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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34O5
Molecular Weight 402.5238
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLASCOTERONE

SMILES

[H][C@@]12CC[C@](OC(=O)CC)(C(=O)CO)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=GPNHMOZDMYNCPO-PDUMRIMRSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H34O5
Molecular Weight 402.5238
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Cortexolone 17α-propionate (WINLEVI, BREEZULA) is a steroid belonging to the family of cortexolone derivatives. It is a topical and peripherally selective androgen antagonist. WINLEVI is used for the treatment of acne and has completed Phase II clinical trials and Phase III trials. BREEZULA is used for the treatment of androgenic alopecia and is currently undergoing a Phase II trial in the US.

CNS Activity

Curator's Comment: The explanation of peripheral selectivity of cortexolone 17α-propionate could be that it poorly penetrates the blood-brain barrier, thus failing to achieve an adequate concentration in CNS. However, this last hypothesis needs to be confirmed as tissue distribution studies will be performed.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BREEZULA

Approved Use

Unknown
Primary
WINLEVI

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Biological profile of cortexolone 17alpha-propionate (CB-03-01), a new topical and peripherally selective androgen antagonist.
2004
Cortexolone 17α-propionate 1% cream, a new potent antiandrogen for topical treatment of acne vulgaris. A pilot randomized, double-blind comparative study vs. placebo and tretinoin 0·05% cream.
2011 Jul
The use of hormonal agents in the treatment of acne.
2016 Jun
Anti-acne drugs in phase 1 and 2 clinical trials.
2017 Jul
Patents

Sample Use Guides

Cortexolone 17α-propionate 1% cream was applied every 12 hours for 2 weeks in children 9-12 years old with acne.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:24:48 GMT 2023
Edited
by admin
on Sat Dec 16 16:24:48 GMT 2023
Record UNII
XN7MM8XG2M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLASCOTERONE
USAN   INN  
Official Name English
Clascoterone [WHO-DD]
Common Name English
PREGN-4-ENE-3,20-DIONE, 17,21-DIHYDROXY-, 17-PROPIONATE
Systematic Name English
CLASCOTERONE [USAN]
Common Name English
WINLEVI
Brand Name English
CLASCOTERONE [MI]
Common Name English
clascoterone [INN]
Common Name English
21-Hydroxy-3,20-dioxopregn-4-en-17-yl propanoate
Systematic Name English
PREGN-4-ENE-3,20-DIONE, 21-HYDROXY-17-(1-OXOPROPOXY)-
Systematic Name English
CORTODOXONE 17.ALPHA.-PROPIONATE
Common Name English
CORTEXOLONE 17.ALPHA.-PROPIONATE
Common Name English
CLASCOTERONE [ORANGE BOOK]
Common Name English
BREEZULA
Brand Name English
CB-03-01
Code English
Code System Code Type Description
ChEMBL
CHEMBL3545016
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
CAS
19608-29-8
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
DAILYMED
XN7MM8XG2M
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
NCI_THESAURUS
C169855
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
FDA UNII
XN7MM8XG2M
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
WIKIPEDIA
Clascoterone
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
USAN
EF-84
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
PUBCHEM
11750009
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID10471883
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
MERCK INDEX
m12233
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
INN
10891
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
RXCUI
2474340
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
SMS_ID
300000005912
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
DRUG BANK
DB12499
Created by admin on Sat Dec 16 16:24:49 GMT 2023 , Edited by admin on Sat Dec 16 16:24:49 GMT 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
clascoterone cream, 1%, has no clinically meaningful effect on the PK of drugs metabolized by CYP 1A2, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1 or 3A4.
BINDER->LIGAND
Plasma protein binding of clascoterone is independent of concentrations, in vitro.
BINDING
METABOLIC ENZYME -> INHIBITOR
clascoterone cream, 1%, has no clinically meaningful effect on the PK of drugs metabolized by CYP 1A2, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1 or 3A4.
IC50
TARGET -> INHIBITOR
METABOLIC ENZYME -> INHIBITOR
clascoterone cream, 1%, has no clinically meaningful effect on the PK of drugs metabolized by CYP 1A2, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1 or 3A4.
Related Record Type Details
ACTIVE MOIETY