(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl 3-phenylpropanoate

• ChemBase ID: 858
• Molecular Formular: C27H34O3
• Molecular Mass: 406.55706
• Monoisotopic Mass: 406.25079495
• 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)CCc1ccccc1
• Canonical SMILES: O=C(O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12)CCc1ccccc1
• 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
• InChIKey: UBWXUGDQUBIEIZ-QNTYDACNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl 3-phenylpropanoate; (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
• IUPAC Traditional name: activin
• Brand Name: Activin; Durabol; Durabolin; Fenobolin; Nandrobolic; Nerobil; Nerobiolil; Nerobolil; Phenobolin; Strabolene; Superanabolon
• Synonyms: (17β)-17-(1-Oxo-3-phenylpropoxy)-estr-4-en-3-one; 17β-(3-Phenylpropionyloxy)-estr-4-en-3-one; 19-Nor-17β-hydroxy-3-ketoandrost-4-ene 17-phenylpropionate; 19-Norandrostenolone phenylpropionate; Nerobil; Nerobolil; Phenobolin; Strabolene; Superanabolon; Nandrolone Phenylpropionate; 19-nortestosterone; Duranox; Dubol-100; Nadrolone phenylpropionate; Nandrolon phenylpropionate; Nandrolone phenylpionate; Nandrolone phenylpropionate; Nortestosterone phenylpropionate; Norandrostenolone phenylpropionate; Norandrolone phenyl propionate; NPP; NTPP; Testosterone phenylpropionate; 19NTPP; Nandrolin; Nandrolone phenpropionate; Testosterone phenylpropionate

Database IDs

• CAS Number: 434-22-0; 1255-49-8; 62-90-8
• PubChem SID: 46506276; 160964321
• PubChem CID: 229455

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.278885
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.78541
• LogD (pH = 7.4): 5.78541
• Log P: 5.78541
• Molar Refractivity: 118.4291 cm^3
• Polarizability: 46.689083 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.22
• LOG S: -5.95
• Solubility (Water): 4.58e-04 g/l

PROPERTIES

Physical Property

• Solubility: 3.09 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]; Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 85-87°C
• Hydrophobicity(logP): 2.62 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: -20°C; Controlled Substance, -20°C Freezer

Product Information

• Purity: 98%
• Salt Data: Phenpropionate

DETAILS

DrugBank - DB00984

• 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.
• 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.
• Half Life: The elimination half-life from plasma is very short.
• Protein Binding: 58%
• References: "InChem Data Sheet":http://www.inchem.org/documents/pims/pharm/pim909.htm
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1310

Related research area: Endocrinology

Toronto Research Chemicals - N315045

Anabolic Steroid.

REFERENCES

• "InChem Data Sheet":http://www.inchem.org/documents/pims/pharm/pim909.htm
• InChem Data Sheet
• www.drugs.com/pro/nandrolone.html
• Thevis, M., et al.: J. Anal. Toxicol., 32, 232 (2008)
• Pagonis, T., et al.: Clin. Toxicol., 46, 57 (2008)
• Zhang, Y., et al.: J. Food Sci., 74, T67 (2008)