Testosterone cypionate

Iupac Name：[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate

CAS No.: 58-20-8

Molecular Weight：412.614

Modify Date.: 2022-10-31 05:56

Introduction: Testosterone cypionate is an anabolic steroid that is classified as a male hormone (androgen). Testosterone cypionate is an injectable solution whose brand name is Depo-testosterone. The generic drug is administered to enhance performance in athletics and bodybuilding, and as a prescription drug that alleviates the symptoms of hypogonadism in men. In most cases, the drug is administered to the muscle or the subcutaneous layer of the skin through an injection based on clinical indications or once every few weeks. The androgenic/anabolic structure of Testosterone cypionate has a score of 100, which makes it an appropriate steroid for strength and size associated gains. Testosterone cypionate influences changes in the size, shape, number, and appearance of muscle fibers. View more+

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1. Names and Identifiers

1.1 Name: Testosterone cypionate
1.2 Synonyms: (17Β)-3-Oxoandrost-4-en-17-yl 3-cyclopentylpropanoate (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 3-cyclopentylpropanoate (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-3-cyclopentylpropanoat 17-(Cyclopentyl-1-oxopropoxy)androst-4-en-3-one 17b-(3-Cyclopentyl-1-oxopropoxy)androst-4-en-3-one 3-cyclopentylpropanoate de (8R,9S,10R,13S,14S,17S)-10,13-diméthyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-1H-cyclopenta[a]phénanthrén-17-yle 4-09-00-00048 Andro-Cyp Androst-4-en-3-one, 17- (3-cyclopentyl-1-oxopropoxy)-, (17Β)- Androst-4-en-3-one, 17-(3-cyclopentyl-1-oxopropoxy)-, (17Β)- Cyclopentanepropanoic acid, (17Β)-3-oxoandrost-4-en-17-yl ester depAndro 100 depAndro 200 Depo Depotest depo-testosterone Depo-testosterone cyclopentylpropionate DEPOVIRIN Dep-Test Durandro EINECS 200-368-4 Jectatest Malogen CYP MFCD00053944 Pertestis Testergon Testex Leo Testodrin prolongatum Testosterone 17b-Cyclopentanepropionate Testosterone 17b-Cypionate TESTOSTERONE 17BETA-CYCLOPENTANEPROPIONATE TESTOSTERONE 17BETA-CYPIONATE Testosterone 17Β-cyclopentanepropionate Testosterone 17Β-cypionate TESTOSTERONE CYCLOPENTANE PROPIONATE TESTOSTERONE CYCLOPENTYLPROPIONATE Testosterone, cyclopentanepropionate testosterone17β-cyclopentylpropionate Testosteronecypionate T-Ionate-P.A VIRILON

1.3 CAS No.: 58-20-8

1.4 CID: 441404

1.5 EINECS(EC#): 200-368-4

1.6 Molecular Formula: C27H40O3 (isomer)

1.7 Inchi: InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1

1.8 InChkey: HPFVBGJFAYZEBE-ZLQWOROUSA-N

1.9 Canonical Smiles: CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=CC(=O)CCC35C

1.10 Isomers Smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C

2. Properties

2.1 Density: 1.1

2.1 Melting point: 98 - 104 C

2.1 Boiling point: 525.9 °C at 760 mmHg

2.1 Refractive index: 1.546

2.1 Flash Point: 223.9 °C

2.1 Precise Quality: 412.29800

2.1 PSA: 43.37000

2.1 logP: 6.40050

2.1 Appearance: white to off-white crystalline powder

2.2 Storage: 2-8°C

2.3 Water Solubility: Insoluble

2.4 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 51 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (21.57%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (21.57%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (21.57%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H350 (45.1%): May cause cancer [Danger Carcinogenicity]
H351 (54.9%): Suspected of causing cancer [Warning Carcinogenicity]
H360 (52.94%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (45.1%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (31.37%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, and P501

3.2 Usage: Testosterone Cypionate is an anabolic steroid with androgenic properties. Testosterone Cypionate is used for testosterone therapy in males with hypogonadism.Controlled Substance.

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R45

4.1 Safety Statements: 53-22-26-36

4.1 Hazard Declaration: H350-H361

4.1 RIDADR: HAZARD

4.1 Caution Statement: P201-P280-P308 + P313

4.1 WGK Germany: 3

4.1 RTECS: XA3066000

4.1 Specification

The IUPAC name of Testosterone cyclopentylpropionate is (10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) 3-cyclopentylpropanoate. With the CAS registry number 58-20-8, it is also named as Testosterone 17beta-cypionate. The classification codes are Anabolic Agents; Androgen; Androgens; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Mutation data; Reproductive Effect. When heated to decomposition it emits acrid smoke and irritating fumes. Additionally, it is steroids which is used as androgen. And this chemical must be stored at 2-8°C.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 6.93; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 3; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 5; (6)Index of Refraction: 1.546; (7)Molar Refractivity: 118.41 cm³; (8)Molar Volume: 373.8 cm³; (9)Polarizability: 46.94×10^-24 cm³; (10)Surface Tension: 43.7 dyne/cm; (11)Enthalpy of Vaporization: 80.01 kJ/mol; (12)Vapour Pressure: 3.78E-11 mmHg at 25°C; (13)Rotatable Bond Count: 5; (14)Tautomer Count: 5; (15)Exact Mass: 412.297745; (16)MonoIsotopic Mass: 412.297745; (17)Topological Polar Surface Area: 43.4; (18)Heavy Atom Count: 30; (19)Complexity: 732.

When you are using Testosterone cyclopentylpropionate, please be cautious about it as the following:
It may cause cancer and?possible risk of harm to the unborn child, so people should?not breathe dust.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing.?Avoid exposure - obtain special instructions before use.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C5\C=C3/[C@]([C@H]2CC[C@@]4([C@@H](OC(=O)CCC1CCCC1)CC[C@H]4[C@@H]2CC3)C)(C)CC5
2.?InChI:InChI=1/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1.

The following?is the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 1gm/kg (1000mg/kg)	?	Drugs in Japan Vol. 6, Pg. 487, 1982.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 1B

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H350 May cause cancer H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

58-20-8Total: 6 Synthesis Route

140-77-2 67 Suppliers

58-20-8 577 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 75, p. 650,652, 6359
Yield: null

17006-07-4

58-20-8 577 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 75, p. 650,652, 6359
Yield: null

58032-37-4

58-20-8 577 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 75, p. 650,652, 6359
Yield: null

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8. Precursor and Product

precursor:

56736-66-4

17006-07-4

58032-37-4

104-97-2

140-77-2

9. Other Information

9.0 Description: Testosterone cypionate is an anabolic steroid that is classified as a male hormone (androgen). Testosterone cypionate is an injectable solution whose brand name is Depo-testosterone. The generic drug is administered to enhance performance in athletics and bodybuilding, and as a prescription drug that alleviates the symptoms of hypogonadism in men. In most cases, the drug is administered to the muscle or the subcutaneous layer of the skin through an injection based on clinical indications or once every few weeks. The androgenic/anabolic structure of Testosterone cypionate has a score of 100, which makes it an appropriate steroid for strength and size associated gains. Testosterone cypionate influences changes in the size, shape, number, and appearance of muscle fibers.

9.1 Mechanism of Action: In humans, the influence of testosterone may take place based on two mechanisms: through alteration of the hormone to estradiol and trigger specific estrogen receptors, and by triggering of the androgen receptor. Free testosterone (T) is transmitted to the cytoplasm of selected cells for attachment with the androgen receptor, or diminution to 5α-dihydrotestosterone (DHT) through the cytoplasmic enzyme 5α-reductase.
DHT creates a strong bond with a similar androgen receptor, one that is stronger than free testosterone to enhance its androgenic potency. The DHT-receptor or the T-receptor undergoes structural modifications that allow its free flow into the nucleus of the cell for binding with certain nucleotide sequences particular to the chromosomal DNA. Notably, these binding spots are referred to as hormone response elements (HREs), and their effect on the transcriptional activity of specific genes results in the androgenic effects.
When Testosterone cypionate is absorbed into the body, the drug is processed in the blood and 40% of the resultant testosterone binds with plasma globulin, the remaining 2% either binds with proteins such as albumin or it remains unbound.

9.2 Information on Dosing: The dosage requirements of Testosterone cypionate are dependent on an individual’s age, the need for testosterone therapy, the intensity of the condition, additional medical conditions and one’s reaction after injection of the first dose. For primary hypogonadism and hypogonadotropic hypogonadism, 50-400mg is injected into one’s gluteal muscle every 2-4weeks.
The administration of Testosterone cypionate to enhance performance may necessitate a weekly injection of the hormone, where two smaller injections could be more effective. Noteworthy, multiple injections ensure that an individual’s blood levels are at a peak, which mitigates the effects of performance level dosage instructions. In this case, the administration of smaller doses of the hormone may range from 200mg-1000mg per week, which is solely dependent on an individual’s needs.

9.3 Interactions: Testosterone cypionate can interact with herbs, vitamins and other medications that one may be taking. Such interactions may inhibit the appropriate functionality of the drug hence to avoid this, it is advisable to consult a doctor for management of medications. Notably, some of the drug interactions may include oral blood thinners, adrenocorticotropic and corticosteroid hormones, oral diabetes drugs and insulin.

9.4 Indications: In men, Testosterone cypionate is indicated for primary or secondary hypogonadism. The testosterone cypionate injection should only be used to treat specific symptoms of testosterone deficiency. Before the initiation of Testosterone cypionate treatment, testosterone deficiency should be validated by clinical features and biochemical assays.

9.5 Contraindications: Testosterone cypionate is contradicted in persons who have known or suspected breast and testicular carcinomas. If one is allergic to testosterone they should refrain from the use of Testosterone cypionate. Females should keep off the drug especially if one is either breastfeeding or pregnant.

9.6 Side Effects: The common side effects associated with testosterone cypionate include headaches, mood swings, erections which last longer than normal, frequent erections, gynecomastia, hair growth, pain and swelling at the point of injection, acne, retention of excess water, and a reduction of the sperm count when one indulges in high dosages of the drug.
Serious side effects of testosterone cypionate use include aromatization, heart attack, stroke, prostate cancer, liver problems, deep vein thrombosis, pulmonary embolism, polycythemia, and enlargement of the prostate gland.
Testosterone cypionate is well-tolerated amongst most men hence the common side effects can be controlled easily while the serious side effects are not guaranteed.

9.7 Testosterone Cypionate Warnings: Before administering Testosterone cypionate, one should take into consideration the fact that people with liver problems may experience liver damage, people with heart and kidney problems may experience water and salt retention. For people with breast cancer, prostate cancer, sleep apnea, polycythemia, high cholesterol levels and blood clots, Testosterone cypionate may amplify their respective conditions.
It is not advisable for seniors above the age of 65 to take Testosterone cypionate as it may increase their chances of contracting prostate cancer, heart disease or an enlarged prostate. The drug should only be used by males.

9.8 Originator: Depo-Testosterone,Upjohn,US,1951

9.9 Uses: Testosterone Cypionate is an anabolic steroid with androgenic properties. Testosterone Cypionate is used for testosterone therapy in males with hypogonadism. Controlled Substance.

9.10 Manufacturing Process: 1 g of crude 3-enol-ethyl ether of testosterone dissolved in 3 cc of pyridine is treated with 2 cc of β-cyclopentylpropionic anhydride (obtained from the β- cyclopentylpropionic acid and acetic anhydride: boiling point 180°C/2 mm Hg). After standing at room temperature overnight the mixture is diluted with water and extracted with ether, the ethereal layer, washed with water to neutrality and dried, is evaporated by vacuum. The oily residue is taken up in petroleum ether and filtered through a layer of aluminum oxide, which is afterwards washed with a further amount of petroleum ether. The solution so filtered and purified is evaporated to dryness; the crystalline residue is recrystallized from a small amount of methanol containing a trace of pyridine: about 1 g of 3-enol-ethyl-ether of the β-cyclopentyl propionate of testosterone, melting point 86°C to 88°C, is so obtained (by further recrystallization melting point 90°C to 91°C). This product (that may be employed either in the crystalline state, or in the oily one, that is, before the purification by filtration through aluminum oxide) by treatment with a small amount of hydrochloric acid in acetone solution yields the β-cyclopentyl propionate of testosterone, melting point 99°C to 101°C (recrystallized from methanol).

9.11 Therapeutic Function: Androgen

9.12 Veterinary Drugs and Treatments: The use of injectable esters of testosterone in veterinary medicine is limited primarily to its use in dogs (and perhaps cats) for the treatment of testosterone-responsive urinary incontinence in neutered males. Testosterone has been used to treat a rare form of dermatitis (exhibited by bilateral alopecia) in neutered male dogs. These drugs are also used in bovine medicine to produce an estrus-detector (teaser) animal in cull cows, heifers, and steers.
The effectiveness of testosterone to increase libido, treat hypogonadism, aspermia, and infertility in domestic animals has been disappointing.

10. Computational chemical data

Molecular Weight: 412.614g/mol
Molecular Formula: C₂₇H₄₀O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 412.29774513
Monoisotopic Mass: 412.29774513
Complexity: 732
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 43.4
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 6
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAYMAAAAwYIAAAAAAAGDAAAAAGgAAAAAADxSggAICCAAABACIAqDSCAAAAAAgAAAACAEAAEgAABIAAQACAAAEgAAIAQOIyPCPgAAAAAAAAACAAAQAACAAAIAADAAAAA==

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