U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H13NO2
Molecular Weight 167.205
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHINAMATE

SMILES

NC(=O)OC1(CCCCC1)C#C

InChI

InChIKey=GXRZIMHKGDIBEW-UHFFFAOYSA-N
InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)

HIDE SMILES / InChI

Molecular Formula C9H13NO2
Molecular Weight 167.205
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Ethinamate was used to treat insomnia (trouble in sleeping) under the brand name VALMID, but then was replaced by other more efficacy medicines. The mechanism of action was not known. However, was studies, which showed that ethinamate inhibits carbonic anhydrases I and did not inhibit II. Nevertheless, even inhibition carbonic anhydrases I is not sufficiently strong to implicate carbonic anhydrases I in the mechanism of action.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P00915
Gene ID: 759.0
Gene Symbol: CA1
Target Organism: Homo sapiens (Human)
2.9 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
valmid

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.9 μg/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
15 g single, oral
Overdose
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
healthy, 24 years
n = 1
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 1
Sources:
Other AEs: Breathing slowed...
Other AEs:
Breathing slowed (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Breathing slowed 1 patient
15 g single, oral
Overdose
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
healthy, 24 years
n = 1
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Reductive metabolism of an alpha,beta-ketoalkyne, 4-phenyl-3-butyn-2-one, by rat liver preparations.
2002 Apr
Patents

Sample Use Guides

In Vivo Use Guide
single oral dose of 1 gram
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:51:39 UTC 2023
Edited
by admin
on Thu Jul 06 00:51:39 UTC 2023
Record UNII
IAN371PP48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHINAMATE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
ETHINAMATE [VANDF]
Common Name English
CYCLOHEXANOL, 1-ETHYNYL-, CARBAMATE
Systematic Name English
ETHINAMATE [HSDB]
Common Name English
NSC-11538
Code English
ethinamate [INN]
Common Name English
ETHINAMATE [MART.]
Common Name English
ETHINAMATE [MI]
Common Name English
VALMID
Brand Name English
ETHINAMATE [ORANGE BOOK]
Common Name English
ETHINAMATE [JAN]
Common Name English
Ethinamate [WHO-DD]
Common Name English
1-Ethynylcyclohexanol carbamate
Systematic Name English
Classification Tree Code System Code
DEA NO. 2545
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
NCI_THESAURUS C29756
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
Code System Code Type Description
MESH
C100198
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
SMS_ID
100000082617
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
INN
549
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
NCI_THESAURUS
C65559
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
CAS
126-52-3
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
RXCUI
24474
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY RxNorm
IUPHAR
7325
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL1576
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
EVMPD
SUB07276MIG
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
WIKIPEDIA
ETHINAMATE
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
PUBCHEM
3284
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
NSC
11538
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
DRUG BANK
DB01031
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
CHEBI
4884
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-789-4
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
DRUG CENTRAL
1081
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
MERCK INDEX
M1137
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY Merck Index
HSDB
3325
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
FDA UNII
IAN371PP48
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID7023013
Created by admin on Thu Jul 06 00:51:39 UTC 2023 , Edited by admin on Thu Jul 06 00:51:39 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY