HEPTABARBITAL

First approved in 1954

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H18N2O3
Molecular Weight	250.2936
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(C(=O)NC(=O)NC1=O)C2=CCCCCC2

InChI

InChIKey=PAZQYDJGLKSCSI-UHFFFAOYSA-N

InChI=1S/C13H18N2O3/c1-2-13(9-7-5-3-4-6-8-9)10(16)14-12(18)15-11(13)17/h7H,2-6,8H2,1H3,(H2,14,15,16,17,18)

HIDE SMILES / InChI

Molecular Formula	C13H18N2O3
Molecular Weight	250.2936
Charge	0
Count

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

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0015443 | https://www.ncbi.nlm.nih.gov/pubmed/13367825 | https://www.ncbi.nlm.nih.gov/pubmed/14116507

HEPTABARBITAL is an intermediate or short term barbiturate. It binds to the GABAA receptor at either the alpha or the beta subunit. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. HEPTABARBITAL was formerly used as a sedative and hypnotic drug.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13367825 https://www.ncbi.nlm.nih.gov/pubmed/26573	Curative		Withdrawn	Medomin Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.94 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9299	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		HEPTABARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
14.6 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9299	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		HEPTABARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23.6 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9299	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		HEPTABARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9299	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		HEPTABARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
2400 mg single, oral Highest studied dose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: https://journals.lww.com/jonmd/Citation/1956/02000/CLINICAL_OBSERVATIONS_ON_THE_SOMNIFACIENT_EFFICACY.4.aspx	unhealthy Health Status: unhealthy Sources: https://journals.lww.com/jonmd/Citation/1956/02000/CLINICAL_OBSERVATIONS_ON_THE_SOMNIFACIENT_EFFICACY.4.aspx	Sources: https://journals.lww.com/jonmd/Citation/1956/02000/CLINICAL_OBSERVATIONS_ON_THE_SOMNIFACIENT_EFFICACY.4.aspx

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY557405	https://www.001chemical.com/chem/509-86-4
ABI Chem	AC1L1VDD
ABI Chem	AC1Q6GAL
BOC Sciences	509-86-4
ChemMol	99117275	http://www.chemmol.com/chemmol/99117275.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0606217
Compound Cloud	10518
LGC Standards	LGCFOR0775.00	https://www.lgcstandards.com/US/en/p/LGCFOR0775.00
Molcore	MC557405	https://www.molcore.com/product/509-86-4
NovoSeek	10518
THE BioTek	bt-437486	https://www.thebiotek.com/product/others/bt-437486
Toronto Research Chemicals	H264900
ZINC	ZINC000005651594	http://zinc15.docking.org/substances/ZINC000005651594

PubMed

Title	Date	PubMed
Clinical observations on the somnifacient efficacy of heptabarbital (medomin) in mentally disturbed patients.	1956 Feb	13367825
A clinical trial of heptabarbitone (Medomin).	1962	13994997
HEPTABARBITONE AS A PRE-OPERATIVE SEDATIVE.	1964 Jan	14116507
Transport of lipophilic drug molecules in a new mucus-secreting cell culture model based on HT29-MTX cells.	2001 Aug	11587485

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:50:24 UTC 2023` Edited by `admin` on `Sat Dec 16 17:50:24 UTC 2023`
Record UNII	V10R70ML23
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HEPTABARBITAL

Common Name

English

5-(1-CYCLOHEPTEN-1-YL)-5-ETHYLBARBITURIC ACID

Systematic Name

English

HEPTABARBITAL [MI]

Common Name

English

Heptabarb [WHO-DD]

Common Name

English

HEPTABARBITONE

Common Name

English

heptabarb [INN]

Common Name

English

HEPTABARB

Official Name

English

Classification Tree Code System Code

WHO-VATC

QN05CA11