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Merck
CN

PZ0002

Maraviroc

≥98% (HPLC), CCR5 chemokine receptor antagonist, powder

Synonym(s):

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, UK-427857

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About This Item

Empirical Formula (Hill Notation):
C29H41F2N5O
CAS Number:
376348-65-1
Molecular Weight:
513.67
UNSPSC Code:
12352200
PubChem Substance ID:
329823671
NACRES:
NA.77
MDL number:
MFCD13188530

Key Documents

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Product Name

Maraviroc, ≥98% (HPLC)

SMILES string

CC(C)c1nnc(C)n1[C@H]2C[C@@H]3CC[C@H](C2)N3CC[C@H](NC(=O)C4CCC(F)(F)CC4)c5ccccc5

InChI key

GSNHKUDZZFZSJB-QYOOZWMWSA-N

InChI

1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25-,26-/m0/s1

assay

≥98% (HPLC)

form

powder

optical activity

[α]-15/D

color

white

solubility

DMSO: >30 mg/mL

storage temp.

room temp

Quality Level

100

Gene Information

human ... CCR5(1234)

Related Categories

Application

Maraviroc has been used as a C-C chemokine receptor type 5 (CCR5-specific) inhibitor in murine monocyte/macrophage cell line J774A.1, porcine uterine luminal epithelial cells and human lung CD4+ T cells.

Biochem/physiol Actions

Maraviroc is a CCR5 chemokine receptor antagonist and antiretroviral entry inhibitor.
Maraviroc is a CCR5 chemokine receptor antagonist, and antiretroviral entry inhibitor. Maraviroc inhibits HIV entry by blocking interaction of viral coat protein gp120 with the receptor.
Maraviroc is metabolised by cytochrome P450 3A4. The transport and absorption of maraviroc in the intestine and bile is regulated by P-glycoprotein (Pgp). Maraviroc binds to the active site pocket of chemokine receptor CCR5 making the receptor inactive.

Features and Benefits

This compound is featured on the Chemokine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000389462
0000389462
0000231530
0000231530
0000055201

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HIV-1 and SIV Infection Are Associated with Early Loss of Lung Interstitial CD4+ T Cells and Dissemination of Pulmonary Tuberculosis
Corleis B, et al.
Testing, 26(6), 1409-1418 (2019)
Characterization of CC motif chemokine ligand 4 in the porcine endometrium during the presence of the maternal-fetal interface
Lim W, et al.
Developmental Biology, 441(1), 146-158 (2018)
Marie Armani-Tourret et al.
PLoS pathogens, 17(4), e1009526-e1009526 (2021-04-20)
HIV-1 infects CD4 T lymphocytes (CD4TL) through binding the chemokine receptors CCR5 or CXCR4. CXCR4-using viruses are considered more pathogenic, linked to accelerated depletion of CD4TL and progression to AIDS. However, counterexamples to this paradigm are common, suggesting heterogeneity in
Laura Pérez-Martínez et al.
The Journal of antimicrobial chemotherapy, 69(7), 1903-1910 (2014-03-22)
Non-alcoholic fatty liver disease (NAFLD) is the most common cause of chronic liver disease in the general population. The NAFLD spectrum ranges from simple steatosis to cirrhosis. The chemokine CCL5/RANTES plays an important role in the progression of hepatic inflammation
Procoagulant and proinflammatory effects of red blood cells on lipopolysaccharide-stimulated monocytes
Osterud B, et al.
Journal of Thrombosis and Haemostasis, 13(9), 1676-1682 (2015)
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