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

• ChemBase ID: 1228
• Molecular Formular: C22H32O3
• Molecular Mass: 344.48768
• Monoisotopic Mass: 344.23514488
• SMILES: O([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)CC2)CC1)C)C(=O)CC
• Canonical SMILES: CCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
• InChIKey: PDMMFKSKQVNJMI-BLQWBTBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl propanoate; (1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl propanoate
• IUPAC Traditional name: androgen; testosterone propionate
• Brand Name: Testex; Agovirin
• Synonyms: Androlon; Androtest P; Androteston; Aquaviron; Bio-testiculina; Enarmon; Hormoteston; NRB 03689; NSC; (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl propionate; 17β-Hydroxy-4-androsten-3-one 17-propionate; 17β-Propionyloxy-4-androsten-3-one; 4-Androsten-17β-ol-3-one 17-propionate; Testosterone propionate; Testosteroni propionas; Testosterone Propionate; (17β)-17-(1-Oxopropoxy)androst-4-en-3-one; 17β-(Propionyloxy)androst-4-en-3-one; Agovirin; Testodrin; Testosterone-17-propionate; Testoviron; Testrex; Virormone; 丙酸睾酮; 丙酸睾丸素

Database IDs

• CAS Number: 57-85-2
• EC Number: 200-351-1
• MDL Number: MFCD00003653
• Beilstein Number: 3221760
• PubChem SID: 24888692; 160964688; 46508693; 24899994
• PubChem CID: 5995

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.086855
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.5070844
• LogD (pH = 7.4): 4.5070844
• Log P: 4.5070844
• Molar Refractivity: 98.2082 cm^3
• Polarizability: 38.92798 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.65
• LOG S: -4.84
• Solubility (Water): 5.02e-03 g/l

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble4.4 mg/mL; ethanol: soluble10 mg/mL; H2O: insoluble
• Apperance: white solid
• Melting Point: 118-123 °C
• Optical Rotation: [α]20/D +86±3°, c = 2% in dioxane

Safety Information

• Storage Condition: -20°C
• RTECS: XA3115000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-63-22
• Safety Statements: 53-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H350-H361
• GHS Precautionary statements: P201-P281-P308 + P313
• 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; USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Target: Androgen Receptor / Estrogen receptor
• Gene Information: human ... CYP17A1(1586)rat ... Ar(24208)

Product Information

• Purity: ≥97.0% (HPLC); 97%
• Grade: Ph Eur; purum; VETRANAL™, analytical standard
• Salt Data: Propionate
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C22H32O3

DETAILS

MP Biomedicals - 05218655

MP Biomedicals Rare Chemical collection

DrugBank - DB01420

• Drug Groups: approved
• Description: An ester of testosterone with a propionate substitution at the 17-beta position. [PubChem]
• Indication: Testosterone propionate is an anabolic steroid and a short ester form of testosterone that becomes active in the body. It is often used for muscle mass building.
• Pharmacology: Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does. In the body, this ester form of testosterone is hydrolyzed rapidly and become actively available as testosterone.
• Toxicity: Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
• Affected Organisms: Humans and other mammals
• Biotransformation: Testosterone propionate is rapidly hydrolysed into testosterone. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).
• Protein Binding: 40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
• Elimination: About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.
• External Links: Drugs.com

Selleck Chemicals - S2558

Biological Activity:
Testosterone propionate (Agovirin) is a direct androgen receptor activator and an indirect certain estrogen receptors activator. Testosterone propionate (Agovirin) increases the level of the IGF-1 hormone which leads to muscle growth. Testosterone propionate (Agovirin) has been used for the increase of the nitrogen in the muscles and this leads to the increase of the proteins in the muscles as well. When the muscle fibers have a lot of proteins, they increase in size and quality. As with other testosterones, testosterone propionate (Agovirin) leads to the increase in the activity of the satellite cells which leads to faster recovery after exercising among others. Testosterone propionate (Agovirin) also prevents muscles from wasting and maintains the quality of the muscles you have gained for some time. When testosterone propionate (Agovirin) comes to fat loss, testosterone propionate (Agovirin) is a leader as testosterone propionate (Agovirin) promotes muscle gain and fat loss. [1][2][3]References on Testosterone propionate (Agovirin)[] TEM, 1998, 9:317-324

Sigma Aldrich - T1875

Biochem/physiol Actions
Androgen.
Physical form
Photosensitive solid

Sigma Aldrich - 86541

Other Notes
Sales restrictions may apply

Sigma Aldrich - 86540

Other Notes
Sales restrictions may apply

Sigma Aldrich - 46925

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T155045

Anabolic steroid. Androgen.Controlled substance.

REFERENCES

• http://en.wikipedia.org/wiki/Testosterone
• Glass, A., et al.: J. Clin. Endocrinol. Metab., 45, 1211 (1977)
• Behre, H., et al.: Eur. J. Endocrinol., 140, 414 (1977)
• Nieschlag, E., et al.: Steroids, 68, 965 (1977)
• Wang, C., et al.: J. Clin. Endocrinol. Metab., 91, 460 (1977)