Raltegravir
Product Features- Product Name
- Raltegravir
- CAS No.
- 518048-05-0
- Chemical Name
- Raltegravir
- Synonyms
- CS-1889;Raltegravir;Reg column wei;Raltegravir(R&D);Raltegravir, >=99%;Raltegravir USP/EP/BP;Raltegravir(free base);Raltegravir (free base) API;MK-0518 518048-05-0 CAS NO.518048-05-0;Raltegravir-d4Q: What is Raltegravir-d4 Q: What is the CAS Number of Raltegravir-d4
- CBNumber
- CB61456530
- Molecular Formula
- C20H21FN6O5
- Formula Weight
- 444.42
- MOL File
- 518048-05-0.mol
Raltegravir Property
- Melting point:
- 216 °C(Solv: isopropanol (67-63-0))
- Density
- 1.46±0.1 g/cm3(Predicted)
- storage temp.
- -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Very Slightly)
- pka
- 4.50±1.00(Predicted)
- form
- Solid
- color
- White to Light Beige
- CAS DataBase Reference
- 518048-05-0(CAS DataBase Reference)
Safety
- Hazardous Substances Data
- 518048-05-0(Hazardous Substances Data)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- SML3670
- Product name
- Raltegravir
- Purity
- ≥98% (HPLC)
- Packaging
- 10MG
- Price
- $79
- Updated
- 2024/03/01
- Product number
- SML3670
- Product name
- Raltegravir
- Purity
- ≥98% (HPLC)
- Packaging
- 50MG
- Price
- $319
- Updated
- 2024/03/01
- Product number
- R100305
- Product name
- Raltegravir
- Packaging
- 100mg
- Price
- $450
- Updated
- 2021/12/16
- Product number
- INB0000049
- Product name
- RALTEGRAVIR
- Purity
- 95.00%
- Packaging
- 250MG
- Price
- $460
- Updated
- 2021/12/16
- Product number
- orb134886
- Product name
- Raltegravir
- Purity
- >99%
- Packaging
- 250mg
- Price
- $1133.9
- Updated
- 2021/12/16
Raltegravir Chemical Properties,Usage,Production
Product Features
Merck's Raltegravir is the first HIV integrase strand transfer inhibitor (referred to as an integrase inhibitor). It is also known as MK-0518, which can treat human immunodeficiency virus (HIV)-1 infection combining with other antiretroviral (ARV) drugs. It slows HIV-1 infection by inhibiting the necessary HIV integrase for viral replication. When raltegravir combines with other anti-HIV drugs, it can reduce the amount of HIV in the blood, while it can increase the number of so-called CD4+ T cells that belong to white blood cells. It helps against other infections. The interaction between raltegravir and ritonavir, efavirenz, tipranavir and tenofovir indicates that there is no drug cross-resistance, and there is a synergistic effect with a variety of drugs. The most common adverse reactions are diarrhea, nausea, headache. In addition, blood tests show that the muscle enzymes abnormally increased in some of patients who taked this drug.
The above information is edited by the chemicalbook of Kui Ming.
Description
Joining maraviroc as a unique approach to battling HIV-1, raltegravir, an inhibitor of HIV-1 integrase, represents the first in its class to be developed and launched as a combination treatment with other antiretroviral agents (NRTIs, NNRTIs, and PIs). HIV-1 integrase is essential for replication of the virus as a virally encoded enzyme that integrates the viral DNA into the genome of the host cell. Inhibition of HIV-1 integrase prevents the two-step process of endonucleolytic removal of the terminal dinucleotide from each 3′end of the viral DNA followed by the covalent integration of the viral DNA, at these modified 3′ends, into the host DNA, thereby representing a viable intervention in the viral life cycle. In vitro, raltegravir inhibited the strand transfer activity of HIV-1 integrase with an IC50 of 2–7nM with ＞ 1,000-fold selectivity over other phosphoryltransferases. In addition, its in vitro IC95 for HIV-1 in 10% fetal bovine serum and 50% human serum was 19 and 33 nM, respectively. Raltegravir was well tolerated with no dose-related toxicities and a safety profile comparable to placebo. The most common clinical adverse events were diarrhea, nausea, vomiting, fatigue, headache, flushing, pruritus, and injection-site reactions.
Originator
Merck (US)
Uses
Raltegravir (MK-0518) is a potent integrase (IN) inhibitor for WT and S217Q PFV IN.
Uses
Raltegravir (MK-0518, Isentress) is a potent integrase (IN) inhibitor for WT and S217Q PFV IN with IC50 of 90 nM and 40 nM, respectively.
Definition
ChEBI: Raltegravir is a pyrimidone that is pyrimidin-4(3H)-one in which the hydrogens at positions 2, 3, 5 and 6 are replaced by 2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl, methyl, hydroxy, and N-[(4-fluorophenyl)methyl]aminoacyl groups, respectively. It is an antiretroviral drug used for treatment of HIV infection. It has a role as an antiviral drug and a HIV-1 integrase inhibitor. It is a 1,2,4-oxadiazole, a dicarboxylic acid amide, a member of monofluorobenzenes, a pyrimidone, a hydroxypyrimidine and a secondary carboxamide.
brand name
Isentress
Acquired resistance
Several characteristic mutations leading to typical amino acid exchanges have been characterized in cell culture studies and confirmed in clinical trial participants with virological failure while receiving raltegravir in combination with other antiretrovirals. Virological failure has generally been associated with mutations at one of three residues – Y143, Q148 or N155 – usually in combination with at least one other mutation.
Pharmaceutical Applications
Formulated as the potassium salt for oral administration.
Pharmacokinetics
Oral absorption: Not known/available
Cmax 400 mg twice daily: c. 2.17 mg/L
Plasma half-life: c. 9 h
Volume of distribution: Not known/available
Plasma protein binding: c. 83%
Absorption and distribution
It may be administered without regard to food. There are few data regarding its capacity to penetrate into genital secretions or breast milk. A study of 25 HIV-infected individuals receiving raltegravir as a component of combination antiretroviral therapy found that 24 had detectable levels and that 50% of these reached a level exceeding the 95% inhibitory concentration reported to inhibit HIV-1 strains fully susceptible to integrase inhibition.
Metabolism and excretion
It is not a substrate, and does not appear to inhibit or induce the cytochrome P450 enzyme complex. It is primarily metabolized through hepatic glucuronidation mediated by the UGT-1A1 enzyme. It is excreted in the feces (51%) and the urine (32%) as unaltered compound and its glucuronide. There are no recommended dose adjustments for weight, sex and race, or for hepatic or renal insufficiency. The pharmacokinetic handling in children has not been determined.
Clinical Use
Treatment of HIV infection (in combination with other antiretroviral drugs)
Side effects
Its toxicity profile to date is remarkably benign. Clinical trial participants experienced similar types and frequencies of adverse events as those receiving placebo. The most frequently reported adverse events were nausea, diarrhea and headache and were mostly mild to moderate in intensity. Myopathy, rhabdomyolysis and elevations of creatinine phosphokinase have been noted in a few trial participants and it should be used cautiously in combination with drugs associated with muscle toxicity.
Synthesis
The synthesis of raltegravir begins with the treatment of acetone cyanohydrin with liquid ammonia in a pressure vessel. The resulting aminonitrile is protected as the benzyl carbamate before reaction of the nitrile moiety with hydroxylamine to afford the amidoxime. The pyrimidone ring is then constructed by condensation with dimethyl acetylenedicarboxylate and subsequent cyclization in hot xylene. Methylation of the pyrimidone is performed next with iodomethane and magnesium methoxide in dimethylsulfoxide followed by conversion of the methyl ester to an amide with 4-fluorobenzylamine. The amine, liberated from hydrogenolytic removal of the carbobenzyloxy-protecting group, is acylated with oxadiazolecarbonyl chloride, prepared in three steps from 5-methyltetrazole, to afford raltegravir.
Drug interactions
Potentially hazardous interactions with other drugs
Antibacterials: concentration reduced by rifampicin,
consider increasing raltegravir dose.
Antivirals: avoid with fosamprenavir.
Orlistat: absorption of raltegravir possibly reduced.
Ulcer-healing drugs: concentration increased by
omeprazole and famotidine.
Metabolism
Metabolised via glucuronidation, catalysed by the enzyme uridine diphosphate glucuronosyltransferase. Raltegravir is excreted in both urine and faeces as unchanged drug and metabolites.
Raltegravir Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Raltegravir manufacturers
- Product
- Raltegravir 518048-05-0
- Price
- US $0.00/kg
- Min. Order
- 25kg
- Purity
- 98%
- Supply Ability
- Inquiry
- Release date
- 2022-10-20
- Product
- Raltegravir 518048-05-0
- Price
- US $35.00-25.00/kg
- Min. Order
- 1kg
- Purity
- 99.8%
- Supply Ability
- 200tons/year
- Release date
- 2024-03-15
- Product
- Raltegravir 518048-05-0
- Price
- US $110.00-90.00/kilogram
- Min. Order
- 1kilogram
- Purity
- 99%
- Supply Ability
- 10 tons/per week
- Release date
- 2024-01-19