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    Ritonavir (ABT-538; Norvir)
    Ritonavir (ABT-538; Norvir)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0729
    CAS #: 155213-67-5 Purity ≥98%

    Description: Ritonavir (previously known as ABT-538; A-84538; RTV; ABT538, trade name: Norvir) is a L-valine derivative and potent inhibitor of HIV-1 protease used to treat HIV infection and AIDS. It is widely used as a booster for other protease inhibitors/PIs such as lopinavir, and makes them work better. More specifically, ritonavir is used to inhibit a particular liver enzyme that normally metabolizes protease inhibitors, CYP3A4. Ritonavir exhibits potent in vitro inhibition against HIV-1 strain as well as HIV-2 strain with 50% effective concentration EC50 values of 0.022 μM and 0.16 μM respectively.

    References: Br J Clin Pharmacol. 1997 Aug;44(2):190-4; J Pharmacol Exp Ther. 1996 Apr;277(1):423-31.

    Related CAS: 176655-55-3 (Desthiazolylmethyloxycarbonyl Ritonavir, a metabolite of Ritonavir)

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    Molecular Weight (MW)720.94
    FormulaC37H48N6O5S2
    CAS No.155213-67-5 (Ritonavir); 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 100 mg/mL (138.7 mM)
    Water: <1 mg/mL
    Ethanol: 3 mg/mL (4.16 mM)
    Solubility (In vivo)30% PEG400+0.5% Tween80+5% propylene glycol: 30 mg/mL
    SynonymsABT-538; A 84538; Norvir; ABT538; A-84538; Norvir Sec; 538, ABT; Ritonavir; ABT 538; 

    Chemical Name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[[(2S)-3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]butanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate

    InChi Key: NCDNCNXCDXHOMX-UHFFFAOYSA-N

    InChi Code: InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(40-29)25(3)4)34(45)39-28(16-26-12-8-6-9-13-26)18-32(44)31(17-27-14-10-7-11-15-27)41-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)

    SMILES Code: CC(C)C1=NC(=CS1)CN(C)C(=O)NC(C(C)C)C(=O)NC(CC2=CC=CC=C2)CC(C(CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)O


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    In Vitro

    In vitro activity: Ritonavir is a very potent inhibitor of CYP3A4 mediated testosterone 6β-hydroxylation with mean Ki of 19 nM and also inhibits tolbutamide hydroxylation with IC50 of 4.2 μM. Ritonavir is found to be a potent inhibitor of CYP3A-mediated biotransformations (nifedipine oxidation with IC50 of 0.07 mM, 17alpha-ethynylestradiol 2-hydroxylation with IC50 of 2 mM; terfenadine hydroxylation with IC50 of 0.14 mM). Ritonavir is also found to be an inhibitor of the reactions mediated by CYP2D6 (IC50 = 2.5 mM) and CYP2C9/10 (IC50 = 8.0 mM). Ritonavir results in an increase in cell viability in uninfected human PBMC cultures. Ritonavir markedly decreases the susceptibility of PBMCs to apoptosis correlated with lower levels of caspase-1 expression, decreases in annexin V staining, and reduces caspase-3 activity in uninfected human PBMC cultures. Ritonavir inhibits induction of tumor necrosis factor (TNF) production by PBMCs and monocytes in a time- and dose-dependent manner at nontoxic concentrations. Ritonavir inhibits p-glycoprotein-mediated extrusion of saquinavir with an IC50 of 0.2 μM, indicating a high affinity of ritonavir for p-glycoprotein. Ritonavir inhibits human liver microsomal metabolism of ABT-378 potently with Ki of 13 nM. Ritonavir combined with ABT-378 (at 3:1 and 29:1 ratios) inhibits CYP3A (IC50 = 1.1 and 4.6 μM), albeit less potently than Ritonavir (IC50 = 0.14 μM).


    Kinase Assay: Ritonavir (ABT 538) is an inhibitor of CYP3A4 mediated testosterone 6β-hydroxylation with mean Ki of 19 nM and also inhibits tolbutamide hydroxylation with IC50 of 4.2 μM. Ritonavir (ABT 538) is found to be a potent inhibitor of CYP3A-mediated biotransformations (nifedipine oxidation with IC50 of 0.07 mM, 17alpha-ethynylestradiol 2-hydroxylation with IC50 of 2 mM; terfenadine hydroxylation with IC50 of 0.14 mM). Ritonavir is also an inhibitor of the reactions mediated by CYP2D6 (IC50=2.5 mM) and CYP2C9/10 (IC50=8.0 mM).


    Cell Assay: Ritonavir results in an increase in cell viability in uninfected human PBMC cultures. Ritonavir markedly decreases the susceptibility of PBMCs to apoptosis correlated with lower levels of caspase-1 expression, decreases in annexin V staining, and reduces caspase-3 activity in uninfected human PBMC cultures. Ritonavir inhibits induction of tumor necrosis factor (TNF) production by PBMCs and monocytes in a time- and dose-dependent manner at nontoxic concentrations. Ritonavir inhibits p-glycoprotein-mediated extrusion of saquinavir with an IC50 of 0.2 μM, indicating a high affinity of ritonavir for p-glycoprotein. Ritonavir inhibits human liver microsomal metabolism of ABT-378 potently with Ki of 13 nM. Ritonavir combined with ABT-378 (at 3:1 and 29:1 ratios) inhibits CYP3A (IC50=1.1 and 4.6 μM), albeit less potently than Ritonavir (IC50=0.14 μM).

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    ReferencesBr J Clin Pharmacol. 1997 Aug;44(2):190-4; J Pharmacol Exp Ther. 1996 Apr;277(1):423-31.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

     

    Ritonavir

     

    Ritonavir

     Biological Activity Ritonavir


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