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    Chemistry

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    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
    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

    Testosterone Cypionate

    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.

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    23-Feb-2021
    09-Sep-2024
    KGS
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