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Chemistry

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Also known as: 19-nortestosterone, 434-22-0, 19-norandrostenolone, Norandrostenolone, Nortestosterone, Menidrabol
Molecular Formula
C18H26O2
Molecular Weight
274.4  g/mol
InChI Key
NPAGDVCDWIYMMC-IZPLOLCNSA-N
FDA UNII
6PG9VR430D

Nandrolone
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.
Nandrolone is an Androgen.
1 2D Structure

Nandrolone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
2.1.3 InChI Key
NPAGDVCDWIYMMC-IZPLOLCNSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@H]34
2.2 Other Identifiers
2.2.1 UNII
6PG9VR430D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17-hydroxy-estr-4-ene-3-one

2. 17beta Hydroxy 19 Nor 4 Androsten 3 One

3. 17beta-hydroxy-19-nor-4-androsten-3-one

4. 19-nortestosterone

5. Estrenolone

6. Norandrostenolone

7. Nortestosterone

2.3.2 Depositor-Supplied Synonyms

1. 19-nortestosterone

2. 434-22-0

3. 19-norandrostenolone

4. Norandrostenolone

5. Nortestosterone

6. Menidrabol

7. 17beta-hydroxy-4-estren-3-one

8. 4-estren-17beta-ol-3-one

9. Nortestosteronum

10. Nandrolon

11. Nortestonate

12. Nandrolona

13. Nandrolonum

14. Oestrenolon

15. Norandrostenolon

16. 17beta-hydroxy-19-nor-4-androsten-3-one

17. 17beta-hydroxyestr-4-en-3-one

18. (17beta)-17-hydroxyestr-4-en-3-one

19. 17-beta-hydroestr-4-en-3-one

20. Nandrolone Ciii

21. (17-beta)-17-hydroxyestr-4-en-3-one

22. Nandrolone (inn)

23. Nandrolone [inn]

24. (8r,9s,10r,13s,14s,17s)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one

25. Chembl757

26. 6pg9vr430d

27. Chebi:7466

28. Estr-4-en-3-one, 17-hydroxy-, (17b)-

29. Nsc 3351

30. Nsc-3351

31. Ncgc00159416-02

32. U 2410

33. Dsstox_cid_3350

34. (+)-19-nortestosterone

35. Dsstox_rid_76987

36. Dsstox_gsid_23350

37. Nandrolonum [inn-latin]

38. Nandrolona [inn-spanish]

39. Decadura

40. Decadura (tn)

41. Cas-434-22-0

42. Smr000058610

43. Hsdb 3368

44. Nandrolone [inn:ban]

45. Einecs 207-101-0

46. Estr-4-en-3-one, 17-hydroxy-, (17beta)-

47. Estr-4-en-3-one, 17beta-hydroxy-

48. 4-estren-17.beta.-ol-3-one

49. Unii-6pg9vr430d

50. Nandrolone Base

51. Ncgc00164479-01

52. 19-nor-testosterone

53. Biobol

54. Estr-4-en-3-one, 17-beta-hydroxy-

55. 17.beta.-nandrolone

56. Nandrolone [mi]

57. Nandrolone Decanoic Acid

58. Estr-4-en-3-one, 17-hydroxy-, (17.beta.)-

59. Enta[a]phenanthren-3-one

60. Nandrolone [hsdb]

61. 17.beta.-nortestosterone

62. Nandrolone [vandf]

63. Ec 207-101-0

64. Nandrolone [mart.]

65. Estr-4-en-3-one, 17-hydroxy-, (17-beta)-

66. Nandrolone [who-dd]

67. Schembl20140

68. Mls001423989

69. Mls002222325

70. 17-hydroxyestr-4-en-3-one

71. Nandrolone(19-nortestosterone)

72. Gtpl6949

73. Dtxsid7023350

74. Deca-durabolin (decanoate Ester)

75. Nandrolone Ciii [usp-rs]

76. Durabolin (phenylpropionate Ester)

77. Hms2051i04

78. Hms2098e05

79. Hms2272p06

80. Hms3715e05

81. Zinc3814379

82. Tox21_113167

83. Tox21_113199

84. Tox21_201212

85. Bdbm50080092

86. Lmst02010044

87. Akos015894933

88. Nandrolone 1.0 Mg/ml In Acetonitrile

89. Tox21_113167_1

90. Ccg-100835

91. Cs-1416

92. Db13169

93. Gs-6819

94. Nc00085

95. 4-estren-3-one-17.beta.-ol

96. Nandrolone 1000 Microg/ml In Methanol

97. Ncgc00159416-03

98. Ncgc00159416-04

99. Ncgc00258764-01

100. (8r,9s,10r,13s,14s,17s)-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3h-cyclopenta[a]phenanthren-3-one

101. Ac-15207

102. Ac-30575

103. Cpd000058610

104. Hy-17432

105. 19-nortestosterone, >=99.0% (hplc)

106. 19-nortestosterone 100 Microg/ml In Methanol

107. C07254

108. D08250

109. Nandrolone, Vetranal(tm), Analytical Standard

110. 434n220

111. Q421709

112. Sr-01000781257

113. Sr-01000781257-3

114. W-106227

115. Nandrolone Decanoate Impurity D [ep Impurity]

116. Nandrolone, British Pharmacopoeia (bp) Reference Standard

117. Nandrolone, United States Pharmacopeia (usp) Reference Standard

118. (1s,2r,10r,11s,14s,15s)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

119. (8~{r},9~{s},10~{r},13~{s},14~{s},17~{s})-13-methyl-17-oxidanyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1~{h}-cyclop

120. (8~{r},9~{s},10~{r},13~{s},14~{s},17~{s})-13-methyl-17-oxidanyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1~{h}-cyclopenta[a]phenanthren-3-one

121. (8r,10r,13s,17s)-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

122. 6vw

123. Nandrolone Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 274.4 g/mol
Molecular Formula C18H26O2
XLogP32.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass274.193280068 g/mol
Monoisotopic Mass274.193280068 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity466
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)


Nandrolone decanoate ... /is/ indicated in conditions such as chronic infections, extensive surgery, corticosteroid-induced myopathy, decubitus ulcers, burns, or severe trauma, which require reversal of catabolic processes or protein-sparing effects. /This agent is/ ... adjunct to, and not replacement for, conventional treatment of these disorders. /NOT included in US product labeling/

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


Nandrolone decanoate is indicated for the treatment of anemia associated with renal insufficiency (and as adjuvant therapy for aplastic and sickle cell anemias /NOT included in US product labeling/) Adequate iron intake is necessary for maximum therapeutic response. /Included in US product labeling/

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


Nandrolone phenpropionate is indicated in the treatment of refractory deficient red cell production anemias. These may include aplastic anemia, myelofibrosis, myelosclerosis, agnogenic myeloid metaplasia, and hypoplastic anemias caused by malignancy or myelotoxic drugs. Anabolic steroid therapy should not replace other supportive measures. /NOT included in US product labeling/

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


For more Therapeutic Uses (Complete) data for NANDROLONE (10 total), please visit the HSDB record page.


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 and 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


Anabolic steroids are not recommended for use during pregnancy, since studies in animals have shown that anabolic steroids cause masculinization of the fetus. Risk-benefit must be carefully considered. /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


Contraindications: Hypersensitivity to anabolic steroids; male patients with prostate or breast carcinoma; carcinoma of the breast in females with hypercalcemia; nephrosis; the nephrotic phase of nephritis; pregnancy; to enhance physical appearance or athletic performance. /Anabolic steroids/

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334


Anabolic agents may accelerate epiphyseal maturation more rapidly than linear growth in children, and the effect may continue for 6 months after the drug has been stopped. Therefore, monitor therapy by x-ray studies at 6 month intervals to avoid the risk of compromising adult height. Safety and efficacy in children with hereditary angioedema or metastatic breast cancer (rarely found) have not be established. /Anabolic steroids/

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334


For more Drug Warnings (Complete) data for NANDROLONE (16 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.)


Androgens

Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
NANDROLONE
5.2.2 FDA UNII
6PG9VR430D
5.2.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Androgen
5.3 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AB - Estren derivatives

A14AB01 - Nandrolone


S - Sensory organs

S01 - Ophthalmologicals

S01X - Other ophthalmologicals

S01XA - Other ophthalmologicals

S01XA11 - Nandrolone


5.4 Absorption, Distribution and Excretion

Metabolic studies of (14)c-labe nortestosterone were carried out in mice and in calves. Radioactivity was quickly eliminated mainly in urine and feces. 10 wk after admin residual levels were low. Rapid absorption and elimination may be important in vet use.

RICO AG ET AL; ANN RECH VET 8(2) 135 (1977)


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


5.5 Metabolism/Metabolites

Isomers of 3-hydroxyestran-17-one estrane-3,17-diol were identified by gas-liq chromatography-mass spectrometry in urine of a crossbred horse given 19-nortestosterone im.

HOUGHTON E; XENOBIOTICA 7(11) 683 (1977)


Metabolic studies of (14)c-labeled nortestosterone were carried out in mice by macroscopic autoradiog and in calves by liq scintillation determination of excretion and organ distribution. Radioactivity quickly eliminated in urine and feces. 10 wk after admin residual levels were low.

RICO AG ET AL; ANN RECH VET 8(2) 135 (1977)


5.6 Mechanism of Action

Functionally overloading rat soleus muscle by synergist ablation induces a rapid increase in mass. Muscle remodeling during the first week of overload is critical for the overload-induced growth. Anabolic steroid modulation of this overload-induced remodeling response is not well understood. The purpose of this study was to determine whether pretreatment with nandrolone decanoate, a clinically administered anabolic steroid, alters muscle morphology and gene expression related to muscle growth during the initiation of functional overload in the rat soleus muscle. Adult (5 mo) male Fisher 344 x Brown Norway rats were randomly assigned to control (Sham), 3-day functional overload (OV), nandrolone decanoate administration (ND), or 3-day functional overload with nandrolone decanoate administration (OV+ND) treatment groups. Morphologically, OV increased the percentage of small (361%) and large (150%) fibers and expanded the ECM 50%. ND administration decreased the 3-day OV induction of small fibers 51% and nuclei associated with the ECM 20%. ND administration also attenuated the induction of cell cycle regulator p21 (64%) and myogenin (37%) mRNAs after 3 days of overload. These data demonstrate that nandrolone decanoate pretreatment can alter morphological and cell cycle regulator expression related to muscle growth at the onset of functional overload.

PMID:15886356 McClung JM et al; Am J Physiol Regul Integr Comp Physiol 288 (6): R1543-52 (2005)


Anabolic-androgenic steroids (AASs) are widely abused by adolescents, although persistent AAS use can cause several adverse physical and mental effects, including drug dependence. The first aim of the present study was to study the action of nandrolone decanoate on dopaminergic and serotonergic activities in the brains of rats. In order to evaluate the anabolic or toxic effects of the dosing regimens used, selected peripheral effects were monitored as well. Male Wistar rats were treated for 2 weeks. Injections containing nandrolone (5 and 20 mg/kg, i.m.) or vehicle were given once daily, 5 days a week. The levels of dopamine (DA), 5-hydroxytryptamine (5-HT) and their metabolites were assayed from dissected brain regions 3 days after the last injection. Blood was collected for chemical assays before, after 1 week treatment and at decapitation. Both doses of nandrolone significantly increased the levels of 3,4-dihydroxyphenylacetic acid (DOPAC), a metabolite of DA in the cerebral cortex, and the higher dose of nandrolone increased the concentrations of 5-HT in the cerebral cortex compared with the vehicle. In addition, after nandrolone treatment, the levels of hemoglobin and erythrocytes increased, and reticulocyte levels decreased. The results suggest that nandrolone at supraphysiological doses, high enough to induce erythropoiesis, induces changes in the dopaminergic and serotonergic neuronal system in the brains of rats. These phenomena may account to some of the observed central stimulatory properties that have been reported following AAS abuse.

PMID:15862791 Kurling S et al; Brain Res 1044 (1): 67-75 (2005)


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


Antianemic: Anemias due to bone marrow failure: Increases production and urinary excretion of erythropoietin. Anemias due to deficient red cell production : Stimulates erythropoietin production and may have a direct action on bone marrow. Anemias associated with renal disease: increases hemoglobin and red blood cell volume. /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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