,14,15,16,17);9-11H,3-8H2,1-2H3/t;9-/m.0/s1

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
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
Name Type Language
BARBEXACLONE
INN   MART.   WHO-DD  
INN  
Official Name English
BARBEXACLONE [MART.]
Common Name English
PROPYLHEXEDRINE L-FORM ETHYLPHENYLBARBITURATE [MI]
Common Name English
MALIASIN
Brand Name English
(-)-N,A-DIMETHYLCYCLOHEXANEETHYLAMINE COMPOUND WITH 5-ETHYL-5-PHENYLBARBITURIC ACID
Common Name English
BARBEXACLONE [INN]
Common Name English
PROPYLHEXEDRINE L-FORM ETHYLPHENYLBARBITURATE
MI  
Common Name English
BARBEXACLONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC N03AA04
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
WHO-VATC QN03AA04
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
NCI_THESAURUS C264
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
Code System Code Type Description
EVMPD
SUB06101MIG
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
MERCK INDEX
M9242
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY Merck Index
PUBCHEM
71196
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
WIKIPEDIA
BARBEXACLONE
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
EPA CompTox
4388-82-3
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
224-504-7
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
NCI_THESAURUS
C77998
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
FDA UNII
291GX1YB65
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
DRUG BANK
DB09001
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
DRUG CENTRAL
4345
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
MESH
C011019
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
RXCUI
46795
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY RxNorm
CAS
4388-82-3
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY
INN
1982
Created by admin on Sat Jun 26 08:11:07 UTC 2021 , Edited by admin on Sat Jun 26 08:11:07 UTC 2021
PRIMARY