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Darunavir Ethanolate

CAS# 635728-49-3

Darunavir Ethanolate

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Quality Control of Darunavir Ethanolate

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Chemical structure

Darunavir Ethanolate

3D structure

Chemical Properties of Darunavir Ethanolate

Cas No. 635728-49-3 SDF Download SDF
PubChem ID 23725083 Appearance Powder
Formula C29H43N3O8S M.Wt 593.73
Type of Compound N/A Storage Desiccate at -20°C
Synonyms TMC114
Solubility DMSO : ≥ 50 mg/mL (84.21 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate;ethanol
SMILES CCO.CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
Standard InChIKey QWSHKNICRJHQCY-VBTXLZOXSA-N
Standard InChI InChI=1S/C27H37N3O7S.C2H6O/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26;1-2-3/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32);3H,2H2,1H3/t22-,23-,24+,25-,26+;/m0./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Darunavir Ethanolate Dilution Calculator

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Darunavir Ethanolate Molarity Calculator

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Preparing Stock Solutions of Darunavir Ethanolate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6843 mL 8.4213 mL 16.8427 mL 33.6853 mL 42.1067 mL
5 mM 0.3369 mL 1.6843 mL 3.3685 mL 6.7371 mL 8.4213 mL
10 mM 0.1684 mL 0.8421 mL 1.6843 mL 3.3685 mL 4.2107 mL
50 mM 0.0337 mL 0.1684 mL 0.3369 mL 0.6737 mL 0.8421 mL
100 mM 0.0168 mL 0.0842 mL 0.1684 mL 0.3369 mL 0.4211 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Darunavir Ethanolate

Darunavir ethanolate (TMC114 ethanolate) is a potent HIV protease inhibitor used to treat and prevent HIV/AIDS. Darunavir has a Ki of 1 nM for wild type HIV-1 protease.

In Vitro:Darunavir is a broad-spectrum potent inhibitor active against HIV-1 clinical isolates with minimal cytotoxicity. Darunavir forms hydrogen bonds with the conserved main-chain atoms of Asp29 and Asp30 of the protease. These interactions are proposed to be critical for the potency of this compound against HIV isolates that are resistant to multiple protease inhibitors[1]. In an in vitro study in MT-2 cells, the potency of darunavir is greater than that of saquinavir, amprenavir, nelfinavir, indinavir, lopinavir and ritonavir. Darunavir is primarily metabolized by the hepatic cytochrome P450 (CYP) enzymes, primarily CYP3A. The ‘boosting’ dose of ritonavir acts an an inhibitor of CYP3A, thereby increasing darunavir bioavailability[2].

In Vivo:Darunavir is effective against wild-type and PI-resistant HIV, and has an oral bioavailability of 37%. It needs to be combined with ritonavir, which increases the bioavailability to 82%[3].

References:
[1]. Tie Y, et al. High resolution crystal structures of HIV-1 protease with a potent non-peptide inhibitor (UIC-94017) active against multi-drug-resistant clinical strains. J Mol Biol. 2004 Apr 23;338(2):341-52. [2]. McKeage K, et al. Darunavir: a review of its use in the management of HIV infection in adults. Drugs. 2009;69(4):477-503. [3]. Bhalekar MR, et al. In-vivo bioavailability and lymphatic uptake evaluation of lipid nanoparticulates of darunavir. Drug Deliv. 2016 Sep;23(7):2581-2586.

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References on Darunavir Ethanolate

Stability-indicating HPLC method for the determination of darunavir ethanolate.[Pubmed:23097581]

J Chromatogr Sci. 2013 May-Jun;51(5):471-6.

A novel stability-indicating reversed-phase high-performance liquid chromatographic (HPLC) method has been developed for the quantitative determination of Darunavir Ethanolate, an HIV-1 protease inhibitor. The chromatographic separation was achieved using an X-Bridge C18 (150 x 4.6 mm x 3.5 microm) HPLC column in isocratic mode employing 0.01M ammonium formate (pH.3.0) buffer and acetonitrile in the ratio of 55:45 (v/v) with a flow rate of 1.0 mL/min. The detector wavelength was monitored at 265 nm and the column temperature was maintained at 30 degrees C. Darunavir Ethanolate was exposed to thermal, photolytic, acid, base and oxidative stress conditions. Considerable degradation of the drug substance was found to occur under acid, base and oxidative stress conditions. The peak homogeneity data of Darunavir Ethanolate obtained by photodiode array detection demonstrated the specificity of the method in the presence of degradants. The degradation products were well resolved from primary peak of darunavir, indicating that the method is specific and stability-indicating. The HPLC method was validated as per International Conference on Harmonization guidelines with respect to specificity, precision, linearity, accuracy and robustness. Regression analysis showed a correlation coefficient value greater than 0.999. The accuracy of the method was established based on the recovery obtained for Darunavir Ethanolate.

Description

Darunavir ethanolate (TMC114 Ethanolate) is a potent HIV protease inhibitor used to treat and prevent HIV/AIDS. Darunavir has a Ki of 1 nM for wild type HIV-1 protease.

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