Setipiprant - CAS 866460-33-5
Catalog number: B0084-474875
Category: Inhibitor
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Molecular Formula:
C24H19FN2O3
Molecular Weight:
402.42
COA:
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Targets:
CRTH2 (GPR44)
Description:
Setipiprant is a potent, orally available and selective CRTH2 antagonist, which is a G protein-coupled receptor for PGD2. It may be a promising target for the treatment of allergic disorders. It was well tolerated and reduced both the allergen-induced LAR and the associated AHR in allergic asthmatics at multiple oral doses. It is a drug originally developed by Actelion, but it failed to show sufficient advantages and was discontinued from further development in this application. Later it was developed as a novel treatment for baldness by Kythera.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-474875 25 mg $198 In stock
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Purity:
>98 %
Appearance:
Solid powder
Synonyms:
2-(2-(1-naphthoyl)-8-fluoro-1,2,3,4-tetrahydropyrido[4,3-b]indol-5-yl)acetic acid;ACT129968;2-[8-fluoro-2-(naphthalene-1-carbonyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl]acetic acid;8-Fluoro-1,2,3,4-tetrahydro-2-(1-naphthalenylcarbonyl)-5H-pyrido[4,3-b]indole-5-acetic acid;KYTH-105
Solubility:
DMSO: ≥ 36 mg/mL
Storage:
-20°C Freezer
MSDS:
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Application:
Setipiprant may be a promising target for the treatment of allergic disorders.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Boiling Point:
690.4±55.0 °C | Condition: Press: 760 Torr
Density:
1.37±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
IHAXLPDVOWLUOS-UHFFFAOYSA-N
InChI:
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)
Canonical SMILES:
C1CN(CC2=C1N(C3=C2C=C(C=C3)F)CC(=O)O)C(=O)C4=CC=CC5=CC=CC=C54
Current Developer:
Setipiprant is a drug originally developed by Actelion, but it failed to show sufficient advantages and was discontinued from further development in this application. Later it was developed as a novel treatment for baldness by Kythera.
1.Single- and multiple-dose tolerability and pharmacokinetics of the CRTH2 antagonist setipiprant in healthy male subjects.
Sidharta PN;Diamant Z;Dingemanse J Fundam Clin Pharmacol. 2014 Dec;28(6):690-9. doi: 10.1111/fcp.12079. Epub 2014 May 11.
Chemoattractant receptor-homologous molecule expressed on T helper (Th) 2 cells (CRTH2) is a G-protein-coupled receptor for prostaglandin D2 (PGD2), a key mediator in inflammatory disorders such as asthma and allergic rhinitis. In this study, we investigated the single- and multiple-dose tolerability and pharmacokinetics (PKs) of setipiprant, an orally active, potent, and selective CRTH2 antagonist. This randomized, double-blind, placebo-controlled study was performed in two parts in healthy male subjects. In study Part A, single oral doses of up to 2000 mg setipiprant or placebo were given to sequential groups of eight subjects each. Additionally, the impact of food on the PKs was investigated in one-dose group. In study Part B, two groups of subjects received 500 or 1000 mg setipiprant or placebo b.i.d. during 5.5 days. At regular intervals, tolerability variables and plasma and urine levels of setipiprant were determined. Setipiprant was well tolerated after single- and multiple-dose administration. Headache was the most frequently reported adverse event. No treatment effect on tolerability variables was observed. After single- and multiple-dose administration, setipiprant was rapidly absorbed and followed a biphasic elimination pattern with an elimination half-life between 10 and 18 h.
2.Disposition and metabolism of setipiprant, a selective oral CRTH2 antagonist, in humans.
Hoch M;Wank J;Kluge I;Wagner-Redeker W;Dingemanse J Drugs R D. 2013 Dec;13(4):253-69. doi: 10.1007/s40268-013-0031-7.
BACKGROUND: ;Setipiprant, a tetrahydropyridoindole derivative, is a CRTH2 (chemoattractant receptor-homologous molecule expressed on T-helper [Th]-2 cells) antagonist that has the potential to be effective in the treatment of patients with diseases with an allergic etiology, such as allergic rhinitis and asthma.;OBJECTIVES: ;This study investigated the disposition, metabolism, and elimination of setipiprant.;STUDY DESIGN: ;In this open-label study, a single oral dose of 1,000 mg (14)C-labeled setipiprant was administered.;PARTICIPANTS: ;Six healthy male subjects were enrolled in this study.;RESULTS: ;The radioactive dose was almost completely recovered in feces (88.2 %) and to a smaller extent in urine (11.7 %). The main recovery route for unchanged setipiprant was feces (50 % of the radioactive dose). The recovered amount of unchanged setipiprant in urine accounted for 3.7 %. The two main metabolites were M7 and M9 with the intact tetrahydropyridoindole core of setipiprant. M7 and M9 are supposedly two distinct dihydroxy-dihydronaphthalene isomers assumed to be formed by intermediate epoxidation of the naphthyl ring followed by a hydrolytic epoxide ring-opening. M7 and M9 accounted for 20.
3.Targeting the PGD
Kupczyk M;Kuna P Drugs. 2017 Aug;77(12):1281-1294. doi: 10.1007/s40265-017-0777-2.
Prostaglandin D;2; (PGD;2;) released by degranulating mast cells is believed to play a key role in orchestrating mechanisms of inflammation in allergies and asthma. The biological effects of PGD;2; are mediated by D-prostanoid (DP1), CRTH2 (DP2), and thromboxane prostanoid (TP) receptors. The CRTH2 receptor is involved in induction of migration and activation of T helper type 2 (Th;2;) lymphocytes, eosinophils, and basophils; up-regulation of adhesion molecules; and promotion of pro-inflammatory Th;2;-type cytokines (interleukin [IL]-4, 5, 13), whereas the DP receptor is associated with relaxation of smooth muscles, vasodilation, inhibition of cell migration, and apoptosis of eosinophils. A number of CRTH2/PGD;2; receptor antagonists have been investigated in asthma and allergic diseases. The CRTH2 antagonist (OC000459) or dual CRTH2 and TP receptor antagonist (ramatroban) were effective in reducing eosinophilia, nasal mucosal swelling, and clinical symptoms of allergic rhinitis, with the latter drug registered for clinical use in this indication. OC000459 and setipiprant reduced the late but not early phase of response in an allergen challenge in atopic asthmatics. In persistent asthma, some molecules induced limited improvement in lung function, quality of life, and asthma symptoms (OC000459, BI671800), but in other trials with AMG 853 and AZ1981 these findings were not confirmed.
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CAS 866460-33-5 Setipiprant

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