CAS 155213-67-5|Ritonavir
| Common Name | Ritonavir | ||
|---|---|---|---|
| CAS Number | 155213-67-5 | Molecular Weight | 720.944 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 947.0±65.0 °C at 760 mmHg |
| Molecular Formula | C37H48N6O5S2 | Melting Point | 120-122°C |
| MSDS | ChineseUSA | Flash Point | 526.6±34.3 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | ritonavir |
|---|---|
| Synonym | More Synonyms |
Ritonavir BiologicalActivity
| Description | Ritonavir is an inhibitor of HIV protease used to treat HIV infection and AIDS. |
|---|---|
| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>HIV ProteaseSignaling Pathways >>Anti-infection >>HIVResearch Areas >>Infection |
| In Vitro | Ritonavir 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[1]. 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 an inhibitor of the reactions mediated by CYP2D6 (IC50=2.5 mM) and CYP2C9/10 (IC50=8.0 mM)[2]. 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[3]. Ritonavir inhibits p-glycoprotein-mediated extrusion of saquinavir with an IC50 of 0.2 μM, indicating a high affinity of ritonavir for p-glycoprotein[4]. 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)[5]. |
| References | [1]. Eagling VA, et al. Differential inhibition of cytochrome P450 isoforms by the protease inhibitors, ritonavir, saquinavir and indinavir. Br J Clin Pharmacol. 1997 Aug;44(2):190-4. [2]. Kumar GN, et al. Cytochrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes. J Pharmacol Exp Ther. 1996 Apr;277(1):423-31. [3]. Weichold FF, et al. HIV-1 protease inhibitor ritonavir modulates susceptibility to apoptosis of uninfected T cells. J Hum Virol. 1999 Sep-Oct;2(5):261-9. [4]. Drewe J, et al. HIV protease inhibitor ritonavir: a more potent inhibitor of P-glycoprotein than the cyclosporine analog SDZ PSC 833. Biochem Pharmacol. 1999 May 15;57(10):1147-52. [5]. Kumar GN, et al. Potent inhibition of the cytochrome P-450 3A-mediated human liver microsomal metabolism of a novel HIV protease inhibitor by ritonavir: A positive drug-drug interaction. Drug Metab Dispos. 1999 Aug;27(8):902-8. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 947.0±65.0 °C at 760 mmHg |
| Melting Point | 120-122°C |
| Molecular Formula | C37H48N6O5S2 |
| Molecular Weight | 720.944 |
| Flash Point | 526.6±34.3 °C |
| Exact Mass | 720.312744 |
| PSA | 202.26000 |
| LogP | 5.28 |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.600 |
| InChIKey | NCDNCNXCDXHOMX-XGKFQTDJSA-N |
| SMILES | CC(C)c1nc(CN(C)C(=O)NC(C(=O)NC(Cc2ccccc2)CC(O)C(Cc2ccccc2)NC(=O)OCc2cncs2)C(C)C)cs1 |
| Storage condition | -20°C Freezer |
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 + H312 + H332 |
| Precautionary Statements | P261-P280-P301 + P312 + P330 |
| Hazard Codes | Xi |
| Risk Phrases | R36/38:Irritating to eyes and skin . |
| Safety Phrases | 26-37/39 |
| RIDADR | NONH for all modes of transport |
| RTECS | XA5310000 |
| HS Code | 2942000000 |
Customs
| HS Code | 2942000000 |
|---|
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Synonyms
| [5S-(5R*,8R*,10R*,11R*)]-10-Hydroxy-2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-4-thiazolyl]-3,6-dioxo-8,11-bis(phenylmethyl)-2,4,7,12-tetraazatridecan-13-oic acid 5-thiazolylmethyl ester |
| Norvir |
| Ritonavir |
| EINECS 208-127-9 |
| N-[(2S,4S,5S)-4-Hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl]-N-{[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}-L-valinamide |
| Ritonavi |
| Carbamic acid, N-[(1S,2S,4S)-2-hydroxy-4-[[(2S)-3-methyl-2-[[[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]amino]-1-oxobutyl]amino]-5-phenyl-1-(phenylmethyl)pentyl]-, 5-thiazolylmethyl ester |
| ABT-538 |
| (1E,2S)-N-[(2S,4S,5S)-4-Hydroxy-5-{(E)-[hydroxy(1,3-thiazol-5-ylmethoxy)methylene]amino}-1,6-diphenyl-2-hexanyl]-2-[(E)-(hydroxy{[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino}methylene)amino]-3-methylbutanimidic acid |
| 1,3-Thiazol-5-ylmethyl-[(1S,2S,4S)-1-benzyl-2-hydroxy-4-({(2S)-3-methyl-2-[(methyl{[2-(1-methylethyl)-1,3-thiazol-4-yl]methyl}carbamoyl)amino]butanoyl}amino)-5-phenylpentyl]carbamat |
| N-[(1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl]-N-(methyl{[2-(1-methylethyl)-1,3-thiazol-4-yl]methyl}carbamoyl)-L-valinamide |
| [(1S,2S,4S)-1-benzyl-2-hydroxy-4-({(2S)-3-méthyl-2-[(méthyl{[2-(1-méthyléthyl)-1,3-thiazol-4-yl]méthyl}carbamoyl)amino]butanoyl}amino)-5-phénylpentyl]carbamate de 1,3-thiazol-5-ylméthyle |
| Butanimidic acid, N-[(1S,3S,4S)-3-hydroxy-4-[[(1E)-hydroxy(5-thiazolylmethoxy)methylene]amino]-5-phenyl-1-(phenylmethyl)pentyl]-2-[[(1E)-hydroxy[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]methylene]amino]-3-methyl-, (1E,2S)- |
| N-[(2S,4S,5S)-4-Hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}-2-hexanyl]-N-{[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}-L-valinamide |
| carbamic acid, [(1S,2S,4S)-2-hydroxy-4-[[(2S)-3-methyl-2-[[[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]amino]-1-oxobutyl]amino]-5-phenyl-1-(phenylmethyl)pentyl]-, 5-thiazolylmethyl es |
| N-[(2S,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl]-N2-(methyl{[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl}carbamoyl)-L-valinamide |
| Liponavir Core |
| 1,3-thiazol-5-ylmethyl [(1S,2S,4S)-1-benzyl-2-hydroxy-4-({(2S)-3-methyl-2-[(methyl{[2-(1-methylethyl)-1,3-thiazol-4-yl]methyl}carbamoyl)amino]butanoyl}amino)-5-phenylpentyl]carbamate |
| A-84538 ABT-538 Abbott 84538 |
| Norvi |
| (2S,3S,5S)-5-[N-[N-[[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]valinyl]amino]-2-[N-[(5-thiazolyl)methoxycarbonyl]amino]-1,6-diphenyl-3-hydroxyhexane |
| RITONA |
| MFCD04115732 |
| carbamic acid, [(1S,2S,4S)-2-hydroxy-4-[[(2S)-3-methyl-2-[[[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]amino]-1-oxobutyl]amino]-5-phenyl-1-(phenylmethyl)pentyl]-, 5-thiazolylmethyl ester |
