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PZ0002

Sigma-Aldrich

Maraviroc

≥98% (HPLC)

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
MDL number:
MFCD13188530
UNSPSC Code:
12352200
PubChem Substance ID:
329823671
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]-15/D

color

white

solubility

DMSO: >30 mg/mL

storage temp.

room temp

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

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

InChI key

GSNHKUDZZFZSJB-QYOOZWMWSA-N

Gene Information

human ... CCR5(1234)

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 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.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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)
Juan G Sierra-Madero et al.
The lancet. HIV, 1(2), e60-e67 (2015-10-02)
Immune reconstitution inflammatory syndrome (IRIS) is a common complication of antiretroviral therapy (ART) in patients with HIV. IRIS is associated with an increased risk of admission to hospital and death. We assessed whether CCR5 blockade with maraviroc reduces the risk
Assessment of the absorption, metabolism and absolute bioavailability of maraviroc in healthy male subjects
Abel S, et al.
British Journal of Clinical Pharmacology, 65, 60-67 (2008)
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
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)
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