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315-37-7

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315-37-7 Usage

Indications and Usage

Testosterone enanthate is a type of androgen drug, and it is a synthetic compound of testosterone proprionate and testosterone enantate. Its effects are the same as those of testosterone acetate, which include promoting the development of male sex organs and secondary sex characteristics and resisting estrogen. It also has protein assimilating effects, which allow it to help muscle growth and weight gain. Testosterone enanthate can inhibit the pituitary gland and promote sex hormone secretion, thus decreasing the endogenous testosterone secreted by Leydig cells, which achieves the purpose of stopping spermatogenesis. Testosterone enanthate can be used as a long-term male birth control drug. It is clinically used to treat male hypogonadism and gonadal insufficiency, sex organ hypogenesis, infertility, eunuchism, and cryptorchidism. It can also be used to treat female dysfunctional uterine bleeding, menopausal syndrome, breast cancer and uterine cancer. It can also treat cirrhosis, aplastic anemia, osteoporosis and other consumptive diseases.

Drug Metabolism

After injection, it creates a blood concentration higher than the physiological level, and then blood concentration decreases rapidly.

Clinical Research

In a trial that injected monkeys with testosterone enanthate every week, the monkeys’ sperm cells began experiencing apoptosis in a week, with apoptosis rates peaking in the fifth week. A clinical trial with 308 participants also showed that testosterone enanthate’s birth-control effects are much more effective on Asian men than on Caucasian men, as over 95% of Asian men achieved azoospermia, while only 40-70% of Caucasian men did. A trial of over 100 volunteers showed that weekly muscle injections of 250mg led to most men developing azoospermia or severe ogliospermia in 10 weeks, and that sperm count could recover after ceasing injection for a certain period of time. If the injection intervals are extended to over 10-12 days, even increasing dosage will not have desired effects. Testosterone enanthate only needs to be injected once a week, which is an advantage over testosterone acetate.

Adverse reactions

Large dosages or extended use can cause water and sodium retention and edema. Young women may exhibit virilism, with characteristics including deepened voice, hair growth, acne, clitoral hypertrophy, etc. Not to be used by patients with prostatic cancer or pregnant patients. Should be used with caution by patients with prostate hypertrophy and liver and kidney dysfunction. When treating breast cancer, drug usage should be stopped immediately if hypercalcemia is detected.

Description

Testosterone enanthate (Item No. 22546) is an analytical reference standard categorized as an anabolic androgenic steroid. It is an ester of the naturally occurring androgen, testosterone (Item Nos. 15645 | ISO60154) with a longer half-life. Formulations containing testosterone enanthate have been tested for use in hypogonadism and as a potential male contraceptive. Formulations containing it have been associated with higher levels of total cholesterol, low density lipoproteins, and triglycerides and lower levels of high density lipoproteins. Anabolic steroids, including testosterone enanthate, have been used to enhance physical performance in racehorses and athletes, and methods to detect steroids, their derivatives, and their metabolites have been developed. This product is intended for research and forensic applications.

Chemical Properties

White or yellowish-white, crystalline powder.

Originator

Delatestryl,Squibb,US,1954

Uses

Testosterone Enanthate is a derivative of testosterone (T155000), the principal hormone of the testes, produced by the interstitial cells.

Definition

ChEBI: Testosterone enanthate is a heptanoate ester and a sterol ester. It has a role as an androgen. It is functionally related to a testosterone.

Manufacturing Process

A mixture of testosterone, pyridine and oenanthic acid anhydride is heated for 1 1/2 hours to 125°C. The cooled reaction mixture is decomposed with water while stirring and cooling. After prolonged standing at a temperature below room temperature, the whole is extracted with ether and the ethereal solution is washed consecutively with dilute sulfuric acid, water, 5% sodium hydroxide solution, and again with water. The crude ester remaining on evaporation of the dried ether solution, after recrystallization from pentane, melts at 36° to 37.5°C.

Therapeutic Function

Androgen

Check Digit Verification of cas no

The CAS Registry Mumber 315-37-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 5 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 315-37:
(5*3)+(4*1)+(3*5)+(2*3)+(1*7)=47
47 % 10 = 7
So 315-37-7 is a valid CAS Registry Number.
InChI:InChI=1/C19H28O.C7H14O2/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18;1-2-3-4-5-6-7(8)9/h12,15-17H,3-11H2,1-2H3;2-6H2,1H3,(H,8,9)/p-1/t15-,16-,17-,18-,19-;/m0./s1

315-37-7 Well-known Company Product Price

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  • Sigma-Aldrich

  • (T0250000)  Testosterone enantate  European Pharmacopoeia (EP) Reference Standard

  • 315-37-7

  • T0250000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001312)  Testosterone enantate for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 315-37-7

  • Y0001312

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001317)  Testosterone enantate for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 315-37-7

  • Y0001317

  • 1,880.19CNY

  • Detail
  • USP

  • (1648004)  Testosteroneenanthate  United States Pharmacopeia (USP) Reference Standard

  • 315-37-7

  • 1648004-200MG

  • 5,736.51CNY

  • Detail

315-37-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Testosterone enanthate

1.2 Other means of identification

Product number -
Other names Atlates

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:315-37-7 SDS

315-37-7Synthetic route

oenanthic acid
111-14-8

oenanthic acid

17β-hydroxy-3-methoxyandrosta-3,5-diene

17β-hydroxy-3-methoxyandrosta-3,5-diene

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Stage #1: oenanthic acid; 17β-hydroxy-3-methoxyandrosta-3,5-diene With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water
97.18%
oenanthic acid
111-14-8

oenanthic acid

17β-hydroxy-3-ethoxyandrosta-3,5-diene
26614-48-2

17β-hydroxy-3-ethoxyandrosta-3,5-diene

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Stage #1: oenanthic acid; 17β-hydroxy-3-ethoxyandrosta-3,5-diene With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 20℃; Inert atmosphere;
Stage #2: With sulfuric acid In water
96.3%
oenanthic acid
111-14-8

oenanthic acid

3,3-(ethylenedioxy)-5-androsten-17β-ol
975-57-5

3,3-(ethylenedioxy)-5-androsten-17β-ol

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Stage #1: oenanthic acid; 3,3-(ethylenedioxy)-5-androsten-17β-ol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 20℃; Inert atmosphere;
Stage #2: With sulfuric acid In water
95.76%
oenanthic acid
111-14-8

oenanthic acid

testosterone
58-22-0

testosterone

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Stage #1: oenanthic acid; testosterone With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 20℃; Inert atmosphere;
Stage #2: With sulfuric acid In water
89.6%
testosterone
58-22-0

testosterone

Heptanoic acid chloride
2528-61-2

Heptanoic acid chloride

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
With pyridine Ambient temperature;57%
With dmap; triethylamine In dichloromethane at 20℃;11.9 g
3-ethoxyandrosta-3,5-dien-17-one
972-46-3

3-ethoxyandrosta-3,5-dien-17-one

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium borohydride; pyridine / ethanol / 60 °C
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium borohydride; pyridine / ethanol / 60 °C
2: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: potassium borohydride; pyridine / ethanol / 60 °C
2: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
3: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
17β-hydroxy-3-ethoxyandrosta-3,5-diene
26614-48-2

17β-hydroxy-3-ethoxyandrosta-3,5-diene

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
2: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
testosterone
58-22-0

testosterone

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine hydrochloride / ethanol / 40 °C / Inert atmosphere
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
Androstenedione
63-05-8

Androstenedione

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridinium p-toluenesulfonate / methanol / 20 °C / Inert atmosphere
2: pyridine; sodium tetrahydroborate / methanol / 40 °C
3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 40 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: pyridinium p-toluenesulfonate / ethanol / 40 °C / Inert atmosphere
2: potassium borohydride; pyridine / ethanol / 60 °C
3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: pyridinium p-toluenesulfonate / ethanol / 40 °C / Inert atmosphere
2: potassium borohydride; pyridine / ethanol / 60 °C
3: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: pyridinium p-toluenesulfonate / ethanol / 40 °C / Inert atmosphere
2: potassium borohydride; pyridine / ethanol / 60 °C
3: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C
4: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere
5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
View Scheme
3-methoxyandrosta-3,5-dien-17-one
57144-06-6

3-methoxyandrosta-3,5-dien-17-one

testosterone heptanoate
315-37-7

testosterone heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; sodium tetrahydroborate / methanol / 40 °C
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 40 °C / Inert atmosphere
View Scheme
testosterone heptanoate
315-37-7

testosterone heptanoate

A

testosterone
58-22-0

testosterone

B

Androstenedione
63-05-8

Androstenedione

Conditions
ConditionsYield
With Fusarium fujikuroi PTCC 5144 In ethanol; water at 26℃; for 312h; Reagent/catalyst; Microbiological reaction;A 20%
B 17%
C 59%
testosterone heptanoate
315-37-7

testosterone heptanoate

A

testosterone
58-22-0

testosterone

C

14alpha-Hydroxytestosterone
4075-20-1

14alpha-Hydroxytestosterone

Conditions
ConditionsYield
With Acremonium chrysogenu PTCC 5271 In ethanol; water at 26℃; for 72h; Reagent/catalyst; Microbiological reaction;A 12%
B 29%
C 53%
2,2,3,3,3-pentafluoropropanoic anhydride
356-42-3

2,2,3,3,3-pentafluoropropanoic anhydride

testosterone heptanoate
315-37-7

testosterone heptanoate

Heptanoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(2,2,3,3,3-pentafluoro-propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Heptanoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(2,2,3,3,3-pentafluoro-propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
at 70℃; for 0.25h;
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
24589-78-4

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

testosterone heptanoate
315-37-7

testosterone heptanoate

Heptanoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Heptanoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With ammonium iodide; 1,4-dithio-erythritol at 60℃; for 0.25h;
testosterone heptanoate
315-37-7

testosterone heptanoate

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

Heptanoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(2,2,2-trifluoro-acetoxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Heptanoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(2,2,2-trifluoro-acetoxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
at 70℃; for 0.25h;
testosterone heptanoate
315-37-7

testosterone heptanoate

heptafluorobutyric anhydride
336-59-4

heptafluorobutyric anhydride

Heptanoic acid (8R,9S,10R,13S,14S,17S)-3-(2,2,3,3,4,4,4-heptafluoro-butyryloxy)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Heptanoic acid (8R,9S,10R,13S,14S,17S)-3-(2,2,3,3,4,4,4-heptafluoro-butyryloxy)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
at 70℃; for 0.25h;
testosterone heptanoate
315-37-7

testosterone heptanoate

Heptanoic acid (8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Heptanoic acid (8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In acetic acid for 1h; Ambient temperature;
testosterone heptanoate
315-37-7

testosterone heptanoate

3-oxo-5α-androstan-17β-yl heptanoate
33776-88-4

3-oxo-5α-androstan-17β-yl heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / PtO2 / acetic acid / 1 h / Ambient temperature
2: Jones reagent / acetone / 0.08 h
View Scheme
testosterone heptanoate
315-37-7

testosterone heptanoate

3-oxo-5β-androstan-17β-yl heptanoate

3-oxo-5β-androstan-17β-yl heptanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / PtO2 / acetic acid / 1 h / Ambient temperature
2: Jones reagent / acetone / 0.08 h
View Scheme
testosterone heptanoate
315-37-7

testosterone heptanoate

testosterone
58-22-0

testosterone

Conditions
ConditionsYield
With Candida antarctica Lipase A In aq. phosphate buffer at 20℃; for 20h; pH=8; Reagent/catalyst; Enzymatic reaction;

315-37-7Relevant articles and documents

Preparation method of alkyl acid testosterone

-

Paragraph 0022-0023, (2020/11/10)

The invention discloses a preparation method of alkyl acid testosterone, and belongs to the technical field of medicine preparation and processing. According to the method, testosterone serves as a raw material and is esterified into testosterone ester, a solvent used in the esterification reaction is a non-water-soluble organic solvent, the amount of wastewater is reduced, the solvent can be recycled, and the process is more environmentally friendly. The method is high in yield, the total molar yield of the final product is higher than 85%, and the method has extremely high commercial competitiveness, is suitable for industrial large-scale production and has good economic benefits.

Long-range effect of 17-substituents in 3-oxo steroids on 4,5-double bond hydrogenation

Sidova, Romana,Stransky, Karel,Kasal, Alexander,Slavikova, Barbora,Kohout, Ladislav

, p. 1528 - 1542 (2007/10/03)

The long-range effect of substituents in the 17-position on the hydrogenation of double bond of the steroidal Δ4-3-ketones in acetic acid on a platinum catalyst is described in a series of testosterone (1) and epitestosterone (5) esters with carboxylic acids of varying alkyl chain length. The ratio 5α-to 5β-products is affected by the nature of substituents in the position 17.

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