Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H19FN2O3 |
Molecular Weight | 402.4177 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CN1C2=C(CN(CC2)C(=O)C3=CC=CC4=C3C=CC=C4)C5=C1C=CC(F)=C5
InChI
InChIKey=IHAXLPDVOWLUOS-UHFFFAOYSA-N
InChI=1S/C24H19FN2O3/c25-16-8-9-21-19(12-16)20-13-26(11-10-22(20)27(21)14-23(28)29)24(30)18-7-3-5-15-4-1-2-6-17(15)18/h1-9,12H,10-11,13-14H2,(H,28,29)
Molecular Formula | C24H19FN2O3 |
Molecular Weight | 402.4177 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Kythera Biopharmaceuticals (a subsidiary of Allergan) is developing setipiprant, an oral prostaglandin D2 (PGD2/CRTH2) receptor antagonist, for the treatment of alopecia. Setipiprant was initially developed as a treatment for allergic rhinitis, but recent hair loss-related discoveries have made it a better candidate for hair loss reversal. As CRTH2 antagonist, setipiprant, blocks the effects of prostaglandin D2 (PGD2) role in inflammation and, in consequence, the amplification and maintenance of allergic reactions. It targets the allergic inflammation at the beginning of the cascade. In clinical trials for allergic rhinitis and asthma, the drug performed quite well in the treatment of allergen-induced airway responses in asthmatic patients. It was also well tolerated by participants. However, its results were similar to those of drugs already on the market, so further trials were discontinued. In 2012, researchers discovered a link between the PGD2 receptor and hair loss. More specifically, this receptor is seen at high levels in the scalps of men diagnosed with Androgenetic Alopecia (AGA). setipiprant steps in before PGD2 attaches to the receptors, and therefore prevents receptor activation and, as a result, hair loss. With the discovery of the possible link to PGD2 receptors, Kythera acquired the drug, and trials began to test the effects of setipiprant on hair loss.
Approval Year
PubMed
Title | Date | PubMed |
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Single- and multiple-dose tolerability and pharmacokinetics of the CRTH2 antagonist setipiprant in healthy male subjects. | 2014 Dec |
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Efficacy and safety of setipiprant in seasonal allergic rhinitis: results from Phase 2 and Phase 3 randomized, double-blind, placebo- and active-referenced studies. | 2017 |
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Does inhibition of aldose reductase contribute to the anti-inflammatory action of setipiprant? | 2017 Sep 22 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02781311
Alopecia: Setipiprant 1000 mg (2 X 500 mg) tablets, orally, BID at 12-hour intervals for 24 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23721423
Setipiprant is highly potent in inhibiting hCRTh2 (IC50 = 6 nM)
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:20:00 GMT 2023
by
admin
on
Sat Dec 16 16:20:00 GMT 2023
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Record UNII |
BHF20LA2GM
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Record Status |
Validated (UNII)
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C574
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