Indinavir

Base Information

• Chemical Name: Indinavir
• CAS No.: 150378-17-9
• Deprecated CAS: 166746-42-5,216884-06-9
• Molecular Formula: C36H47N5O4
• Molecular Weight: 613.8
• UNII: 9MG78X43ZT
• DSSTox Substance ID: DTXSID4043802
• Nikkaji Number: J566.361J
• Wikipedia: Indinavir
• Wikidata: Q425490
• NCI Thesaurus Code: C74585
• Pharos Ligand ID: 3WRTT7LPSHQR
• Metabolomics Workbench ID: 42626
• ChEMBL ID: CHEMBL115
• Mol file: 150378-17-9.mol

Synonyms:Crixivan;Indinavir;Indinavir Sulfate;Indinavir, Sulfate (1:1);L 735 524;L 735,524;L-735 524;L-735,524;L735 524;L735,524;MK 639;MK-639;MK639;Sulfate, Indinavir

Chemical Property of Indinavir

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 150-153 °C
• Refractive Index: 1.636
• Boiling Point: 877.9 °C at 760 mmHg
• PKA: pKa 3.8/6.2(H2O,t undefined,Iundefined) (Uncertain)
• Flash Point: 484.7 °C
• PSA: 118.03000
• Density: 1.25 g/cm³
• LogP: 3.52450
• Water Solubility.: 70mg/L(temperature not stated)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 613.36280500
• Heavy Atom Count: 45
• Complexity: 952

Purity/Quality:

99% ^*data from raw suppliers

Indinavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(C)(C)NC(=O)C1CN(CCN1CC(CC(CC2=CC=CC=C2)C(=O)NC3C(CC4=CC=CC=C34)O)O)CC5=CN=CC=C5
• Isomeric SMILES: CC(C)(C)NC(=O)[C@@H]1CN(CCN1C[C@H](C[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H]3[C@@H](CC4=CC=CC=C34)O)O)CC5=CN=CC=C5
• Recent ClinicalTrials: Use of Combined Antiretroviral Therapy to Determine Sites of Persistent HIV Infection
• Recent EU Clinical Trials: Raltegravir-based regimen versus raltegravir-based regimen plus atorvastatin for reducing ?inflamaging? (aging-related complication) in HIV-infected patients older than 60 years.
• Description: Crixivan was launched in Australia, Switzerland, the UK and the US as an orally-bioavailable HIV-1 protease inhibitor. The compound can be prepared by coupling an optically active piperazine derivative with an epoxide derivative (now commercially available). The synthesis of the proteins, reverse transcriptase, integrase, structural proteins and a protease, required by the virus to complete its lifecycle, can be interupted if the protease enzyme is not capable of cleaving a proform polypeptide chain into these components. lndinavir inhibits this process and is more potent than the first approved protease inhibitor saquinavir. This effect was noted by the increase in CD4+ cells and a decrease in HIV RNA levels. Since indinavir is metabolized by the CYP3A4 isozyme, care must be taken with patients with hepatic insufficiency and to sex-related differences in the level of this enzyme. Other than nephrolithiasis (5%), indinavir is relatively safe and well tolerated.
• Uses: Indinavir is a member of the novel hydroxyaminopentane amide class of HIV-1 protease inhibitors. Indinavir is used as an antiviral. It is a COVID19-related research product. Indinavir is a member of the novel hydroxyaminopentane amide class of HIV-1 protease inhibitors. Indinavir is used as an antiviral.
• Indications: Indinavir (Crixivan) is a potent inhibitor of HIV reverse transcriptase. It produces the side effects common to all protease inhibitors and also may produce nephrolithiasis, urolithiasis, and possibly renal insufficiency or renal failure. This problem occurs more frequently in children (approximately 30%) than adults (approximately 10%) and can be minimized by drinking at least 1.5 L of water daily. Additional side effects include asymptomatic hyperbilirubinemia, alopecia, ingrown toenails, and paronychia. Hemolytic anemia rarely occurs. Rifampin should not be given with indinavir.
• Clinical Use: Treatment of adult HIV infection (in combination with other antiretroviral drugs)
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: possibly increased amiodarone and flecainide concentration - avoid. Antibacterials: rifampicin increases metabolism - avoid concomitant use; increased rifabutin concentration - avoid; avoid with telithromycin in severe renal and hepatic failure. Anticoagulants: avoid with apixaban and rivaroxaban. Antidepressants: concentration reduced by St John’s wort - avoid. Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin, phenytoin, primidone and phenobarbital, also concentration of carbamazepine, fosphenytoin and phenytoin increased. Antifungals: itraconazole and ketoconazole inhibits metabolism - reduce dose of indinavir to 600 mg every 8 hours. Antimalarials: use artemether/lumefantrine with caution; possibly increased quinine concentration. Antipsychotics: possibly increased risk of ventricular arrhythmias with pimozide - avoid; possibly inhibits aripiprazole metabolism - reduce aripiprazole dose; possibly increases lurasidone and quetiapine concentration - avoid. Antivirals: avoid with atazanavir; concentration reduced by efavirenz, nevirapine and possibly etravirine, avoid with etravirine; concentration of both drugs increased with darunavir; concentration of maraviroc increased, consider reducing maraviroc dose; concentration increased by ritonavir; saquinavir concentration increased. Anxiolytics and hypnotics: increased risk of prolonged sedation with alprazolam and midazolam - avoid. Avanafil: concentration of avanafil possibly increased - avoid. Ciclosporin: concentration of ciclosporin increased. Colchicine: possibly increases risk of colchicine toxicity, avoid in hepatic or renal impairment. Cytotoxics: possibly increases concentration of axitinib, reduce dose of axitinib; possibly increases bosutinib, cabazitaxel and docetaxel concentration - avoid or reduce dose of bosutinib, cabazitaxel and docetaxel; possibly increases concentration of crizotinib and everolimus - avoid; possibly increases ibrutinib concentration, reduce dose of ibrutinib; avoid with olaparib and pazopanib; reduce dose of ruxolitinib. Ergot alkaloids: risk of ergotism - avoid. Guanfacine: possibly increases guanfacine concentration, halve dose of guanfacine. 5HT1 agonists: concentration of eletriptan increased - avoid. Lipid-regulating drugs: avoid with lomitapide increased risk of myopathy with rosuvastatin and simvastatin - avoid; and possibly with atorvastatin. Naloxegol: possibly increases naloxegol concentration - avoid. Orlistat: absorption possibly reduced by orlistat. Ranolazine: possibly increases ranolazine concentration - avoid. Sildenafil: concentration of sildenafil increased - reduce initial sildenafil dose. Vardenafil: concentration of vardenafil increased - avoid.

Technology Process of Indinavir

There total 33 articles about Indinavir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

C36H50BN5O4 → indinavir (150378-17-9)

Guidance literature:

With methanol; hydrogen; platinum(IV) oxide; In tetrahydrofuran; for 3h;

Reference yield: 83.6%

nicotinyl chloride (3099-31-8) + [14C]-N-Dealkyl Indinavir (150323-38-9) → indinavir (150378-17-9)

Guidance literature:

at 20 ℃; for 0.5h;

Reference yield: 76.0%

3-chloromethylpyridinium chloride (6959-48-4) + [14C]-N-Dealkyl Indinavir (150323-38-9) → indinavir (150378-17-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 12h;

DOI:10.1021/jm00047a001

upstream raw materials:

nicotinyl chloride

[14C]-N-Dealkyl Indinavir

3-chloromethylpyridinium chloride

3-pyridinecarboxaldehyde

Downstream raw materials:

1-[4-benzyl-5-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

C₈₂H₁₁₃N₇O₁₆

Refernces

• 1、 -. "Methods for predicting the response to statins". . . Retrieved 2011/10/13.
• 2、 Myers,Barbay,Zhong. "Asymmetric synthesis of chiral organofluorine compounds: Use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors". . p. 7207 - 7219. Retrieved 2007/10/03.