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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O2
Molecular Weight 312.4458
Optical Activity ( + )
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6-DEHYDROPROGESTERONE

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C=CC4=CC(=O)CC[C@]34C

InChI

InChIKey=JGMOKGBVKVMRFX-LEKSSAKUSA-N
InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

HIDE SMILES / InChI

Description

6-Dehydroprogesterone (Pregna-4,6-diene-3,20-dione) is a synthetic derivative and natural metabolite of progesterone and major impurity of dehydrogesterone. 6-Dehydroprogesterone derivatives has been used in hormone replacement therapy for menopausal symptoms and in the treatment of gynecological disorders, but 6-Dehydroprogesterone has never marketed.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Four liter culture medium was prepared for Aspergillus niger, and distributed equally in 40 Erlenmeyer flasks of 250 mL i.e., each flasks contain 100 mL of culturing medium. Seed flaks were prepared by inoculating with A. niger spores and incubated at 26 _C for 3 days. Within two to three days, fungus growth was observed. The remaining flasks were inoculated by transferring spores from seed flasks. 6-Dehydroprogesterone (1) (300 mg) was dissolved in methanol (20 mL), and distributed to 40 flasks containing 3–4 days old cultures of A. niger (7.5 mg in each flask). These flasks were placed over rotary shaker for fermentation for 12 days at 26 _C. On completion of fermentation reaction, the fungal mass was filtered off, and extracted three times with CH2Cl2 (24 L). The extract was dried over Na2SO4 (anhydrous) and concentrated under reduced pressure to obtain a brown gum (2.1 g). This gum was fractionated with silica gel column chromatography with hexane: acetone mixtures of increasing polarity. The fractions were compiled together through comparative TLC analysis, which yielded five main fractions (1–5). Further purification was carried out using recycling HPLC.