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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15646372
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Biological profile of cortexolone 17alpha-propionate (CB-03-01), a new topical and peripherally selective androgen antagonist. | 2004 |
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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 |
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The use of hormonal agents in the treatment of acne. | 2016 Jun |
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Anti-acne drugs in phase 1 and 2 clinical trials. | 2017 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21428978
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
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 16:24:48 GMT 2023
by
admin
on
Sat Dec 16 16:24:48 GMT 2023
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Record UNII |
XN7MM8XG2M
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Record Status |
Validated (UNII)
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Record Version |
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CHEMBL3545016
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19608-29-8
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XN7MM8XG2M
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C169855
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XN7MM8XG2M
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Clascoterone
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EF-84
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11750009
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DTXSID10471883
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m12233
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10891
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2474340
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300000005912
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DB12499
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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.
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BINDER->LIGAND |
Plasma protein binding of clascoterone is independent of concentrations, in vitro.
BINDING
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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
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TARGET -> INHIBITOR | |||
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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.
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ACTIVE MOIETY |