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PZ0002

Sigma-Aldrich

Maraviroc

≥98% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C29H41F2N5O
Numero CAS:
376348-65-1
Peso molecolare:
513.67
Numero MDL:
MFCD13188530
Codice UNSPSC:
12352200
ID PubChem:
329823671
NACRES:
NA.77
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Saggio

≥98% (HPLC)

Stato

powder

Attività ottica

[α]-15/D

Colore

white

Solubilità

DMSO: >30 mg/mL

Temperatura di conservazione

room temp

Stringa SMILE

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
GSNHKUDZZFZSJB-QYOOZWMWSA-N

Informazioni sul gene

human ... CCR5(1234)

Applicazioni

Maraviroc has been used as a C-C chemokine receptor type 5 (CCR5-specific) inhibitor in murine monocyte/macrophage cell line J774A.1,[1] porcine uterine luminal epithelial cells[2] and human lung CD4+ T cells.[3]

Azioni biochim/fisiol

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).[4] Maraviroc binds to the active site pocket of chemokine receptor CCR5 making the receptor inactive.[5]

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
0000389462
0000389462
0000231530
0000231530
0000055201

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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)
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)
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
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
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