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Chemistry

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Also known as: Ethyl carbamate, 51-79-6, Urethan, Carbamic acid, ethyl ester, Ethylurethane, Carbamic acid ethyl ester
Molecular Formula
C3H7NO2
Molecular Weight
89.09  g/mol
InChI Key
JOYRKODLDBILNP-UHFFFAOYSA-N
FDA UNII
3IN71E75Z5

Urethane
Antineoplastic agent that is also used as a veterinary anesthetic. It has also been used as an intermediate in organic synthesis. Urethane is suspected to be a carcinogen.
1 2D Structure

Urethane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl carbamate
2.1.2 InChI
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
2.1.3 InChI Key
JOYRKODLDBILNP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC(=O)N
2.2 Other Identifiers
2.2.1 UNII
3IN71E75Z5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Carbamate, Ethyl

2. Ethyl Carbamate

3. Urethan

2.3.2 Depositor-Supplied Synonyms

1. Ethyl Carbamate

2. 51-79-6

3. Urethan

4. Carbamic Acid, Ethyl Ester

5. Ethylurethane

6. Carbamic Acid Ethyl Ester

7. Pracarbamine

8. Leucethane

9. Ethylcarbamate

10. Ethyl Urethane

11. O-ethylurethane

12. Pracarbamin

13. Ethyl Urethan

14. U-compound

15. Aethylcarbamat

16. Aethylurethan

17. Ethylurethan

18. Leucothane

19. Estane 5703

20. Uretan

21. Uretano [dcit]

22. Uretan Etylowy

23. Ethyl Aminoformate

24. Nsc 746

25. Aethylurethan [german]

26. Aethylcarbamat [german]

27. O-ethyl Urethane

28. Carbamidsaeure-aethylester

29. Rcra Waste Number U238

30. Ethyl Ester Of Carbamic Acid

31. Ethylester Kyseliny Karbaminove

32. X 41

33. Mfcd00007966

34. A 11032

35. Nsc-746

36. Nh2cooc2h5

37. Nsc746

38. Chebi:17967

39. Urethane + Ethanol (combination)

40. 3in71e75z5

41. Aethylurethan (german)

42. Ncgc00095041-01

43. Aethylcarbamat (german)

44. Dsstox_cid_1427

45. Urethanum [inn-latin]

46. Uretan Etylowy [polish]

47. Dsstox_rid_76156

48. Dsstox_gsid_21427

49. Ethyl Carbamate;carbamic Acid Ethyl Ester;ethylurethane

50. Uretano

51. Urethanum

52. Carbamate, Ethyl

53. Carbamidsaeure-aethylester [german]

54. O-ethyl Carbamate

55. Ethyl Carbamate (urethane)

56. Cas-51-79-6

57. Urethane [inn:ban:dcf]

58. Ccris 619

59. Ethylester Kyseliny Karbaminove [czech]

60. Hsdb 2555

61. Urethane [inn:dcf]

62. Sr-05000001854

63. Einecs 200-123-1

64. Rcra Waste No. U238

65. Ethyl-carbamate

66. Unii-3in71e75z5

67. Ai3-00553

68. Urethane, Inn

69. Spectrum_001685

70. Urethane, >=99%

71. Urethane [hsdb]

72. Urethane [inn]

73. Urethan [mi]

74. Spectrum2_000909

75. Spectrum3_000965

76. Spectrum4_001082

77. Spectrum5_001651

78. Urethane [who-dd]

79. Wln: Zvo2

80. Bspbio_002569

81. Kbiogr_001464

82. Kbioss_002165

83. Urethane, Analytical Standard

84. Bidd:er0508

85. Divk1c_000060

86. Spectrum1503304

87. Spbio_000758

88. Ethyl Carbamate [iarc]

89. Chembl462547

90. Dtxsid9021427

91. Hms500c22

92. Kbio1_000060

93. Kbio2_002165

94. Kbio2_004733

95. Kbio2_007301

96. Kbio3_001789

97. Ninds_000060

98. Urethane, >=99.0% (gc)

99. Hms1922a10

100. Hms2093c21

101. Hms3885f08

102. Pharmakon1600-01503304

103. Zinc901020

104. Hy-b1207

105. Tox21_111398

106. Tox21_201761

107. Tox21_300494

108. Ccg-39905

109. Nsc758452

110. S4544

111. Stl257390

112. Akos000118772

113. Tox21_111398_1

114. Cs-4731

115. Db04827

116. Nsc-758452

117. Idi1_000060

118. Ncgc00095041-02

119. Ncgc00095041-03

120. Ncgc00095041-04

121. Ncgc00095041-05

122. Ncgc00095041-06

123. Ncgc00095041-08

124. Ncgc00254522-01

125. Ncgc00259310-01

126. Sbi-0051812.p002

127. Sbi-0051812.p003

128. Db-052027

129. Ethyl Carbamate 100 Microg/ml In Methanol

130. Am20100253

131. Ft-0626365

132. Ft-0675741

133. C01537

134. F21294

135. Ab00052344_04

136. Q422884

137. Sr-05000001854-1

138. Sr-05000001854-2

139. Brd-k24297741-001-01-1

140. Carbamic Acid Ethyl Ester;ethyl Carbamate;ethylurethane

141. Z33546369

142. F0001-1333

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 89.09 g/mol
Molecular Formula C3H7NO2
XLogP3-0.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass89.047678466 g/mol
Monoisotopic Mass89.047678466 g/mol
Topological Polar Surface Area52.3 Ų
Heavy Atom Count6
Formal Charge0
Complexity52.8
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anesthetics, Intravenous; Antineoplastic Agents; Carcinogens

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


/It was/ ... reported in 1968 that urethane had found use in human medicine as an anti-neoplastic agent & formerly was used as a hypnotic, an adjunct to sulfonamide therapy, a component (with quinine) of sclerosing soln for varicose veins, & as a topical bacteriocide.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V7 112 (1974)


A more recent source states that large doses of urethane produce bone marrow depression, & that for a time it was used in treatment of chronic leukemia & multiple myeloma. No evidence was found that urethane presently finds use in USA in human medicine.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V7 112 (1974)


Medication (vet): reported ... exposures of urethane incl its infrequent use as a hypnotic & its more frequent use as an anesthetic for lab animals.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V7 113 (1974)


For more Therapeutic Uses (Complete) data for ETHYL CARBAMATE (7 total), please visit the HSDB record page.


4.2 Drug Warning

Overdosage with any /anticancer agents which include urethane/ causes leukopenia, granulocytopenia, thrombocytopenia, hypoplasia of all elements of bone marrow, nausea ... & anorexia. /From table/

Dreisbach, R. H. Handbook of Poisoning. 9th ed. Los Altos, California: Lange Medical Publications, 1977., p. 433


Medication (vet): ... Hepatotoxic. Contraindicated in nephritis or hepatitis. Hematopoietic depressant. May be teratogenic (hamsters) & carcinogenic (rats & mice). Continued use may depress white cell counts. May increase blood glucose levels. ... Usually reserved for terminal experiments, as pulmonary edema may occur during long lasting anesthesia and recovery periods.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 632


Although positive evidence of teratogenicity in humans is not available for all antineoplastic agents, it is considered that they are best avoided during pregnancy, especially during the first trimester, and should not be used in mothers who are breast feeding. /Anti-neoplastic agents/

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 175


... Urethane can occur as a contaminant in two anticonvulsant drugs (trimethadione and paramethadione), with an allowable limit of 1 ppm; these anticonvulsant drugs may be used only to treat epilepsy ... .

DHHS/NTP; Fourth Annual Report On Carcinogens p.198 (1985) NTP 85-002


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Carcinogens

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)


5.2 Absorption, Distribution and Excretion

The distribution of radiolabelled urethane administered in water or ethanolic solution, was compared in mice by whole-body autoradiography. Two fasted male A/JAX mice were administered 6 uCi (ethyl-1-(14)C)urethane by oral intubation. One mouse received urethane in 1 mL of an aqueous solution, the other in a 12% ethanol solution. One hour after treatment, the mice were frozen and processed for whole body autoradiography. When urethane was administered in water, the radioactivity localized in the salivary, seromucous, and Harderian glands, medullary bone, liver, bile, and epithelia of the stomach and intestine. Lower levels were seen in brown fat, and in the thymus and esophagus. When urethane was administered in ethanol, localization of urethane at each of these sites was almost completely inhibited; high concentrations were still found in the lumen of the stomach and intestine. No evidence was found of transesterification at pH 1.5 in 12% ethanol.

PMID:3623342 Waddell WJ et al; Food Chem Toxicol 25 (7): 527-31 (1987)


In an attempt to understand route of administration dependency, (3)H-benzo(a)pyrene, (14)C-urethane and (14)C-acrylamide were administered as single doses orally or topically to male Sencar mice. Distribution in skin, stomach, liver, and lung was determined for time periods up to 48 hr. The binding of these compounds to DNA, RNA, and protein in these tissues was determined 6 and 48 hr after administration. For all three compounds, high concentrations were found in the skin following topical application, but very little material reached this target organ following oral administration. The internal organs generally contained more material after oral administration compared to topical application, whereas the opposite was true for the skin. Differences in distribution to the skin and binding to macromolecules following oral or topical administration cannot explain the greater tumorigenicity of urethane and acrylamide after oral administration in the Sencar mouse.

PMID:3780633 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1474256 Carlson GP et al; Environ Health Perspect 68: 53-60 (1986)


In mice, urethane is active by transplacental route & is passed to offspring in milk.

Doull, J., C.D.Klassen, and M.D. Amdur (eds.). Casarett and Doull's Toxicology. 3rd ed., New York: Macmillan Co., Inc., 1986., p. 123


After oral administration to rats and mice, /carbamic acid, ethyl ester/ is completely absorbed from the GI tract and rapidly distributed throughout the body. ...Mice eliminated /carbamic acid, ethyl ester/ as /carbon dioxide/ more rapidly than rats.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 59


For more Absorption, Distribution and Excretion (Complete) data for ETHYL CARBAMATE (6 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

In rats, rabbits & humans (patients with multiple myeloma treated with urethane in conjunction with alkylating agent), urinary metabolites are: urethane (0.5-1.7% of admin dose), n-hydroxy urethane (0.02-0.15%), acetyl-n-hydroxy urethane (0.1-0.6%), ethyl mercapturic acid (0.1-0.2%) & N-acetyl-s-ethoxy carbonylcysteine (0.9-2.1%).

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V7 127 (1974)


Reactivity of ... /n-hydroxyurethane/ in vitro and in vivo favors its consideration as being a proximal carcinogenic metabolite of ... /urethane/ ...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 263


It is metabolized to ethyl alcohol and carbamic acid, and the latter acts as a weak diuretic.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 632


Biotransformation of urethane in rats and rabbits and in man affords n-hydroxyurethane, N-acetyl-s-carboxyethylcysteine, and ethylmercapturic acid as urinary metabolites, and thus urethane is converted into an alkylating agent through n-hydroxylation.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 262


For more Metabolism/Metabolites (Complete) data for ETHYL CARBAMATE (10 total), please visit the HSDB record page.


Urethane has known human metabolites that include Vinyl carbamate.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.4 Mechanism of Action

The clonal origin of pulmonary tumors by treatment with the chemical carcinogens, urethane and 4-nitroquinoline-1-oxide, were verified by PGK-isozyme mosaicism in DS strain mice. Six pulmonary tumors (12.5%) in 48 mice treated with urethane, and one (3.4%) in 23 mice treated with 4-nitroquinoline 1-oxide, were observed respectively. A single band, either PGK-la or PGK-lb occurred in two out of 7 tumors; and 5 remaining tumors showed either band la and lb associated with a trace band of the other isozyme. Though traces of stromal element and/or blood cells seem to be mixed among the neoplastic tissue, the pulmonary tumor could have originated from a single cell, when one takes into account the significantly higher expression in one band.

Inayama Y et al; Yokohama Med Bull 38 (5-6): 133-40 (1987)


The suitability of urethane anesthesia for physiopharmacological investigations is reviewed. Total dose administered and route of administration are recognized as factors having a great influence on both resting parameters and biological responses to drugs. A peculiar characteristic of urethane is represented by its ability to induce a surgical plane of anesthesia without affecting neurotransmission in various subcortical areas and the peripheral nervous system. This makes urethane a suitable general anesthetic nervous systems and accounts for the preservation of a number of reflex responses in urethane anesthetized animals.

PMID:2868911 Maggi CA, Meli A; Experientia 42 (2): 109-14 (1986)


The carbamates alone weakly activated estrogen- or progesterone-responsive reporter genes in breast and endometrial cancer cells. All of the carbamates decreased estradiol- or progesterone-induced reporter gene activity in the breast and endometrial cancer cells. In whole cell competition binding assays, the carbamates demonstrated a limited capacity to displace radiolabeled estrogen or progesterone from /estrogen receptor/ or /progesterone receptor/. /Carbamates/

PMID:9126867 Klotz D et al; Life Sciences 60 (17): 1467-1475 (1997)


... Urethane potentiated the functions of neuronal nicotinic acetylcholine, gamma-aminobutyric acid(A), and glycine receptors, and it inhibited N-methyl-D-aspartate and alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid receptors in a concentration-dependent manner. At concentrations close to anesthetic 50% effective concentration, urethane had modest effects on all channels tested. ... A large concentration of urethane exerts marked effects on all channels.

PMID:11812690 Hara K, Harris RA; Anesth Analg 94 (2): 313-8 (2002)


For more Mechanism of Action (Complete) data for ETHYL CARBAMATE (7 total), please visit the HSDB record page.


ABOUT THIS PAGE

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Urethane manufacturers, exporters & distributors 1

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Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Urethane manufacturer or Urethane supplier.

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API | Excipient name

Urethane

Synonyms

Ethyl carbamate, 51-79-6, Urethan, Carbamic acid, ethyl ester, Ethylurethane, Carbamic acid ethyl ester

Cas Number

51-79-6

Unique Ingredient Identifier (UNII)

3IN71E75Z5

About Urethane

Antineoplastic agent that is also used as a veterinary anesthetic. It has also been used as an intermediate in organic synthesis. Urethane is suspected to be a carcinogen.

Urethane Manufacturers

A Urethane manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Urethane, including repackagers and relabelers. The FDA regulates Urethane manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Urethane API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Urethane Suppliers

A Urethane supplier is an individual or a company that provides Urethane active pharmaceutical ingredient (API) or Urethane finished formulations upon request. The Urethane suppliers may include Urethane API manufacturers, exporters, distributors and traders.

Urethane GMP

Urethane Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Urethane GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Urethane GMP manufacturer or Urethane GMP API supplier for your needs.

Urethane CoA

A Urethane CoA (Certificate of Analysis) is a formal document that attests to Urethane's compliance with Urethane specifications and serves as a tool for batch-level quality control.

Urethane CoA mostly includes findings from lab analyses of a specific batch. For each Urethane CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Urethane may be tested according to a variety of international standards, such as European Pharmacopoeia (Urethane EP), Urethane JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Urethane USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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