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Chemistry

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Also known as: 57-85-2, Agovirin, Androlon, Androteston, Aquaviron, Hormoteston
Molecular Formula
C22H32O3
Molecular Weight
344.5  g/mol
InChI Key
PDMMFKSKQVNJMI-BLQWBTBKSA-N
FDA UNII
WI93Z9138A

Testosterone Propionate
An ester of TESTOSTERONE with a propionate substitution at the 17-beta position.
1 2D Structure

Testosterone Propionate

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] propanoate
2.1.2 InChI
InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
2.1.3 InChI Key
PDMMFKSKQVNJMI-BLQWBTBKSA-N
2.1.4 Canonical SMILES
CCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
2.1.5 Isomeric SMILES
CCC(=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
WI93Z9138A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Agovirin

2. Eifelfango, Testosteron Propionat

3. Testosteron Propionat Eifelfango

4. Virormone

2.3.2 Depositor-Supplied Synonyms

1. 57-85-2

2. Agovirin

3. Androlon

4. Androteston

5. Aquaviron

6. Hormoteston

7. Enarmon

8. Bio-testiculina

9. Androtest P

10. Androsteston

11. Sterandryl

12. Testonique

13. Andronate

14. Masenate

15. Orchiol

16. Orchistin

17. Pantestin

18. Propiokan

19. Solvotest

20. Synandrol

21. Synerone

22. Telipex

23. Testaform

24. Testodet

25. Testodrin

26. Testogen

27. Testolets

28. Testormol

29. Testosid

30. Testoxyl

31. Testrex

32. Tostrin

33. Uniteston

34. Nasdol

35. Vulvan

36. Enarmon-oil

37. Neo-hombreol

38. Okasa-mascul

39. Andrusol-p

40. Oreton Propionate

41. Recthormone Testosterone

42. Orchisterone

43. Androgen

44. Testosteroni Propionas

45. Nsc 9166

46. Testosteron Propionate

47. Homandren (amps)

48. Nsc-9166

49. Testosteron 17-propionate

50. Testosterone-17-propionate

51. Testosterone Propionate Ciii

52. Chembl1170

53. Chebi:9466

54. Testosterone 17.beta.-propionate

55. Testosterone-17.beta.-propionate

56. Wi93z9138a

57. Nrb-03689

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

59. [(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] Propanoate

60. Ncgc00016254-01

61. (17beta)-3-oxoandrost-4-en-17-yl Propanoate

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

63. 17-propionyl-17beta-hydroxyandrost-4-en-3-one

64. Dsstox_cid_16515

65. Dsstox_rid_79286

66. Dsstox_gsid_36515

67. Cas-57-85-2

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

69. Ccris 575

70. Testoviron (ampule)

71. Testosteron-17-propionat

72. Testosterone-17beta Propionate

73. Testosterone-17beta-propionate

74. Testosterone-17-beta-propionate

75. Einecs 200-351-1

76. 17beta-(propionyloxy)androst-4-en-3-one

77. Unii-wi93z9138a

78. Ai3-26378

79. 17beta-hydroxyandrost-4-en-3-one Propionate

80. 17beta-hydroxy-4-androsten-3-one 17-propionate

81. Testosterone Propionate [usp:jan]

82. Androst-4-en-3-one, 17beta-hydroxy-, Propionate

83. Delta(sup 4)-androstene-17-beta-propionate-3-one

84. Prestwick_432

85. 17beta-hydroxyandrost-4-en-3-one-17beta-propionate

86. Testex (tn)

87. 17.beta.-(propionyloxy)androst-4-en-3-one

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

89. .delta.4-androstene-17.beta.-propionate-3-one

90. 17.beta.-hydroxyandrost-4-en-3-one, Propionate

91. 3-oxoandrost-4-en-17-yl Propionate, (17.beta.)-

92. Prestwick0_000401

93. Prestwick1_000401

94. Prestwick2_000401

95. Prestwick3_000401

96. Androst-4-en-3-one, 17.beta.-hydroxy-, Propionate

97. 17-(1-oxopropoxy)androst-4-en-3-one, (17.beta.)-

98. Schembl4044

99. Bspbio_000322

100. Mls002153796

101. Testosterone Propionate, Solid

102. Spbio_002261

103. Bpbio1_000356

104. Gtpl7100

105. Testosterone-17.beta.propionate

106. Dtxsid9036515

107. Testosterone Propionate [androgenic (anabolic) Steroids]

108. Nsc9166

109. Hms1569a04

110. Hms2096a04

111. Hms2272k06

112. Hms3713a04

113. Testosterone Propionate (agovirin)

114. Zinc490791

115. Hy-b1269

116. Testosterone Propionate [mi]

117. Tox21_110330

118. Tox21_302270

119. Bbl029912

120. Bdbm50215709

121. Lmst02020076

122. Mfcd00003653

123. Stk801834

124. Testosterone Propionate (jp17/usp)

125. Testosterone Propionate [jan]

126. Akos005622513

127. Akos015842719

128. Tox21_110330_1

129. Ccg-220401

130. Cs-4905

131. Db01420

132. Testosterone Propionate [mart.]

133. Testosterone Propionate [vandf]

134. Testosterone Propionate [who-dd]

135. Testosterone Propionate [who-ip]

136. Ncgc00179602-01

137. Ncgc00179602-03

138. Ncgc00179602-06

139. Ncgc00255481-01

140. Ac-12172

141. Ac-33160

142. Smr000058348

143. Vs-09499

144. Bcp0726000215

145. Testosterone Propionate [green Book]

146. T0028

147. Testosterone Propionate [orange Book]

148. Testosteroni Propionas [who-ip Latin]

149. Testosterone Propionate [ep Monograph]

150. Testosterone Propionate [usp Impurity]

151. C08158

152. D00959

153. Testosterone Propionate [usp Monograph]

154. 003t653

155. Testosterone Propionate 1.0 Mg/ml In Acetonitrile

156. Testosterone Propionate, Tested According To Ph.eur.

157. W-105436

158. Brd-k90553655-001-03-6

159. Q10354588

160. Testosterone 17-propionate 100 Microg/ml In Methanol

161. Wln: L E5 B666 Ov Mutj A E Fo52 -b&aef

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

163. Testosterone Propionate, British Pharmacopoeia (bp) Reference Standard

164. Testosterone Propionate, European Pharmacopoeia (ep) Reference Standard

165. Testosterone Propionate, United States Pharmacopeia (usp) Reference Standard

166. (1s,3as,3br,9ar,9bs,11as)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-1-yl Propanoate

167. Propionic Acid (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 Ester

168. Propionic Acid 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 Ester

169. Propionic Acid 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 Ester(testosterone Propionate)

170. Testosterone Propionate For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 344.5 g/mol
Molecular Formula C22H32O3
XLogP34.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass344.23514488 g/mol
Monoisotopic Mass344.23514488 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count25
Formal Charge0
Complexity621
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 propionate is used in veterinary practice in heifers in order to stimulate maximal growth.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The administration of testosterone propionate can induce production of proteins related to male sexual development. Clinical trials have shown a decrease in plasma LH after the administration of testosterone propionate.


5.2 Absorption, Distribution and Excretion

Absorption

Testosterone propionate presents a slow absorption from the intramuscular site of administration. This slow absorption is due to the presence of the less polar ester group. The absorption rate of testosterone propionate generates a frequent injection requirement when compared with testosterone enanthate or testosterone cypionate. It presents absorption parameters of AUC and residence time of 180-210 ng h/ml and 40-60 h, respectively.


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. From the rest of the dose, approximately 6% of a dose is excreted in the feces, mostly in the unconjugated form.


Volume of Distribution

The registered volume of distribution for testosterone propionate is in the range of 75-120 L/kg.


Clearance

Testosterone propionate has a reduced clearance rate compared to testosterone. The reported clearance rate is of approximately 2000 ml/min.


5.3 Metabolism/Metabolites

As all testosterone esters, testosterone propionate is rapidly hydrolysed into free testosterone in plasma. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).


5.4 Biological Half-Life

Testosterone propionate possesses a relatively short half-life compared with other testosterone esters at approximately 4.5 days.


5.5 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 5alpha-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5alpha-reductase. 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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22-Jan-2021
24-Aug-2024
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