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Aspen Testosterone Enanthate

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Chemistry

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Also known as: 315-37-7, Testosterone heptanoate, Androtardyl, Testosterone enantate, Testosterone heptylate, Atlatest

Molecular Formula

C₂₆H₄₀O₃

Molecular Weight

400.6 g/mol

InChI Key

VOCBWIIFXDYGNZ-IXKNJLPQSA-N

FDA UNII

7Z6522T8N9

Testosterone Enanthate is a long-acting intramuscular form of the androgen testosterone. Testosterone inhibits gonadotropin secretion from the pituitary gland and ablates estrogen production in the ovaries, thereby decreasing endogenous estrogen levels. In addition, this agent promotes the maintenance of male sex characteristics and is indicated for testosterone replacement in hypogonadal males, delayed puberty, and metastatic mammary cancer. (NCI04)

1 2D Structure

Testosterone Enanthate

2 Identification

2.1 Computed Descriptors

2.1.1 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] heptanoate

2.1.2 InChI

InChI=1S/C26H40O3/c1-4-5-6-7-8-24(28)29-23-12-11-21-20-10-9-18-17-19(27)13-15-25(18,2)22(20)14-16-26(21,23)3/h17,20-23H,4-16H2,1-3H3/t20-,21-,22-,23-,25-,26-/m0/s1

2.1.3 InChI Key

VOCBWIIFXDYGNZ-IXKNJLPQSA-N

2.1.4 Canonical SMILES

CCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C

2.1.5 Isomeric SMILES

CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

2.2 Other Identifiers

2.2.1 UNII

7Z6522T8N9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Andropository

2. Delatestryl

3. Durathate

4. Primoteston Depot

5. Testosteron Depot-rotexmedica

6. Testosteron-depot Eifelfango

7. Testosteron-depot Jenapharm

8. Testosterone Heptanoate

9. Testosterone Heptylate

10. Testrin P.a.

11. Theramex

2.3.2 Depositor-Supplied Synonyms

1. 315-37-7

2. Testosterone Heptanoate

3. Androtardyl

4. Testosterone Enantate

5. Testosterone Heptylate

6. Atlatest

7. Testanthate

8. Testinon

9. Testoenant

10. Testostroval

11. Everone

12. Orquisteron-e

13. Exten Test

14. Depo-testro Med

15. Testosterone Oenanthate

16. Andropository

17. Durathate

18. Testenate

19. Testosterone Heptoate

20. Reposo-tmd

21. Primotestone

22. Malogen L.a.

23. Depatestrye

24. Testosterone 17-enanthate

25. Nsc-17591

26. Malogen L.a.200

27. Reposo Tmd

28. Testonenant

29. Ditate

30. Andro L.a. 200

31. 17-hydroxyandrost-4-en-3-one, 17-heptanoate

32. Delatest

33. Testate

34. Xyosted

35. Testosterone, Heptanoate

36. Heptanoic Acid, Ester With Testosterone

37. 17-((1-oxoheptyl)oxy)androst-4-en-3-one

38. 17beta-enanthoxyandrost-4-en-3-one

39. 4-androsten-3-one 17beta-enanthate

40. Androgyn L.a.

41. Androst-4-en-3-one, 17-[(1-oxoheptyl)oxy]-, (17b)-

42. Dea No. 4000

43. 17beta-hydroxyandrost-4-en-3-one Enanthate

44. Androst-4-en-3-one, 17-((1-oxoheptyl)oxy)-, (17beta)-

45. Testosterone Enanthate Ciii

46. Chebi:9464

47. 7z6522t8n9

48. [(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] Heptanoate

49. 17-heptanoyl-17beta-hydroxyandrost-4-en-3-one

50. (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 Heptanoate

51. Testosterone Ethanate

52. Ccris 7082

53. 17-[(1-oxoheptyl)oxy]androst-4-en-3-one

54. Einecs 206-253-5

55. Brn 3170544

56. Androst-4-en-3-one, 17-[(1-oxoheptyl)oxy]-, (17.beta.)-

57. Unii-7z6522t8n9

58. Testosterone Enanthate [usp:jan]

59. Delatestryl (tn)

60. Androst-4-en-3-one, 17beta-hydroxy-, Heptanoate

61. Testosteroni Enantas

62. Ditate (salt/mix)

63. Androst-4-en-3-one, 17-(1-oxoheptyl)oxy-, (17beta)-

64. Deladumone (salt/mix)

65. Testosterone Heptoic Acid

66. Enanthic Acid Testosterone

67. Schembl42687

68. Androgyn L.a. (salt/mix)

69. 4-08-00-00979 (beilstein Handbook Reference)

70. Testosterone 17beta-heptanoate

71. Chembl1200335

72. Androst-4-en-3-one, Heptanoate

73. Dtxsid701016540

74. Testosterone 17beta-heptanoic Acid

75. Testosterone Enanthate [mi]

76. Nsc17591

77. Zinc3876080

78. Testosterone Enanthate (jp17/usp)

79. Testosterone Enanthate [jan]

80. Lmst02020075

81. S3717

82. Androst-4-en-3-one,(17.beta.)-

83. Testosterone Enantate [mart.]

84. Testosterone Enanthate [vandf]

85. Akos015960945

86. Testosterone Enantate [who-ip]

87. Ccg-268655

88. Db13944

89. Testosterone Enanthate [usp-rs]

90. Testosterone Enanthate [who-dd]

91. 4-androsten-3-one 17.beta.-enanthate

92. 3-oxoandrost-4-en-17beta-yl Heptanoate

93. Ac-12599

94. Ds-11585

95. Testosterone Enanthate, Analytical Standard

96. 4-androsten-17beta-ol-3-one 17-enanthate

97. Testosterone Enantate [ep Monograph]

98. Testosterone Enanthate [orange Book]

99. Testosteroni Enantas [who-ip Latin]

100. 17beta-hydroxyandrost-4-en-3-one Heptanoate

101. Testosterone Enanthate Ciii [usp-rs]

102. Testosterone Enanthate [usp Monograph]

103. Wln: L E5 B666 Ov Mutj A E Fov6

104. C08157

105. D00958

106. Ditate-ds Component Testosterone Enanthate

107. 17-hydroxyandrost-4-en-3-one, 17-heptanoic Acid

108. 315t377

109. Sr-01000942262

110. Sr-01000942262-1

111. Testosterone Enanthate Component Of Ditate-ds

112. W-106891

113. Androst-4-en-3-one, 17.beta.-hydroxy-, Heptanoate

114. Q27108402

115. 3-oxoandrost-4-en-17-yl Heptanoate, (17.beta.)- #

116. 17.beta.-(heptanoyloxy)androst-4-en-3-one [who-ip]

117. Androst-4-en-3-one, 17-(1-oxoheptyl)oxy-, (17.beta.)-

118. Testosterone Enantate, European Pharmacopoeia (ep) Reference Standard

119. Testosterone Enanthate, United States Pharmacopeia (usp) Reference Standard

120. Testosterone Enantate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

121. Testosterone Enantate For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₄₀O₃
Molecular Weight	400.6 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	7
Exact Mass	400.29774513 g/mol
Monoisotopic Mass	400.29774513 g/mol
Topological Polar Surface Area	43.4 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	679
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

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Testosterone enanthate
Drug Label	DELATESTRYL (Testosterone Enanthate Injection, USP) provides testosterone enanthate, a derivative of the primary endogenous androgen testosterone, for intramuscular administration. In their active form, androgens have a 17-beta-hydroxy group. Ester...
Active Ingredient	Testosterone enanthate
Dosage Form	Injectable
Route	Injection
Strength	200mg/ml
Market Status	Prescription
Company	Hikma Farmaceutica; Watson Labs; Paddock; Mylan Institutional

2 of 2
Drug Name	Testosterone enanthate
Drug Label	DELATESTRYL (Testosterone Enanthate Injection, USP) provides testosterone enanthate, a derivative of the primary endogenous androgen testosterone, for intramuscular administration. In their active form, androgens have a 17-beta-hydroxy group. Ester...
Active Ingredient	Testosterone enanthate
Dosage Form	Injectable
Route	Injection
Strength	200mg/ml
Market Status	Prescription
Company	Hikma Farmaceutica; Watson Labs; Paddock; Mylan Institutional

4.2 Drug Indication

Testosterone enanthate in males is indicated as a replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone. Some of the treated conditions are 1) primary hypogonadism, defined as testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome or orchidectomy; 2) hypogonadotropic hypogonadism due to an idiopathic gonadotropin or luteinizing hormone-releasing hormone deficiency or due to a pituitary-hypothalamic injury from tumors, trauma or radiation, in this case it is important to accompany the treatment with adrenal cortical and thyroid hormone replacement therapy; 3) to stimulate puberty in patients with delayed puberty not secondary to a pathological disorder. If the conditions 1 and 2 occur prior to puberty, the androgen replacement therapy will be needed during adolescent years for the development of secondary sexual characteristics and prolonged androgen treatment might be needed it to maintain sexual characteristics after puberty. In females, testosterone enanthate is indicated to be used secondarily in presence of advanced inoperable metastatic mammary cancer in women who are from one to five years postmenopausal. It has also been used in premenopausal women with breast cancer who have benefited from oophorectomy and are considered to have a hormone-responsive tumor. Testosterone enanthate injections that are currently formulated for subcutaneous use are specifically indicated only for primary hypogonadism and hypogonadotropic hypogonadism. The use of such formulations is limited because the safety and efficacy of these subcutaneous products in adult males with late-onset hypogonadism and males less than 18 years old have not yet been established. Moreover, subcutaneously administered testosterone enanthate is indicated only for the treatment of men with hypogonadal conditions associated with structural or genetic etiologies, considering the medication could cause blood pressure increases that can raise the risk of major adverse cardiovascular events like non-fatal myocardial infarction, non-fatal stroke, and cardiovascular death.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Administration of ester derivatives of testosterone as testosterone enanthate generates an increase in serum testosterone to levels reaching 400% from the baseline within 24 hours of administration. These androgen levels remain elevated for 3-5 days after initial administration. Continuous administration of testosterone enanthate shows a significant suppression of dihydrotestosterone, serum PSA, HDL and FSH, as well as a slight increase in serum estradiol. The levels of dihydrotestosterone and FSH can remain suppressed even 14 days after treatment termination. There are no changes in mood and sexual activity by the presence of testosterone enanthate.

5.2 MeSH Pharmacological Classification

Androgens

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. (See all compounds classified as Androgens.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Androgen [EPC]; Androstanes [CS]; Androgen Receptor Agonists [MoA]

5.4 Absorption, Distribution and Excretion

Absorption

The pharmacokinetic profile of testosterone enanthate was studied in a regime of multiple dosing and the testosterone level was reported to present a Cmax above 1200 ng/dl after 24 hours of the last dose. The concentration decreased sequentially until it reached 600 ng/dl after one week. The pharmacokinetic profile of testosterone enanthate presented differences depending on the administered dose in which the tmax was shifted to a range of 36-48 hours. The plasma testosterone level plateaued below the therapeutic range after 3-4 weeks. This reports showed that the different formulation of testosterone enanthate and testosterone cypionate generates a different profile and thus, they are not therapeutically equivalent.

Route of 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. The inactivation of testosterone occurs primarily in the liver.

Volume of Distribution

The volume of distribution following intravenous administration of testosterone is of approximately 1 L/kg.

5.5 Metabolism/Metabolites

To start its activity, testosterone enanthate has to be processed by enzymes in the bloodstream. These enzymes will catalyze the molecule at the ester location of the moiety. Once processed in this manner, the testosterone enanthate molecule is metabolized to various 17-keto steroids through two different pathways. Subsequently, the major active metabolites are estradiol and DHTd. Testosterone is metabolized to DHT by steroid 5-reductase in skin, liver and urogenital tract. In reproductive tissues DHT is further metabolized to androstanediol.

5.6 Biological Half-Life

Testosterone enanthate presents a long half-life in the range of 7-9 days.

5.7 Mechanism of Action

The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing androgen effects. Such activities are useful as endogenous androgens like testosterone and dihydrotestosterone are responsible for the normal growth and development of the male sex organs and for maintenance of secondary sex characteristics. These effects include the growth and maturation of the prostate, seminal vesicles, penis, and scrotum; the development of male hair distribution, such as facial, pubic, chest, and axillary hair; laryngeal enlargement, vocal cord thickening, and alterations in body musculature and fat distribution. Male hypogonadism, a clinical syndrome resulting from insufficient secretion of testosterone, has two main etiologies. Primary hypogonadism is caused by defects of the gonads, such as Klinefelters syndrome or Leydig cell aplasia, whereas secondary hypogonadism is the failure of the hypothalamus (or pituitary) to produce sufficient gonadotropins (FSH, LH).

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Aspen Oss Bv

Netherlands

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Testosterone Enanthate

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 3877

Submission : 1980-06-25

Status : Active

Type : II

02

Symbiotec Pharmalab Private Ltd

India

AES 2024

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Symbiotec: Global API manufacturer, specializing in Cortico-Steroids & Steroid-Hormone APIs.

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India

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Testosterone Enanthate, Usp

GDUFA

DMF Review : Complete

Rev. Date : 2018-09-26

Pay. Date : 2018-04-17

DMF Number : 26166

Submission : 2012-06-19

Status : Active

Type : II

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Roussell Uclaf

France

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Sanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

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France

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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 3781

Submission : 1980-04-15

Status : Inactive

Type : II

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Bayer Ag

Germany

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Biovet Joint Stock Co

Bulgaria

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Pharmacia And Upjohn

U.S.A

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Steroid Spa

Italy

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Zhejiang Xianju Pharmaceutical Co Lt...

China

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Aspen API

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About the Company : Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen...

Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen API works tirelessly to deliver top-quality APIs to clients worldwide. Aspen API has a portfolio of over 58 high-quality APIs, including high potency, oncology, peptides, narcotics, analgesics, botanical extractions, and biochemicals. Aspen API places a strong emphasis on sustainability. It employs eco-friendly technologies and solvents in its chemical processes, ensuring responsible and environmentally conscious manufacturing.

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Symbiotec Pharmalab

India

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About the Company : Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable...

Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable operations, and innovation has driven their commitment to improving global healthcare access. With a state-of-the-art manufacturing facility inaugurated in 2004, Symbiotec has become a trusted provider in the industry. Their certifications including WHO-GMP, ISO, US FDA, and EU GMP showcase their dedication to quality and excellence. Over two decades, they've maintained their position through adaptability, efficiency, and competitive pricing.

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Hubei Gedian Humanwell Pharmaceutic...

China

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Hubei Gedian Humanwell focuses on R&D, production, & sales of fertility regulation drugs & steroidal APIs.

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China

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About the Company : Hubei Gedian Humanwell Pharmaceutical Co., Ltd. is a modern high-tech pharmaceutical company with a focus on the research and development, production, and sales of fertility regula...

Hubei Gedian Humanwell Pharmaceutical Co., Ltd. is a modern high-tech pharmaceutical company with a focus on the research and development, production, and sales of fertility regulation drugs and steroidal APIs. It operates as a wholly-owned subsidiary of Humanwell Healthcare Group (Stock Code: 600079), one of the leading pharmaceutical conglomerates in China. The company operates two APIs manufacturing sites, one formulation factory, and one excipients factory, showcasing its commitment to integrating the reproductive health industry chain from raw materials and active pharmaceutical ingredients (APIs) to finished dosage forms.

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AASraw Biochemical Technology Co., ...

China

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ASG Biochem

India

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Nanjing Bold Chemical

China

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Italy

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Zhejiang Xianju Pharmaceutical Co. ...

China

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API Reference Price

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