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Chemistry

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Also known as: Maxibolin, Orabolin, Ethylnandrol, Duraboral, Durabolin-o, Ethylestrenolum
Molecular Formula
C20H32O
Molecular Weight
288.5  g/mol
InChI Key
AOXRBFRFYPMWLR-XGXHKTLJSA-N
FDA UNII
ADC79EK5Q8

Ethylestrenol
An anabolic steroid with some progestational activity and little androgenic effect.
1 2D Structure

Ethylestrenol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,10R,13S,14S,17S)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
2.1.2 InChI
InChI=1S/C20H32O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h6,15-18,21H,3-5,7-13H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1
2.1.3 InChI Key
AOXRBFRFYPMWLR-XGXHKTLJSA-N
2.1.4 Canonical SMILES
CCC1(CCC2C1(CCC3C2CCC4=CCCCC34)C)O
2.1.5 Isomeric SMILES
CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CCCC[C@H]34)C)O
2.2 Other Identifiers
2.2.1 UNII
ADC79EK5Q8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ethyloestrenol

2. Maxibolin

2.3.2 Depositor-Supplied Synonyms

1. Maxibolin

2. Orabolin

3. Ethylnandrol

4. Duraboral

5. Durabolin-o

6. Ethylestrenolum

7. Etilestrenol

8. Ethyloestrenol

9. 965-90-2

10. Neodurabolin

11. Maxibalin

12. Orgabolin

13. Orgaboral

14. 17alpha-ethylestr-4-en-17beta-ol

15. 17alpha-ethyl-17beta-hydroxy-4-estrene

16. 19-nor-17alpha-pregn-4-en-17beta-ol

17. 17beta-hydroxy-17alpha-ethyl-19-nor-4-androstene

18. (17alpha)-19-norpregn-4-en-17-ol

19. Adc79ek5q8

20. Chebi:31578

21. Ethylnandrol (jan)

22. Nsc-37726

23. Ncgc00167514-01

24. Org-483

25. Ethyloestrenolum

26. Nsc 37726

27. Dsstox_cid_3024

28. Ethylnandrol [jan]

29. Dsstox_rid_76835

30. Dsstox_gsid_23024

31. (8r,9s,10r,13s,14s,17s)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ol

32. Etilestrenolo [dcit]

33. Etilestrenolo

34. (17beta)-17-ethylestr-4-en-17-ol

35. Etilestrenol [inn-spanish]

36. Ethylestrenolum [inn-latin]

37. Cas-965-90-2

38. Smr000238204

39. Hsdb 3327

40. 19-norpregn-4-en-17-ol, (17alpha)-

41. Einecs 213-523-6

42. Estr-4-en-17beta-ol, 17-ethyl-

43. Unii-adc79ek5q8

44. (17-alpha)-19-norpregn-4-en-17-ol

45. Ethylestrenol [usan:inn:ban]

46. Orabolin (tn)

47. 19-nor-17alpha-pregn-4-en-17-ol

48. 19-nor-17.alpha.-pregn-4-en-17.beta.-ol

49. 19-nor-17-alpha-pregn-4-en-17-ol

50. 19-norpregn-4-en-17-ol, (17-alpha)-

51. Ethylestrenol [mi]

52. Ethylestrenol [inn]

53. Ethylestrenol (usan/inn)

54. Ethylestrenol [hsdb]

55. Ethylestrenol [usan]

56. Ethylestrenol [vandf]

57. Mls000759411

58. Mls001424123

59. Ethylestrenol [mart.]

60. Schembl147908

61. Ethylestrenol [who-dd]

62. Gtpl6948

63. Chembl1200623

64. Dtxsid6023024

65. Hms2051p08

66. Ethylestrenol [orange Book]

67. Zinc4215863

68. Tox21_112512

69. Tox21_112512_1

70. Ccg-101014

71. Db01493

72. Nc00264

73. Ncgc00167514-02

74. D01414

75. Q764283

76. 19-norpregn-4-en-17-ol, (17.alpha.)

77. W-100138

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 288.5 g/mol
Molecular Formula C20H32O
XLogP35.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass288.245315640 g/mol
Monoisotopic Mass288.245315640 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count21
Formal Charge0
Complexity453
Isotope Atom Count0
Defined Atom Stereocenter Count6
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

Anabolic Steroids

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


/Ethylestrenol/ has been used in for the promotion of growth in boys with short stature or delayed bone growth.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 1554


4.2 Drug Warning

Use of anabolic steroids by athletes is not recommended. Objective evidence is conflicting and inconclusive as to whether these medications significantly increase athletic performance by increasing muscle strength. Weight gains reported by athletes are due in part to fluid retention, which is a potentially hazardous side effect of anabolic steroid therapy. The risk of other unwanted effects, such as testicular atrophy and suppression of spermatogenesis in males; menstrual disturbances and virilization, such as deepening of voice, development of acne, and unnatural growth of body hair in females; peliosis hepatis or other hepatotoxicity; and hepatic cancer outweigh any possible benefit received from anabolic steroids and make their use in athletes inappropriate. /Anabolic Steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140


Hepatocellular carcinoma has been associated rarely with long-term, high-dose anabolic steroid therapy. /Anabolic Steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


Hepatic neoplasms have been associated rarely with long-term, high-dose anabolic steroid therapy. /Anabolic Steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


FDA Pregnancy Category X. /CONTRAINDICATED IN PREGNANCY. Studies in animals and or humans, or investigational or post-marketing reports, have demonstrated positive evidence of fetal abnormalities or risk which clearly outweighs any possible benefit to the patient./

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


For more Drug Warnings (Complete) data for ETHYLESTRENOL (17 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anabolic Agents

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)


5.2 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AB - Estren derivatives

A14AB02 - Ethylestrenol


5.3 Absorption, Distribution and Excretion

The absorption, distribution, metabolism and excretion of [3H]ethylestrenol were studied in the rat. 2. Approximately one third of an intragastric dose was absorbed; 17% of the dose was excreted in urine and 83% in faeces within 10 days. 3. The dose is distributed throughout the rat, and kidney and liver were found to contain respectively 2.5-3 and 5-7 times the average specific activity of all other tissues. 4. Unchanged ethylestrenol was the only component detected in urine. Ethylestrenol was also found in faeces, along with two different dihydroxylated dihydro derivatives and one trihydroxylated dihydro derivative.

PMID:7233967 Stelle JW et al; Xenobiotica 11(2):103-15 (1981)


It is not known whether anabolic steroids are distributed into breast milk. /Anabolic Steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


5.4 Metabolism/Metabolites

Ethylestrenol incubated with a post-mitochondrial supernatant fraction of rat liver plus co-factors gives norethandrolone as the major metabolite. A second (minor) metabolite was tentatively identified as 17 alpha-ethyl-5 epsilon-estrane-3 epsilon,17 beta-diol. A pathway is suggested for the metabolism of ethylestrenol in the rat.

PMID:7233968 Steele JW et al; Xenobiotica. 1981 Feb;11(2):117-21.


Orabolin was oxidized at C-3 to form nilevar which in turn was metabolized in man by a ring reduction and side chain hydroxylation to form a 19-norpregnatriol. Identification of this metabolite, detection in urine is test for athletes suspected of drug misuse.

PMID:410996 Ward et al; J Steroid Biochem 8 (10): 1057-63 (1977)


5.5 Mechanism of Action

Anabolic steroids reverses catabolic processes and negative nitrogen balance by promoting protein anabolism and stimulating appetite if there is concurrently a proper intake of calories and proteins. /Anabolic Steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


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Ethylestrenol manufacturers, exporters & distributors 1

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API | Excipient name

Ethylestrenol

Synonyms

Maxibolin, Orabolin, Ethylnandrol, Duraboral, Durabolin-o, Ethylestrenolum

Cas Number

965-90-2

Unique Ingredient Identifier (UNII)

ADC79EK5Q8

About Ethylestrenol

An anabolic steroid with some progestational activity and little androgenic effect.

Ethylestrenol Manufacturers

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

click here to find a list of Ethylestrenol manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Ethylestrenol Suppliers

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

click here to find a list of Ethylestrenol suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Ethylestrenol USDMF

A Ethylestrenol DMF (Drug Master File) is a document detailing the whole manufacturing process of Ethylestrenol active pharmaceutical ingredient (API) in detail. Different forms of Ethylestrenol DMFs exist exist since differing nations have different regulations, such as Ethylestrenol USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Ethylestrenol DMF submitted to regulatory agencies in the US is known as a USDMF. Ethylestrenol USDMF includes data on Ethylestrenol's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Ethylestrenol USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Ethylestrenol suppliers with USDMF on PharmaCompass.

Ethylestrenol GMP

Ethylestrenol 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 Ethylestrenol 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 Ethylestrenol GMP manufacturer or Ethylestrenol GMP API supplier for your needs.

Ethylestrenol CoA

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

Ethylestrenol CoA mostly includes findings from lab analyses of a specific batch. For each Ethylestrenol 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.

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