Testosterone metabolite, structure

STRUCTURE DETERMINATION USING HSQC AND HMBC 11.6.1 Testosterone Metabolites... 

FIGURE 4.20 Structures of the CYP3A4 substrates, erythromycin, nifedipine, testosterone, and midazolam, and their metabolites. 

Men also have chemical stimulants. [14] Prelog and Ruzicka resolved the structure of 5a-androst- 16-en-3-one, the sex pheromone ofthe boar Sus scrofa domestica), [15] and, as it became clear later, also of men. [16] It is a metabolite of testosterone and its odour was described as a scent of receptacles , which had been used over a longer period to store urine. In waiting rooms, women preferred to sit rather on androstenone-impregnated chairs than on those which were untreated. Also, photographs of men, animals and houses primed with traces of 5a-androst- 16-en-3-one were considered more warm and friendlythan those which lacked the boar pheromone. 

Urinary Studies. If the 19-carbon urinary steroids in Table VI are arranged in orderly stepwise oxidation or reduction products of testosterone, a scheme (Fig. 10) is obtained which affords a reasonable summary of the chemical pathways potentially involved in the transformation of testosterone to its urinary metabolites. This scheme accounts for the majority of the 19-earbon-ll-desoxysteroids listed in Table VI with a few notable exceptions. These include A -androstene-SjlT-dione (LXVIII), a compound isolated in small amount after the administration of large amounts of testosterone. The close structural resemblance to A -andro-stene-3,17-dione (LV) might lead to the belief that it is derived from this... 

Figure 4.5 Structures of selected steroidal analytes 5a-androstan-17P-ol-3-one (1), 5P-androstan-17P-ol-3-one (2), 17a-methyl-5a-androstan-17P-ol-3-one (3), la-methyl-5a-androstan-17P-ol-3-one (4), testosterone (5), nandrolone (6), 1-testosterone (7), metenolone (8), 5a-androst-l-ene-3,17-dione (9), metandienone (10), 18-nor-17P-hydroxymethyl,17a-methyl-androst-l,4,13-trien-3-one (metandienone metabolite) (11), androsta-4,6-dien-17P-ol-3-one (12), androsta-4,9-dien-17P-ol-3-one (13), trenbo-lone (14), methyltrienolone (15), tetrahydrogestrinone (THG, 16), and stanozolol (17).

Kuuranne, T., Aitio, O., Vahermo, M., et al. (2002) Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of methyl-testosterone (17a-methylandrost-4-en-17b-ol-3-one) andnandrolone (estr-4-en-17b-ol-3-one) metabolites. Bioconjugate Chemistry, 13,194-199. 

---