19608-29-8

Basic information

• Product Name: 17alpha-propionate
• Synonyms: 17alpha-propionate;21-Hydroxy-17-(1-oxopropoxy)pregn-4-ene-3,20-dione;CB-03-01;Cortexolone 17-alpha-propionate;17 alpha-propionate (CB-03-01);CB-03-1;17alpha-propio17-(1-oxopropoxy)pregn-4-ene-3,20-dione;CB-03-01 17alpha-propionate
• CAS NO: 19608-29-8
• Molecular Formula: C₂₄H₃₄O₅
• Molecular Weight: 402.52
• EINECS: 1533716-785-6
• Product Categories: APIS
• Mol File: 19608-29-8.mol

Chemical Properties

• Boiling Point: 538.898 °C at 760 mmHg
• Flash Point: 179.292 °C
• Appearance: /
• Density: 1.19
• Solubility: Soluble in DMSO
• PKA: 12.98±0.10(Predicted)
• CAS DataBase Reference: 17alpha-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: 17alpha-propionate(19608-29-8)
• EPA Substance Registry System: 17alpha-propionate(19608-29-8)

Safety Data

• Hazardous Substances Data: 19608-29-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
17Alpha-propionate is used as a novel antagonist of androgen receptors for the treatment of acne vulgaris and androgenetic alopecia. It works by competing with androgens for binding to androgen receptors, blocking the androgen receptor signaling cascades that promote acne pathogenesis, such as sebaceous gland proliferation, excess sebum production, and inflammatory pathways.
2. Used in Dermatology:
17Alpha-propionate is used as a first-in-class topical treatment for acne vulgaris in male and female patients aged 12 years and older. It received FDA approval in August 2020 and is being investigated as a novel treatment for androgenetic alopecia.
3. Used in Cosmetic Industry:
17Alpha-propionate is being developed as a topical cream by Cassiopea for androgen-dependent skin disorders, which may include various cosmetic applications targeting skin health and appearance.

Biological Activity

Clascoterone is a high-affinity androgen receptor (AR) antagonist (antiandrogen) that antagonizes testosterone-stimulated transcription activity (in reporter cells) as well as DHT-induced production of lipids and inflammatory cytokines (in human sebocytes) in cultures. When applied topically, clascoterone is as active as cyproterone acetate, and 2-, 3-, and 4-times, respectively, more active than finasteride, flutamide, and progesterone in vivo (local antiandrogenic activity in hamster′s flank organ; 100-400 μg/50 μL acetone/animal).

Safety

Clascoterone(Winlevi) is the only topical acne product with a warning about hypothalamic-pituitary-adrenal (HPA) axis suppression. This may result when Winlevi is used over large surface areas or if use is prolonged. In addition, pediatric patients may be more susceptible. This adverse event was not observed in the pivotal studies or in the long-term open-label extension study. However, it was observed in a small group of patients on Day 14 in a pharmacokinetic study. Normal HPA axis function was observed at follow-up at 4 weeks after end of treatment.

Mode of action

Clascoterone is an androgen receptor inhibitor. The mechanism of action of WINLEVI cream for the topical treatment of acne vulgaris is unknown.

Upstream product

• 19608-30-1 cortexolone 17α,21-dipropionate 

Relevant articles and documents

ENZYMATIC PROCESS FOR OBTAINING 17 ALPHA- MONOESTERS OF CORTEXOLONE AND/OR ITS 9,11- DEHYDRODERIVATIVES

The present invention refers to a new enzymatic process for obtaining 17α-monoesters of cortexolone and/or its 9,11-dehydroderivatives starting from the corresponding 17α,21-diesters which comprises an enzymatic alcoholysis reaction. Furthermore, the present invention refers to new crystalline forms of cortexolone 17α-propionate and 9,11-dehydro-cortexolone 17α-butanoate.

Lipase-catalyzed preparation of corticosteroid 17α-esters endowed with antiandrogenic activity

Several 17α-monoesters of cortexolone and its Δ9-derivative are endowed with antiandrogenic activity. Their synthesis can be accomplished by means of a lipase-catalyzed chemoselective alcoholysis of the corresponding 17α,21-diesters.