Identification

Name
Ritonavir
Accession Number
DB00503  (APRD00312)
Type
Small Molecule
Groups
Approved, Investigational
Description

Ritonavir is an HIV protease inhibitor that interferes with the reproductive cycle of HIV. Although it was initially developed as an independent antiviral agent, it has been shown to possess advantageous properties in combination regimens with low-dose ritonavir and other protease inhibitors. It is now more commonly used as a booster of other protease inhibitors and is available in both liquid formulation and as capsules.

While ritonavir is not an active antiviral agent against hepatitis C virus (HCV) infection, it is added in combination therapies indicated for treatment of HCV infections as a booster. Ritonavir is a potent CYP3A inhibitor that increases peak and trough plasma drug concentrations of other protease inhibitors such as Paritaprevir and overall drug exposure. American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) guidelines recommend ritonavir-boosted combination therapies as a first-line therapy for HCV Genotype 1a/b and 4 treatment-naïve patients with or without cirrhosis.

Ritonavir is found in a fixed-dose combination product with Ombitasvir, Dasabuvir, and Paritaprevir as the FDA-approved product Viekira Pak. First approved in December 2014, Viekira Pak is indicated for the treatment of HCV genotype 1b without cirrhosis or with compensated cirrhosis, and when combined with Ribavirin for the treatment of HCV genotype 1a without cirrhosis or with compensated cirrhosis.

Ritonavir is also available as a fixed-dose combination product with Ombitasvir and Paritaprevir as the FDA- and Health Canada-approved product Technivie. First approved in July 2015, Technivie is indicated in combination with Ribavirin for the treatment of patients with genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis or with compensated cirrhosis.

In Canada, ritonavir is also available as a fixed-dose combination product with Ombitasvir, Dasabuvir, and Paritaprevir as the Health Canada-approved, commercially available product Holkira Pak. First approved in January 2015, Holkira Pak is indicated for the treatment of HCV genotype 1b with or without cirrhosis, and when combined with Ribavirin for the treatment of HCV genotype 1a with or without cirrhosis. Inclusion of ritonavir can can select for HIV-1 protease inhibitor resistance-associated substitutions. Any HCV/HIV-1 co-infected patients treated with ritonavir-containing combination therapies should also be on a suppressive antiretroviral drug regimen to reduce the risk of HIV-1 protease inhibitor drug resistance.

Structure
Thumb
Synonyms
  • Ritonavir
  • Ritonavirum
External IDs
A-84538 / Abbott 84538 / ABBOTT-84538 / ABT 538 / ABT-538 / NSC-693184
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NorvirSolution80 mgOralAbbvie1996-09-25Not applicableCanada
NorvirTablet, film coated100 mg/1OralAvera McKennan Hospital2016-03-14Not applicableUs
NorvirTablet, film coated100 mg/1OralAbbvie2010-05-06Not applicableUs
NorvirTablet, film coated100 mg/1OralA-S Medication Solutions2010-05-06Not applicableUs
NorvirCapsule100 mgOralAbbvie1996-09-162012-11-08Canada
NorvirPowder100 mg/1OralAbbvie2017-06-07Not applicableUs
NorvirTablet, film coated100 mg/1OralA-S Medication Solutions2010-05-06Not applicableUs
NorvirCapsule100 mg/1OralPhysicians Total Care, Inc.2003-07-142007-12-10Us
NorvirTablet, film coated100 mg/1OralRemedy Repack2015-08-06Not applicableUs
NorvirTablet100 mgOralAbbvie2010-12-17Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RitonavirTablet100 mg/1OralCamber Pharmaceuticals, Inc.2018-09-17Not applicableUs
RitonavirTablet, film coated100 mg/1OralWest-Ward Pharmaceuticals Corp.2018-03-20Not applicableUs
RitonavirTablet100 mg/1OralAmneal Pharmaceuticals LLC2018-09-21Not applicableUs
RitonavirTablet, film coated100 mg/1OralAmerincan Health Packaging2018-05-01Not applicableUs
RitonavirTablet, film coated100 mg/1OralAurobindo Pharma Limited2018-09-17Not applicableUs
RitonavirTablet, film coated100 mg/1OralRemedy Repack2018-03-29Not applicableUs
RitonavirTablet100 mg/1OralREMEDYREPACK INC.2018-10-11Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Holkira PakRitonavir (50 mg) + Dasabuvir (250 mg) + Ombitasvir (12.5 mg) + Paritaprevir (75 mg)Kit; TabletOralAbbvie2015-01-06Not applicableCanada
KaletraRitonavir (50 mg) + Lopinavir (200 mg)TabletOralAbbvie2006-09-08Not applicableCanada
KaletraRitonavir (20 mg/1mL) + Lopinavir (80 mg/1mL)SolutionOralAbbvie2010-06-18Not applicableUs
KaletraRitonavir (50 mg/1) + Lopinavir (200 mg/1)Tablet, film coatedOralRemedy Repack2008-09-052017-01-16Us
KaletraRitonavir (50 mg/1) + Lopinavir (200 mg/1)Tablet, film coatedOralCardinal Health2010-06-18Not applicableUs
KaletraRitonavir (50 mg/1) + Lopinavir (200 mg/1)Tablet, film coatedOralRemedy Repack2016-12-29Not applicableUs
KaletraRitonavir (50 mg/1) + Lopinavir (200 mg/1)Tablet, film coatedOralHHS/Program Support Center/Supply Service Center2010-06-18Not applicableUs
KaletraRitonavir (33.3 mg) + Lopinavir (133.3 mg)CapsuleOralAbbvie2001-03-092012-11-02Canada
KaletraRitonavir (25 mg/1) + Lopinavir (100 mg/1)Tablet, film coatedOralAbbvie2010-06-18Not applicableUs
KaletraRitonavir (50 mg/1) + Lopinavir (200 mg/1)Tablet, film coatedOralDispensing Solutions, Inc.2010-06-18Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
KaletraRitonavir (50 mg/1) + Lopinavir (200 mg/1)TabletOralRemedy Repack2010-09-272013-05-16Us
International/Other Brands
Busvir (Conifarma) / Empetus (Emcure) / Normune (Grey Inversiones) / Norvir
Categories
UNII
O3J8G9O825
CAS number
155213-67-5
Weight
Average: 720.944
Monoisotopic: 720.312760056
Chemical Formula
C37H48N6O5S2
InChI Key
NCDNCNXCDXHOMX-XGKFQTDJSA-N
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
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}butanamido]-1,6-diphenylhexan-2-yl]carbamate
SMILES
CC(C)[C@H](NC(=O)N(C)CC1=CSC(=N1)C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)OCC1=CN=CS1)CC1=CC=CC=C1

Pharmacology

Indication

Indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection.

Associated Conditions
Pharmacodynamics

Ritonavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Ritonavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. Modern protease inhibitors require the use of low-dose ritonavir to boost pharmacokinetic exposure through inhibition of metabolism via the cytochrome P450 3A4 enzyme pathway.

Mechanism of action

Ritonavic inhibits the HIV viral proteinase enzyme that normally cleaves the structural and replicative proteins that arise from major HIV genes, such as gag and pol. Gag encodes proteins involved in the core and the nucleocapsid, while pol encodes the the HIV reverse transcriptase, ribonuclease H, integrase, and protease [1]. The pol-encoded proteins are initially translated in the form of a larger precursoe polypeptide, gag-pol, and needs to be cleaved by HIV protease to form other complement proteins [1]. Ritonavir prevents the cleavage of the gag-pol polyprotein, which results in noninfectious, immature viral particles. Ritonavir is a potent inhibitor of cytochrome P450 CYP3A4 isoenzyme present both in the intestinal tract and liver [1]. It is a type II ligand that perfectly fits into the CYP3A4 active site cavity and irreversibly binds to the heme iron via the thiazole nitrogen, which decreases the redox potential of the protein and precludes its reduction with the redox partner, cytochrome P450 reductase [3]. Ritonavir may also play a role in limiting cellular transport and efflux of other protease inhibitors via the P-glycoprotein and MRP efflux channels [1].

TargetActionsOrganism
AHuman immunodeficiency virus type 1 protease
inhibitor
Human immunodeficiency virus 1
UNuclear receptor subfamily 1 group I member 2
activator
Human
Absorption

The absolute bioavailability of ritonavir has not been determined.

Volume of distribution
Not Available
Protein binding

Highly protein-bound, 98-99% [1].

Metabolism

Ritonavir circulates in the plasma predominantly as unchanged drug. Five metabolites have been identified. The isopropylthiazole oxidation metabolite (M-2) is the major metabolite in low plasma concentrations and retains similar antiviral activity to unchanged ritonavir. The cytochrome P450 enzymes CYP3A and CYP2D6 are primarily involved in the metabolism of ritonavir.

Route of elimination

The metabolites are detected in the urine and feces.

Half life

3-5 hours [1].

Clearance
Not Available
Toxicity

Human experience of acute overdose with ritonavir is limited. One patient in clinical trials took ritonavir 1500 mg/day for two days. The patient reported paresthesias which resolved after the dose was decreased. A post-marketing case of renal failure with eosinophilia has been reported with ritonavir overdose. The approximate lethal dose was found to be greater than 20 times the related human dose in rats and 10 times the related human dose in mice. Oral LD value in rats is >2500 mg/kg. Adverse effects of ritonavir may arise from drug-drug interactions. Other effects include hepatotoxicity, pancreatitis, and allergic reactions/hypersensitivity.

Affected organisms
  • Human Immunodeficiency Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ritonavir.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Ritonavir.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Ritonavir.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Ritonavir.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Ritonavir.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Ritonavir.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with Ritonavir.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Ritonavir.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Ritonavir.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Ritonavir.
Food Interactions
  • Avoid St.John's Wort.
  • Take with food.

References

Synthesis Reference
US5484801
General References
  1. Hull MW, Montaner JS: Ritonavir-boosted protease inhibitors in HIV therapy. Ann Med. 2011 Aug;43(5):375-88. doi: 10.3109/07853890.2011.572905. Epub 2011 Apr 18. [PubMed:21501034]
  2. Myers RP, Shah H, Burak KW, Cooper C, Feld JJ: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver. Can J Gastroenterol Hepatol. 2015 Jan-Feb;29(1):19-34. Epub 2015 Jan 13. [PubMed:25585348]
  3. Sevrioukova IF, Poulos TL: Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir. Proc Natl Acad Sci U S A. 2010 Oct 26;107(43):18422-7. doi: 10.1073/pnas.1010693107. Epub 2010 Oct 11. [PubMed:20937904]
  4. Rock BM, Hengel SM, Rock DA, Wienkers LC, Kunze KL: Characterization of ritonavir-mediated inactivation of cytochrome P450 3A4. Mol Pharmacol. 2014 Dec;86(6):665-74. doi: 10.1124/mol.114.094862. Epub 2014 Oct 1. [PubMed:25274602]
  5. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
External Links
Human Metabolome Database
HMDB0014646
KEGG Drug
D00427
KEGG Compound
C07240
PubChem Compound
392622
PubChem Substance
46505050
ChemSpider
347980
BindingDB
520
ChEBI
45409
ChEMBL
CHEMBL163
Therapeutic Targets Database
DAP000169
PharmGKB
PA451260
HET
RIT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ritonavir
ATC Codes
J05AX67 — Ombitasvir, paritaprevir and ritonavirJ05AR10 — Lopinavir and ritonavirJ05AE03 — RitonavirJ05AX66 — Dasabuvir, ombitasvir, paritaprevir and ritonavir
AHFS Codes
  • 08:18.08.08 — HIV Protease Inhibitors
PDB Entries
1hxw / 1n49 / 1rl8 / 1sh9 / 2b60 / 3ndw / 3ndx / 3nxu / 3prs / 3q70
show 6 more
FDA label
Download (960 KB)
MSDS
Download (26.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedOtherHealthy Volunteers1
0CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
0Unknown StatusTreatmentPulmonary Arterial Hypertension (PAH)1
1Active Not RecruitingOtherHealthy Volunteers1
1Active Not RecruitingTreatmentAnemias / Chronic Lymphocytic Leukemia (CLL) - Refractory / Chronic, recurrent Lymphocytic Leukemia / Fevers / Lymphadenopathy / Lymphocytosis / Night Sweats / Obese experiencing rapid weight loss / Recurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma / Splenomegaly / Thrombocytopenias / Tiredness1
1Active Not RecruitingTreatmentGlioblastomas1
1Active Not RecruitingTreatmentNeoplasms Metastasis1
1CompletedNot AvailableDrug Abuse / Human Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailableHealthy Volunteers13
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Isavuconazole / Pharmacokinetics of Lopinavir/Ritonavir1
1CompletedNot AvailableHepatitis C Viral Infection1
1CompletedNot AvailableHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections4
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceHealthy Volunteers / Human Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)2
1CompletedBasic SciencePharmacokinetics1
1CompletedDiagnosticCancer, Breast1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
1CompletedOtherDrug-induced QT Interval Prolongation / Pharmacodynamics / Pharmacokinetics1
1CompletedOtherFenofibrate / Glucuronosyltransferase / Human Immunodeficiency Virus (HIV) / Hypertriglyceridemias / Protease Inhibitors1
1CompletedOtherHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedPreventionAsthma Bronchial / Human Immunodeficiency Virus (HIV)1
1CompletedSupportive CareHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
1CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentAntivirals/HIV1
1CompletedTreatmentCardiovascular Disease (CVD) / High Blood Pressure (Hypertension) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection4
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentErectile Dysfunction (ED)1
1CompletedTreatmentHCV Infections3
1CompletedTreatmentHCV / Healthy Volunteers1
1CompletedTreatmentHealthy Volunteers48
1CompletedTreatmentHealthy Volunteers / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHepatic Insufficiency2
1CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) / Telaprevir1
1CompletedTreatmentHepatitis C Viral Infection / Thrombocytopenias1
1CompletedTreatmentHepatitis C Virus (HCV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)3
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections26
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Fungal1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Opioid Dependency1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Pregnancy1
1CompletedTreatmentInfections, Human Immunodeficiency Virus and Herpesviridae1
1CompletedTreatmentInsulin Resistance1
1CompletedTreatmentPlasmodium Infections1
1CompletedTreatmentTuberculosis1
1Enrolling by InvitationTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1RecruitingTreatmentHepatitis B Chronic Infection1
1RecruitingTreatmentProstatic Neoplasms1
1SuspendedTreatmentHuman Immunodeficiency Virus (HIV)1
1TerminatedOtherHealthy Volunteers1
1TerminatedTreatmentHealthy Volunteers2
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis1
1Unknown StatusNot AvailableHuman Immunodeficiency Virus (HIV) / Hyperlipidemias1
1Unknown StatusBasic ScienceAtazanavir1
1WithdrawnBasic SciencePulmonary Arterial Hypertension (PAH)1
1, 2CompletedTreatmentHepatitis C Viral Infection1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections8
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
1, 2CompletedTreatmentInfection, Human Immunodeficiency Virus I / Pf Subclinical Parasitemia1
1, 2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2WithdrawnNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections4
2Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedNot AvailableHealthy Volunteers1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentChronic Delta Hepatitis1
2CompletedTreatmentChronic Hepatitis C Virus1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection14
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / HCV / Hepatitis C Genotype 1 / Hepatitis C Viral Infection2
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C (HCV) / Hepatitis C Genotype 11
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C (HCV) / Hepatitis C Genotype 1a1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C Viral Infection / Hepatitis C Virus (HCV)1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C Virus (HCV)1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Compensated liver disease / Hepatitis C Virus (HCV)1
2CompletedTreatmentChronic Hepatitis D Infection2
2CompletedTreatmentFibrosis, Liver / Hepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentHepatitis C Virus (HCV)1
2CompletedTreatmentHepatitis D1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV)2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections42
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I3
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
2CompletedTreatmentInfection, Human Immunodeficiency Virus I8
2CompletedTreatmentSarcomas1
2Not Yet RecruitingTreatmentChronic Delta Hepatitis1
2RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
2RecruitingTreatmentContraception / HIV-1-infection1
2RecruitingTreatmentHIV-1-infection1
2RecruitingTreatmentHepatitis B Chronic Infection1
2RecruitingTreatmentHepatitis D / Liver Diseases1
2RecruitingTreatmentMaternal-fetal Infection Transmission1
2TerminatedTreatmentAnaplastic Astrocytoma (AA) / Anaplastic Ependymoma / Anaplastic Oligodendroglioma (AO) / Brain Stem Gliomas / Giant Cell Glioblastoma / Glioblastomas / Gliosarcoma / Mixed Gliomas / Neoplasms, Brain1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
2TerminatedTreatmentInfection, Human Immunodeficiency Virus I1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Viral Hepatitis B1
2Unknown StatusTreatmentCancers1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections5
2WithdrawnTreatmentChronic Hepatitis C Virus (HCV) Infection1
2WithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3Active Not RecruitingTreatmentHCV1
2, 3CompletedTreatmentAcute HIV Infection1
2, 3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Compensated Cirrhosis and Non-cirrhotics / Hepatitis C Virus Infection / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
2, 3RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / HBV Coinfection / Hepatitis B Reactivation1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Pediatric AIDS1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Pregnancy1
3Active Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentAcute HIV Infection1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I2
3CompletedNot AvailableDirectly Observed Therapy / Human Immunodeficiency Virus (HIV) Infections1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
3CompletedOtherHepatitis C Viral Infection1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections4
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
3CompletedPreventionMumps / Rubella / Rubeola / Varicella1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAcquired Immunodeficiency Syndrome (AIDS) Virus / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentChronic Hepatitis C Virus (HCV Infection Genotype 1)1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection11
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Cirrhosis, Decompensated / Hepatitis C Virus (HCV)1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Compensated liver disease / End-Stage Renal Disease (ESRD) / Hepatitis C Virus (HCV) / Severe Renal Impairment1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C (HCV) / Hepatitis C Genotype 1a1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C Virus (HCV)1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatitis C Virus (HCV) / Liver Cirrhosis1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Compensated liver disease / Hepatitis C Virus (HCV)1
3CompletedTreatmentChronic Hepatitis C Virus / Chronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentChronic Hepatitis C Virus / Hepatitis C Virus (HCV)2
3CompletedTreatmentChronic Kidney Disease (CKD) / Genotype 1a / Genotype 4 / HCV / Hepatitis C Viral Infection / Hepatitis C Virus (HCV) / IFN / PegIFN1
3CompletedTreatmentHIV-Infected Children1
3CompletedTreatmentHepatitis C Infection / Hepatitis C Virus (HCV)1
3CompletedTreatmentHepatitis C Virus (HCV)2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections37
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Infectious1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I3
3RecruitingTreatmentHepatitis C, Acute1
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
3TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
3TerminatedTreatmentInfection, Human Immunodeficiency Virus I / Treatment Resistant Disorders / Viral sepsis1
3Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3WithdrawnPreventionBreastfeeding / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
3WithdrawnTreatmentChronic Hepatitis C Virus1
3WithdrawnTreatmentHuman Immunodeficiency Virus (HIV)1
4Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection2
4Active Not RecruitingTreatmentChronic Infection With HIV1
4Active Not RecruitingTreatmentHepatitis C Virus (HCV)1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHealthy Volunteers3
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV)3
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Proteinuria1
4CompletedBasic ScienceCardiovascular Disease (CVD) / Dyslipidemias / Glucose Metabolism Disorders / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases1
4CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticAIDS-Related Opportunistic Infections / Human Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedOtherHuman Immunodeficiency Virus (HIV)1
4CompletedPreventionHuman Immunodeficiency Virus (HIV)1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Tuberculosis1
4CompletedTreatmentCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHIV, Combination Therapy1
4CompletedTreatmentHIV, Pediatric1
4CompletedTreatmentHIV/AIDS Treatment / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHIV/HCV Co-infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHealthy Volunteers2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)11
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections23
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Hyperlipidemias1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Hypertriglyceridemias1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Mitochondrial Toxicity1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)4
4CompletedTreatmentInfection, Human Immunodeficiency Virus I2
4Not Yet RecruitingTreatmentAntiviral Drug Adverse Reaction1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Tuberculosis1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentEnd-Stage Renal Disease (ESRD) / HCV Coinfection / Hepatis C and End-stage Kidney Disease1
4RecruitingTreatmentHCV Coinfection1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Osteopenia1
4TerminatedNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
4TerminatedPreventionHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentAIDS-Related Dementia Complex1
4TerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4TerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections8
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mitochondrial Dysfunction1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusPreventionHIV-Associated Lipodystrophy Syndrome / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / HIV-1 Adults Patients / Triple Class Failure1
4Unknown StatusTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections5
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4WithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
Not AvailableApproved for MarketingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableChronic Hepatitis C Virus (HCV) Infection / Liver Cirrhosis1
Not AvailableCompletedNot AvailableHealthy Volunteers3
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV)4
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections9
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I3
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedOtherEndothelial Dysfunction1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Pregnancy1
Not AvailableCompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections26
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Wasting Disease1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
Not AvailableCompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
Not AvailableRecruitingNot AvailableMinor Patient Treated by One or More Antiretroviral and for Which a Blood Test Has Been Performed1
Not AvailableRecruitingTreatmentHCV Coinfection1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableUnknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV)1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnNot AvailableHIV-infected Patients1
Not AvailableWithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentLymphoma, Hodgkins / Stage I Adult Hodgkin Lymphoma / Stage II Adult Hodgkin Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage IV Adult Hodgkin Lymphoma1

Pharmacoeconomics

Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Abbott laboratories
Packagers
  • Abbott Laboratories Ltd.
  • Atlantic Biologicals Corporation
  • Cardinal Health
  • Catalent Pharma Solutions
  • DHHS Program Support Center Supply Service Center
  • Dispensing Solutions
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Southwood Pharmaceuticals
Dosage forms
FormRouteStrength
Kit; tabletOral
CapsuleOral
Capsule, liquid filledOral
SolutionOral
Tablet, film coatedOral
CapsuleOral100 mg/1
CapsuleOral100 mg
PowderOral100 mg/1
SolutionOral80 mg
SolutionOral80 mg/1mL
TabletOral100 mg
Tablet, film coatedOral100 mg/1
TabletOral100 mg/1
Kit
TabletOral
Prices
Unit descriptionCostUnit
Norvir 100 mg softgel cap10.29USD softgel capsule
Norvir 100 mg tablet10.29USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5541206No1993-07-302013-07-30Us
CA2178632No2006-04-112015-01-03Canada
CA2135890No1996-08-272013-12-16Canada
US6703403Yes1996-12-262016-12-26Us
US6037157Yes1996-12-262016-12-26Us
US6232333Yes1998-05-072018-05-07Us
US7432294Yes2000-11-222020-11-22Us
US7141593Yes2000-11-222020-11-22Us
US5914332Yes1996-06-132016-06-13Us
US6284767Yes1996-08-152016-08-15Us
US7364752Yes2001-05-102021-05-10Us
US8309613Yes2005-06-242025-06-24Us
US8377952Yes2008-04-222028-04-22Us
US8691878Yes2005-02-252025-02-25Us
US8025899Yes2008-06-142028-06-14Us
US7148359Yes2000-01-192020-01-19Us
US8470347Yes2007-03-172027-03-17Us
US8268349Yes2005-02-252025-02-25Us
US8399015Yes2005-02-252025-02-25Us
US6458818Yes1998-05-072018-05-07Us
US6521651Yes1998-05-072018-05-07Us
US6911214Yes2002-05-282022-05-28Us
US8501219No2001-11-282021-11-28Us
US9139536No2008-11-092028-11-09Us
US8685984No2012-09-042032-09-04Us
US8466159No2012-09-042032-09-04Us
US8642538No2009-09-102029-09-10Us
US8501238No2008-09-172028-09-17Us
US8680106No2012-09-042032-09-04Us
US8492386No2012-09-042032-09-04Us
US8188104No2009-05-172029-05-17Us
US9006387No2010-06-102030-06-10Us
US9044480No2011-04-102031-04-10Us
US8686026No2011-06-092031-06-09Us
US8420596Yes2011-10-102031-10-10Us
US8691938No2012-04-132032-04-13Us
US9629841No2013-10-182033-10-18Us
US9333204No2015-01-022035-01-02Us
US9744170No2015-01-022035-01-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityPractically insolubleMSDS
logP3.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00126 mg/mLALOGPS
logP4.24ALOGPS
logP5.22ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)13.68ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.78 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity194.59 m3·mol-1ChemAxon
Polarizability77.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7195
Blood Brain Barrier-0.9717
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8307
P-glycoprotein inhibitor IInhibitor0.8317
P-glycoprotein inhibitor IINon-inhibitor0.8753
Renal organic cation transporterNon-inhibitor0.9009
CYP450 2C9 substrateNon-substrate0.694
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5973
CYP450 1A2 substrateNon-inhibitor0.67
CYP450 2C9 inhibitorNon-inhibitor0.6229
CYP450 2D6 inhibitorNon-inhibitor0.8424
CYP450 2C19 inhibitorInhibitor0.5399
CYP450 3A4 inhibitorInhibitor0.5843
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5946
Ames testNon AMES toxic0.7378
CarcinogenicityNon-carcinogens0.8664
BiodegradationNot ready biodegradable0.9633
Rat acute toxicity2.6154 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9774
hERG inhibition (predictor II)Inhibitor0.8457
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-carbamoyl-alpha amino acids and derivatives
Alternative Parents
Valine and derivatives / Alpha amino acid amides / Amphetamines and derivatives / 2,4-disubstituted thiazoles / N-acyl amines / Carbamate esters / Heteroaromatic compounds / Secondary carboxylic acid amides / Ureas / Secondary alcohols
show 6 more
Substituents
Valine or derivatives / N-carbamoyl-alpha-amino acid or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / 2,4-disubstituted 1,3-thiazole / Monocyclic benzene moiety / Fatty amide / Fatty acyl / N-acyl-amine / Benzenoid
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
carbamate ester, ureas, 1,3-thiazole, carboxamide, L-valine derivative (CHEBI:45409)

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Aspartic-type endopeptidase activity
Specific Function
Not Available
Gene Name
pol
Uniprot ID
Q72874
Uniprot Name
Pol polyprotein
Molecular Weight
10778.7 Da
References
  1. Garriga C, Perez-Elias MJ, Delgado R, Ruiz L, Najera R, Pumarola T, Alonso-Socas Mdel M, Garcia-Bujalance S, Menendez-Arias L: Mutational patterns and correlated amino acid substitutions in the HIV-1 protease after virological failure to nelfinavir- and lopinavir/ritonavir-based treatments. J Med Virol. 2007 Nov;79(11):1617-28. [PubMed:17854027]
  2. Das A, Rao DR, Hosur MV: X-ray structure of HIV-1 protease tethered dimer complexed to ritonavir. Protein Pept Lett. 2007;14(6):565-8. [PubMed:17627597]
  3. Wittayanarakul K, Hannongbua S, Feig M: Accurate prediction of protonation state as a prerequisite for reliable MM-PB(GB)SA binding free energy calculations of HIV-1 protease inhibitors. J Comput Chem. 2008 Apr 15;29(5):673-85. [PubMed:17849388]
  4. Markowitz M, Saag M, Powderly WG, Hurley AM, Hsu A, Valdes JM, Henry D, Sattler F, La Marca A, Leonard JM, et al.: A preliminary study of ritonavir, an inhibitor of HIV-1 protease, to treat HIV-1 infection. N Engl J Med. 1995 Dec 7;333(23):1534-9. [PubMed:7477168]
  5. Hoetelmans RM, Meenhorst PL, Mulder JW, Burger DM, Koks CH, Beijnen JH: Clinical pharmacology of HIV protease inhibitors: focus on saquinavir, indinavir, and ritonavir. Pharm World Sci. 1997 Aug;19(4):159-75. [PubMed:9297727]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [PubMed:14977870]
  2. Smith CM, Faucette SR, Wang H, LeCluyse EL: Modulation of UDP-glucuronosyltransferase 1A1 in primary human hepatocytes by prototypical inducers. J Biochem Mol Toxicol. 2005;19(2):96-108. [PubMed:15849716]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Duan SX, Fogelman SM, Daily JP, Harmatz JS, Shader RI: Protease inhibitors as inhibitors of human cytochromes P450: high risk associated with ritonavir. J Clin Pharmacol. 1998 Feb;38(2):106-11. [PubMed:9549640]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Foisy MM, Yakiwchuk EM, Hughes CA: Induction effects of ritonavir: implications for drug interactions. Ann Pharmacother. 2008 Jul;42(7):1048-59. doi: 10.1345/aph.1K615. Epub 2008 Jun 24. [PubMed:18577765]
  2. Yeh RF, Gaver VE, Patterson KB, Rezk NL, Baxter-Meheux F, Blake MJ, Eron JJ Jr, Klein CE, Rublein JC, Kashuba AD: Lopinavir/ritonavir induces the hepatic activity of cytochrome P450 enzymes CYP2C9, CYP2C19, and CYP1A2 but inhibits the hepatic and intestinal activity of CYP3A as measured by a phenotyping drug cocktail in healthy volunteers. J Acquir Immune Defic Syndr. 2006 May;42(1):52-60. doi: 10.1097/01.qai.0000219774.20174.64. [PubMed:16639344]
  3. Ritonavir FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Hughes CA, Freitas A, Miedzinski LJ: Interaction between lopinavir/ritonavir and warfarin. CMAJ. 2007 Aug 14;177(4):357-9. doi: 10.1503/cmaj.061284. [PubMed:17698824]
  3. Tseng A, Hughes CA, Wu J, Seet J, Phillips EJ: Cobicistat Versus Ritonavir: Similar Pharmacokinetic Enhancers But Some Important Differences. Ann Pharmacother. 2017 Nov;51(11):1008-1022. doi: 10.1177/1060028017717018. Epub 2017 Jun 19. [PubMed:28627229]
  4. von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Duan SX, Fogelman SM, Daily JP, Harmatz JS, Shader RI: Protease inhibitors as inhibitors of human cytochromes P450: high risk associated with ritonavir. J Clin Pharmacol. 1998 Feb;38(2):106-11. [PubMed:9549640]
Details
4. Cytochrome P450 2B6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Tanabe M, Hashimoto M, Ono H: Imidazoline I(1) receptor-mediated reduction of muscle rigidity in the reserpine-treated murine model of Parkinson's disease. Eur J Pharmacol. 2008 Jul 28;589(1-3):102-5. doi: 10.1016/j.ejphar.2008.06.013. Epub 2008 Jun 7. [PubMed:18602099]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
  4. Fahmi OA, Shebley M, Palamanda J, Sinz MW, Ramsden D, Einolf HJ, Chen L, Wang H: Evaluation of CYP2B6 Induction and Prediction of Clinical Drug-Drug Interactions: Considerations from the IQ Consortium Induction Working Group-An Industry Perspective. Drug Metab Dispos. 2016 Oct;44(10):1720-30. doi: 10.1124/dmd.116.071076. Epub 2016 Jul 15. [PubMed:27422672]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Vourvahis M, Kashuba AD: Mechanisms of pharmacokinetic and pharmacodynamic drug interactions associated with ritonavir-enhanced tipranavir. Pharmacotherapy. 2007 Jun;27(6):888-909. doi: 10.1592/phco.27.6.888. [PubMed:17542771]
  3. Eagling VA, Back DJ, Barry MG: Differential inhibition of cytochrome P450 isoforms by the protease inhibitors, ritonavir, saquinavir and indinavir. Br J Clin Pharmacol. 1997 Aug;44(2):190-4. [PubMed:9278209]
  4. FDA, ritonavir [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. List of drugs that may have potential CYP2E1 interactions [File]
Details
8. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Drug Interactions & Labeling - FDA [Link]
  2. Flockhart Table - Indiana University [Link]
Details
9. Cytochrome P450 3A5
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Flockhart Table - Indiana University [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inhibitor
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table - Indiana University [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Interactions [Link]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [PubMed:15814459]
  2. Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [PubMed:16336266]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Perloff MD, Von Moltke LL, Marchand JE, Greenblatt DJ: Ritonavir induces P-glycoprotein expression, multidrug resistance-associated protein (MRP1) expression, and drug transporter-mediated activity in a human intestinal cell line. J Pharm Sci. 2001 Nov;90(11):1829-37. [PubMed:11745741]
  2. Choo EF, Leake B, Wandel C, Imamura H, Wood AJ, Wilkinson GR, Kim RB: Pharmacological inhibition of P-glycoprotein transport enhances the distribution of HIV-1 protease inhibitors into brain and testes. Drug Metab Dispos. 2000 Jun;28(6):655-60. [PubMed:10820137]
  3. Kumar S, Kwei GY, Poon GK, Iliff SA, Wang Y, Chen Q, Franklin RB, Didolkar V, Wang RW, Yamazaki M, Chiu SH, Lin JH, Pearson PG, Baillie TA: Pharmacokinetics and interactions of a novel antagonist of chemokine receptor 5 (CCR5) with ritonavir in rats and monkeys: role of CYP3A and P-glycoprotein. J Pharmacol Exp Ther. 2003 Mar;304(3):1161-71. [PubMed:12604693]
  4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389]
  5. Yamazaki M, Neway WE, Ohe T, Chen I, Rowe JF, Hochman JH, Chiba M, Lin JH: In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther. 2001 Mar;296(3):723-35. [PubMed:11181899]
  6. Huisman MT, Smit JW, Wiltshire HR, Hoetelmans RM, Beijnen JH, Schinkel AH: P-glycoprotein limits oral availability, brain, and fetal penetration of saquinavir even with high doses of ritonavir. Mol Pharmacol. 2001 Apr;59(4):806-13. [PubMed:11259625]
  7. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019]
  8. Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Perloff MD, Von Moltke LL, Marchand JE, Greenblatt DJ: Ritonavir induces P-glycoprotein expression, multidrug resistance-associated protein (MRP1) expression, and drug transporter-mediated activity in a human intestinal cell line. J Pharm Sci. 2001 Nov;90(11):1829-37. [PubMed:11745741]
  2. Olson DP, Scadden DT, D'Aquila RT, De Pasquale MP: The protease inhibitor ritonavir inhibits the functional activity of the multidrug resistance related-protein 1 (MRP-1). AIDS. 2002 Sep 6;16(13):1743-7. [PubMed:12218384]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Dussault I, Lin M, Hollister K, Wang EH, Synold TW, Forman BM: Peptide mimetic HIV protease inhibitors are ligands for the orphan receptor SXR. J Biol Chem. 2001 Sep 7;276(36):33309-12. Epub 2001 Jul 20. [PubMed:11466304]
  2. Huisman MT, Smit JW, Crommentuyn KM, Zelcer N, Wiltshire HR, Beijnen JH, Schinkel AH: Multidrug resistance protein 2 (MRP2) transports HIV protease inhibitors, and transport can be enhanced by other drugs. AIDS. 2002 Nov 22;16(17):2295-301. [PubMed:12441801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Gupta A, Zhang Y, Unadkat JD, Mao Q: HIV protease inhibitors are inhibitors but not substrates of the human breast cancer resistance protein (BCRP/ABCG2). J Pharmacol Exp Ther. 2004 Jul;310(1):334-41. Epub 2004 Mar 8. [PubMed:15007102]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Tirona RG, Leake BF, Wolkoff AW, Kim RB: Human organic anion transporting polypeptide-C (SLC21A6) is a major determinant of rifampin-mediated pregnane X receptor activation. J Pharmacol Exp Ther. 2003 Jan;304(1):223-8. [PubMed:12490595]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Annaert P, Ye ZW, Stieger B, Augustijns P: Interaction of HIV protease inhibitors with OATP1B1, 1B3, and 2B1. Xenobiotica. 2010 Mar;40(3):163-76. doi: 10.3109/00498250903509375. [PubMed:20102298]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 11:51