ChemicalBook
Chinese Japanese Germany Korea

Maraviroc

Maraviroc
Maraviroc structure
CAS No.
376348-65-1
Chemical Name:
Maraviroc
Synonyms
maroviroc;Celsentri;Maraviroc;Maraviroc API;Maraviroc, >=99%;Maraviroc(UK427857);Maraviroc(Selzentry);Maraviroc(Selzentry, UK-427857);Maraviroc cas 376348-65-1(whatsapp:+8618830163278);4,4-Difluoro-N-((1S)-3-((1R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.
CBNumber:
CB71270957
Molecular Formula:
C29H41F2N5O
Formula Weight:
513.67
MOL File:
376348-65-1.mol

Maraviroc Properties

Melting point:
79-81°C
storage temp. 
Store at +4°C
solubility 
DMSO: >30mg/mL
pka
7.3(at 25℃)
form 
white powder
optical activity
[α]-15/D
CAS DataBase Reference
376348-65-1(CAS DataBase Reference)

SAFETY

Hazard Codes  Xn
Risk Statements  48/22
Safety Statements  22-36
WGK Germany  1

Maraviroc price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PZ0002 Maraviroc ≥98% (HPLC) 376348-65-1 5mg $119 2018-11-13 Buy
Sigma-Aldrich PZ0002 Maraviroc ≥98% (HPLC) 376348-65-1 25mg $476 2018-11-13 Buy
Cayman Chemical 14641 Maraviroc ≥98% 376348-65-1 5mg $65 2018-11-13 Buy
Cayman Chemical 14641 Maraviroc ≥98% 376348-65-1 10mg $124 2018-11-13 Buy
Cayman Chemical 14641 Maraviroc ≥98% 376348-65-1 25mg $244 2018-11-13 Buy

Maraviroc Chemical Properties,Uses,Production

Description

Maraviroc is the first CCR5 receptor antagonist that has been developed and launched for the treatment of HIV-1. Maraviroc binds in a slowly reversible, allosteric manner to CCR5, which is one of two principle chemokine co-receptors for viral entry into the host cell, the other being CXCR4. Binding of maraviroc to CCR5 induces conformational changes within the chemokine receptor, thereby preventing CCR5 binding to the viral gp120 protein and the ultimate CCR5- mediated virus-cell fusion that is a prerequisite for HIV invasion. Maraviroc, with its unique mechanism of action as a fusion inhibitor, joins the greater than 20 marketed antiretrovirals, including nucleotide reverse transcriptase inhibitors (NRTIs), non-nucleoside reverse transcriptase inhibitors (NNRTIs), and PIs. It is approved for use in combination with these other antiretroviral drugs in adult patients with R5-tropic HIV-1 infection (but not X4 or dual/mixed tropic HIV-1).

Chemical Properties

Brown Solid

Originator

Pfizer (US)

Uses

Potent, non-competitive CCR5 receptor antagonist; inhibits binding of HIV viral coat protein gp120. Antiviral

Uses

Maraviroc is a CCR5 antagonist for MIP-1α, MIP-1β and RANTES with IC50 of 3.3 nM, 7.2 nM and 5.2 nM, respectively

Definition

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4,4-difluorocyclohexanecarboxylic acid and the primary amino group of (1S)-3-[(3-exo)-3-(3-isopropyl-5-methyl-4H-1,2,4- riazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropylamine. An antiretroviral drug, it prevents the interaction of HIV-1 gp120 and chemokine receptor 5 (CCR5) necessary for CCR5-tropic HIV-1 to enter cells.

brand name

Selzentry

Acquired resistance

In most patients (c. 60%) failure of response is associated with the selection of virus that can use CXCR4 as its entry co-receptor. Evidence for the selection of virus that continues to use CCR5 has also been described.

Pharmaceutical Applications

A spirodiketopiperazine formulated as tablets for oral use.

Pharmacokinetics

Oral absorption: c. 33% (300 mg dose)
Cmax 150 mg twice daily: c. 332 μg/L*
Cmin 150 mg twice daily: c. 101 μg/L*
Plasma half-life: c. 13.2 h (30 mg iv administration)
Volume of distribution: c. 194 L
Plasma protein binding: c. 76%
Absorption
The absolute bioavailability of a 100 mg dose is 23% and is predicted to be 33% after a 300 mg dose. Co-administration of a 300 mg tablet and a high-fat meal has resulted in reduced Cmax and AUC by 33% in healthy volunteers. However, because no food restrictions were enacted during clinical trials, maraviroc may be taken with or without food.
Distribution
Animal experiments suggest low CSF concentrations around 10% of free plasma concentrations. It is not known whether it passes into breast milk. A study of genital tract secretions and vaginal tissue in healthy HIV-uninfected female volunteers suggest a concentration in cervicovaginal fluid more than four-fold higher than that in plasma.
Metabolism
It is a substrate for CYP3A4 and P-glycoprotein, but does not appear to inhibit or induce CYP3A4.
Excretion
Seventy-six and 19% of a radiolabeled maraviroc dose were recovered in the feces and urine, respectively.

Clinical Use

Treatment of HIV infection (in combination with other antiretroviral drugs) in treatment-experienced patients
On November 20, 2009, the US Food and Drug Administration approved a supplemental new drug application to expand the indication for maraviroc to include combination antiretroviral treatment of treatmentnaive adults infected with CCR5-tropic HIV virus

Side effects

There has been some concern that CCR5 blockade may result in decreased immune surveillance and a subsequent increased risk of development of malignancies (e.g. lymphomas). Genetic deficiency of the CCR5 co-receptor is also known to be a risk factor for the development of symptomatic West Nile virus infection. No evidence for an increase in either of these potential risks has so far emerged.
The toxicity profile appears relatively benign. The most common adverse events described so far include diarrhea, fatigue, headache and nausea. In placebo-controlled studies the only differences to emerge were fever (6% versus 4% in the placebo group) and headache (2% versus 6% with placebo). Discontinuation because of adverse events was uncommon and the same in both groups.

Side effects

Overall, maraviroc was well tolerated with the most common adverse events being cough, fever, colds, rash, muscle and joint pain, stomach pain, and dizziness. While some patients did experience liver enzyme elevation, these events did not appear to be doserelated. Since hepatotoxicity did occur in one patient with prior liver function abnormalities, maraviroc s label warns of a potentially increased risk of hepatoxicity with treatment. Postural hypotension was also observed in a dosedependent manner; however, no patients discontinued therapy as a result. As a substrate for CYP3A4, the dose of maraviroc should be reduced by 50% in the presence of strong CYP3A4 inhibitors. Conversely, concomitant use of strong CYP3A4 inducers requires a 50% increase in maraviroc dose. While there are no contraindications, maraviroc should be used with caution in patients with liver dysfunction, high risk of cardiovascular events, and pre-existing postural hypotension.

Chemical Synthesis

The synthesis of maraviroc involves the convergent connection of a triazole-substituted tropane moiety, a phenylpropyl fragment with a benzylic chiral center, and a 4,4-difluorocyclohexyl unit. In the presence of aqueous HCl and sodium acetate, 2,5-dimethoxytetrahydrofuran is cyclized with benzylamine and 2-oxomalonic acid to afford 8-benzyl-8-azabicyclo[3.2.1]octan-3-one. The ketone is converted to an amine via reduction of an intermediate oxime. Carbodiimide-mediated coupling of this amine with isobutyric acid yields the isobutyramide that is subsequently cyclized to the 1,2,4-triazole with acetic hydrazide. The benzyl-protected amine is then liberated by transfer hydrogenation (ammonium formate and palladium hydroxide) and subjected to reductive amination with 3(S)-(tert-butoxycarbonylamino)-3-phenylpropionaldehyde by means of sodium triacetoxyborohydride. Removal of the BOC-protecting group establishes the handle for the final amide coupling with 4,4-difluorocyclohexane carboxylic acid to provide maraviroc.

Maraviroc Preparation Products And Raw materials

Raw materials

Preparation Products


Maraviroc Suppliers

Global( 134)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19919 60
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21930 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070;product@chemlin.com.cn
product@chemlin.com.cn CHINA 3015 60
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20516 58
Hebei Huanhao Biotechnology Co., Ltd.
86-0311-83975816 whatsapp +8618034554576
86-0311-83975816 grace@hbhuanhao.com CHINA 701 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 955 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23982 58
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20094 58

View Lastest Price from Maraviroc manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-24 Maraviroc
376348-65-1
US $2.00 / kg 1kg 99% 100kg career henan chemical co
2019-04-18 Maraviroc
376348-65-1
US $10.00 / KG 1KG 99% 10mt Hebei Guanlang Biotechnology Co., Ltd.
2019-01-04 Maraviroc cas 376348-65-1(whatsapp:+8618830163278)
376348-65-1
US $14.00 / kg 1kg 99.9% 15tons Hebei Huanhao Biotechnology Co., Ltd.

376348-65-1(Maraviroc)Related Search:


  • maroviroc
  • 4,4-Difluoro-N-{(1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl}cyclohexanecarboxamide
  • Maraviroc(Selzentry)
  • 4,4-difluoro-N-[(1S)-3-[(1R,3R,5S)-3-[3-Methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxaMide
  • Celsentri
  • 4,4-difluoro-N-((1R)-3-(3-(3-isopropyl-5-Methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)cyclohexanecarboxaMide
  • 4,4-difluoro-N-(3-(3-(3-isopropyl-5-Methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)cyclohexanecarboxaMide
  • Maraviroc API
  • 4,4-difluoro-N-((S)-3-((1S,3R,5R)-3-(3-isopropyl-5-Methyl-4H-1,2,4-triazol-4-yl)-8-aza-bicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)cyclohexanecarboxaMide
  • Maraviroc(Selzentry, UK-427857)
  • 4,4-difluoro-N-((S)-3-(3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-aza-bicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)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]cyclohexanecarboxamide
  • Maraviroc, >=99%
  • 4,4-Difluoro-N-((1S)-3-((1R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.
  • Anti-AIDS
  • Chiral Reagents
  • 376348-65-1
  • Maraviroc
  • Maraviroc(UK427857)
  • 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
  • Maraviroc cas 376348-65-1(whatsapp:+8618830163278)
  • -
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Pfizer compounds
  • UK-427857, Celsentri
  • Other APIs
Copyright 2017 © ChemicalBook. All rights reserved