L. Stallion, Ram, Bull, and Rat Urine
X. Possible Androgenic Activity of Other Hormones and Pregneninolone A large number of androgenic substances which are not naturally
occurring have been synthesized. These steroid compounds are closely related to testosterone (200). In addition to this class of compounds, claims of androgenic activity have been made for progesterone, preg-neninolone, and desoxycorticosterone.
Progesterone has been claimed to be inactive by Albrieux, Bruno, Engel, and Morato (2), by Desseau (53), and by Desclin (51). Evidence for androgenic activity of progesterone has been presented by Greene, Burrell, and Thomas (94), who showed increases up to 400% in the weights of the prostates of immature castrated rats which received 2 mg.
of progesterone for ten days. It was also possible to show significant stimulations of the prostates of adrenalectomized castrated immature rats. However, since the total dosage was 20*mg. of material it still is
540
likely that a contaminant of perhaps as little as 1 % may be responsible for these androgenic effects. Other reports have been published claim-ing androgenic activity for progesterone \vhen administered at levels of 20 t o 30 m g . / d a y (41,119).
Pregneninolone has been claimed t o possess androgenic activity under various conditions i n castrated male rats (41), and i n a Lebistes reticulatus (186). I n one experiment pregneninolone was administered to t h e tadpoles of Rana pipiens f r o m the early larval stage through metamorphoses. I t did n o t effect larval growth or differentiation b u t markedly affected sexual development. A l l treated tadpoles became males, a n d genetic females could n o t be identified. This action is identical w i t h that found w i t h testosterone.
Whether desoxycorticosterone is androgenically active is still t h e subject of some debate. Negative results on the capon's comb (33,134) and the castrated male rat have been reported (201). On the other hand, androgenic activity has been reported for desoxycorticosterone i n cas-trated male rats (35,41).
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17- Methy l-A4-androstenol-17-one-3 Isoandrosterone
XII. BIOCHEMISTRY OF ANDROGENS 547
Number Compound
X X Δδ-Androstenediol-3 (β), 17(α)-17 monobenzoate X X I Adrenosterone
X X I I A4-Androstenedione-3,17 X X I I I Androstanediol-3 {β), 11-one-17 X X I V 17-Hydroxyprogesterone X X V Testosterone
X X V I Δ2 or A3-Androstenone-17 X X V I I Δ 3·6-Androstadienone-17 X X V I I I A6-Androstenediol-3(/S),17(A) X L 11-Hydroxyandrosterone X L I Androstanetrione-3,11,17 X L I I Δ9 or n-Androstenol-3(A)-one-17 X L I I I Androstanediol-3 (A), 17 (A) X L I V Δ6-Androstenetriol·-3G3), 16,17 X L V Androstanetriol-3 (β), 16,17 X L V I 3-Ketoetioallobilianic acid
X L V I I 16-Benzilidinandrostanol-3 (β) -one-17 X L V I I I β-3-Hydroxyetioallobilianic acid
X L I X A6-Androstenetriol-3 (/3), 16,17-3-monoacetate L /3-3-Hydroxy^6-etiobilienic acid
LI Allopregnanol-3(/S)-one-20-al-21 L I I Pregnanol-3(/8)-one-20-al-21 L I I I A6-Pregnenol-3(/3)-one-20 L I V Allopregnanol-3(ß)-one-20 L V Δ1 6-Androstenol-3 (a) L V I A1 6-Androstenol-3(/3)
L V I I Androstanol-17 (/3)-one-3 hexahydrobenzoate L V I I I Δ1 6- Androstenone-3
L I X Estranediol-A
L X 11-Ketoisoandrosterone
L X I 11 - H y d r o x y d e h y droisoandrosterone L X I I 11-Ketodehydroisoandrosterone L X I I I Δ4-Androstenol-l l-dione-3,17 L X I V Etiocholanediol-3(a), l l - o n e - 1 7 L X V 11-Ketoandrosterone
L X V I Etiocholanol-3 (a)-dione-l 1,17 L X V I I Androstanol-17(a)-one-3 L X V I I I Δ5-Androstenol-3 (a)-one-17 L X I X Δ5-Androstenediol-3 (A), 17(A) L X X Androstanedione-3,17 L X X I Etiochoianedione-3,17 L X X I I Etiocholanol-l7(A)-one-3 L X X I I I Etiocholanediol-3(A),17(A)
L X X I V Allopregnanediol-3(fl), (21)-dione-l 1,20 L X X V Allopregnanetriol-3 (0), 11 (β), 20(A) L X V I Δ6-Pregnenetriol-3 (β), 11 (β), 20 (Α) L X X V I I Pregnanediol-3 (Α), 20 (Α)
L X X V I I I Δ 4-Pregnenediol-20,21-dione-3,11 L X X I X Δ4- Ρ ^ η β η 6 ά ί ο 1 - 1 1 (/3),21-dione 3,20 L X X X A4-Pregnenol-21-trione-3,11,20
Number Compound L X X X VII Desoxycorticosterone L X X X V I I I Allopregnanol-3 (0)-one-20
X C V A6-Methylandrostenediol-3(0),17(A) X C V I Meth y It estosterone
X C V I I Androstanediol-3 (0), 17 (A) X C I X Etiocholanediol-3 (0), 17 (A) C A5-Pregnenediol-3(0),17-one-2O CI A5-Pregnenetriol-3(0), 17,20 C I I Allopregnanediol-3 (Α), 20 (A) C M Androsterone sulfate
CIV Dehydroisoandrosterone benzoate C V Dehydroisoandrosterone sulfate C V I Pregnanediol-3(A),17-one-20 C V I I 3-Chloro^5-androstenol-17(A) C V I I I Pregnanetriol-3 (A) ,17,20 C I X A5-Pregnenediol-3 (0), 17-one-20 C X Androstanediol-3 (0), 17 (A)
C X I Allopregnanetetrol-3(A),ll,17(0),21-one-2O C X I I A5-Pregnenediol-3 (0), 20 (A)
C X I I I AllopregnanetetiOl-3(0),ll(0),17(0),21-one-2O C X I V Allopregnanepentol-3(0),11(0),17(0),20,21 CXV Allopregnanetetrol-3(0),17(0),2O,21-one-l 1 C X V I Allopregnanetriol-3 (0), 17 (0), 21-dione-11,20 C X V I I A n d r o s t a n o l- 3( 0) - d i o n e - l l , 1 7
C X V I I I û5-Androstenediol-3(0),ll-one-17 C X I X Δ5-Androstenol-3(0)-dione-ll,17 C X X A4-Androstenol-ll(0)-dione-3,17 C X X 1 E t i o c h o l a n e d i o l- 3( A) , l l( 0) - o n e - 1 7 C X X I J 11-Ketoandrosterone
C X X I I i 1 l-Ketoetiocholanol-3 (A)
C X X I V A4-Pregnenetetrol-Il(0), 17(0),2O,21-one-3 C X X V A4-Pregnenetriol-17(0),2O,21-dione-3,ll C X X V I A4-Pregnenetriol-ll(0),17(0),21-dione-3,2O C X X V I I Δ4-Pregnenediol-17(0),21-trione-3,ll,2O C X X V I I I Allopregnanetetrol-3 (0), 17 (0), 20,21 C X X I X Allopregn anetriol-3 (0), 17 (0), 2 l-one-3 C X X X Allopregnanetriol-3(0),ll(0),21-one-2O