STEROID SEX HORMONES 649 



EXCRETORY PRODUCTS 



c=o 



Progesterone 



1 3 



HCOH 



HO H 



Pregnanediol 



CH, 



-OH 



17 Hydroxy progesterone 



CH, 



^ H-C-OH 



■OH 



HO H 



Pregnanetriol 



OH 



Testosterone 



Androsterone 



HO 



/ 



androstenedione 



HO H 



Etiocholanolone 



Dehydroepiandrosterone 



Fk;. 11.3. Excretory products of progesterone and androgen 



(Iroxy progesterone is converted to pregnane- 

 3a:17a:20a-triol (Fig. 11.3). Testosterone 

 and dehydrocpiandroesterone are both con- 

 verted to A4-androstenedione and the reduc- 

 tion of its A4-3-ketone group results in a 

 mixture of androsterone (3a,5a-configura- 

 tion) and ctiochohmolone (3a,5/?-configu- 

 ration ) . 



The catabohsm of estradiol is not com- 

 pletely known. Estradiol, estrone, and es- 

 triol are found in the urine but they account 

 for less than half of an administered dose of 

 labeled estradiol. The /3-isomer, 16-epies- 

 triol, and two other phenolic steroids, 16-a- 

 hydroxy estrone and 2-methoxyestrone, 

 have recently been isolated from normal 



