(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

• ChemBase ID: 6404
• Molecular Formular: C28H44O3
• Molecular Mass: 428.64716
• Monoisotopic Mass: 428.32904527
• SMILES: O([C@@H]1[C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CC(=O)CC2)CC3)CC1)C)C(=O)CCCCCCCCC
• Canonical SMILES: CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• 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
• InChIKey: JKWKMORAXJQQSR-MOPIKTETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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; (1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl decanoate
• IUPAC Traditional name: nandrolone decanoate
• Brand Name: Deca-Durabol; Deca-durabolin; Deca Durabolin; Retabolil
• Synonyms: Norandrostenolone decanoate; Nortestosterone decanoate; Nandrolone decanoate; 17β-Hydroxy-19-nor-4-androsten-3-one 17-decanoate; 17β-Hydroxy-4-estren-3-one 17-decanoate; 4-Estren-17β-ol-3-one 17-decanoate; Decadurabolin; Nandrolone decanoate; 19-Nortestosterone 17-decanoate; 17β-Hydroxy-19-norandrost-4-en-3-one 17-Decanoate; 17β-Hydroxyestr-4-en-3-one 17-Decanoate; 17β-Hydroxyestr-4-en-3-one Decanoate; 17β-Nandrolone laureate; 17β-Nortestosterone laureate; 19-Nor-17β-hydroxy-3-ketoandrost-4-ene 17-Decanoate; 19-Norandrostenolone Decanoate; 19-Nortestosterone 17β-Decanoate; 19-Nortestosterone Decanoate; Anabolicum; Anabolin Forte; Deca-Durabol; Deca-Durabolin; Deca-Hybolin; Decanofort; Extraboline; Hybolin Decanoate; Nandrobolic LA; Retabolil; 19-Nortestosterone 17-decanoate

Database IDs

• CAS Number: 360-70-3
• EC Number: 206-639-3
• MDL Number: MFCD00135100
• PubChem SID: 160969711
• PubChem CID: 9677

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.278885
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 7.319018
• LogD (pH = 7.4): 7.319018
• Log P: 7.319018
• Molar Refractivity: 125.9401 cm^3
• Polarizability: 49.98545 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.96
• LOG S: -6.44
• Solubility (Water): 1.57e-04 g/l

PROPERTIES

Physical Property

• Solubility: 3.09 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.8 mg/mL; DMSO: soluble10 mg/mL; ethanol: soluble5 mg/mL; H2O: insoluble
• Apperance: white to light yellow powder
• Hydrophobicity(logP): 2.62 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: KG7967000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: 98%

DETAILS

DrugBank - DB08804

• Drug Groups: illicit; approved
• Description: 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.
• 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.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Nandrolone is unusual in that unlike most anabolic steroids, it is not broken down into the more reactive DHT by the enzyme 5α-reductase, but rather into a less effective product known as Dihydronandrolone.
• Protein Binding: 58%
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - N6633

Biochem/physiol Actions
Anabolic steroid with a stimulatory effect on bone mass, muscle ultrastructure, and immune response.

Toronto Research Chemicals - N315020

Nandrolone Decanoate is an anabolic steroid. Nandrolone decanoate is used in the treatment of osteoporosis in postmenopausal women. Nandrolone Decanoate is also used for some aplastic anemias.Controlled Substance.

REFERENCES

• Dhem, A. et al.: Curr. Med. Res. Opin., 6, 606 (1980)
• Lippi, G. et al.: Scand. J. Clin. Lab. Invest., 57, 507 (1980)
• Frisoli, A. et al.: J. Gerontol. Ser. A Biol. Sci. Med. Sci., 60A, 648 (1980)
• Sheashaa, H. et al.: Nephron, 99, c102 (1980)