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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
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 Weight 402.5 g/mol
Molecular Formula C24H34O5
XLogP33.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass402.24062418 g/mol
Monoisotopic Mass402.24062418 g/mol
Topological Polar Surface Area80.7 Ų
Heavy Atom Count29
Formal Charge0
Complexity769
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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

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Symbiotec Pharmalab

India

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Seqens

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Wavelength Pharmaceuticals

Israel

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Hubei Gedian Humanwell Pharmaceuti...

China

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Curia

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Curia

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Teva Pharmaceutical Industries

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Beijing Mesochem Technology

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Kimia Biosciences

India

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Teva API

Israel

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Teva API

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Bulat Pharmaceutical

India

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Curia Spain Sau

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

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Clascoterone

About the Company : Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable...

Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable operations, and innovation has driven their commitment to improving global healthcare access. With a state-of-the-art manufacturing facility inaugurated in 2004, Symbiotec has become a trusted provider in the industry. Their certifications including WHO-GMP, ISO, US FDA, and EU GMP showcase their dedication to quality and excellence. Over two decades, they've maintained their position through adaptability, efficiency, and competitive pricing.
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Seqens

France
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About the Company : Since its inception in 2003, Seqens has grown to become a global leader in pharmaceutical solutions and specialty ingredients. Seqens supports its customers in developing, scaling ...

Since its inception in 2003, Seqens has grown to become a global leader in pharmaceutical solutions and specialty ingredients. Seqens supports its customers in developing, scaling up and manufacturing drug substances from the pre-clinical phase to the commercial phase. It offers a large portfolio of APIs and proprietary products. Seqens also develops custom solutions and ingredients for the most demanding industries, such as healthcare, electronics and cosmetics. Its unique range of technologies enables it to manufacture complex molecules for small- and large-scale demands. It operates 24 industrial plants and 10 R&D centres across the globe.
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Virtual BoothHubei Gedian Humanwell focuses on R&D, production, & sales of fertility regulation drugs & steroidal APIs.

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Clascoterone

About the Company : Hubei Gedian Humanwell Pharmaceutical Co., Ltd. is a modern high-tech pharmaceutical company with a focus on the research and development, production, and sales of fertility regula...

Hubei Gedian Humanwell Pharmaceutical Co., Ltd. is a modern high-tech pharmaceutical company with a focus on the research and development, production, and sales of fertility regulation drugs and steroidal APIs. It operates as a wholly-owned subsidiary of Humanwell Healthcare Group (Stock Code: 600079), one of the leading pharmaceutical conglomerates in China. The company operates two APIs manufacturing sites, one formulation factory, and one excipients factory, showcasing its commitment to integrating the reproductive health industry chain from raw materials and active pharmaceutical ingredients (APIs) to finished dosage forms.
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Clascoterone

About the Company : Beijing Mesochem Technology Co. Ltd., which is located in the national economic and technological development area of Yizhuang, China, manufactures pharmaceutical chemicals, fine c...

Beijing Mesochem Technology Co. Ltd., which is located in the national economic and technological development area of Yizhuang, China, manufactures pharmaceutical chemicals, fine chemicals and fundamental chemical materials. It has an efficient research and development team. Beijing Mesochem provides its customers customized development, craft optimization, contract customization and outsourcing services. The company has a well-established industrial base in Weinan, Shanxi Province. The production base features a 20,000 ㎡ plant with a production capacity of over 8,000 MT per year.
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Clascoterone

About the Company : Beijing Sjar Technology Development Co., Ltd. founded in 2014, it is a high-tech enterprise which specialized in the research and development of active pharmaceutical ingredients a...

Beijing Sjar Technology Development Co., Ltd. founded in 2014, it is a high-tech enterprise which specialized in the research and development of active pharmaceutical ingredients and their intermediates, electronic chemical materials and intermediates, large-scale production, sales and services, and provide customized synthetic services according to customer requirements. Sjar-Tech locates in Beijing Economic and Technological Development Zone, has its own R&D and development laboratory. Sjar-Tech has set up a R&D team with rich experience and strong technical strength, most of the practitioners have more than ten years' experience.
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Clascoterone

About the Company : Bulat Pharmaceutical is a fast growing pharmaceutical company, founded in the year 2017, Bulat Pharmaceutical is engaged in the manufacturing and sales of high quality APIs and Int...

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Clascoterone

About the Company : Guangzhou Topwork Chemical Co., Ltd. Specializes in manufacturing corticosteroid and relative intermediates. We provide high quality products and excellent service to our clients a...

Guangzhou Topwork Chemical Co., Ltd. Specializes in manufacturing corticosteroid and relative intermediates. We provide high quality products and excellent service to our clients and have gained a high business reputation in the world market. Topwork gathers a group of energetic, hardworking and much experienced experts. They dedicate their entire efforts to research and development of new products. To guarantee the quality of our products, we have established an international standard quality control system. All of our products conform the latest standard of USP, EP, BP and CP.
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Clascoterone

About the Company : Kimia Biosciences, established in 1993, is focused on manufacturing bulk drugs for various therapeutic segments. With a strong emphasis on excellence and advanced technologies, Kim...

Kimia Biosciences, established in 1993, is focused on manufacturing bulk drugs for various therapeutic segments. With a strong emphasis on excellence and advanced technologies, Kimia aims to become a globally recognized company in both APIs and FDFs while upholding clean business practices. Kimia's state-of-the-art facilities at Village Bhondsi, Gurugram enable it to produce a wide range of APIs. Kimia also plans to establish its own facilities for lifestyle segments, adhering to international regulatory standards. Kimia aims to provide the best pharmaceutical products and support to consumers and healthcare professionals.
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Sterling Spa

Italy
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Sterling Spa

Italy
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Clascoterone

About the Company : The Quality Assurance department is the Guardian of Quality within the Company. We have a team dedicated to identifying and implementing new ICH guidelines. Our team is prepared ...

The Quality Assurance department is the Guardian of Quality within the Company. We have a team dedicated to identifying and implementing new ICH guidelines. Our team is prepared to obtain quality objectives which have been universally recognized by Inspection Authorities and the most important Pharmaceutical Companies from around the globe. This system is periodically verified through internal, national and international inspectors who have been able to recognize the high level obtained by the system and the actual achievement of quality objectives multiple times. Sterling has been inspected three times by FDA .
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Teva API

Israel
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Teva API

Israel
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Clascoterone

About the Company : Teva API is a standalone business unit within Teva Pharmaceutical Industries, the world’s largest generic drug manufacturer. Employing over 4,000 professionals at 15 internationa...

Teva API is a standalone business unit within Teva Pharmaceutical Industries, the world’s largest generic drug manufacturer. Employing over 4,000 professionals at 15 international plant sites and 6 R&D centers, Teva API is a leading international supplier of active pharmaceutical ingredients (APIs) with the industry’s broadest portfolio of over 350 products. Its leadership in cutting-edge development, large-scale production capacity and global support make it an ideal API partner of choice. Over its more than 85 years of existence, Teva API has acquired and established top-rated manufacturing and development facilities around the world.
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API Reference Price

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P.O.BOX 3158, 4970602 ISRAELSDNF Israel","customerAddress":"PLOT NO.2, MAITRIVIHAR,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1704133800,"product":"FOC - CLASCOTERONE CAS NO.: 19608-29-8","address":"NO. 5\/55 KAMDHENU COMPLEX HARI OM,","city":"MUMBAI,MAHARASHTRA","supplier":"WAVELENGTH PHARMACEUTICALS","supplierCountry":"ISRAEL","foreign_port":"TEL AVIV YAFO","customer":"MONOLOM INDIA PHARMA ","customerCountry":"INDIA","quantity":"0.25","actualQuantity":"250","unit":"GMS","unitRateFc":"9.4","totalValueFC":"2369.5","currency":"USD","unitRateINR":"787.7","date":"02-Jan-2024","totalValueINR":"196930","totalValueInUsd":"2369.5","indian_port":"Bombay Air","hs_no":"29349990","bill_no":"9503207","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"ISRAEL","selfForZScoreResived":"Pharma Grade","supplierPort":"TEL AVIV YAFO","supplierAddress":"SHLOMO SHMELTZER94 OFER (HI-TECH) PARK PETAH TIKVA ISRAEL Israel, , Israel Israel","customerAddress":"NO. 5\/55 KAMDHENU COMPLEX HARI OM,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1706121000,"product":"CLASCOTERONE","address":"3RD FLOOR, PLOT NO.2, MAITRIVIHAR,","city":"HYDERABAD, ANDHRA PRADESH","supplier":"WAVELENGTH PHARMACEUTICALS","supplierCountry":"ISRAEL","foreign_port":"TEL AVIV-YAFO","customer":"APL HEALTHCARE","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"18000","totalValueFC":"36428.1","currency":"USD","unitRateINR":"1513800","date":"25-Jan-2024","totalValueINR":"3027600","totalValueInUsd":"36428.1","indian_port":"SEZ\/Mahaboobnagar","hs_no":"29349990","bill_no":"1000269","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"ISRAEL","selfForZScoreResived":"Pharma Grade","supplierPort":"TEL AVIV-YAFO","supplierAddress":"N\/A","customerAddress":"3RD FLOOR, PLOT NO.2, MAITRIVIHAR,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1706553000,"product":"(N.C.V) CLASCOTERONE ( FOR TESTING PURPOSE ONLY)","address":"159, C.S.T. ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"WAVELENGTH PHARMACEUTICALS","supplierCountry":"ISRAEL","foreign_port":"TEL AVIV YAFO","customer":"LUPIN LTD","customerCountry":"INDIA","quantity":"0.02","actualQuantity":"0.02","unit":"KGS","unitRateFc":"50000","totalValueFC":"1011.9","currency":"USD","unitRateINR":"4205000","date":"30-Jan-2024","totalValueINR":"84100","totalValueInUsd":"1011.9","indian_port":"Bombay Air","hs_no":"29372900","bill_no":"9896030","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"ISRAEL","selfForZScoreResived":"Pharma Grade","supplierPort":"TEL AVIV YAFO","supplierAddress":"94 SHLOMO SHMELTZER ROAD, PETACH-TIKVA PO BOX NO 3158, 4970602 , ISRAEL Israel","customerAddress":"159, C.S.T. 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P.O.BOX 3158, 4970602 ISRAELSDNF Israel","customerAddress":"PLOT NO.2, MAITRIVIHAR,"}]
06-Apr-2023
19-Mar-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
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