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Testosterone ( CASNO:58-22-0 )

Identification and Related Records
Name:
Testosterone
CAS Registry number:
58-22-0
Iupac name:
(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,
15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
17beta-Hydroxyandrost-4-en-3-one
testosterone--dea schedule iii
testosterone standard solution
testosterone gamma-irradiated cell*culture tested
testosterone cell culture tested--dea*schedule ii
Testosterone,99%
17-hydroxyandrost-4-en-3-one
EINECS(EC#):
200-370-5
Molecular Formula:
C19H28O2
Molecular Weight:
288.43
Inchi:
InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
Canonical SMILES:
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
Isomers smiles:
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@]34C
Chemical and Physical Properties
Appearance:
white crystalline odourless solid
Density:
1.12 g/cm3
Melting Point:
153-157℃
Boiling Point:
432.9 °C at 760mmHg
Refractive Index:
1.56
Flash Point:
432.9 °C at 760mmHg
Alpha:
101 o (C=1, DIOXANE 25 oC)
Solubilities:
Insoluble
Color/Form:
White needles from dil acetone
White or cream white crystalline powder
Crystals
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
Storage temp:
2-8°C
Spectral properties:
Specific optical rotation: +109 deg at 24 deg C/D (concentration by volume = 4 g in 100 ml alcohol)
Max absorption: 238 nm
SADTLER REFERENCE NUMBER: 727 (IR, PRISM); 13203 (IR, PRISM), 3128 (NMR)
IR: 5450 (Coblentz Society Spectral Collection)
UV: 7-851 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 11900 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 483 FT (Johnson and Jankowski, Carbon 13 NMR Spectra, John Wiley and Sons, NY)
MASS: 62026 (NIST/EPA/MSDC Mass Spectral Data Base, 1990 Version)
Intense mass spectral peaks: 124 m/z, 246 m/z, 288 m/z
Computed Properties:
Molecular Weight:288.42442 [g/mol]
Molecular Formula:C19H28O2
XLogP3:3.3
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:0
Tautomer Count:5
Exact Mass:288.20893
MonoIsotopic Mass:288.20893
Topological Polar Surface Area:37.3
Heavy Atom Count:21
Formal Charge:0
Complexity:508
Isotope Atom Count:0
Defined Atom Stereocenter Count:6
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Ring Count:4
Effective Rotor Count:1.8
Conformer Sampling RMSD:0.6
CID Conformer Count:1
Safety and Handling
Hazard Codes:
Xn:Harmful
Risk Statements:
R40
Safety Statements:
S24/25
HazardClass:
4.1
PackingGroup:
II; III
Transport:
5kgs
Formulations/Preparations:
Parenteral: Injection (in oil): 100 mg/mL (C-III), (available by nonproprietary name). /Testosterone propionate/
Parenteral: Injection (in oil): 200 mg/mL Delatestryl (C-III; with chlorobutanol; available as Unimatic disposable syringes and multiple-dose vials), (BTG). /Testosterone enanthate/
Parenteral: Injection (in oil): 100 mg/mL Depo-Testosterone (C-III with benzyl alcohol), (Pfizer); 200 mg/mL Depo-Testosterone (C-III; with benzyl alcohol), (Pfizer), Virilon IM (C-III; with benzyl alcohol), (Star). /Testosterone cypionate/
Topical: Transdermal System: 2.5 mg/24 hour (12.2 mg/37 sq cm) Androderm (C-III; with alcohol), (Watson); 4 mg/24 hour (10 mg/40 sq cm) Testoderm (C-III; available with or without adhesive), (Ortho-McNeil); 5 mg/24 hour (24.3 mg/44 sq cm) Androderm (C-III; with alcohol), (Watson); 5 mg/24 hour (328 mg/60 sq cm) Testoderm TTS (C-III; with 1.2 mL alcohol), (Ortho-McNei);l 6 mg/24 hour (15 mg/60 sq cm) Testoderm (C-III; available with or without adhesive), (Ortho-McNeil).
Topical: Gel: 1% (25 and 50 mg) AndroGel (C-III; with alcohol 68.9%), (Unimed); 1% (50 mg) Testim (C-III; with alcohol 74%), (Auxilium)
TESTOSTERONE (TESTOJECT-50) AQUEOUS SUSPENSION FOR IM USE: 10-50 MG; TESTOSTERONE PROPIONATE (TESTEX) OILY SOLN FOR IM USE : 10 TO 25 MG; TESTOSTERONE ENANTHATE (DELATESTRYL) OILY SOLN FOR IM USE: 50-400 MG.
TESTOSTERONE CYPIONATE (DEPO-TESTOSTERONE): OILY SOLN FOR IM USE: 50-400 MG; NANDROLONE DECANOATE (DECA-DURABOLIN) OILY SOLN FOR IM USE: 50-100 MG; NANDROLONE PHENPROPIONATE (DURABOLIN) OILY SOLN FOR IM USE: 50-100 MG
Grade: National Formulary
Parenteral: Implants, for subcutaneous use: 75 mg Testopel Pellets (C-III; with povidone), (Bartor); Injectable suspension: 100 mg/mL (C-III) (available by nonproprietary name).
0.015 MG= 1 INTERNATIONAL UNIT
Exposure Standards and Regulations:
Tolerances for residues of new animal drugs in food. Testosterone propionate. No residues of testosterone, resulting from the use of testosterone propionate, are permitted in excess of the following increments above the concentrations of testosterone naturally present in untreated animals:(a) In uncooked edible tissues of heifers: (1) 0.64 part per billion in muscle. (2) 2.6 parts per billion in fat. (3) 1.9 parts per billion in kidney. (4) 1.3 parts per billion in liver.
Specification:
The Testosterone is a steroid hormone from the androgen group and is found in mammals, reptiles, birds, and other vertebrates. The IUPAC name of this chemical is?(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one. With the?CAS registry number 58-22-0,?it is also named as 17-Hydroxy-(17-beta)-androst-4-en-3-one.?The product's categories are?MI; TPI; steroids; intermediates & fine chemicals; pharmaceuticals; intracellular receptor. It is?white crystalline odourless solid?which is soluble in ethanol (1:5) and chloroform (1:2), dissolved in ether (1:100), and insoluble in water.?When heated to decomposition it emits acrid smoke and irritating fumes. The other characteristics of this product can be summarized as:?(1)ACD/LogP: 3.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.48; (4)ACD/LogD (pH 7.4): 3.48; (5)ACD/BCF (pH 5.5): 257.74; (6)ACD/BCF (pH 7.4): 257.74; (7)ACD/KOC (pH 5.5): 1851.51; (8)ACD/KOC (pH 7.4): 1851.51; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.56; (13)Molar Refractivity: 83.11 cm3; (14)Molar Volume: 256.9 cm3; (15)Polarizability: 32.94×10-24 cm3; (16)Surface Tension: 44.4 dyne/cm; (17)Enthalpy of Vaporization: 79.52 kJ/mol; (18)Vapour Pressure: 2.6E-09 mmHg at 25°C; (19)Tautomer Count: 5; (20)Exact Mass: 288.20893; (21)MonoIsotopic Mass: 288.20893; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 21. Preparation of Testosterone:?The?Androst-4-enedione is restored?by lithium aluminum hydride, and oxidated by manganese dioxide.?Then we can get the product. Uses of Testosterone: In mammals,?it is primarily secreted in the testes of males and the ovaries of females, although small amounts are also secreted by the adrenal glands. It is the principal male sex hormone and an anabolic steroid.?Testosterone is used for the treatment of?eunuchism,?male menopause syndrome,?impotence and other diseases. When you are using this chemical, please be cautious about it as the following:
It is highly flammable and harmful by inhalation. It is also may form explosive peroxides and has limited evidence of a carcinogenic effect.?Additionally, Testosterone may impair fertility and?cause harm to the unborn child, so people should?avoid contact with skin and eyes.?If you want to contact this product, you must wear suitable protective clothing and gloves.?In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?Avoid exposure - obtain special instructions before use.? People can use the following data to convert to the molecule structure.
1. SMILES:O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
2.?InChI:InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1. The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral > 5gm/kg (5000mg/kg) ? Toksikologicheskii Vestnik. Vol. (2), Pg. 6, 1996.
rat LDLo intraperitoneal 326mg/kg (326mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Proceedings of the Society for Experimental Biology and Medicine. Vol. 46, Pg. 116, 1941.
Octanol/Water Partition Coefficient:
log Kow = 3.32
Report:
IARC Cancer Review: Animal Sufficient Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 ,1974,p. 209.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) , IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 519.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 519.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

PREPD BY CONVERSION OF OTHER STEROIDS SUCH AS CHOLESTEROL. THE IMPORTANT INTERMEDIATE DEHYDROANDROSTERONE IS EFFICIENTLY TRANSFORMED INTO TESTOSTERONE BY MICROBIAL PROCESS.
Isolation from extract of testis, synthesis ... from the plant steroid.
Testosterone is synthesized from androstenolone acetate which is reduced to the 17beta-alcohol with Raney nickel and then esterified with benzoyl chloride in pyridine. This protecting ester group permits partial saponification of the 3-acetate with methanolic sodium hydroxide solution to yield the 3-hydroxy compound. Subsequent Oppenauer oxidation produces the testosterone benzoate, which is then subjected to alkaline hydrolysis to give testosterone.
Usage:
Secreted by the testis and is converted to dihydrotestosterone in the target tissue where is appears to mediate many of the biological actions of testosterone. CONTROLLED SUBSTANC
Biomedical Effects and Toxicity
Biological Activity:
Endogenous androgen receptor agonist.
Pharmacological Action:
- 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.
Therapeutic Uses:
Androgens /systemic testosterone/ are primarily indicated in males as replacement therapy when congenital or acquired endogenous androgen absence or deficiency is associated with primary or secondary hypogonadism. Primary hypogonadism includes conditions such as: testicular failure due to cryptorchidism, bilateral torsion, orchitis, or vanishing testis syndrome; orchidectomy, Klinefelter's syndrome, chemotherapy, or toxic damage from alcohol or heavy metals. Hypogonadotropic hypogonadism (secondary hypogonadism) conditions include idiopathic gonadotropin or LHRH deficiency, or pituitary-hypothalamic injury as a result of tumors, trauma, or radiation and are the most common forms of hypogonadism seen in older adults. /Included in US product labeling/
Testosterone is used for the development and maintenance of secondary sexual characteristics in female-to-male transsexuals. /NOT included in US product labeling/
Extemporaneously compounded topical testosterone is used for the treatment of itching resulting from lichen scierosus. /NOT included in US product labeling/
Intramuscular preparations of testosterone and testosterone esters, and extemporaneously compounded topical testosterone are used in the treatment of microphallus. /NOT included in US product labeling/
Male hypogonadism is a clinical situation characterised by a low serum testosterone level in combination with a diversity of symptoms and signs such as reduced libido and vitality, decreased muscle mass, increased fat mass and depression. Similar symptoms in combination with subnormal testosterone levels are seen in some elderly men. Several publications have suggested that testosterone treatment in hypogonadal men may have beneficial effects, but it is still uncertain whether testosterone substitution in the aging man is indicated. Despite this uncertainty the sale of testosterone have increased enormously over the last few years, hence it seems important to discuss what we now know about such treatment. The result from placebo-controlled studies of testosterone substitution in elderly men differ substantially, but it seems to improve, among other things, bone mineral density, body composition, perception of physical strength, and maybe libido. In the short term there have been few problems or complications with testosterone treatment, but effects on the cardiovascular system and the prostate over the long term remain uncertain. Before any general recommendation could be given, big prospective studies have to be performed. Treatment should, however, be considered in men with testosterone in the hypogonadal range accompanied by clinical symptoms. Treatment needs to be individualized and should preferably be initiated by specialists in andrology, endocrinology or urology. [Svartberg J; Tidsskr Nor Laegeforen 125 (7): 879-82 (2005)]
Biomedical Effects and Toxicity:
Testosterone is absorbed systemically through the skin following topical application as a gel or transdermal system. Following topical application of a hydroalcoholic gel formulation of testoterone (AndroGel 1%) to the skin, the gel quickly dries on the skin surface, which serves as a reservoir for sustained release of the hormone into systemic circulation. Approximately 10% of a testosterone dose applied topically to the skin as the 1% gel is absorbed percutaneously into systemic circulation. The manufacturer states that increases in serum testosterone concentrations were apparent within 30 minutes of topical application of a 100-mg testosterone dose of the 1% gel, with physiologic concentrations being achieved in most patients within 4 hours (pretreatment concentrations were not described); percutaneous absorption continues for the entire 24-hour dosing interval. Serum testosterone concentrations approximate steady-state levels by the end of the initial 24 hours and are at steady state by the second or third day of dosing of the 1% gel. With daily topical application of the 1% gel, serum testosterone concentrations 30, 90, and 180 days after initiating treatment generally are maintained in the eugonadal range. Following discontinuance of such topical therapy, serum testosterone concentrations remain within the normal range for 24-48 hours but return to pretreatment levels by the fifth day after the last application. The manufacturer states that mean concentrations of the active metabolite dihydrotestosterone (DHT) were within or about 7% above the normal range 180 days after initiating daily topical application of 50 or 100 mg, respectively, of testosterone as the gel. Increases in DHT concentrations appeared to parallel those of testosterone, and the mean steady-state ratio of DHT to testosterone was maintained in the normal range during the 180-day treatment period.
Following subcutaneous implantation of testosterone pellets, approximately 33% of an implanted dose is absorbed systemically during the first month, 25% during the second month, and 17% during the third month. The duration of action of subcutaneous testosterone implants (pellets) is usually 3-4 months but occasionally may be up to 6 months.
Esterification of testosterone generally results in less polar compounds. The cypionate and enanthate esters of testosterone are absorbed slowly from the lipid tissue phase at the IM injection site, achieving peak serum concentrations about 72 hours after IM injection; thus, these esters have a prolonged duration of action (i.e., up to 2-4 weeks) following IM administration. Testosterone propionate, however, reportedly has a shorter duration of action than that of testosterone following IM administration. Because IM injection of testosterone or its esters causes local irritation, the rate of absorption may be erratic. /Testosterone esters/
The distribution of bioactive and nonbioactive androgen is determined by the amount sex hormone binding globulin in the serum and the total testosterone level.
Elimination: Renal: about 90% excreted in urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites. Fecal: about 6% unconjugated form.
Duration of elevation of plasma testosterone levels following single dose of testosterone esters varies from testosterone propionate, with duration of 1-3 days, to testosterone enanthate with duration of 14 to 21 days ... .
Following oral administration of testosterone, only small amounts of the drug reach systemic circulation unchanged. The low bioavailability of orally administered testosterone results from metabolism of the drug in the GI mucosa during absorption and on first pass through the liver.
In serum, testosterone is bound with high affinity to SHBG and with low affinity to albumin. The amount of SHBG in serum and the total testosterone concentration determine the distribution of pharmacologically active and non-active forms of the androgen. SHBG-binding capacity is high in prepubertal children, declines during puberty and adulthood, and increases again during the later decades of life. Approximately 30-40% of testosterone in plasma is bound to SHBG, 2% remains unbound (free), and the rest is bound to albumin and other proteins.
Protein binding: Moderate (approximately 40% to sex hormone-binding globulin); 2% remains free and the rest is bound to albumin and other proteins. However, the albumin-bound testosterone easily dissociates and is presumed to be bioactive, while the portion bound to the sex hormone-binding globulin is not considered biologically active.
It is not known whether testosterone is distributed into milk.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 2,188(2), indicates that testosterone is expected to have low mobility in soil(SRC). Volatilization of testosterone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Testosterone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-8 mm Hg(SRC), determined from a fragment constant method(4). Sewage treatment plant removal rates of 58-65%(5,6) suggest that biodegradation may be an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), a Koc value of 2,188(2), indicates that testosterone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.5X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 72(SRC), from an a log Kow 3.32(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Sewage treatment plant removal rates of 58-65%(8,9), with 95% removal reported for the aqueous phase of treatment(8) suggest that biodegradation may be an important environmental fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), testosterone, which has an estimated vapor pressure of 1.7X10-8 mm Hg at 25 deg C (SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase testosterone may be removed from the air by wet and dry deposition(SRC). Testosterone does not absorb light at wavelengths >290 nm(3) and therefore should not be susceptible to direct photolysis by sunlight(SRC).
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