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DSSTox_CID_3352
Also known as: 360-70-3, Retabolil, 19-nortestosterone decanoate, Norandrostenolone decanoate, Deca-hybolin, Nortestosterone decanoate
Molecular Formula
C28H44O3
Molecular Weight
428.6  g/mol
InChI Key
JKWKMORAXJQQSR-MOPIKTETSA-N
FDA UNII
H45187T098

Decanoic acid ester of nandrolone that is used as an anabolic agent to prevent or treat WASTING SYNDROME associated with severe chronic illness or HIV infection (HIV WASTING SYNDROME). It may also be used in the treatment of POSTMENOPAUSAL OSTEOPOROSIS.
1 2D Structure

DSSTox_CID_3352

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] decanoate
2.1.2 InChI
InChI=1S/C28H44O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h19,22-26H,3-18H2,1-2H3/t22-,23+,24+,25-,26-,28-/m0/s1
2.1.3 InChI Key
JKWKMORAXJQQSR-MOPIKTETSA-N
2.1.4 Canonical SMILES
CCCCCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C
2.1.5 Isomeric SMILES
CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C
2.2 Other Identifiers
2.2.1 UNII
H45187T098
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17 Beta Hydroxyestr 4 En 3 One 17 Decanoate

2. 17 Beta-hydroxyestr-4-en-3-one 17-decanoate

3. 19 Nor 4 Androstene 17 Beta Ol 3 One 17 Decanoate

4. 19 Nortestosterone Decanoate

5. 19-nor-4-androstene-17 Beta-ol-3-one 17-decanoate

6. 19-nortestosterone Decanoate

7. Decadurabolin

8. Decadurobolin

9. Retabolil

10. Retabolyl

2.3.2 Depositor-Supplied Synonyms

1. 360-70-3

2. Retabolil

3. 19-nortestosterone Decanoate

4. Norandrostenolone Decanoate

5. Deca-hybolin

6. Nortestosterone Decanoate

7. Hybolin Decanoate

8. Estr-4-en-3-one, 17-[(1-oxodecyl)oxy]-, (17b)-

9. Nandrolone Decanoate Ciii

10. Chebi:7467

11. [(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] Decanoate

12. Retabolyl

13. Nandrobolic L.a.

14. 19-norandrostenolone Decanoate

15. Naboline

16. 19-nortestosterone 17-decanoate

17. Ncgc00159403-02

18. Salistoperm

19. Dimapolan

20. Palactin

21. Rougerol

22. Superbolan

23. Ziremilon

24. Anaboline Depot

25. Anabolin Depot

26. Ndrolone-d

27. H45187t098

28. Dsstox_cid_3352

29. Dsstox_rid_76988

30. Dsstox_gsid_23352

31. (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 Decanoate

32. Estr-4-en-3-one, 17-[(1-oxodecyl)oxy]-, (17.beta.)-

33. (1s,2r,10r,11s,14s,15s)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl Decanoate

34. Cas-360-70-3

35. Drg 0264

36. Einecs 206-639-3

37. Brn 2228051

38. 17beta-hydroxyestr-4-en-3-one Decanoate

39. Deca-durobolin

40. 17-beta-hydroxyestr-4-en-3-one Decanoate

41. Estr-4-en-3-one, 17-((1-oxodecyl)oxy)-, (17.beta.)-

42. 17beta-hydroxyestr-4-en-3-one 17-decanoate

43. Unii-h45187t098

44. (17-beta)-17-((1-oxodecyl)oxy)estr-4-en-3-one

45. Nandrolone Decanoate [usan:usp:jan]

46. Deca-durabolin (tn)

47. Nandrolonedecanoate

48. (17beta)-3-oxoestr-4-en-17-yl Decanoate

49. Nandrolone 17beta-decanoate

50. Estr-4-en-3-one, 17-beta-hydroxy-, Decanoate

51. Schembl27975

52. Chembl1200946

53. Dtxsid7023352

54. Nandrolone Decanoate (jan/usp)

55. Estr-4-en-3-one, 17-((1-oxodecyl)oxy)-, (17beta)-

56. Nandrolone Decanoate [mi]

57. Nandrolone Decanoate [jan]

58. Nandrolone Decanoate [usan]

59. Zinc8214619

60. Nandrolone Decanoate [vandf]

61. Tox21_111638

62. Mfcd00135100

63. Nandrolone Decanoate [mart.]

64. Nandrolone Decanoate [who-dd]

65. Akos025311438

66. Tox21_111638_1

67. 19-nortestosterone-17.beta.-decanoate

68. Ac-1484

69. Cs-4613

70. Db08804

71. Gs-3155

72. Ncgc00159403-04

73. Ncgc00263561-01

74. Hy-13698

75. Nandrolone Decanoate [ep Impurity]

76. Nandrolone Decanoate [orange Book]

77. Nandrolone Decanoate [ep Monograph]

78. Nandrolone Decanoate Ciii [usp-rs]

79. Nandrolone Decanoate [usp Monograph]

80. 17b-hydroxyestr-4-en-3-one Decanoate.

81. C08154

82. D00955

83. 360n703

84. A823112

85. Q16634231

86. 17.beta.-hydroxyestr-4-en-3-one 17-decanoate

87. Nandrolone Decanoate, European Pharmacopoeia (ep) Reference Standard

88. Nandrolone Decanoate, United States Pharmacopeia (usp) Reference Standard

89. Nandrolone Decanoate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

90. Nandrolone Decanoate For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 428.6 g/mol
Molecular Formula C28H44O3
XLogP37.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count10
Exact Mass428.32904526 g/mol
Monoisotopic Mass428.32904526 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count31
Formal Charge0
Complexity680
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 Information
1 of 2  
Drug NameNandrolone decanoate
Drug LabelA sterile oleaginous solution containing per mL: Nandrolone Decanoate 100 mg with Benzyl Alcohol 10% as solubilizer/preservative, in Sesame Oil q.s., and Nandrolone Decanoate 200 mg with Benzyl Alcohol 5% as solubilizer/preservative, in Sesame Oil q....
Active IngredientNandrolone decanoate
Dosage FormInjectable
RouteInjection
Strength200mg/ml
Market StatusPrescription
CompanyPharmaforce

2 of 2  
Drug NameNandrolone decanoate
Drug LabelA sterile oleaginous solution containing per mL: Nandrolone Decanoate 100 mg with Benzyl Alcohol 10% as solubilizer/preservative, in Sesame Oil q.s., and Nandrolone Decanoate 200 mg with Benzyl Alcohol 5% as solubilizer/preservative, in Sesame Oil q....
Active IngredientNandrolone decanoate
Dosage FormInjectable
RouteInjection
Strength200mg/ml
Market StatusPrescription
CompanyPharmaforce

4.2 Drug Indication

Nandrolone decanoate is indicated in the management of anemia of renal insufficiency. In Canada, it is also indicated as an adjunct therapy in the treatment of senile and postmenopausal osteoporosis.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nandrolone decanoate is an alkylated anabolic steroid indicated in the management of anemia of renal insufficiency and as an adjunct therapy in the treatment of senile and postmenopausal osteoporosis. It has a long duration of action as it is given every 3-4 weeks, and a wide therapeutic window as acute overdoses are rare. Patients should be counselled regarding the risks of giving this drug to patients with cardiac, renal, or hepatic diseases.


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.)


Bone Density Conservation Agents

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)


5.3 Absorption, Distribution and Excretion

Absorption

A 50 mg intramuscular dose of nandrolone decanoate reaches a mean Cmax 2.14 ng/mL, with a mean Tmax of 30 hours, and a mean AUC of 400 h\*ng/mL. A 100 mg intramuscular dose of nandrolone decanoate reaches a mean Cmax 4.26 ng/mL, with a mean Tmax of 30 hours, and a mean AUC of 862 h\*ng/mL. A 150 mg intramuscular dose of nandrolone decanoate reaches a mean Cmax 5.16 ng/mL, with a mean Tmax of 72 hours, and a mean AUC of 1261 h\*ng/mL.


Route of Elimination

Nandrolone decanoate is eliminated as urinary metabolites, however data regarding elimination in the feces are not readily available. Data in cattle shows that [nandrolone] is 30% eliminated in the feces.


Clearance

50 mg, 100 mg, and 150 mg doses of nadrolone decanoate had mean apparent clearances of 80.0 L/h, 74.3 L/h, and 76.2 L/h respectively.


5.4 Metabolism/Metabolites

Nandrolone decanoate is hydrolyzed to [nandrolone], possibly by PDE7B. Nandrolone is further metabolized to the urinary metabolites 19-norandrosterone, 19-noretiocholanolone, and 19-norepiandrosterone. 19-norandrosterone is 3-O-glucuronidated by UGT2B7, UGT 1A4, UGT2B4, UGT1A3, and UGT1A1. 19-noretiocholanolone is 3-O-glucuronidated by UGT2B7, UGT2B4, UGT1A4, UGT1A10, UGT1A3, and UGT1A1.


5.5 Biological Half-Life

Nandrolone decanoate has an absorption half life of 6 days and an elimination half life of 4.3 hours. Alternate studies have shown that nandrolone decanoate has a terminal half life of 7.1, 11.7, and 11.8 hours for doses of 50, 100, and 150 mg respectively.


5.6 Mechanism of Action

Nandrolone decanoate is hydrolyzed to [nandrolone], possibly by PDE7B. Nandrolone is brought into cells by receptor mediated endocytosis, where it interacts with the androgen receptor. After binding to the androgen receptor, a conformational change occurs, the androgen receptor enters the nucleus, dimerizes, and can then bind to segments of DNA to regulate transcription. Androgens can also regulate transcription through activation of ERK, Akt, and MAPK; or binding to and competitively inhibiting transcription factors.


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