Hydroxyprogesterone
[CAS# 68-96-2]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Birth control pills
• Name: Hydroxyprogesterone
• Synonyms: 17a-Hydroxyprogesterone; 4-Pregnen-17a-ol-3,20-dione; 17a-Hydroxypregn-4-ene-3,20-dione
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.47
• CAS Registry Number: 68-96-2
• EC Number: 200-699-4
• SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O

Properties

• Solubility: 40mg/mL (DMSO)
• Melting point: 276 °C

Safety Data

• Hazard Symbols: HGS08 Danger
• Risk Statements: H360
• Safety Statements: P203-P280-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	2	H361

Discovery and Applications

Hydroxyprogesterone, also known as 17α-hydroxyprogesterone, is a synthetic progestin that plays an important role in medical treatment and reproductive health. Hydroxyprogesterone is a derivative of progesterone, a natural female hormone that is essential for menstrual cycle regulation and pregnancy maintenance. It is first synthesized by modifying the progesterone molecule to enhance its pharmacological properties, especially its duration of action and bioavailability. The synthesis involves selective hydroxylation at the 17α position of the progesterone molecule, resulting in hydroxyprogesterone.

Hydroxyprogesterone has various physiological effects similar to natural progesterone: It acts primarily as a progestin, binding to progesterone receptors in the uterus and other reproductive tissues, promoting the maintenance of pregnancy and preparing the uterus for implantation. Hydroxyprogesterone helps maintain the integrity of the endometrium, which is essential for implantation and early pregnancy development.

Hydroxyprogesterone is widely used in obstetrics and gynecology practice: It is mainly used in pregnant women with a history of spontaneous preterm birth to reduce the risk of recurrent preterm birth. Hydroxyprogesterone is injected once a week from the 16th to the 36th week of pregnancy to help maintain pregnancy until term. For women in menopause, hydroxyprogesterone can be used as part of hormone replacement therapy (HRT) to replenish declining progesterone levels, support estrogen therapy, and reduce the risk of endometrial hyperplasia.

Hydroxyprogesterone is used to regulate the menstrual cycle and control conditions such as irregular menstruation and abnormal uterine bleeding. It can be used to correct hormonal imbalances in conditions such as polycystic ovary syndrome (PCOS) or dysfunctional uterine bleeding.

Hydroxyprogesterone is usually given by intramuscular injection under physician supervision. Dosing regimens vary depending on the indication, patient medical history, and response to treatment. Regular monitoring is essential to assess treatment effectiveness and manage potential side effects.

Common side effects of hydroxyprogesterone include injection site reactions such as pain and swelling, and mild systemic reactions such as headache and fatigue. Serious adverse reactions, while rare, can include thromboembolic events (blood clots) and allergic reactions. Hydroxyprogesterone should be used with caution in patients with a history of hormone-sensitive cancers or certain cardiovascular diseases.

Ongoing studies are aimed at optimizing the formulation and dosing of hydroxyprogesterone to improve efficacy and patient compliance. Emerging research explores its potential use in fertility treatments, hormone-related cancers, and other reproductive health conditions.

References

1987. Morning Salivary 17-Hydroxyprogesterone Is a Useful Screening Test for Nonclassical 21-Hydroxylase Deficiency. The Journal of clinical endocrinology and metabolism, 65(2).
DOI: 10.1210/jcem-65-2-227

1984. Source and regulation of 17 alpha-hydroxyprogesterone during baboon pregnancy. Biology of Reproduction, 31(3).
DOI: 10.1095/biolreprod31.3.471

1986. Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Oxygenative lactonization of androstenedione to testololactone. The Journal of Biochemistry, 99(3).
DOI: 10.1093/oxfordjournals.jbchem.a135541