Progesterone

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Cat Number

API57830

CAS Number

57-83-0

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CAS Number

57-83-0

EINECS

200-350-6

Storage

Store at room temperature

Synonyms

Pregn-4-ene-3,20-dione; Agolutin; Crinone; Progestin; Utrogestan; Luteol

Molecular Formula

C21H30O2

Molecular Weight

314.46

Smiles

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

Appearance

White to off-white crystalline powder

Melting Point

128-132℃

Boiling Point

447.2℃

General Description

Progesterone is a naturally occurring C21 steroid hormone produced primarily by the corpus luteum and placenta. It is available in multiple formulations, including oral capsules, intramuscular injections, vaginal gels, and intrauterine devices. This agent is essential for the maintenance of pregnancy and the regulation of the menstrual cycle, serving as the principal progestogen in the body.

Mechanism of Action

Upon binding to nuclear progesterone receptors (PR-A and PR-B) in target tissues, the hormone-receptor complex dimerizes and translocates to the nucleus, where it regulates gene transcription. This action promotes secretory transformation of the endometrium, increases vascular permeability, and maintains endometrial stability. Additionally, it exerts negative feedback on the hypothalamic-pituitary axis to suppress gonadotropin secretion.

Application

It is used for a wide range of indications, including luteal phase support in assisted reproductive technology, secondary amenorrhea, abnormal uterine bleeding, and hormone replacement therapy in menopausal women. The micronized oral formulation is also approved for the prevention of endometrial hyperplasia in postmenopausal women receiving estrogen therapy. In pregnancy, it is utilized for the prevention of preterm birth in women with a short cervix.

This review synthesizes current understanding of how progesterone exerts opposing effects on neuronal excitability through distinct mechanisms. Progesterone activates its cognate receptors to enhance AMPA receptor expression, producing excitatory effects. Conversely, its metabolite allopregnanolone potentiates synaptic and extrasynaptic GABAA receptors, mediating sedative, anxiolytic, and anticonvulsant actions. These dual mechanisms have important clinical implications for catamenial epilepsy, where progesterone withdrawal at the end of the menstrual cycle may precipitate seizure exacerbation. The authors conclude that progesterone’s bidirectional modulation of neuronal excitability—excitatory via nuclear receptors and inhibitory via neurosteroid metabolites—explains its complex role in seizure regulation and provides a framework for understanding hormone-related seizure disorders.

Fig. 1 A schematic illustrating the cellular actions of progesterone. Four progesterone effector molecules, THP, PRs, mPRs, and PGRMC1 are present in the brain. (Kapur J, Joshi S, 2021)

References

Kapur J, Joshi S. Progesterone modulates neuronal excitability bidirectionally. Neurosci Lett. 2021; 744:135619.

A double‑blind, placebo‑controlled trial randomized 278 women with threatened miscarriage before 10 weeks to vaginal progesterone 400 mg nightly or placebo until 12 weeks. Live birth rates were 82.4% with progesterone versus 84.2% with placebo (RR 0.98, 95% CI 0.88‑1.09; P=0.683).

Fig. 2 Recruitment, randomization, and follow-up of participants. (McLindon LA, et al., 2023)

References

McLindon LA, et al. Progesterone for women with threatened miscarriage (STOP trial): a placebo-controlled randomized clinical trial. Hum Reprod. 2023; 38(4):560-568.

Does Progesterone require protection from light during long-term storage?

Yes, it is photosensitive. Prolonged exposure to light can cause photodegradation and isomerization. Store in light-resistant containers in a cool, dark place.

What is the recommended storage temperature for Progesterone?

Store at controlled room temperature, between 15°C and 25°C. Avoid excessive heat, which can cause melting or softening of the crystalline material.

Is Progesterone stable in lipid-based formulations for injectable or topical use?

Yes, it is lipophilic and stable in oil-based vehicles. We provide compatibility data for various excipients, including sesame oil, castor oil, and benzyl alcohol.

How is the polymorphic form of Progesterone controlled during storage?

Progesterone exhibits polymorphism. We manufacture the stable Form I and monitor polymorphic transformation using X-ray diffraction during stability testing.