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2D Structure
Also known as: 58-20-8, Depo-testosterone, Depovirin, Jectatest, Testosterone cyclopentylpropionate, Testosterone cyclopentanepropionate
Molecular Formula
C27H40O3
Molecular Weight
412.6  g/mol
InChI Key
HPFVBGJFAYZEBE-ZLQWOROUSA-N
FDA UNII
M0XW1UBI14

Testosterone Cypionate is an eight-carbon ester form of Testosterone. The number of ester carbon atoms correlate with the half-life of the prodrug. 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. (NCI04)
1 2D Structure

2D Structure

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] 3-cyclopentylpropanoate
2.1.2 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
2.1.3 InChI Key
HPFVBGJFAYZEBE-ZLQWOROUSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=CC(=O)CCC35C
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C
2.2 Other Identifiers
2.2.1 UNII
M0XW1UBI14
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Andronate

2. Depo-testosterone

3. Depo-testosterone Cypionate

4. Deposteron

5. Depostomead

6. Duratest

7. Testa-c

8. Testex Elmu

9. Testosterone 17 Beta-cyclopentanepropionate

10. Testosterone 17 Beta-cyclopentylpropionate

11. Testosterone 17 Beta-cypionate

2.3.2 Depositor-Supplied Synonyms

1. 58-20-8

2. Depo-testosterone

3. Depovirin

4. Jectatest

5. Testosterone Cyclopentylpropionate

6. Testosterone Cyclopentanepropionate

7. Pertestis

8. Testosterone 17beta-cypionate

9. Andro-cyp

10. Dep-test

11. Malogen Cyp

12. Depandro 100

13. Depandro 200

14. T-ionate-p.a

15. Testodrin Prolongatum

16. Testosterone Cipionate

17. Depo-testadiol

18. Durandro

19. Nsc 9157

20. Testosterone Cypionate Ciii

21. M0xw1ubi14

22. Testosterone 17beta-cyclopentylpropionate

23. Testosterone Cypionate [usp]

24. Chebi:9463

25. Testosterone 17.beta.-cyclopentanepropionate

26. Androst-4-en-3-one, 17-(3-cyclopentyl-1-oxopropoxy)-, (17b)-

27. Testosterone, Cyclopentanepropionate

28. Nsc-9157

29. Testosterone 17beta-cyclopentanepropionate

30. Androst-4-en-3-one, 17-(3-cyclopentyl-1-oxopropoxy)-, (17.beta.)-

31. Depo-testosterone Cypionate

32. [(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

33. Testosterone Cypionate (usp)

34. 17-(3-cyclopentyl-1-propionyl)-17beta-hydroxyandrost-4-en-3-one

35. Unii-m0xw1ubi14

36. Testosterone 17.beta.-cypionate

37. Depotest

38. Testosterone 17-beta-cypionate

39. (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

40. Einecs 200-368-4

41. Testosterone 17.beta.-cyclopentylpropionate

42. Depo-testosterone Cyclopentylpropionate

43. Brn 3174363

44. Depo-testosterone (tn)

45. Schembl40862

46. 17beta-hydroxyandrost-4-en-3-one Cyclopentylpropionate

47. Chembl1201101

48. Dtxsid901015617

49. Zinc4097468

50. Androst-4-en-3-one, 17-(3-cyclopentyl-1-oxopropoxy)-, (17beta)-

51. Lmst02020074

52. Testosterone Cypionate [vandf]

53. Akos007930349

54. Akos015895326

55. Testosterone Cipionate [mart.]

56. Db13943

57. Ds-3318

58. Testosterone Cipionate [who-dd]

59. Testosterone Cypionate [orange Book]

60. Testosterone Cypionate Ciii [usp-rs]

61. Testosterone Cypionate [usp Monograph]

62. C08156

63. D00957

64. Ab01274709-01

65. 053t944

66. W-105407

67. 3-oxoandrost-4-en-17beta-yl 3-cyclopentylpropanoate

68. Depo-testadiol Component Testosterone Cypionate

69. Q27108401

70. Testosterone Cypionate 100 Microg/ml In Acetonitrile

71. Testosterone Cypionate Component Of Depo-testadiol

72. (17beta)-3-oxoandrost-4-en-17-yl 3-cyclopentylpropanoate

73. 17.beta.-hydroxyandrost-4-en-3-one Cyclopentylpropionate

74. Testosterone 17.beta.-cyclopentanepropionate [mi]

75. 17-(cyclopentyl-1-oxopropoxy)androst-4-en-3-one, (17.beta.)-

76. 3-oxoandrost-4-en-17-yl 3-cyclopentylpropanoate, (17.beta.)- #

77. Testosterone Cypionate, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 412.6 g/mol
Molecular Formula C27H40O3
XLogP36.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass412.29774513 g/mol
Monoisotopic Mass412.29774513 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count30
Formal Charge0
Complexity732
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Testosterone cypionate is used in males that present conditions derived from a deficiency or absence of endogenous testosterone. These conditions are 1) primary hypogonadism, defined as the testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome or orchidectomy; and 2) hypogonadotropic hypogonadism characterized by idiopathic gonadotropin, LHRH deficiency or pituitary-hypothalamic injury from tumors, trauma or radiation.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Administration of ester derivatives of testosterone as testosterone cypionate 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. The continuous variation in plasma testosterone after intramuscular administration of testosterone cypionate results in fluctuations in mood and libido as well as some local inflammation.


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.)


Anabolic Agents

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)


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

Testosterone cypionate is an esterified anabolic which allows it to present a greater degree of solubility in fats and thus, the release and absorption occur in a slow rate compare to homologous molecules. Intramuscular administration of 200 mg of testosterone cypionate produced a mean supratherapeutic Cmax of 1122 ng/dl which occurred 4-5 days post-injection. After the fifth day, the levels of testosterone cypionate in plasma went down reaching an average of 400 ng/dl.


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.


Volume of Distribution

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


Clearance

Testosterone cypionate presents a lower clearance rate after intramuscular administration compared to other analogs of testosterone.


5.5 Metabolism/Metabolites

To start its activity, testosterone cypionate has to be processed by enzymes in the bloodstream. These enzymes will break the bond between the cypionate ester moiety and the testosterone. Once separated, testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT). 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

The half-life of testosterone cypionate is one of the longest, being approximately of 8 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 5-alpha-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha-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 the androgen effects.