METHARBITAL

First approved in 1952

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H14N2O3
Molecular Weight	198.2191
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FWJKNZONDWOGMI-UHFFFAOYSA-N

InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)

HIDE SMILES / InChI

Molecular Formula	C9H14N2O3
Molecular Weight	198.2191
Charge	0
Count

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

Description
Sources: Shorvon, S. (2004). The Treatment of Epilepsy 2nd Ed. Retrieved from Shorvon, S. (2004). The Treatment of Epilepsy 2nd Ed. Retrieved from | https://books.google.ru/books?hl=ru&id=YBCQCgAAQBAJ&dq=isbn%3A0632060468&q=metharbital#v=snippet&q=metharbital&f=false

Methbarbital is a barbiturate anticonvulsant, discovered by Merck in 1905. It was introduced to market for treatment of epolepsy by Abbott in 1952, and discontinued in 1990.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/209272	Binding Agent 1064		10.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: http://www.ncbi.nlm.nih.gov/pubmed/13902356	Primary		Approved 8429	GEMONIL Approved Use Long-acting barbiturate that is demethylated to barbital in the liver; has broad-spectrum anticonvulsant action, but used mainly to treat myoclonic spasms in infants.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B1 26 CYP2B2 15 CYP3A 129 CYP2C11 14

Drug as perpetrator

Target	Modality	Activity
CYP2B1 41	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8638929/	yes
CYP2B2 16	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8638929/	yes
CYP2C11 15	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8638929/	yes
CYP3A 298	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8638929/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY556869	https://www.001chemical.com/chem/50-11-3
3B Scientific (Wuhan) Corp	3B2-1194	http://www.3bsc.com/index/pro_info.php?id=54910
AA Blocks	AA00DC9B	http://www.aablocks.com/goods/Goods/detail?id=AA00DC9B
AHH Chemical co.,ltd	MT-53565	http://www.ahhchemical.com/product/MT-53565.html
Ambinter	Amb22731852	http://www.ambinter.com/reference/22731852
Aurora Fine Chemicals LLC	A14.690.930	http://online.aurorafinechemicals.com/info?ID=A14.690.930
Aurora Fine Chemicals LLC	K14.818.590	http://online.aurorafinechemicals.com/info?ID=K14.818.590
BOC Sciences	50-11-3	https://www.bocsci.com/metharbital-cas-50-11-3-item-69753.html
Enamine	Z2205958937	https://www.enaminestore.com/catalog/Z2205958937
Finetech	FT-0692647	http://www.finetechnology-ind.com/prod/detail/pub/50-11-3.html
LGC Standards	LGCAMP1656.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1656.00-01
LGC Standards	LGCFOR1656.00	https://www.lgcstandards.com/US/en/p/LGCFOR1656.00
LGC Standards	MM1656.00	https://www.lgcstandards.com/US/en/p/MM1656.00
Molcore	MC556869	https://www.molcore.com/product/50-11-3
Smolecule	S575246	https://www.smolecule.com/products/s575246
THE BioTek	bt-366227	https://www.thebiotek.com/product/others/bt-366227
mcule	MCULE-9702939099	https://mcule.com/MCULE-9702939099/

PubMed

Title	Date	PubMed
Evaluation of pyridine-3-carboxylic acid as a drug carrier by utilizing multivariate methods, structure property correlations, and pattern recognition techniques.	2004	15204036
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.	2009	20111734

Patents

Sample Use Guides

In Vivo Use Guide

Metharbital is administered orally. Effective dose, causing a reduction in seizure score by 225, is 110 mg.

Route of Administration: Oral

In Vitro Use Guide

The binding of [3H]DHP (dihydropicrotoainin) to rat brain membrane fragments was measured by a centrifugation assay. Assay condition involved incubating 1-3 mg of protein at 0° for 15 min with 63 nM [3H]DHP with or without a given concentration of barbiturate in a total incubation medium of 2 ml. Following incubation, the vials were centrifuged, supernatant discarded, pellets rapidly rinsed, solubilized and prepared for counting as previously described (26) . Specific binding was obtained by subtracting from the total radioactivity in the pellet the background, i .e . the amount not displaced by high concentrations (0.1 mM) of unlabeled DHP. Metharbital inhibits binding of [3H]DHP to GABAA receptor with IC50 of 10 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:33:36 GMT 2023` Edited by `admin` on `Sat Dec 16 17:33:36 GMT 2023`
Record UNII	02OS7K758T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHARBITAL

Official Name

English

metharbital [INN]

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5,5-DIETHYL-1-METHYL-

Systematic Name

English

NSC-27156

Code

English

METHARBITONE

Brand Name

English

METHARBITAL [MART.]

Common Name

English

5,5-Diethyl-1-methylbarbituric acid

Systematic Name

English

Metharbital [WHO-DD]

Common Name

English

METHARBITAL [VANDF]

Common Name

English

METHARBITAL CIII

Common Name

English

METHARBITAL [ORANGE BOOK]

Common Name

English

METHARBITAL [JAN]

Common Name

English

GEMONIL

Brand Name

English

METHARBITAL [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67084