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Barbexaclone

HCID 71196
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Basic information

CAS
4388-82-3
Standard SMILES
CCC1(c2ccccc2)C(=O)NC(=O)NC1=O.CN[C@@H](C)CC1CCCCC1
InChIKey
MJCBWPMBFCUHBP-NPULLEENSA-N
Molecular formula
C22H33N3O3
Average molar mass
387.5 g/mol
Monoisotopic mass
387.25219192

Overview

Barbexaclone, a salt compound of propylhexedrine and phenobarbital, is a potent antiepileptic. By weight, barbexaclone is 40% propylhexedrine and 60% phenobarbital. While barbexaclone has sedative properties, propylhexedrine has psychostimulant properties intended to offset these sedative effects. Pharmacokinetic studies have demonstrated that the pharmacokinetics of phenobarbital given as barbexaclone are not affected by propylhexedrine. Several reports from Spanish and Italian literature suggest that barbexaclone is at least as effective as phenobarbital in adults and children, while being better tolerated and having less sedative properties. These reports were conducted in a small series of patients in the 1970s and 1980s, and have yet to be confirmed by larger controlled trials. Despite the lack of controlled trials, barbexaclone was used widely in Turkey until it was discontinued in 2009. Barbexaclone exists in 25mg and 100mg tablets. 100mg of barbexaclone is equivalent to 60mg of phenobarbital. With this difference in potency in mind, other pharmacokinetic considerations such as dose titration, daily dosing, and optimal plasma concentration can be considered the same as for the equivalent amount of phenobarbital. There has been a case of barbexaclone abuse due to the amphetamine like properties of propylhexedrine, although the comparative abuse potential is much lower than amphetamine.

Names & identifiers

Preferred name
Barbexaclone
IUPAC
(2S)-1-cyclohexyl-N-methylpropan-2-amine;5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
English name
barbexaclone
Molecular formula
C12H12N2O3.C10H21N
Molecular weight
387.521

Names & synonyms

BarbexacloneMaliasinBarbexaclonum4388-82-3Barbexaclona291GX1YB65Propylhexedrine l-form ethylphenylbarbiturateDTXSID90195974CHP phenobarbitalphenobarbital propylhexedrine saltRefChem:116470DTXCID30118465
Show more names
MJCBWPMBFCUHBP-UHFFFAOYSA-Nl-Form ethylphenylbarbiturate
N03AA045-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione; ((2S)-1-cyclohexylpropan-2-yl)(methyl)amine224-504-7BarbexaclonBarbexaclone [INN]Barbexaclone (INN)(2S)-1-cyclohexyl-N-methylpropan-2-amine;5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trionechp-Phenobarbitalat

Database identifiers

CAS
4388-82-3
PubChem CID
71196
DTXSID
DTXSID90195974
ChEMBL
CHEMBL3833301
UNII
291GX1YB65
EC Number
224-504-7

Properties

Computed structural properties

Topological polar surface area
87.3 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
28
Formal charge
0
Complexity
434

Experimental & physicochemical properties

DrugsPharmaceuticals -> Barbiturates

Physicochemical properties

FDA UNII
291 GX1YB65 · 291GX1YB65
ATC code
3 AA04 · N03AA04

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Mechanism of ActionPhenobarbitol targets GABA receptors in the CNS. Propylhexedrine is a TAAR1 agonist.
Biological Half-LifeAfter IV administration in mice, levels of phenobarbital declined exponentially with a half life of 7.5h. [3] For propylhexedrine t0.5a = 0.31h and t0.5b = 2.5h.
Absorption, Distribution and Excretion · 2 items

After oral administration of barbexaclone in mice the maximum plasma levels of prophylhexedrine appeared after 4 minutes, and propylhexedrine was seen to penetrate the blood brain barrier rapidly. Bioavailability (AUC oral / AUC iv) = 0.37. [3] Phenobarbital was observed to reach the blood more slowly, and brain uptake was a slow process. Equilibrium concentrations with plasma reached after 30 minutes after i.v injection. [3]

In mice, the volume of distribution was 0.78L/kg of phenobarbital, and 19.3L/kg for propylhexedrine, after i.v. administration. [3] High but unequal tissue accumulation of propylhexedrine was observed in mice: lung = kidney > liver = brain > spleen > heart > skeletal muscle. [3]

Upstream & downstream products

Upstream raw materials

Phenobarbital

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Compound notes

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