Urethane

US Previously Marketed

First marketed in 1921

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 Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29329860
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28818685 | https://www.ncbi.nlm.nih.gov/pubmed/18921082 https://www.ncbi.nlm.nih.gov/pubmed/2188890

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 By US FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use.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 Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11848977	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18921082	Primary		Approved 8583	URETHANE Approved Use Unknown
Metastatic malignant tumor 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18921082	Primary		Approved 8583	URETHANE Approved Use Unknown

Doses

Dose	Population	Adverse events
0.5 g 3 times / day multiple, oral Studied dose Dose: 0.5 g, 3 times / day Route: oral Route: multiple Dose: 0.5 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18911201	unhealthy, 2 year Health Status: unhealthy Age Group: 2 year Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18911201	Other AEs: Vomiting, White blood cell increased... Other AEs: Vomiting (1 patient) White blood cell increased (grade 5, 1 patient) Hemorrhage (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18911201
10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Sources: https://pubmed.ncbi.nlm.nih.gov/13366677	unhealthy, 21 years Health Status: unhealthy Age Group: 21 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13366677	Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Vomiting (1 patient) Leukopenia (grade 5, 1 patient) Hemorrhage (grade 5, 1 patient) Renal disorder NOS (grade 5, 1 patient) Liver injury (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13366677
6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18911201	unhealthy, 51-76 years Health Status: unhealthy Age Group: 51-76 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18911201	Other AEs: Anorexia, Leukopenia... Other AEs: Anorexia (4 patients) Leukopenia (1 patient) Weight loss (severe, 1 patient) Neutrophilia (1 patient) Nausea (1 patient) Vomiting (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18911201
10 g multiple, intravenous Dose: 10 g Route: intravenous Route: multiple Dose: 10 g Sources: https://pubmed.ncbi.nlm.nih.gov/18911201	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/18911201	Other AEs: Drowsiness... Other AEs: Drowsiness (slight) Sources: https://pubmed.ncbi.nlm.nih.gov/18911201

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 227		CYP2E1 131 CYP1A 59

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S094029939980027X Page: 1.0	yes
CYP2E1 1146	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S094029939980027X Page: 1.0	yes
CYP3A 317	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/S094029939980027X	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY557495	https://www.001chemical.com/chem/51-79-6
3B Scientific (Wuhan) Corp	3B3-030400	http://www.3bsc.com/index/pro_info.php?id=51664
AA Blocks	AA0035PL	http://www.aablocks.com/goods/Goods/detail?id=AA0035PL
Aaron Chemicals	AR0036HD	http://www.aaronchem.com/51-79-6
abcr GmbH	AB139082	http://www.abcr.com/shop/en/AB139082
AbMole Bioscience	M6045	http://www.abmole.com/products/urethane.html
Acadechem	ACDS-021133	http://www.acadechemical.com/product/95832
Achemica	ACMC-209kw3	http://www.achemica.com/prodinfo/?id=128444
Achemtek	0104-001101	http://www.achemtek.com/51-79-6
Acros Organics	AC325540010	https://www.fishersci.com/shop/products/urethane-97-acros-organics-2/AC325540010
Acros Organics	AC325540500	https://www.fishersci.com/shop/products/urethane-97-acros-organics/AC325540500
Acros Organics	AC325542500	https://www.fishersci.com/shop/products/urethane-97-acros-organics/AC325542500
AHH Chemical co.,ltd	MT-12134	http://www.ahhchemical.com/product/MT-12134.html
AK Scientific, Inc. (AKSCI)	67552	http://www.aksci.com/item_detail.php?cat=67552
Alfa Aesar	44804	https://www.alfa.com/en/catalog/044804/
Alfa Chemistry	AP51796	https://reagents.alfa-chemistry.com/product/urethane-cas-51-79-6-12388.html
Alichem	490015805	http://www.alichem.com/en/products/51-79-6.html
Anward	ANW-31345	http://www.anward.com/pro_result/30290
Aronis	ARONIS27009	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=19905
Aurora Fine Chemicals LLC	A00.151.192	http://online.aurorafinechemicals.com/info?ID=A00.151.192
Aurora Fine Chemicals LLC	K02.096.319	http://online.aurorafinechemicals.com/info?ID=K02.096.319
Aurum Pharmatech LLC	K-9500	http://www.Aurumpharmatech.com/Product/ProductDetails/K_9500
Avantor Inc	200008-042	https://us.vwr.com/store/product/7519276/urethane-97
BLD Pharm	BD156218	http://www.bldpharm.com/products/51-79-6.html
BOC Sciences	73962-07-9	https://www.bocsci.com/urethane-d5-cas-73962-07-9-item-131954.html
Chem Scene	CS-4731	http://www.chemscene.com/51-79-6.html
Chemenu	CM100840	http://www.chemenu.com/products/CM100840
ChemMol	49417194	http://www.chemmol.com/chemmol/49417194.html
ChemMol	99097773	http://www.chemmol.com/chemmol/99097773.html
Chemspace	CSSB00000162152	https://chem-space.com/CSSB00000162152
DC Chemicals	DC37116	http://www.dcchemicals.com//product_show-Urethane.html
Debye Scientific	DB-052027	http://www.debyesci.com/cas_51-79-6.html
Enamine	Z33546369	https://www.enaminestore.com/catalog/Z33546369
eNovation Chemicals	D376574	http://www.enovationchem.com/productDetails.asp?productID=D376574
Finetech	FT-0626365	http://www.finetechnology-ind.com/prod/detail/pub/51-79-6.html
Finetech	FT-0675741	http://www.finetechnology-ind.com/prod/detail/pub/73962-07-9.html
Glentham Life Sciences	GE8815	http://www.glentham.com/products/product/GE8815/
Hairui	HR123919	http://www.hairuichem.com/en/product/51-79-6.html
iChemical	EBD16140	http://www.ichemical.com/products/51-79-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00194423	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00194423
LGC Standards	DRE-C13322000	https://www.lgcstandards.com/US/en/p/DRE-C13322000
LGC Standards	LGCFOR2535.00	https://www.lgcstandards.com/US/en/p/LGCFOR2535.00
Matrix Scientific	139265	https://www.matrixscientific.com/139265.html
mcule	MCULE-1776877276	https://mcule.com/MCULE-1776877276/
MedChem Express	HY-B1207	https://www.medchemexpress.com/Urethane.html
Molcore	MC557495	https://www.molcore.com/product/51-79-6
MuseChem	I003869	https://www.musechem.com/product/I003869.html
Oakwood	99367	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=130780&ExtHyperLink=1
Otava	2825409	https://search.otavachemicals.com/#!/search?query=2825409&type=code&base=dbb
Parchem	35919	http://www.parchem.com/chemical-supplier-distributor/Ethyl-Carbamate-025919.aspx
Renno Tech	RP18512	http://www.rennotech.com/product_show.asp?id=24310
Sigma-Aldrich	76607_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/76607?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	94300_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/94300?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	U2500_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/u2500?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S005476	http://www.sinfoobiotech.com/product/1008874
Smolecule	S546446	http://www.smolecule.com/products/s546446
TCI (Tokyo Chemical Industry)	C0028	http://www.tcichemicals.com/eshop/en/us/commodity/C0028/index.html
THE BioTek	bt-285396	https://www.thebiotek.com/product/inhibitors/bt-285396
VladaChem	VL269301-250G	https://www.vladachem.com/product.php?products=51-79-6
Yuhao Chemical	RT0197	http://www.chemyuhao.com/51-79-6.html

PubMed

Title	Date	PubMed
Enzyme-induced biodegradation of polycarbonate polyurethanes: dependence on hard-segment concentration.	2001-09-15	11400129
Excitatory stimulation of neurons in the arcuate nucleus inhibits gastric acid secretion via vagal pathways in anesthetized rats.	2001-09-14	11532242
Discrete regions in the laterodorsal tegmental area of the rat regulating the urinary bladder and external urethral sphincter.	2001-09-07	11532432
Loss of p16Ink4a with retention of p19Arf predisposes mice to tumorigenesis.	2001-09-06	11544531
GDNF improves cerebellar Purkinje neuron function in aged F344 rats.	2001-09-01	11514987
The release of spinal prostaglandin E2 and the effect of nitric oxide synthetase inhibition during strychnine-induced allodynia.	2001-09	11524348
Abrogation of alpha-adrenergic vasoactivity in chronically inflamed rat knee joints.	2001-09	11506997
The application of magnetic resonance microimaging to the visible light curing of dental resins. 3. Stray-field nuclear magnetic resonance imaging (STRAFI).	2001-09	11445204
In vitro comparison of cuspal fracture resistances of posterior teeth restored with various adhesive restorations.	2001-08-18	11508095
Indomethacin reduces lung adenoma number in A/J mice.	2001-08-11	11497255
Extracellular signal-regulated kinases 1 and 2 phosphorylated neurons in the tele- and diencephalon of rat after visceral pain stimulation: an immunocytochemical study.	2001-08-10	11479017
Shear bond strength of denture reline polymers to denture base polymers.	2001-08-04	11484577
Clinical wear performance of eight experimental dental composites over three years determined by two measuring methods.	2001-08	11531074
Capillary zone electrophoresis for the characterization of latex particles.	2001-08	11519952
Anesthetic induction agents, sympathetic nerve activity and baroreflex sensitivity: a study in rabbits comparing thiopental, propofol and etomidate.	2001-08	11512561
Cardiovascular effects of the methanol and dichloromethanol extracts from Mentha suaveolens Ehrh.	2001-08	11507742
Involvement of a urethane-sensitive system in timing the onset of gastrulation in Xenopus laevis embryos.	2001-08	11473547
Effects of anesthesia on cystometry and leak point pressure of the female rat.	2001-07-27	11508351
Macroporous copolymer matrix. IV. Expanded bed adsorption application.	2001-07-13	11486892
Anesthesia alters NO-mediated functional hyperemia.	2001-07-13	11430881
Fine chromosomal localization of the mouse Par2 gene that confers resistance against urethane-induction of pulmonary adenomas.	2001-07-05	11494126
Utilization of an intramolecular hydrogen bond to increase the CNS penetration of an NK(1) receptor antagonist.	2001-07-05	11428921
Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres.	2001-07	11515988
Occupational hypersensitivity pneumonitis due to isocyanates: mechanisms of action and case reports in Japan.	2001-07	11500003
Effect of nitric oxide synthase inhibition on fos expression in the hypothalamus of female rats following central oxytocin and systemic urethane administration.	2001-07	11442774
Flexural behaviour of post-cured composites at oral-simulating temperatures.	2001-07	11422699
Denture base polymer Alldent Sinomer: mechanical properties, water sorption and release of residual compounds.	2001-07	11422690
Use of a simplified method of optical recording to identify foci of maximal neuron activity in the somatosensory cortex of white rats.	2001-06-05	11388374
Delayed-type hypersensitivity and humoral immunity modulation by dietary lipids in a murine model of pulmonary tumorigenesis induced by urethan.	2001-06	11484837
Azo-containing urethane analogues for colonic drug delivery: synthesis, characterization and in-vitro evaluation.	2001-06	11428667
Copper(II) catalysis in cyanide conversion into ethyl carbamate in spirits and relevant reactions.	2001-06	11409971
Topical bicuculline to the rat spinal cord induces highly localized allodynia that is mediated by spinal prostaglandins.	2001-06	11376908
Sympathetic nerve and cardiovascular responses to chemical activation of the midbrain defense region.	2001-06	11353674
Muscarinic dependence of nucleus basalis induced conditioned receptive field plasticity.	2001-05-25	11388444
[Liver angiosarcoma in humans: epidemiologic considerations].	2001-05-23	11367826
2-Chloroacetaldehyde induces epsilondA DNA adducts in DNA of Raji cells as demonstrated by an improved HPLC-fluorimetry method.	2001-05	11393245
An in vitro wear study of posterior denture tooth materials on human enamel.	2001-05	11380779
Optimization of an exogenous metabolic activation system for FETAX. II. Preliminary evaluation.	2001-05	11360430
Adrenomedullin acts in the rat paraventricular nucleus to decrease blood pressure.	2001-05	11328458
The role of alpha(1)-adrenoceptors and 5-HT(1A) receptors in the control of the micturition reflex in male anaesthetized rats.	2001-05	11325795
Telomerase activation and p53 mutations in urethane-induced A/J mouse lung tumor development.	2001-05	11323394
Two unusual glycerophospholipids from a filamentous fungus, Absidia corymbifera.	2001-04-30	11325609
Stimulatory effects of centrally injected kappa-opioid receptor agonists on gastric acid secretion in urethane-anesthetized rats.	2001-04-27	11343688
A novel traceless resin-bound guanidinylating reagent for secondary amines to prepare N,N-disubstituted guanidines.	2001-04-19	11348177
Monoclonal antibody to rat galanin: production, characterization, and in vivo immunoneutralization activity.	2001-04	11394529
The effects of moisture on the dielectric relaxation of urethane dimethacrylate polymer and composites.	2001-04	11350592
Modulation of diaspirin crosslinked hemoglobin induced systemic and regional hemodynamic response by ethanol in normal rats.	2001-02-09	11388690
Differences in parasympathetic vasodilator and salivary responses in the cat submandibular gland between lingual and chorda-lingual nerve stimulation.	2001-02	11332537
A role of proton transfer in peroxidase-catalyzed process elucidated by substrates docking calculations.	2001	11545682
[A plastic property in the change of rat muscle potentials clarified in the presence of neostigmine: a conjecture on the recycling process of ACh].	2001	11544757

Patents

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 Created by `admin` on `Wed Apr 02 09:16:41 GMT 2025` Edited by `admin` on `Wed Apr 02 09:16:41 GMT 2025`
Record UNII	3IN71E75Z5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Urethane

Official Name

English

URETHAN

Preferred Name

English

ETHYL-CARBAMATE

Systematic Name

English

Urethane [WHO-DD]

Common Name

English

CARBAMIC ACID, ETHYL ESTER

Common Name

English

URETHAN [MI]

Common Name

English

NSC-746

Code

English

O-ETHYLURETHANE

Common Name

English

ETHYL CARBAMATE

Systematic Name

English

PRACARBAMINE

Common Name

English

ETHYL AMINOFORMATE

Systematic Name

English

urethane [INN]

Common Name

English

URETHANE [HSDB]

Common Name

English

LEUCETHANE

Common Name

English

ETHYL CARBAMATE [IARC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45176