[CAS NO. 376348-65-1] Maraviroc (UK-427857)

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PRODUCTS SPECIFICATIONS [376348-65-1]

Catalog

SLK-S2003

Brand

Selleck

CAS

376348-65-1

DESCRIPTION [376348-65-1]

Overview

MDL	MFCD13188530
Molecular Weight	513.67
Molecular Formula	C29H41F2N5O
SMILES	C(C[C@H](NC(=O)C1CCC(F)(F)CC1)C2=CC=CC=C2)N3[C@@H]4C[C@@H](C[C@H]3CC4)N5C(C(C)C)=NN=C5C

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	1.9468 mL	9.7339 mL	19.4678 mL
5 mM	0.3894 mL	1.9468 mL	3.8936 mL
10 mM	0.1947 mL	0.9734 mL	1.9468 mL
50 mM	0.0389 mL	0.1947 mL	0.3894 mL

Description

Maraviroc (Celsentri,UK-427857) is a CCR5 antagonist for , and with of 3.3 nM, 7.2 nM and 5.2 nM in cell-free assays, respectively. Maraviroc is used in the treatment of infection.

Targets

CCR5 ^[3] (Cell-free assay)	MIP-1α ^[1] (Cell-free assay)	RANTES ^[1] (Cell-free assay)	MIP-1β ^[1] (Cell-free assay)
	3.3 nM	5.2 nM	7.2 nM

In vitro

Maraviroc inhibits MIP-1β-stimulated γ-S-GTP binding to HEK-293 cell membranes, indicating its ability to inhibit chemokine-dependent stimulation of GDP-GTP exchange at the CCR5/G protein complex. Maraviroc also inhibits the downstream event of chemokine-induced intracellular calcium redistribution, with IC50s ranging from 7 to 30 nM obtained against MIP-1β, MIP-1α and RANTES. In the same experiments, Maraviroc does not trigger release of intracellular calcium at concentrations up to 10 μM, indicating that it is devoid of CCR5 agonist activity. Consistent with this, Maraviroc fails to induce CCR5 internalization. Maraviroc is active at low nanomolar concentrations against HIV-1 Ba-L. Maraviroc inhibits all 200 pseudotyped viruses with a geometric mean IC90 of 13.7 nM. At concentrations >1000 times the 50% inhibitory concentration, maraviroc did not inhibit other chemokine receptors (CCR1, 2, 3, 4, 7, and 8; CXCR1 and 2) to a clinically relevant degree.

References

[1] Dorr P, et al. Antimicrob Agents Chemother. 2005, 49(11), 4721-4732.
[2] Neff CP, et al. PLoS One. 2011, 6(6), e20209.
[3] Lieberman-Blum SS, et al. Clin Ther. 2008, 30(7):1228-50.

Synonyms

Cyclohexanecarboxamide, 4,4-difluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]-

4,4-Difluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]cyclohexanecarboxamide

Maraviroc

UK 427857

Celsentri

Selzentry

4,4-Difluoro-N[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide