5p-Androstane

L., Ragg, E., Rossi, R., Santagostino, M., Schiavone, A., Serra, F., Zappavigna, M.P., and Melloni, P., 17P-O-Aminoalkyloximes of 5P-androstane-3p,14P-diol with digitafis-Uke activity. Synthesis, cardiotonic activity, structure-activity relationships, and molecular modeling of the Na, K -ATPase receptor, J. Med. Chem., 43, 2332, 2000. 

Many of the organic contaminants which were found in Lippe river water were also present in the source samples (see Table 3). The sewage effluent sample and the Seseke river showed the best accordance with the compound spectrum of the Lippe river. However, also in the two tributaries from the rural upper reaches of the river, numerous specific contaminants like 9-methylacridine (No. 8), alkyl phosphates (Nos. 31, 32) and chlorinated alkyl phosphates (Nos. 34, 36) appeared. In the effluent of a pharmaceutical plant, only a few Lippe river contaminants like n-alkanes (No. 1), naphthalene (No. 3), TXIB (No. 21) and caffeine (No. 67) were detected (see Table 3). Therein, mainly structural relatives of androstanone like 3p-hydroxy-5p-androstan-17-one, 3a-hydroxy-5p-androstan-17-one and androstan-50-3,17-dione were present. These compounds are probably by-products of the synthesis of hormone preparations. Some polycyclic aromatic compounds, halogenated compounds and terpenoids were not detected in the source samples (see the underlined compounds in Table 3) and probably have another origin. Representative sampling of various input sources have to be carried out to prove the origin of these compounds. Hexachlorobutadiene (No. 38) and bis(chloropropyl)ethers (No. 44) appear exclusively at the lower reaches of the Lippe river (see Table 1), downstream the chemical plants in Marl. They are attributed to inputs of the chlorochemical industry (see section 3.1). Hence, this suggests their input by an industrial point source. 

De Munari S, Barassi P, Cerri A, Fedrizzi G, Gohhini M, Mahilia M, Mellon P. A new approach to the design of novel inhibitors of Na- -,K- —ATPase 17a-substituted seco-D 5p-androstane as cassaine analogues. J. Med. Chem. 1998 41 3033-3040. 

Hilgeis, G. and Scharf, H.-D., Synthese von 5P-Androstan-3,17-dion aus Cholsaure, Liebigs Ann. Chem., 1498,1985. 

The phase-I-metabolism of testosterone leads primarily to 5a-androstan-17P-ol-3-one (dihydrotestosterone), 5a-androstan-3a-ol-17-one (androsterone), and 5P-androstan-3a-ol-17-one (etiocholanolone) (Fig. 3.6,2-4, respectively), which represent important parameters of the so-called urinary steroid profile in sports drug testing (see Chapter 6). 

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).

Methyltestosterone 17a-methyl-5a-androstane-3a,17P-diol 17a-methyl-5P-androstane-3a,17P-diol 17P-methyl-androst-4,6-dien-17a-ol-3-one... 

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