MEPHOBARBITAL

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H14N2O3
Molecular Weight	246.2619
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCC1(C(=O)NC(=O)N(C)C1=O)C2=CC=CC=C2

InChI

InChIKey=ALARQZQTBTVLJV-UHFFFAOYSA-N

InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)

HIDE SMILES / InChI

Molecular Formula	C13H14N2O3
Molecular Weight	246.2619
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Mephobarbital us a barbiturate derivative used primary as an anticonvulsant, but also as a sedative and anxiolytic. Marketing of mephobarbital was discontinued in 2012.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203	Activator 1,447		19.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275	Primary		Approved 8,583	MEBARAL
Epilepsy 121	Primary		Approved 8,583	MEBARAL

C_max

Value	Dose	Co-administered	Analyte	Population
0.73 μg/mL	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens
0.24 μg/mL	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
7.95 μg × h/mL	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens
1.29 μg × h/mL	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.94 h	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens
3.05 h	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
32.6%	400 mg single, oral		MEPHOBARBITAL plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193	substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2,052 MRP1 113 CYP2C19 1,119 CYP2B6 776 CYP1A1 389 CYP1A2 1,197 CYP2A6 626 CYP2C8 810 CYP2E1 729

Drug as victim

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Target	Modality	Activity
CYP1A1 389	substrate 4,014	no
CYP1A2 1,197	substrate 4,014	no
CYP2A6 626	substrate 4,014	no
CYP2C8 810	substrate 4,014	no
CYP2C9 1,193	substrate 4,014	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6758	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6758
eMolecules	2729386	https://www.emolecules.com/cgi-bin/more?vid=2729386

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PubMed

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Title	Date	PubMed
Myasthenia gravis syndrome associated with trimethadione.	1970 Jun 29	4987393
Ependymoblastoma associated with prenatal exposure to diphenylhydantoin and methylphenobarbitone.	1985 May 1	3978571
Prediction of adsorption from multicomponent solutions by activated carbon using single-solute parameters. Part II--Proposed equation.	2002	12916938
Withdrawal of methylphenobarbitone.	2003 Jan 6	12492392
Determination of two ternary mixtures containing phenobarbitone by second derivative of the ratio spectrum-zero-crossing and HPLC methods.	2003 May	12729832

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Patents

Sample Use Guides

In Vivo Use Guide

Mephobarbital shoudl be administered orally. For treatment of epilepsy the average dose for adults and children 12 years of age and older: 400 mg to 600 mg daily.

Route of Administration: Oral

In Vitro Use Guide

Uptake of [36]Cl- ions by membranes from mouse brain was measured using liquid scintillation spectrometry. Mephobarbital simulated GABA-dependent Cl- uptake with EC50 of 19 uM.

Substance Class	Chemical
Record UNII	5NC67NU76B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYLPHENOBARBITAL

Preferred Name

English

MEPHOBARBITAL

Common Name

English

MEPHOBARBITAL [USP MONOGRAPH]

Common Name

English

ISONAL

Common Name

English

MEPHOBARBITAL CIV [USP-RS]

Common Name

English

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Classification Tree

Code System

Code

Sec. 1308.11 Schedule IV.

DEA NO.

2250

Barbiturates and derivatives

WHO-ATC

N03AA01

Sedative and Hypnotic

NCI_THESAURUS

C67084

Barbiturates and derivatives

WHO-VATC

QN03AA01

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Code System

Code

Type

Description

RXCUI

6758

PRIMARY

RxNorm

DRUG BANK

DB00849

PRIMARY

DRUG CENTRAL

1696

PRIMARY

EVMPD

SUB08871MIG

PRIMARY

CAS

115-38-8

PRIMARY

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PHENOBARBITAL

IMPURITY -> PARENT

Interaction Type:

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Qualification:

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Amount:

[<0.5] PERCENT PEAK AREA (limits)

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					5NC67NU76B

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.drugs.com/pro/mephobarbital.html">https://www.drugs.com/pro/mephobarbital.html</a></span></span></div></div>

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description

C_max

T_1/2

F_unbound