Biotransformation of drospirenone, a contraceptive drug, with Cunninghamella elegans

•Biotransformation of drospirenone by Cunninghamella elegans afforded six compounds.•Five metabolites were undescribed products in the chemical bibliography.•Microbial transformation of drospirenone involves oxidation at C-11, -12 and -14.•Biotransformation of drospirenone is a good tool for addition of CO and OH groups.

Biotransformation of an orally active contraceptive drug, drospirenone (1), by Cunninghamella elegans ATCC 36114 yielded four new metabolites, 6β,7β,15β,16β-dimethylene-3-oxo-14α-hydroxy-17α-pregn-4-ene-21,17-carbolactone (2), 6β,7β,15β,16β-dimethylene-3,11-dioxo-17α-pregn-4-ene-21,17-carbolactone (3), 6β,7β,15β,16β-dimethylene-3,12-dioxo-17α-pregn-4-ene-21,17-carbolactone (4), and 6β,7β,15β,16β-dimethylene-3-oxo-11β,14α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone (5), along with a known metabolite, 6β,7β,15β,16β-dimethylene-3-oxo-11α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone (6). This study provides not only new analogues of orally active contraceptive drug, drospirenone, but also help in understanding the metabolism of this important drug.

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