Ritonavir

Category	HIV Protease
CAS	155213-67-5
Description	Ritonavir is an HIV protease inhibitor. It is often used in a low dose with another protease inhibitor lopinavir. Ritonavir was approved for COVID-19 treatment in combination with Nirmatrelvir.

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Product Information

Synonyms	Norvir; ABT-538; A-84538; 538, ABT; ABT 538; ABT-538; ABT538; Abbott 84538
IUPAC 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
Molecular Weight	720.95
Molecular Formula	C37H48N6O5S2
Canonical SMILES	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
InChI	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)/t28-,31-,32-,33-/m0/s1
InChIKey	NCDNCNXCDXHOMX-XGKFQTDJSA-N
Boiling Point	947.0±65.0 °C at 760 mmHg
Melting Point	120-122°C
Flash Point	526.6°C
Purity	≥98%
Density	1.239 g/cm³
Solubility	In Vitro: DMSO: 25 mg/mL (34.68 mM; Need ultrasonic) H2O: < 0.1 mg/mL (insoluble) In Vivo: 1.Add each solvent one by one: 10% DMSO >> 90% corn oil Solubility: 2.5 mg/mL (3.47 mM); Clear solution; Need warming 2.Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline) Solubility: 2.5 mg/mL (3.47 mM); Suspended solution; Need ultrasonic
Appearance	White Solid
Storage	Store at -20°C
Complexity	1040
Exact Mass	720.31276100
Index Of Refraction	1.600
In Vitro	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). Ritonavir results in an increase in cell viability in uninfected human PBMC cultures. It can also markedly decreases the susceptibility of PBMCs to Apoptosis, 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. 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 inhibits CYP3A (IC50=1.1 and 4.6 μM).
PSA	22.26
Target	HIV Protease; HIV; SARS-CoV, SARS-CoV 3CLpro inhibitor with an IC50 of 1.61 μM; Apoptosis
Vapor Pressure	0.0±0.3 mmHg at 25°C
XLogP3-AA	6