Chinese english Japanese Germany Korea
ChemicalBook > Product Catalog >API >Synthetic Anti-infective Drugs >Antiviral drugs >Maraviroc

Maraviroc

Maraviroc Structure
CAS No.
376348-65-1
Chemical Name:
Maraviroc
Synonyms
CS-49;Celsentri;maroviroc;Maraviroc;634 Hexilure;Maraviroc API;Maraviroc, >=99%;Maraviroc(UK427857);Maraviroc USP/EP/BP;Maraviroc(Selzentry)
CBNumber:
CB71270957
Molecular Formula:
C29H41F2N5O
Molecular Weight:
513.68
MOL File:
376348-65-1.mol
MSDS File:
SDS
Modify Date:
2024/6/7 16:07:22
Request For Quotation

Maraviroc Properties

Melting point 79-81°C
Density 1.29±0.1 g/cm3(Predicted)
storage temp. room temp
solubility DMSO: >30mg/mL
pka 7.3(at 25℃)
form white powder
color White
optical activity [α]-15/D
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey GSNHKUDZZFZSJB-RWJISDSDNA-N
SMILES C(N1[C@@H]2CC[C@H]1C[C@H](N1C(=NN=C1C(C)C)C)C2)C[C@@H](C1C=CC=CC=1)NC(C1CCC(F)(F)CC1)=O |&1:2,5,7,19,r|
CAS DataBase Reference 376348-65-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P280-P305+P351+P338
Hazard Codes  Xn
Risk Statements  48/22
Safety Statements  22-36
WGK Germany  1

Maraviroc price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) PZ0002 Maraviroc ≥98% (HPLC) 376348-65-1 5MG ₹15458.1 2022-06-14 Buy
Sigma-Aldrich(India) PZ0002 Maraviroc ≥98% (HPLC) 376348-65-1 25MG ₹62081.38 2022-06-14 Buy
Product number Packaging Price Buy
PZ0002 5MG ₹15458.1 Buy
PZ0002 25MG ₹62081.38 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

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.

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

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.

Maraviroc Preparation Products And Raw materials

Raw materials

N-Benzyltropinone (1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-1-propanamine 4,4-Difluorocyclohexanecarboxylic acid 4,4-DIFLUORO-N-((1S)-3-OXO-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE 8-Benzyl-3-exo-(5-isopropyl-3-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane
METHYL (3S)-3-AMINO-3-PHENYLPROPANOATE (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate (1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane ((S)-3-[3-(3-ISOPROPYL-5-METHYL-[1,2,4]TRIAZOL-4-YL)-8-AZA-BICYCLO[3.2.1]OCT-8-YL]-1-PHENYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER Cyclohexanecarbonyl chloride, 4,4-difluoro- (9CI)
3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-p-toluenesulfonate ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE Methyl (3S)-3-Boc-amino-3-phenylpropionate
chevron_left

1of3

chevron_right

Preparation Products

Maraviroc Suppliers

Global( 264)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
Aurona Med Pharma Private Limited +91-9618434204 +91-8074941863 Hyderabad, India 24 58 Inquiry
Rivashaa Agrotech Biopharma Pvt. Ltd. +91-26463395 +91-7926462688 Gujarat, India 1615 58 Inquiry
Cohance Lifesciences (Previously RA Chem Pharma Ltd) +91-4044758595 +91-4044758595 Telangana, India 47 58 Inquiry
Ralington Pharma +91-7948911722 +91-9687771722 Gujarat, India 1350 58 Inquiry
HETERO LABS LTD (630) 931-6800 New Delhi, India 97 58 Inquiry
A.J Chemicals 91-9810153283 New Delhi, India 6124 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
SynZeal Research Pvt Ltd +1 226-802-2078 Gujarat, India 6522 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
Manus Aktteva +91 (79) 6512-3395 New Delhi, India 581 34 Inquiry
Supplier Advantage
Aurona Med Pharma Private Limited 58
Rivashaa Agrotech Biopharma Pvt. Ltd. 58
Cohance Lifesciences (Previously RA Chem Pharma Ltd) 58
Ralington Pharma 58
HETERO LABS LTD 58
A.J Chemicals 58
CLEARSYNTH LABS LTD. 58
SynZeal Research Pvt Ltd 58
Pharmaffiliates Analytics and Synthetics P. Ltd 58
Manus Aktteva 34

Related articles

  • Side effects of Maraviroc
  • Maraviroc was synthesized by Pfizer Inc as UK-427,857 (4, 4-difluoro- N-[(1S)-3-[exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-....
  • Apr 2，2022

Maraviroc Spectrum

Maraviroc(376348-65-1)1HNMR

376348-65-1(Maraviroc)Related Search:

Methyl acrylate Methanol Kresoxim-methyl Methylparaben Basic Violet 1
Paraquat dichloride Acetonitrile Methyl acetate Methyl Methyl bromide
1-Piperidinepropanamine, -phenyl- 4-(3,5-DIMETHYL-4H-1,2,4-TRIAZOL-4-YL)PIPERIDINE 3-(2,6-DIMETHYL-PIPERIDIN-1-YL)-PROPYLAMINE Maraviroc Des[1-(4,4-difluorocyclohexanecarboxamido)-1-phenylpropyl] Maraviroc
3-Hydroxymethyl Maraviroc Cyclohexanecarboxamide, 4,4-difluoro- Cyclohexanecarboxaldehyde, 4,4-difluoro- (9CI)
chevron_left

1of4

chevron_right
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 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 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(Selzentry, UK-427857) 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. UK-427857; CELSENTRI CS-49 4,4-Difluoro-N-((S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)cyclohexane-1-carboxamide Maraviroc USP/EP/BP Maraviroc (10mM in DMSO) MaravirocQ: What is Maraviroc Q: What is the CAS Number of Maraviroc Q: What is the storage condition of Maraviroc Q: What are the applications of Maraviroc 634 Hexilure Maraviroc UK427857 UK-427857 376348-65-1 4,4-difluoro-N-((S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropyl)cyclohexanecarboxamide 376348-65-1 UK-427857, Celsentri Other APIs Pfizer compounds Anti-AIDS Chiral Reagents Inhibitors Intermediates & Fine Chemicals Pharmaceuticals