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Details

Stereochemistry ACHIRAL
Molecular Formula C3H7NO2
Molecular Weight 89.0932
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URETHANE

SMILES

CCOC(N)=O

InChI

InChIKey=JOYRKODLDBILNP-UHFFFAOYSA-N
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)

HIDE SMILES / InChI

Molecular Formula C3H7NO2
Molecular Weight 89.0932
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Urethane (Ethyl carbamate) is is an ethyl ester of carbamic acid, that has been found in many fermented food products and alcoholic beverages such as cheese, bread, yogurt, wine, whiskey, soya sauce etc. An in vitro study indicated that Urethane has a potential to inhibit the growth of bacteria, plant tissue, and rat carcinoma. Urethane has been used for many years as an antineoplastic agent for medical purposes but this application ended after it was discovered to be carcinogenic in 1943. Urethane can produce long-lasting anesthesia without affecting blood gases or blood pressure, it has been used in acute studies. In earlier studies, Urethane was also used as a co-solvent for water-insoluble analgesic and sedative drugs in Japan. By US FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anesthetic for animals.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
URETHANE
Primary
URETHANE

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
In the 1940s, ethyl carbamate was used in man at doses of 1 g/person/day
Route of Administration: Oral
In Vitro Use Guide
HepG2 cells were cultured in DMEM medium containing 10% fetal bovine serum and 1% mixture of penicillin (100 IU/ml) and streptomycin (100g/ml) at 37 °C in the presence of 5% CO2. Cells at 80% confluent were treated with 100 mM (dissolved in DMEM medium) for different times and cell viability and mortality were timely examined. Cells without EC (Urethane) treatment were grown at the same time as control. For metabolomics and transcriptomic analyses, cells were collected at 4 h and 12 h after treatment, respectively, digested with trypsin and centrifuged in 2 mL Eppendorf tubes at 1000 rpm for 5 min in 4 °C. The cell pellets were washed with ice-cold PBS solution twice, frozen immediately in liquid nitrogen and stored at −80 °C until analysis.
Substance Class Chemical
Record UNII
3IN71E75Z5
Record Status Validated (UNII)
Record Version