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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
Structure of SETIPIPRANT

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)

HIDE SMILES / InChI

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9Y5Y4
Gene ID: 11251.0
Gene Symbol: PTGDR2
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Single- and multiple-dose tolerability and pharmacokinetics of the CRTH2 antagonist setipiprant in healthy male subjects.
2014 Dec
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
Does inhibition of aldose reductase contribute to the anti-inflammatory action of setipiprant?
2017 Sep 22
Patents

Patents

Sample Use Guides

Alopecia: Setipiprant 1000 mg (2 X 500 mg) tablets, orally, BID at 12-hour intervals for 24 weeks.
Route of Administration: Oral
Setipiprant is highly potent in inhibiting hCRTh2 (IC50 = 6 nM)
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:20:00 GMT 2023
Edited
by admin
on Sat Dec 16 16:20:00 GMT 2023
Record UNII
BHF20LA2GM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SETIPIPRANT
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
setipiprant [INN]
Common Name English
Setipiprant [WHO-DD]
Common Name English
[8-Fluoro-2-(naphthalene-1-carbonyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl]acetic acid
Systematic Name English
ACT-129968
Code English
KYTH-105
Code English
5H-PYRIDO(4,3-B)INDOLE-5-ACETIC ACID, 8-FLUORO-1,2,3,4-TETRAHYDRO-2-(1-NAPHTHALENYLCARBONYL)-
Common Name English
SETIPIPRANT [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C574
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
Code System Code Type Description
SMS_ID
300000034373
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
CAS
866460-33-5
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
INN
9330
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
PUBCHEM
49843471
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
WIKIPEDIA
Setipiprant
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
DRUG BANK
DB12562
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL2386081
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID00235739
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
FDA UNII
BHF20LA2GM
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
NCI_THESAURUS
C152348
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
USAN
ZZ-22
Created by admin on Sat Dec 16 16:20:00 GMT 2023 , Edited by admin on Sat Dec 16 16:20:00 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY