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PZ0002

Sigma-Aldrich

Maraviroc

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C29H41F2N5O
Numéro CAS:
376348-65-1
Poids moléculaire :
513.67
Numéro MDL:
MFCD13188530
Code UNSPSC :
12352200
ID de substance PubChem :
329823671
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

[α]-15/D

Couleur

white

Solubilité

DMSO: >30 mg/mL

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

GSNHKUDZZFZSJB-QYOOZWMWSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Structure of the CCR5 chemokine receptor-HIV entry inhibitor maraviroc complex
Tan Q, et al.
Science, 341(6152), 1387-1390 (2013)
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)
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
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
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