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2D Structure
Also known as: Nandrolone phenylpropionate, 62-90-8, Nortestosterone phenylpropionate, Nadrolone phenylpropionate, Nandrolon phenylpropionate, Fenobolin
Molecular Formula
C27H34O3
Molecular Weight
406.6  g/mol
InChI Key
UBWXUGDQUBIEIZ-QNTYDACNSA-N
FDA UNII
KF7Z9K2T3W

C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] 3-phenylpropanoate
2.1.2 InChI
InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/m0/s1
2.1.3 InChI Key
UBWXUGDQUBIEIZ-QNTYDACNSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2OC(=O)CCC4=CC=CC=C4)CCC5=CC(=O)CCC35
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4=CC=CC=C4)CCC5=CC(=O)CC[C@H]35
2.2 Other Identifiers
2.2.1 UNII
KF7Z9K2T3W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17 Beta-hydroxyestr-4-en-3-one Hydrocinnamate

2. Durabolin

3. Fenobolin

4. Nandrolone Phenpropionate, (17alpha)-isomer

5. Nerobolil

6. Nerobolyl

7. Norandrolone Phenylpropionate

8. Nortestosterone Phenylpropionate

9. Nsc-23162e

2.3.2 Depositor-Supplied Synonyms

1. Nandrolone Phenylpropionate

2. 62-90-8

3. Nortestosterone Phenylpropionate

4. Nadrolone Phenylpropionate

5. Nandrolon Phenylpropionate

6. Fenobolin

7. Nandrolin

8. Nerobolil

9. Norandrostenolone Phenylpropionate

10. Superanabolon

11. Durabolin

12. Phenobolin

13. Norandrolone Phenyl Propionate

14. Ntpp

15. 19ntpp

16. Norandrolone Phenylpropionate

17. Nandrolone Phenylpionate

18. Nandrobolic

19. Strabolene

20. 19-nortestosterone, Hydrocinnamate

21. 19-nortestosterone Phenylpropionate

22. 19-nortestosterone Phenyl Propionate

23. 19-norandrostenolone Phenylpropionate

24. Kf7z9k2t3w

25. Activin

26. Nerobil

27. Sk 22271

28. Chebi:7468

29. [(8r,9s,10r,13s,14s,17s)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl] 3-phenylpropanoate

30. Nandrolone Phenpropionate [usp]

31. (17beta)-3-oxoestr-4-en-17-yl 3-phenylpropanoate

32. Nsc-23162

33. Anticatabolin

34. Estr-4-en-3-one, 17-(1-oxo-3-phenylpropoxy)-, (17b)-

35. Dsstox_cid_3353

36. 17-(1-oxo-3-phenylpropoxy)estr-4-en-3-one

37. Dsstox_rid_76989

38. Dsstox_gsid_23353

39. Nandrolone Phenpropionate (usp)

40. Nandrolone Phenylpropionate (jan)

41. Sintabolin

42. Anabosan

43. Equibolin

44. Norandrol

45. Cas-62-90-8

46. Durabolin-50

47. Nandrolone Phenylpropionate [jan]

48. 17b-hydroxyestr-4-en-3-one 17-(3-phenylpropionate)

49. Unii-kf7z9k2t3w

50. Activine

51. Durabolin (tn)

52. Ncgc00159356-02

53. Einecs 200-551-9

54. Nsc 23162

55. 17.beta.-phenylpropionyloxy-4-estrene-3-one

56. Brn 3170861

57. 17-.beta.-hydroxyestr-4-en-3-one Hydrocinnamate

58. 17-beta-phenylpropionyloxy-4-estren-3-one

59. 17beta-phenylpropionyloxy-4-estrene-3-one

60. 17beta-hydroxyestr-4-en-3-one Hydrocinnamate

61. 17-beta-hydroxyestr-4-en-3-one Hydrocinnamate

62. Schembl8443

63. 3-oxo-4-estren-17beta-yl-(3-phenylpropionat)

64. 4-09-00-01758 (beilstein Handbook Reference)

65. Nortestosterone Furanpropionate

66. 17-beta-hydroxy-estra-4-en-3-one, 17-phenylpropionate

67. Chembl1200412

68. Dtxsid2023353

69. 17-beta-hydroxyestr-4-en-3-one 17-(3-phenylpropionate)

70. Estr-4-ene-3-one, 17-beta-hydroxy-, 3-phenylpropionate

71. Estr-4-en-3-one, Hydrocinnamate

72. Estr-4-en-3-one, 17-(1-oxo-3-phenylpropoxy)-, (17beta)-

73. (8r,9s,10r,13s,14s,17s)-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl 3-phenylpropanoate

74. Nsc23162

75. Zinc3881613

76. Tox21_113342

77. Nandrolone Phenpropionate Ciii

78. Nandrolone Phenpropionate [mi]

79. Akos015888240

80. Tox21_113342_1

81. Db00984

82. Ds-3294

83. Nandrolone Phenpropionate [vandf]

84. Ncgc00274069-01

85. Nandrolone Phenpropionate [who-dd]

86. Nandrolone Phenylpropionate [mart.]

87. 3-oxoestr-4-en-17beta-yl 3-phenylpropanoate

88. C08155

89. D00956

90. Nandrolone Phenpropionate [orange Book]

91. Nandrolone Phenpropionate [usp Impurity]

92. 198n407

93. Estr-4-en-3-one, 17beta-hydroxy-, Hydrocinnamate

94. Nandrolone Phenpropionate 100 Microg/ml In Methanol

95. Q4312826

96. W-104946

97. Estr-4-en-3-one, 17-beta-hydroxy-, Hydrocinnamate

98. (1s,2r,10r,11s,14s,15s)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 406.6 g/mol
Molecular Formula C27H34O3
XLogP35.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass406.25079494 g/mol
Monoisotopic Mass406.25079494 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count30
Formal Charge0
Complexity703
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 Drug Indication

For the treatment of refractory deficient red cell production anemias, breast carcinoma, hereditary angioedema, antithrombin III deficiency, fibrinogen excess, growth failure and Turner's syndrome. It is also indicated in the prophylaxis of hereditary angioedema.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone increases production and urinary excretion of erythropoietin. It may also have a direct action on bone marrow. Nandrolone binds to the androgen receptor to a greater degree than testosterone, but due to its inability to act on the muscle in ways unmediated by the receptor, has less overall effect on muscle growth.


5.2 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.)


5.3 Absorption, Distribution and Excretion

Absorption

The absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions.


5.4 Metabolism/Metabolites

Nandrolone is unusual in that unlike most anabolic steroids, it is not broken down into the more reactive DHT by the enzyme 5-reductase, but rather into a less effective product known as Dihydronandrolone.


5.5 Biological Half-Life

The elimination half-life from plasma is very short.


5.6 Mechanism of Action

Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.