Ritonavir

drug
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Also known as A-84538ABBOTT-84538ABT-538EmpetusNorvirNSC-693184RitomuneRitonavir component of kaletraRitonavir component of paxlovidRitonavir component of technivieRitonavir component of viekiraxRitonavir component of xiannuoxinRitonavir mylanRitonavir related compounds mixtureRitonavirumRitovirViekiraxViritonRitomavir

Summary

Ritonavir (CHEMBL163) is an approved small-molecule antiviral drug (ATC J05AE03) targeting CYP3A4, CYP3A5, and UGT1A1; indicated across 38 conditions including chronic hepatitis c virus infection and hiv infectious disease.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: J05AE03
  • Targets: 6 (CYP3A4, CYP3A5, UGT1A1…)
  • Indications: 38 conditions
  • Clinical trials: 593
  • Chemistry: 720.9 Da · C37H48N6O5S2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL163
NameRitonavir
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID392622
ChEBICHEBI:45409
ATCJ05AE03
Molecular formulaC37H48N6O5S2
Molecular weight720.9
InChIKeyNCDNCNXCDXHOMX-XGKFQTDJSA-N

SMILES: CC(C)C1=NC(=CS1)CN(C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC2=CC=CC=C2)C[C@@H]([C@H](CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)O

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

ChEBI definition: An L-valine derivative that is L-valinamide in which α-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.

Pharmacological roles (ChEBI): antiviral drug, HIV protease inhibitor.

Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.

Also known as: A-84538, ABBOTT-84538, ABT-538, Empetus, Norvir, NSC-693184, Ritomune, Ritonavir, Ritonavir component of kaletra, Ritonavir component of paxlovid, Ritonavir component of technivie, Ritonavir component of viekirax

Patent coverage: 14,327 distinct patent families (53,773 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CYP3A4CYP3A4Inhibition70%P08684
CYP3A5CYP3A5Inhibition6.920.2%P20815
UGT1A1UDP glucuronosyltransferase family 1 member A1Inhibition5.770%P22309
TAS2R1TAS2R1Agonist0%Q9NYW7
TAS2R8TAS2R8Agonist0%Q9NYW2
TAS2R14TAS2R14Agonist0.1%Q9NYV8

Broader ChEMBL bioactivity targets: 54 (assay-derived). Sample: UDP-glucuronosyltransferase 1A1, Microtubule-associated protein tau, Nuclear receptor ROR-gamma, Ferritin light chain, Solute carrier organic anion transporter family member 1B1, Solute carrier organic anion transporter family member 1B3, Solute carrier family 22 member 2, Solute carrier organic anion transporter family member 2B1, Multidrug and toxin extrusion protein 1, Multidrug and toxin extrusion protein 2.

Bioactivity

ChEMBL activities: 60 potent at pChembl ≥ 5 of 101 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
CYP3A47.89Ki13nMCHEMBL_ACT_25708379
CYP2C97.8IC5016nMCHEMBL_ACT_7809133
CYP3A47.8IC5016nMCHEMBL_ACT_7809139
CYP3A47.72Ki19nMCHEMBL_ACT_25708373
CYP3A47.52IC5030nMCHEMBL_ACT_1167663
CYP3A47.3IC5050nMCHEMBL_ACT_3230667
TBXAS17.12IC5076nMCHEMBL_ACT_7813336
SLC47A17.1IC5080nMCHEMBL_ACT_12636136
CYP3A47IC50100nMCHEMBL_ACT_10926484
CYP3A47Ki100nMCHEMBL_ACT_6075106
CYP3A46.96IC50110nMCHEMBL_ACT_13913757
CYP3A56.92Ki120nMCHEMBL_ACT_6075240
CYP3A46.89IC50130nMCHEMBL_ACT_20657649
CYP3A46.85IC50140nMCHEMBL_ACT_25708382
CYP3A46.77Ki170nMCHEMBL_ACT_12163653
CYP3A46.6IC50250nMCHEMBL_ACT_598943
CYP3A46.26IC50550nMCHEMBL_ACT_12719306
SLCO1B16.16IC50700nMCHEMBL_ACT_15448329
TACR26.06Ki874nMCHEMBL_ACT_7813333
SLCO1B16IC501000nMCHEMBL_ACT_15448319
CYP3A45.96IC501100nMCHEMBL_ACT_25708381
TACR15.94AC501144nMCHEMBL_ACT_25128730
SLCO1B15.89Ki1300nMCHEMBL_ACT_12088873
SLCO1B15.89IC501300nMCHEMBL_ACT_12088874
NR1I25.85AC501400nMCHEMBL_ACT_25188117
ABCB15.82IC501500nMCHEMBL_ACT_1167666
UGT1A15.77IC501700nMCHEMBL_ACT_15454222
P152075.77AC501700nMCHEMBL_ACT_25187405
ABCB115.76IC501740nMCHEMBL_ACT_18129083
CYP2B65.7IC502000nMCHEMBL_ACT_3496280

Target pathways

Aggregated over 6 target gene(s): CYP3A4, CYP3A5, UGT1A1, TAS2R1, TAS2R8, TAS2R14.

Top Reactome pathways

20 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction3TAS2R1, TAS2R14, TAS2R8
Signaling by GPCR3TAS2R1, TAS2R14, TAS2R8
GPCR downstream signalling3TAS2R1, TAS2R14, TAS2R8
G alpha (i) signalling events3TAS2R1, TAS2R14, TAS2R8
Class C/3 (Metabotropic glutamate/pheromone receptors)3TAS2R1, TAS2R14, TAS2R8
GPCR ligand binding3TAS2R1, TAS2R14, TAS2R8
Sensory Perception3TAS2R1, TAS2R14, TAS2R8
Sensory perception of taste3TAS2R1, TAS2R14, TAS2R8
Sensory perception of sweet, bitter, and umami (glutamate) taste3TAS2R1, TAS2R14, TAS2R8
Xenobiotics2CYP3A4, CYP3A5
Aflatoxin activation and detoxification2CYP3A4, CYP3A5
Aspirin ADME2CYP3A4, UGT1A1
Glucuronidation1UGT1A1
Heme degradation1UGT1A1
Phase I - Functionalization of compounds1CYP3A4
Defective UGT1A1 causes hyperbilirubinemia1UGT1A1
Biosynthesis of maresin-like SPMs1CYP3A4
Paracetamol ADME1UGT1A1
Atorvastatin ADME1CYP3A4
Prednisone ADME1CYP3A4

Dominant GO biological processes

GO termTargets
lipid metabolic process3
xenobiotic metabolic process3
steroid metabolic process3
estrogen metabolic process3
retinoic acid metabolic process3
detection of chemical stimulus involved in sensory perception of bitter taste3
signal transduction3
G protein-coupled receptor signaling pathway3
sensory perception of taste3
lipid hydroxylation2
alkaloid catabolic process2
xenobiotic catabolic process2
retinol metabolic process2
aflatoxin metabolic process2
oxidative demethylation2

Indications & clinical

Indications

38 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
chronic hepatitis C virus infection4MONDO:0005354EFO:0004220
HIV infectious disease4MONDO:0005109EFO:0000764
hepatitis C virus infection4MONDO:0005231EFO:0003047
viral infectious disease4MONDO:0005108EFO:0000763
hepatitis D virus infection3MONDO:0005789EFO:0007304
AIDS3MONDO:0012268EFO:0000765
Orthocoronavirinae infectious disease3MONDO:0020753MONDO:0100116
severe acute respiratory syndrome3MONDO:0005091EFO:0000694
pneumonia3MONDO:0005249EFO:0003106
influenza3MONDO:0005812EFO:0007328
Kaposi’s sarcoma2MONDO:0005055EFO:0000558
sarcoma2MONDO:0005089EFO:0000691
hepatitis B virus infection2MONDO:0005344EFO:0004197
Mycobacterium avium complex disease2MONDO:0005866EFO:0007386
neoplasm2MONDO:0005070MONDO:0004992
long COVID-192MONDO:0100233MONDO:0100233
pulmonary arterial hypertension1MONDO:0015924EFO:0001361
glioblastoma1MONDO:0018177EFO:0000519
hypertensive disorder1MONDO:0005044EFO:0000537
malaria1MONDO:0005136EFO:0001068
erectile dysfunction1MONDO:0005362EFO:0004234
liver disorder1MONDO:0005154EFO:0001421
acute respiratory distress syndrome1MONDO:0006502EFO:1000637
kidney disorder1MONDO:0005240EFO:0003086
anus neoplasm1MONDO:0003046EFO:0003835
amyotrophic lateral sclerosis1MONDO:0004976MONDO:0004976
tuberculosis1MONDO:0018076MONDO:0018076
prostate adenocarcinoma1MONDO:0005082EFO:0000673
glioma1MONDO:0021042MONDO:0100342

9 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 593.

Phase distribution

PhaseTrials
PHASE1179
PHASE2130
PHASE389
PHASE481
Not specified79
PHASE1/PHASE219
PHASE2/PHASE313
EARLY_PHASE13

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02460133PHASE4ACTIVE_NOT_RECRUITINGUnderstanding HCV Reinfection Rates in an Incarcerated Population After Cure With Interferon Free HCV Treatment
NCT06792214PHASE4RECRUITINGAntiviral Strategies in the Prevention of Long-term Cardiovascular Outcomes Following COVID-19: The paxloviD/Remdesivir Effectiveness For the prEvention of loNg coviD Clinical Trial
NCT00005017PHASE4UNKNOWNEffectiveness and Safety of Epivir/Ziagen/Zerit (3TC/ABC/d4T) Versus Epivir/Ziagen/Sustiva (3TC/ABC/EFV) Versus Epivir/Ziagen/Agenerase/Norvir (3TC/ABC/APV/RTV) in HIV Patients Who Have Never Received Treatment
NCT00055120PHASE4COMPLETEDWhen to Start Anti-HIV Drugs in Patients With Opportunistic Infections
NCT00148785PHASE4COMPLETEDA Pharmacokinetic (PK) Study of a Combination of Indinavir, Ritonavir, and Amprenavir
NCT00162643PHASE4UNKNOWNPI Vs. NNRTI Based Therapy for HIV Advanced Disease
NCT00192660PHASE4COMPLETEDHIV Infection And Metabolic Abnormalities Protocol 1 (HAMA001)
NCT00207142PHASE4COMPLETEDInduction-Maintenance With Atazanavir in HIV Naïve Patients (The INDUMA Study)
NCT00224445PHASE4COMPLETEDBoosted Atazanavir and Truvada Given Once-Daily - BATON Study
NCT00234962PHASE4TERMINATEDStudy of Adherence Effects and Clinical Outcomes of Kaletra Based HIV Antiviral Therapy
NCT00234975PHASE4COMPLETEDSafety of Lopinavir/Ritonavir (Kaletra) in HIV/HCV Co-infected Subjects vs Baseline Liver Biopsy Metavir Score
NCT00281606PHASE4COMPLETEDA Multicenter Study to Assess the Tolerability of Once Daily Lopinavir/Ritonavir (LPV/r) Liquid Versus Capsules
NCT00335270PHASE4COMPLETEDA Randomized, Prospective Study of the Efficacy, Safety and Tolerability of Two Doses of GW433908Ritonavir Given With Abacavir/Lamivudine Fixed Dose Combination
NCT00342355PHASE4COMPLETEDAntiretroviral Therapy for Advanced HIV Disease in South Africa
NCT00355719PHASE4COMPLETEDStudy to Evaluate the Influence of Nevirapine to Atazanavir in Steady State Equilibrium in HIV Patients
NCT00384904PHASE4COMPLETEDDrug Interaction Study of Famotidine and Atazanavir With Ritonavir in HIV-Infected Patients
NCT00386659PHASE4TERMINATEDImmune Reconstitution in naïve HIV Patients With CD4 <100 Cells/mL When Treated With Lopinavir or Efavirenz.
NCT00389402PHASE4COMPLETEDBASIC: Boosted Atazanavir or Saquinavir Induced Lipid Changes
NCT00420355PHASE4TERMINATEDPharmacokinetic Study of Two HIV Protease Inhibitors in Patients
NCT00426296PHASE4UNKNOWNSHARE: Simple HAART With Abacavir, Reyataz, and Epivir
NCT00531557PHASE4COMPLETEDDouble Protease Inhibitor to Darunavir Switch Study
NCT00540137PHASE4COMPLETEDThe CogNaive Study: Assessing Changes in Neurocognitive Function in Treatment Naïve HIV-1 Positive Subjects
NCT00544128PHASE4COMPLETEDComparison of Epzicom and Truvada for the Initial Once Daily HIV Treatment
NCT00552240PHASE4COMPLETEDNevirapine vs. Atazanavir Boosted With Ritonavir on a Background of Truvada in Human Immunodeficiency Virus (HIV) Infected Naive Patients (NEwArT)
NCT00564772PHASE4COMPLETEDRaltegravir Kaletra Pharmacokinetics
NCT00605098PHASE4COMPLETEDPharmacokinetics of the Tablet Formulation of Lopinavir/r as Standard and Increased Dosage During Pregnancy
NCT00630734PHASE4COMPLETEDGenetic Predictors of Variability in the Drug-drug Interaction Between Darunavir/Ritonavir and Pravastatin
NCT00632970PHASE4TERMINATEDRaltegravir vs. Lopinavir/Ritonavir, Both in Combination With Truvada, in HIV+ Treatment Naive Individuals
NCT00648999PHASE4COMPLETEDSafety and Efficacy of Kaletra in ARV Therapy Experienced Patients
NCT00661349PHASE4TERMINATEDTrial About Hepatic Security of Antiretroviral Treatment Based on Kaletra Versus Nevirapine in Co-infected HIV/HCV Patients
NCT00677300PHASE4COMPLETEDRaltegravir And Darunavir Antiretroviral in Antiretroviral Naive Patients
NCT00717067PHASE4COMPLETEDPharmacokinetics, Safety And Toleration Of Maraviroc Administered To Subjects With Various Degrees Of Renal Impaired And Normal Renal Function
NCT00757783PHASE4COMPLETEDChanges in Triglyceride and Other Lipids (Levels of Fats Found in Blood) When Taking Darunavir Compared to Atazanavir in HIV-infected Patients That Have Never Received Treatment
NCT00759070PHASE4UNKNOWNEffects of 2 Initial Standard Antiretroviral Combinations Therapies on Lipid Metabolism
NCT00765154PHASE4TERMINATEDNNRTI/PI Toxicity Switch to Darunavir Study
NCT00855413PHASE4TERMINATEDHIV Viremia and Persistence in Acutely HIV-Infected Patients Treated With Darunavir/Ritonavir and Etravirine
NCT00866021PHASE4COMPLETEDTreatment of HIV/HCV Coinfection With Peg-IFN and Ribavirin in Patients Receiving ART Monotherapy With Lopinavir/r
NCT00869960PHASE4COMPLETEDImpact of Menstrual Cycle on Antiretroviral Pharmacokinetics in Healthy Women
NCT00885482PHASE4COMPLETEDAtazanavir and Lamivudine for Treatment Simplification
NCT00994344PHASE4COMPLETEDClinical Study to Evaluate the Efficacy and Safety of Lopinavir/Ritonavir Monotherapy Versus Darunavir/Ritonavir Monotherapies as Simplification Switching Strategies of PI/NNRTI-Triple Therapy Based-Regimens

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 19 clinical and 74 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

658 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
CYCLOSPORINEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5, UGT1A1
DiclofenacChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5, UGT1A1
KETOCONAZOLEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5, UGT1A1
MIDAZOLAMChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5, UGT1A1
ISOPROTERENOLChEMBLPhase 4 (approved)TAS2R1, TAS2R14, TAS2R8
QUERCETINChEMBL + PubChemPhase 3 (approved)CYP3A4, CYP3A5, UGT1A1
ACETAMINOPHENChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
AMIODARONEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
AmitriptylineChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
AmpicillinChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
APREPITANTChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
BUDESONIDEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
CARFILZOMIBChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
CHLORAMPHENICOLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
CHOLECALCIFEROLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
CLOBETASOL PROPIONATEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
CLOZAPINEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
DAPSONEChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
DAUNORUBICINChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
DIETHYLSTILBESTROLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
DOLUTEGRAVIRChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
DoxorubicinChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
ESTRADIOLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
ESTRONEChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
ETHINYL ESTRADIOLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
EZETIMIBEChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
FLUCONAZOLEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
HALOPERIDOLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
HYDRALAZINEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
KETOPROFENChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
LAPATINIBChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
MITOXANTRONEChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
PACLITAXELChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
PazopanibChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
PioglitazoneChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
POSACONAZOLEChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
PROPOFOLChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
QUINIDINEChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
SAQUINAVIRChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
SAXAGLIPTINChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
TacrolimusChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
TELITHROMYCINChEMBL + PubChemPhase 4 (approved)CYP3A4, CYP3A5
TESTOSTERONEChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
TRETINOINChEMBL + PubChemPhase 4 (approved)CYP3A4, UGT1A1
AMPRENAVIRChEMBLPhase 4 (approved)CYP3A4, CYP3A5
CANNABIDIOLChEMBLPhase 4 (approved)CYP3A4, CYP3A5
NELFINAVIRChEMBLPhase 4 (approved)CYP3A4, CYP3A5
VORICONAZOLEChEMBLPhase 4 (approved)CYP3A4, CYP3A5
SEROTONINChEMBL + PubChemPhase 3 (approved)CYP3A4, UGT1A1
RELACORILANTChEMBLPhase 3CYP3A4, CYP3A5
GENISTEINChEMBL + PubChemPhase 2 (approved)CYP3A4, CYP3A5
COFROGLIPTINChEMBLPhase 2CYP3A4, CYP3A5
GLECIRASIBChEMBLPhase 2CYP3A4, CYP3A5
NIFLUMIC ACIDChEMBLPhase 2CYP3A4, UGT1A1
BosentanPubChemApprovedCYP3A4, CYP3A5
CarbamazepinePubChemApprovedCYP3A5, UGT1A1
PhenobarbitalPubChemApprovedCYP3A5, UGT1A1
rifampinPubChemApprovedCYP3A5, UGT1A1
VorapaxarPubChemApprovedCYP3A4, CYP3A5
ATAZANAVIRChEMBL + PubChemPhase 4 (approved)UGT1A1