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Testosterone Undecanoate

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58 US Patents, 4 US Exclusivities, 1 Health Canada Patents

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58 US Patents
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1 Health Canada Patents

Aspen Testosterone Undecanoate

Synopsis

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3EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 5949-44-0, Andriol, Testosterone undecylate, Nebido, Testosterone (undecanoate), Aveed

Molecular Formula

C₃₀H₄₈O₃

Molecular Weight

456.7 g/mol

InChI Key

UDSFVOAUHKGBEK-CNQKSJKFSA-N

FDA UNII

H16A5VCT9C

Testosterone Undecanoate is the undecanoate ester form of the androgen testosterone, with gonadotropin-secretory inhibiting and hormone replacement activity. As testosterone inhibits the secretion of gonadotropins from the pituitary gland, administration of testosterone decreases the secretion of luteinizing hormone (LH). By inhibiting LH secretion, the growth of Leydig cells, which are normally stimulated by LH to produce testosterone, may be suppressed. In addition, this agent promotes the maintenance of male sex characteristics and can be used for testosterone replacement in hypogonadal males.

1 2D Structure

Testosterone Undecanoate

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] undecanoate

2.1.2 InChI

InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1

2.1.3 InChI Key

UDSFVOAUHKGBEK-CNQKSJKFSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

CCCCCCCCCCC(=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

H16A5VCT9C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Andriol

2. Nebido

3. Pantestone

4. Restandol

5. Testosterone Undecylate

6. Undestor

2.3.2 Depositor-Supplied Synonyms

1. 5949-44-0

2. Andriol

3. Testosterone Undecylate

4. Nebido

5. Testosterone (undecanoate)

6. Aveed

7. Org 538

8. Testosterone Undeconate

9. Jatenzo

10. Testosterone Undecanoate [usan]

11. Testosterone, Undecanoate (ester)

12. Undestor

13. H16a5vct9c

14. Org-538

15. Testosterone 17.beta.-undecylate

16. Tsx-011

17. [(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] Undecanoate

18. Mk-3033

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

20. Pantestone

21. Restandol

22. T Undecanoate

23. Testosterone Undecanoate (usan)

24. Rextoro

25. Nebido-r

26. Reandron 1000

27. Einecs 227-712-6

28. Unii-h16a5vct9c

29. Brn 3176734

30. 17beta-hydroxyandrost-4-en-3-one Undecanoate

31. Andriol (tn)

32. Aveed (tn)

33. 5-alpha-androstan-3-one, 17-beta-hydroxy-, Undecanoate

34. Bay 86-5037

35. 3-oxoandrost-4-en-17beta-yl Undecanoate

36. Androst-4-en-3-one, 17-((1-oxoundecyl)oxy)-, (17-beta)-

37. Testosterone, Undecanoate

38. 4-08-00-00981 (beilstein Handbook Reference)

39. Schembl147620

40. Chembl2107067

41. Clr-610

42. Dtxsid90863661

43. Chebi:135741

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

45. (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 Undecanoate

46. Bcp11921

47. Hy-b0626

48. Zinc8214690

49. Mfcd00468114

50. Testosterone Undecanoate [mi]

51. Akos016010255

52. Cs-4342

53. Db13946

54. Gs-6598

55. Testosterone Undecylate [mart.]

56. 17beta-undecanoyloxy-4-androsten-3-one

57. Testosterone Undecanoate [vandf]

58. Ncgc00484056-01

59. Testosterone Undecanoate [who-dd]

60. Testosterone Undecanoate [orange Book]

61. D06087

62. (17beta)-3-oxoandrost-4-en-17-yl Undecanoate

63. (17-beta)-3-oxoandrost-4-en-17-yl Undecanoate

64. 949t440

65. 3-oxoandrost-4-en-17.beta.-yl Undecanoate

66. W-105318

67. Q15410178

68. 17.beta.-hydroxyandrost-4-en-3-one Undecanoate

69. (17.beta.)-17-hydroxyandrost-4-en-3-one Undecanoate

70. 5-.alpha.-androstan-3-one, 17-.beta.-hydroxy-, Undecanoate

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

72. .delta.(sup 4)-androsten-17.beta.-ol-3-one Undecanoate

73. Androst-4-en-3-one, 17-((1-oxoundecyl)oxy)-(17.beta.)

74. (1s,2r,10r,11s,14s,15s)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl Undecanoate

75. (1s,2r,10r,11s,14s,15s)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl Undecanoate

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₈O₃
Molecular Weight	456.7 g/mol
XLogP3	8.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	11
Exact Mass	456.36034539 g/mol
Monoisotopic Mass	456.36034539 g/mol
Topological Polar Surface Area	43.4 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	739
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	Aveed
PubMed Health	Testosterone (Injection)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Aveed (testosterone undecanoate) injection contains testosterone undecanoate (17-undecanoyloxy-4-androsten-3-one) which is an ester of the androgen, testosterone. Testosterone is formed by cleavage of the ester side chain of testosterone undecanoat...
Active Ingredient	Testosterone undecanoate
Dosage Form	Injectable
Route	Intramuscular
Strength	750mg/3ml (250mg/ml)
Market Status	Prescription
Company	Endo Pharms

2 of 2
Drug Name	Aveed
PubMed Health	Testosterone (Injection)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Aveed (testosterone undecanoate) injection contains testosterone undecanoate (17-undecanoyloxy-4-androsten-3-one) which is an ester of the androgen, testosterone. Testosterone is formed by cleavage of the ester side chain of testosterone undecanoat...
Active Ingredient	Testosterone undecanoate
Dosage Form	Injectable
Route	Intramuscular
Strength	750mg/3ml (250mg/ml)
Market Status	Prescription
Company	Endo Pharms

4.2 Drug Indication

Testosterone undecanoate is indicated for replacement therapy in adult males with conditions that are linked with an absence or deficiency in endogenous testosterone production.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Testosterone plays a key role in male sexual differentiation and is involved in regulation of hematopoiesis, body composition, and bone metabolism. As a result, testosterone replacement therapy in males with hypogonadism can result in improved sexual function, increased lean body mass, bone density, erythropoiesis, prostate size, and changes in lipid profiles.

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 absorption of testosterone undecanoate varies based on the formulation. The intramuscular formulation of testosterone esters is suspended in oil and is absorbed from the lipid phase. Testosterone is released when tissue esterases cleave the undecanoic acid side chain. The oral formulation of testosterone undecanoate is also formulated as a prodrug, is best absorbed with food and ideal absorption occurs when taken with a meal containing at least 30 g of fat.

Route of Elimination

The majority (~90%) of an intramuscularly administered dose of testosterone is conjugated and eliminated in the urine. Approximately 6% of the dose is eliminated primarily unconjugated in the feces.

5.5 Metabolism/Metabolites

The side chain of testosterone undecanoate is cleaved by non specific esterases when it enters circulation and the undecanoic acid side chain is metabolized by the beta-oxidation pathway. The resulting Testosterone molecule is then metabolized to dihydrotestosterone (DHT) by the enzyme 5-alpha reductase. DHT is reduced by 3-alpha-hydroxysteroid dehydrogenase (major) and 3-beta-hydroxysteroid dehydrogenase prior to being glucuronidated and cleared by the kidneys. It should be noted that testosterone is metabolized to several other 17-keto steroids in the body.

5.6 Biological Half-Life

Based on one source, Testosterone undecanoate in castor oil (for intramuscular injection) has a half life of 33.9 days, allowing it to maintain serum levels in the normal range for over 6 weeks. It should be noted that the half life of testosterone reported in the literature is inconsistent.

5.7 Mechanism of Action

Testosterone is produced by Leydig cells and exerts it's effects by binding to androgen receptors throughout the body. Testosterone affects the voice, genitalia, mood, and influences muscle growth and protein expression. Accordingly, males with low levels of testosterone often experience decreased libido, fatigue, mood changes and dysphoria. Exogenous sources of testosterone are designed to mimic the effects of endogenous testosterone.

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