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Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02 Page 23 of 50

Figure 38. Microbial transformation of oxandrolone (184) with Cunninghamella blakesleeana, M. phaseolina, Glomerella fusarioides, and
Rhizopus stolonifer.

197-202 were found to be new [Figure 39]. Compounds 194, 196, 199, 200, 201, and 202 showed
[61]
significant anti-inflammatory activity with the IC values of 202, 117, 250, 183, 295, 50, and 127 μM,
50
respectively, as compared to the standard drug prednisolone (IC = 83 μM). Metabolite 195 was found to be
50
inactive .
[61]
Similarly, Cunninghamella blakesleeana-mediated fermentation of mesterolone (194) (0.60%) yielded seven
new compounds, 1α-methyl-11β, 14α, 17β-trihydroxy-5α-androstan-3-one (204), 1α-methyl-7β, 17β-
dihydroxy-5α-androstan-3-one (205) (0.70%), 1α-methyl-17β-hydroxy-5α-androstan-3, 7-dione (206) (1.0%)
[62] [Figure 40], 1α-methyl-1β, 11α, 17β-trihydroxy-5α-androstan-3-one (207) (0.90%), 1α-methyl-7α, 11β,17β-
trihydroxy-5α-androstan-3-one (208) (0.40%), 1α-methyl-1β, 6α, 17β-trihydroxy-5α-androstan-3-one (209)
(0.40%), and 1α-methyl-1β, 11β, 17β-trihydroxy-5α-androstan-3-one (210) (0.50%), along with three known
[63]
metabolites, 197, 198, and 199 [Figure 40]. Fermentation of mesterolone (194) with Macrophomina
phaseolina afforded the new compound, 1α-methyl, 17β-hydroxy-5α-androstan-3, 6-dione (211) (0.40%)
[63]
[Figure 40].

Biotransformation of mibolerone (212)
Mibolerone (212) is a potent synthetic anabolic steroid, marketed by Upjohn Company (USA) under the
brand name Cheque Drops, for the treatment of estrous (heat) in female dogs. Biotransformation of
mibolerone (212) was carried out at room temperature using Cunninghamella echinulata, and
Macrophomina phaseolina. This afforded six new metabolites, 10β, 17β-dihydroxy-7α, 17α-dimethylestr-4-
en-3-one (213) (4.0%), 6 , 17 -dihydroxy-7 , 17 -dimethylestr-4-en-3-one (214) (2.0%), 6 , 10 , 17 -
trihydroxy-7 , 17 -dimethylestr-4-en-3-one (215) (30.0%), 11β, 17β, 20-trihydroxy-7α, 17α-dimethylestr-4-
en-3-one (216) (0.4%), 1α, 17β-dihydroxy-7α, 17α-dimethylestr-4-en-3-one (217) (0.24%), 1α, 11β, 17β-
trihydroxy-7α, 17α-dimethylestr-4-en-3-one (218) (0.34%), and a known metabolite, 11β, 17β-dihydroxy-7α,
[64]
17α-dimethylestr-4-ene-3-one (219) (3.0%) [Figure 41].
Biotransformation of metenolone acetate (220)
Metenolone acetate (220) is another synthetic steroidal anabolic drug, sold under the brand names Nibal
and Primobolan Depot, for the treatment of anemia. Drug 220 is also used by athletes, and for sports
animals, to enhance their muscular strength and physical performances. Microbial transformation of