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Cortexolone 17alpha-propionate

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10 Listed Suppliers
$ API Reference Price

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Synopsis

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Chemistry

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Also known as: Clascoterone, 19608-29-8, Cb-03-01, 17 alpha-propionate, 17alpha-propionate, Winlevi

Molecular Formula

C₂₄H₃₄O₅

Molecular Weight

402.5 g/mol

InChI Key

GPNHMOZDMYNCPO-PDUMRIMRSA-N

FDA UNII

XN7MM8XG2M

Clascoterone (cortexolone 17-propionate, CB-03-01) is a novel antagonist of androgen receptors. It binds to androgen receptors with high affinity. By competing with androgens for binding to androgen receptors, clascoterone works by blocking the androgen receptor signalling cascades that promote acne pathogenesis, such as sebaceous gland proliferation, excess sebum production, and inflammatory pathways. In August 2020, FDA approved clascoterone for the first-in-class topical treatment of acne (acne vulgaris) in male and female patients 12 years and older. Clascoterone is also being investigated as a novel treatment for androgenetic alopecia.

Clascoterone is an Androgen Receptor Inhibitor. The mechanism of action of clascoterone is as an Androgen Receptor Antagonist.

1 2D Structure

Clascoterone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(8R,9S,10R,13S,14S,17R)-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] propanoate

2.1.2 InChI

InChI=1S/C24H34O5/c1-4-21(28)29-24(20(27)14-25)12-9-19-17-6-5-15-13-16(26)7-10-22(15,2)18(17)8-11-23(19,24)3/h13,17-19,25H,4-12,14H2,1-3H3/t17-,18+,19+,22+,23+,24+/m1/s1

2.1.3 InChI Key

GPNHMOZDMYNCPO-PDUMRIMRSA-N

2.1.4 Canonical SMILES

CCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)CO

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

XN7MM8XG2M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cb-03-01

2. Clascoterone

3. Winlevi

2.3.2 Depositor-Supplied Synonyms

1. Clascoterone

2. 19608-29-8

3. Cb-03-01

4. 17 Alpha-propionate

5. 17alpha-propionate

6. Winlevi

7. Cortexolone 17 Alpha-propionate

8. Clascoterone [usan]

9. Xn7mm8xg2m

10. Pregn-4-ene-3,20-dione, 21-hydroxy-17-(1-oxopropoxy)-

11. Cortexolone 17.alpha.-propionate

12. Cortodoxone 17.alpha.-propionate

13. Clascoterone (usan)

14. Pregn-4-ene-3,20-dione, 17,21-dihydroxy-, 17-propionate

15. (8r,9s,10r,13s,14s,17r)-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl Propionate

16. [(8r,9s,10r,13s,14s,17r)-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Propanoate

17. Breezula

18. Unii-xn7mm8xg2m

19. Cortodoxone 17alpha-propionate

20. 17

21. A-propionate

22. Clascoterone [mi]

23. Clascoterone [inn]

24. Cortexolone 17a-propionate

25. Clascoterone [who-dd]

26. Schembl1231152

27. Chembl3590187

28. Gtpl11215

29. Dtxsid10471883

30. Clascoterone [orange Book]

31. Bcp02565

32. Ex-a1953

33. Zinc6716459

34. 11-deoxycortisol 17alpha-propionate

35. S6896

36. Akos030526694

37. At22231

38. Bcp9000062

39. Cb-0301

40. Cs-1151

41. Db12499

42. 17alpha-(propionyloxy)deoxycorticosterone

43. Ac-31957

44. Hy-13331

45. Clascoterone; 19608-29-8; Cb-03-1

46. D11451

47. A854304

48. Q27293917

49. 21-hydroxy-3,20-dioxopregn-4-en-17-yl Propanoate

50. Cortexolone 17alpha-propionate;(8r,9s,10r,13s,14s,17r)-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl Propionate;cortexolone 17 Alpha-propionate

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₄O₅
Molecular Weight	402.5 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	402.24062418 g/mol
Monoisotopic Mass	402.24062418 g/mol
Topological Polar Surface Area	80.7 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	769
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Clascoterone is indicated for the topical treatment of acne vulgaris in patients 12 years of age and older.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Clascoterone exerts anti-androgenic effects by working as an antagonist at androgen receptors (ARs) expressed throughout the skin, including sebaceous glands, sebocytes, and dermal papilla cells. Clascoterone blocks the effects of testosterone and dihydrotestosterone (DHT), which are androgens that bind to the ARs and contribute to the development of androgen-dependent conditions such as acne and alopecia. _In vitro_, the antiandrogenic effects of clascoterone in human primary sebocytes occurred in a dose-dependent manner. Clascoterone mediates selective topical activity by mainly targeting androgen receptors at the site of application. It has limited systemic effects. In clinical trials, HPA axis suppression was observed as a 30-minute post-stimulation serum cortisol level of 18 mcg/dL in 5% of adult subjects and 9% of adolescent subjects with acne vulgaris following two weeks of topical treatment of clascoterone. HPA axis function returned to normal following the discontinuation of drug treatment.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

CLASCOTERONE

5.2.2 FDA UNII

XN7MM8XG2M

5.2.3 Pharmacological Classes

Androgen Receptor Inhibitor [EPC]; Androgen Receptor Antagonists [MoA]

5.3 ATC Code

D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AX - Other anti-acne preparations for topical use

D10AX06 - Clascoterone

5.4 Absorption, Distribution and Excretion

Absorption

Upon topical application, clascoteronet permeates the skin to the dermal levels with minimal systemic absorption. In clinical trials, adult subjects with moderate to severe facial acne vulgaris received twice-daily topical application of six grams of clascoterone. The steady-state concentrations of the drug were reached within five days. Following two weeks, the mean SD Cmax was 4.5 2.9 ng/mL and the mean SD area under the plasma concentration-time over the dosing interval (AUC) was 37.1 22.3 h*ng/mL. The mean SD average plasma concentration (Cavg) was 3.1 1.9 ng/mL.

Route of Elimination

Excretion of clascoterone has not been fully characterized in humans. Upon topical application, clascoterone is quickly hydrolyzed in the epidermis.

Volume of Distribution

There is no information available on the volume of distribution.

Clearance

There is limited information on clearance of clascoterone.

5.5 Metabolism/Metabolites

According to _in vitro_ and clinical studies, the main possible primary metabolite of clascoterone is cortexolone, which is an inactive metabolite. The plasma concentrations of cortexolone were generally below or near the lower limit of quantitation (0.5 ng/mL). Although clascoterone penetrates the skin, the systemic activity of the drug is limited due to rapid hydrolysis of clascoterone into the inactive metabolite by skin and plasma esterases, namely carboxylesterase.

5.6 Biological Half-Life

There is limited information on the half life of clascoterone.

5.7 Mechanism of Action

Acne is a multifactorial skin condition characterized by excess sebum production, epithelial hyperkeratinization, proliferation of the skin commensal bacteria, and inflammation. Circulating and locally synthesized natural ligands, testosterone and dihydrotestosterone (DHT), serve as causative factors in both males and females. Upon binding of DHT, the DHT-androgen receptor complex dimerizes and translocates to the nucleus where it promotes the transcription of genes involved in acne pathogenesis, including proliferation and differentiation of sebocytes, excess sebum production, and inflammatory cytokine production. Clascoterone is a potent antagonist at ARs and competes for androgens in binding to the receptor, thereby inhibiting downstream signalling of ARs that promote acne. Androgenetic alopecia is also an androgen-dependent and highly genetic condition. Dihydrotestosterone (DHT) binds to ARs expressed on dermal papilla cells (DPC) in the scalp to induce AR-mediated transcription of genes that contribute to androgenic alopecia. By blocking the interaction between DHT and aARs, clascoterone inhibits AR-regulated transcription and DHT-induced IL-6 synthesis.

API SUPPLIERS

01

Symbiotec Pharmalab

India

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CPhI India 2024

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Symbiotec: Global API manufacturer, specializing in Cortico-Steroids & Steroid-Hormone APIs.

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India

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02

Seqens

France

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

SupplySide West 2024

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Seqens is an integrated global leader in pharmaceutical solutions & specialty ingredients & provides custom-made solutions.

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France

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03

Wavelength Pharmaceuticals

Israel

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SupplySide West 2024

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04

Hubei Gedian Humanwell Pharmaceuti...

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI India 2024

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Hubei Gedian Humanwell focuses on R&D, production, & sales of fertility regulation drugs & steroidal APIs.

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05

Teva Pharmaceutical Industries

Israel

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Not Confirmed

06

Curia

U.S.A

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Not Confirmed

07

Bulat Pharmaceutical

India

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08

Teva API

Israel

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Not Confirmed

09

Beijing Mesochem Technology

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

SupplySide West 2024

Not Confirmed

10

Kimia Biosciences

India

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SupplySide West 2024

Not Confirmed

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API Reference Price

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