1863-39-4

Usage

Uses

Used in Hormonal Contraceptives:
3-beta,17-alpha-dihydroxypregn-5-en-20-one 3-acetate is used as a contraceptive agent for preventing pregnancy. It acts on the lining of the uterus, inhibiting the release of the egg during the menstrual cycle and creating an environment that is less conducive for sperm to reach the egg, thereby reducing the chances of fertilization.
Used in Hormone Replacement Therapy:
In hormone replacement therapy, 3-beta,17-alpha-dihydroxypregn-5-en-20-one 3-acetate is used as a hormone supplement to alleviate symptoms of menopause. It helps regulate hormonal imbalances and provides relief from menopausal symptoms such as hot flashes, night sweats, and mood swings.
Used in Regulating Irregular Menstrual Cycles:
3-beta,17-alpha-dihydroxypregn-5-en-20-one 3-acetate is used as a menstrual cycle regulator for women experiencing irregular periods. By mimicking the effects of progesterone, it helps to stabilize hormone levels and promote a more regular menstrual cycle.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-beta,17-alpha-dihydroxypregn-5-en-20-one 3-acetate is used as an active pharmaceutical ingredient in the development of various hormonal medications. Its stability and solubility, enhanced by the acetate group, make it a suitable candidate for formulation into tablets, injections, or other dosage forms for effective delivery to patients.

InChI:InChI=1/C23H34O4/c1-14(24)23(26)12-9-20-18-6-5-16-13-17(27-15(2)25)7-10-21(16,3)19(18)8-11-22(20,23)4/h5,17-20,26H,6-13H2,1-4H3

Upstream product

• 387-79-1 17-Hydroxypregnenolone 
• 108-24-7 acetic anhydride 
• 34209-81-9 Acetic acid (3S,8R,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester 
• 979-02-2 16-dehydropregnenolone acetate 
• 117773-23-6 bromohydrin acetate 
• 3517-42-8 17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one 
• 114417-72-0 Acetic acid (3S,8R,9S,10R,13S,14S,17R)-17-acetyl-16-bromo-17-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 75-16-1 methylmagnesium bromide 
• 95910-95-5 3-acetate of the 17-trimethylsilyl ether of 17β-cyanoandrost-5-ene-3β,17α-diol 

Downstream Products

• 4596-16-1 17-heptanoyloxy-pregn-4-ene-3,20-dione 
• 903-67-3 Δ⁵-pregnene-3β,17α,20α-triol 
• 2204-13-9 Δ⁵-pregnene-3β,17α,20S-triol 
• 3517-42-8 17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one 
• 387-79-1 17-Hydroxypregnenolone 
• 853-23-6 prasterone acetate 
• 3517-38-2 3β,17α-diacetoxypregn-5-en-20-one 
• 17291-60-0 17-hydroxy-20-oxopregn-5-en-3β-yl p-toluenusulfonate 
• 135300-59-3 11α,17-dihydroxy-3β-triphenylmethoxypregn-5-en-20-one 
• 135300-60-6 17-hydroxy-3β-triphenylmethoxy-20-oxopregn-5-en-11α-yl hydrogen butanedioate 
• 3517-33-7 3β,17,21-triacetoxy-pregn-5-en-20-one 
• 986-96-9 3,17-diacetoxy-6-methyl-pregna-3,5-dien-20-one 
• 3386-03-6 21-acetoxy-17-hydroxy-6α-methyl-pregn-4-ene-3,20-dione 
• 982-89-8 17-acetoxy-6-methyl-pregna-1,4,6-triene-3,20-dione 

Relevant academic research and scientific papers

SYNTHESIS OF PREGNANE DERIVATIVES

Pregnane derivatives have been obtained from the cyanohydrins of androst-4-en-3,17-dione and of 3β-acetoxyandrost-5-en-17-one.It has been shown that when both a nitrile group and an ethylenedioxy group are present in a androstane derivative a Grignard reaction in anisole takes place simultaneously at the two groups.

Effects of fluorine substitution on substrate conversion by cytochromes P450 17A1 and 21A2

Cytochromes P450 17A1 (CYP7A1) and 21A2 (CYP21A2) catalyze key reactions in the production of steroid hormones, including mineralocorticoids, glucocorticoids, and androgens. With the ultimate goal of designing probes that are selectively metabolized to each of these steroid types, fluorinated derivatives of the endogenous substrates, pregnenolone and progesterone, were prepared to study the effects on CYP17A1 and CYP21A2 activity. In the functional assays, the hydroxylase reactions catalysed by each of these enzymes were blocked when fluorine was introduced at the site of metabolism (positions 17 and 21 of the steroid core, respectively). CYP17A1, furthermore, performed the 17,20-lyase reaction on substrates with a fluorine installed at the 21-position. Importantly, none of the substitutions examined herein prevented compound entry into the active sites of either CYP17A1 or CYP21A2 as demonstrated by spectral binding assays. Taken together, the results suggest that fluorine might be used to redirect the metabolic pathways of pregnenolone and progesterone to specific types of steroids.

Further syntheses of cyproterone acetate

The present invention relates to improved methods for synthesising cyproterone acetate (17α-Acetoxy-6-chloro-1α, 2α-methylene-4,6-pregnadiene-3,20-dione) from solasodine. The methods of the invention are shorter as those of the prior art and therefore more economic.

3β-11α-17-TRIHYDROXY-5-PREGNEN-20-ONE 11-HEMISUCCINATE AS A HAPTENE FOR RIA OF ''17α-HYDROXYPREGNENOLONE''

6β,17-Dihydroxy-3α,5-cyclo-5α-pregnan-20-one (VII) and 17-hydroxy-6β-methoxy-3α,5-cyclo-5α-pregnan-20-one (IX) were hydroxylated into the position 11α using Rhizopus nigricans fungi culture, and then selectively converted into haptene XIII for the RIA determination of 3β,17-dihydroxypregn-5-en-20-one (IV).