26439-43-0

Usage

Type of medication

Synthetic progestin

Uses

Treatment of preterm labor, menstrual disorders, and hormone replacement therapy

Mechanism of action

Binds to and activates progesterone receptors in the body

Regulation

Regulates the menstrual cycle and maintains pregnancy

Forms available

Oral tablets, injections, and vaginal suppositories

Potential side effects

Nausea, breast tenderness, and changes in menstrual bleeding patterns

Upstream product

• 64-17-5 ethanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 95006-63-6 21-bromo-17-hydroxy-5β-pregnane-3,20-dione 
• 570-58-1 5β-17α-hydroxy-preganene-3,20-dione 
• 640-87-9 cortexolone 21-acetate 

Downstream Products

• 640-87-9 cortexolone 21-acetate 
• 601-03-6 3β,5β-Tetrahydro Reichstein's Substance S 
• 68-60-0 tetrahydrodeoxycortisol 
• 566-42-7 5β-pregnan-17α,21-diol-3,20-dione 
• 56162-40-4 17,21-dihydroxy-20-oxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid 

Relevant academic research and scientific papers

Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5 α- and 5 β-series

Here, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5 α- and 5 β-series. The principal reactions involved are: (1) selective protection of a specific hydroxy group in substrates; (2) catalytic hydrogenation at C-5 of Δ4-3-ketosteroids with 10% Pd(OH) 2/C to yield 3-oxo-5 β-steroids and reductive allomerization with 10% Pd/C to yield 3-oxo-5 α-isomers; (3) reduction of the resulting 3-oxo-5 β- and 3-oxo-5 α-steroids to the corresponding 3 α-hydroxy-compounds with Zn(BH4)2 and K-Selectride, respectively; and (4) sulfation of hydroxy groups at C-3 and/or C-21 in the tetrahydrocorticosteroid derivatives with sulfur trioxide-triethylamine complex.

The scarlet letter: Reichstein's substance S. A comparison of the angiostatic properties of 5α-tetrahydro S and 5β-tetrahydro S

5β-Tetrahydro-Reichtein's Substance S (3α, 5β-THS) from different sources yielded variable bioassays activity in the chick chorio-allantoic membrane assay system. Physical characterization showed impure products. Synthesis of this compound by two different routes yielded active and inactive 3α,5β-THS. Of the other two epimers, 3β,5β-THS (epi-THS) and 3α,5α-THS (allo-THS), only the latter was active. These results suggest that the impurities present in 3α,5β-THS synthesized by reduction of the α,β-unsaturated ketone of Substance S might be either or both the epi- lallo-epimers (3β,5β-THS and 3α,5α-THS, respectively), with only the latter contributing the positive angiostatic activity to the mixture. Of the two synthetically derived compounds, only the latter was shown to maintain the activity, whereas 3α,5β-THS was not antiangiogenic.