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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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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)
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
Xinhuai Liu et al.
eLife, 10 (2021-01-20)
The necessity and functional significance of neurotransmitter co-transmission remains unclear. The glutamatergic 'KNDy' neurons co-express kisspeptin, neurokinin B (NKB), and dynorphin and exhibit a highly stereotyped synchronized behavior that reads out to the gonadotropin-releasing hormone (GnRH) neuron dendrons to drive

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