596-63-4

Usage

Uses

Used in Medical Diagnostics:
19-Hydroxyprogesterone is used as a biomarker for congenital adrenal hyperplasia, aiding in the early detection and diagnosis of this genetic disorder in newborns.
Used in Endocrinology:
19-Hydroxyprogesterone is used as a precursor hormone in the synthesis of cortisol and sex hormones, playing a significant role in the endocrine system's regulation.
Used in Obstetrics:
19-Hydroxyprogesterone is used as a therapeutic agent for preventing preterm labor, helping to prolong pregnancy and improve neonatal outcomes.
Used in Reproductive Medicine:
19-Hydroxyprogesterone is used as a treatment for infertility, potentially improving fertility rates by addressing hormonal imbalances.
Used in Oncology:
19-Hydroxyprogesterone is used as a potential therapeutic agent in the treatment of certain types of cancer, with ongoing research exploring its effects on tumor growth and progression.

InChI:InChI=1/C21H30O3/c1-13(23)17-5-6-18-16-4-3-14-11-15(24)7-10-21(14,12-22)19(16)8-9-20(17,18)2/h11,16-19,22H,3-10,12H2,1-2H3/t16-,17+,18-,19-,20+,21+/m0/s1

Upstream product

• 114127-09-2 19-hydroxyprogesterone acetate 
• 2205-86-9 6β,19-epoxypregn-4-en-3,20-dione 
• 53286-90-1 Acetic acid (4S,5R,8S,9S,10S,13S,14S,17S)-4-acetoxy-17-acetyl-13-methyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester 
• 41767-48-0 3β-acetoxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one 
• 88204-48-2 3β-hydroxy-19-(tetrahydropyran-2-yloxy)pregn-5-en-20-one 
• 26360-40-7 3β-acetoxy-19-hydroxy-Δ5-pregnen-20-one 
• 5490-69-7 5α-bromo-6β,19-epoxypregnan-3,20-dione 
• 5563-20-2 3β-hydroxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one 
• 41767-48-0 5-Bromo-20-oxo-6β,19-epoxy-5α-pregnan-3β-yl acetate 
• 2723-07-1 5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate 
• 145-13-1 Pregnenolone 
• 1778-02-5 Pregnenolone acetate 
• 102290-89-1 3,20-Diethylendioxy-6β,19-oxido-5α-pregnan 
• 88204-49-3 19-(tetrahydropyran-2-yloxy)pregn-4-en-3,20-dione 

Downstream Products

• 2394-23-2 19,21-dihydroxypregn-4-ene-3,20-dione 
• 974-38-9 19-Oxo-progesteron 

Relevant academic research and scientific papers

Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones

A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Δ4-3-keto steroids with a 19-mesylate in the presence of KOH in isopropanol. Three 6,19-cyclopregnanes were prepared (4, 5, 9); in the rat, 6,19-cycloprogesterone (4) and its 21-hydroxy derivative 5 displaced [3H]-dexamethasone from glucocorticoid receptors, the former compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. This journal is The Royal Society of Chemistry.

Sulphur analogues of 21-hydroxy-6,19-oxidoprogesterone (21oh-6op) for treating excess of glucocorticoids

The present invention is related to novel 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) analogues, their use as antiglucocorticoids for the treatment and/or prophylaxis of diseases associated to an excess of glucocorticoids. In particular, the invention relates to the use of novel 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) analogues having the formula FORMULAwherein X is S, SO and SO2, and R is either M or OH, for treating Cushing's syndrome, iatrogenic hypercortisolism or depression. Also the present invention is related to methods of preparing the novel 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) analogues.

SYNTHESIS OF 19-HYDROXYSTEROIDS II. NEW SYNTHESIS OF 19-HYDROXYPROGESTERONE

19-Hydroxyprogesterone has been synthesized in seven stages from pregnenolone with an overall yield of 11percent.

An Improved Route to 19-Hydroxypregn-4-ene-3,20-dione and Synthesis of its Analogue

3β-Acetoxy-5-bromo-6β,19-epoxy-5α-pregnane-20-one is more reliably converted into 19-hydroxyprogesterone via reductive opening of the epoxide to give 3β-acetoxy-19-hydroxypregn-5-en-20-one than by a previously published procedure. 19-Hydroxyprogesterone has been converted into its analogue in good yield.