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Chemical Compound Review:

CHEBI:799 (8R,9S,10R,13S,14S)-13- methyl-3,17-dioxo-2...

Synonyms: NSC-76985, NSC76985, CTK8D5872, LMST02020083, ZINC04063367, ...

Miyairi, S. et al., Beusen, D.D. et al., Miyairi, S. et al., McRobie, D.J. et al.

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High impact information on NSC 76985

The essential role of the C-19 hydroxylation in aromatization is supported by the observation that the 3-methylene derivatives of 19-hydroxy- and 19-oxoandrostenedione showed time-dependent inhibition, but the corresponding 19-methyl compound did not [1].
Neither the androstenedione analogue [10-ethylestr-4-ene-3,17-dione (1c)] nor the 19-oxoandrostenedione analogue [10-acetylestr-4-ene-3,17-dione (3c)] was converted to estrogens or oxygenated metabolites by placental microsomes [2].

Anatomical context of NSC 76985

Incubation of a mixture of [19-C3H3]- and [4-14C]androstenedione with human placental microsomes yielded 19-hydroxy- and 19-oxoandrostenedione, respectively, products of one and two hydroxylations at C-19 [3].

Analytical, diagnostic and therapeutic context of NSC 76985

A statistical difference was detected in the percentage of 19-oxoandrostenedione formed between the overt and control groups (P < 0.05) [4].

References

3-Methylene-substituted androgens as novel aromatization inhibitors. Evidence of a requirement for C-3 oxygen in C-19 hydroxylations. Miyairi, S., Fishman, J. J. Biol. Chem. (1986) [Pubmed]
Metabolism of 19-methyl-substituted steroids by human placental aromatase. Beusen, D.D., Carrell, H.L., Covey, D.F. Biochemistry (1987) [Pubmed]
Radiometric analysis of oxidative reactions in aromatization by placental microsomes. Presence of differential isotope effects. Miyairi, S., Fishman, J. J. Biol. Chem. (1985) [Pubmed]
The effects of diabetes on placental aromatase activity. McRobie, D.J., Korzekwa, K.R., Glover, D.D., Tracy, T.S. J. Steroid Biochem. Mol. Biol. (1997) [Pubmed]

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