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S5192

Sigma-Aldrich

SB 222200

≥98% (HPLC), solid

Synonym(s):

(S)-3-Methyl-2-phenyl-N-(1-phenylpropyl)-4-quinolinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C26H24N2O
CAS Number:
174635-69-9
Molecular Weight:
380.48
MDL number:
MFCD00944072
UNSPSC Code:
12352200
PubChem Substance ID:
24278254
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

light yellow

solubility

DMSO: soluble ~28 mg/mL
H2O: insoluble

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

CC[C@H](NC(=O)c1c(C)c(nc2ccccc12)-c3ccccc3)c4ccccc4

InChI

1S/C26H24N2O/c1-3-22(19-12-6-4-7-13-19)28-26(29)24-18(2)25(20-14-8-5-9-15-20)27-23-17-11-10-16-21(23)24/h4-17,22H,3H2,1-2H3,(H,28,29)/t22-/m0/s1

InChI key

MQNYRKWJSMQECI-QFIPXVFZSA-N

Gene Information

human ... TACR2(6865) , TACR3(6870)

Application

The pharmacodynamics profile of SB 222200 enables its use as a tool to study physiological and pathophysiological roles of NK-3 receptor in CNS-modulated behaviors.

Biochem/physiol Actions

SB 222200 is a 2-phenyl-4-quinolinecarboxamides and a selective, reversible and competitive antagonist of human NK-3 receptor that effectively crosses the blood-brain barrier. It inhibits the NK-3 receptor-induced miosis or pupil constriction in conscious rabbits.1,2
Non-peptide NK3 tachykinin receptor antagonist.

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes under agreement from Glaxo­Smith­Kline

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H M Sarau et al.
The Journal of pharmacology and experimental therapeutics, 295(1), 373-381 (2000-09-19)
The pharmacological and pharmacokinetic profile of SB-222200 [(S)-(-)-N-(alpha-ethylbenzyl)-3-methyl-2-phenylquinoline-4-car boxami de], a human NK-3 receptor (hNK-3R) antagonist, was determined. SB-222200 inhibited (125)I-[MePhe(7)]neurokinin B (NKB) binding to Chinese hamster ovary (CHO) cell membranes stably expressing the hNK-3 receptor (CHO-hNK-3R) with a K(i)
A D Medhurst et al.
British journal of pharmacology, 122(3), 469-476 (1997-11-14)
1. Inhibition of NK3 receptor agonist-induced contraction in the rabbit isolated iris sphincter muscle was used to assess the in vitro functional activity of three 2-phenyl-4-quinolinecarboxamides, members of a novel class of potent and selective non-peptide NK3 receptor antagonists. In
J García-Ortega et al.
Human reproduction (Oxford, England), 29(12), 2736-2746 (2014-10-16)
Are neurokinin B (NKB), NK3 receptor (NK3R), kisspeptin (KISS1) and kisspeptin receptor (KISS1R) expressed in human ovarian granulosa cells? The NKB/NK3R and kisspeptin/KISS1R systems are co-expressed and functionally active in ovarian granulosa cells. The NKB/NK3R and KISS1/KISS1R systems are essential

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