U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H48N6O5S2
Molecular Weight 720.944
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RITONAVIR

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](CC2=CC=CC=C2)NC(=O)OCC3=CN=CS3)CC4=CC=CC=C4

InChI

InChIKey=NCDNCNXCDXHOMX-XGKFQTDJSA-N
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

HIDE SMILES / InChI

Description

Ritonavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Ritonavir binds to the protease active site and inhibits the activity of the enzyme. It is FDA approved for the treatment of HIV-1 infection. In patients receiving medications metabolized by CYP3A or initiation of medications metabolized by CYP3A in patients already receiving Ritonavir, may increase plasma concentrations of medications metabolized by CYP3A. The most frequently reported adverse drug reactions among patients receiving Ritonavir alone or in combination with other antiretroviral drugs were gastrointestinal (including diarrhea, nausea, vomiting, abdominal pain (upper and lower)), neurological disturbances (including paresthesia and oral paresthesia), rash, and fatigue/asthenia.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.01 nM [Ki]
2.2 µM [IC50]
0.14 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Saquinavir soft gelatin capsule: a comparative safety review.
2001
Comparison of P-triglyceride levels among patients with human immunodeficiency virus on randomized treatment with ritonavir, indinavir or ritonavir/saquinavir.
2001
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.
2001 Apr
Vertical HIV-1 transmission: prophylaxis and paediatric follow-up.
2001 Apr
P-glycoprotein limits oral availability, brain, and fetal penetration of saquinavir even with high doses of ritonavir.
2001 Apr
Anti-human immunodeficiency virus activity of YK-FH312 (a betulinic acid derivative), a novel compound blocking viral maturation.
2001 Apr
Persistent dyslipidemia in HIV-infected individuals switched from a protease inhibitor-containing to an efavirenz-containing regimen.
2001 Apr 1
Impact of HIV type 1 protease, reverse transcriptase, cleavage site, and p6 mutations on the virological response to quadruple therapy with saquinavir, ritonavir, and two nucleoside analogs.
2001 Apr 10
Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport.
2001 Apr 13
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology.
2001 Apr 15
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.
2001 Apr 15
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection.
2001 Apr 15
Effect of drug efficacy and the eclipse phase of the viral life cycle on estimates of HIV viral dynamic parameters.
2001 Apr 15
[An option even for patients with multiple pretreatment].
2001 Apr 2
[Overcoming weaknesses in therapy. Protease inhibitors with high IQ].
2001 Apr 2
[Possible complication of HIV therapy. Protease inhibitor-induced femur head necrosis].
2001 Apr 2
[Improving the pharmacokinetics of protease inhibitors in a more innovative manner. HIV drugs administered in a more clever way].
2001 Apr 2
[No resistance even after 1 year. New drug combination against HIV].
2001 Apr 2
[Indinavir-ritonavir combination: pharmacologic results and tolerance in patients infected by HIV].
2001 Apr 21
Antiviral drugs: current state of the art.
2001 Aug
Pharmacology and clinical experience with saquinavir.
2001 Feb
Use of HIV protease inhibitors as pharmacoenhancers.
2001 Feb
Pharmacokinetics of ritonavir and saquinavir in a haemodialysis patient.
2001 Feb
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
CMVR diagnoses and progression of CD4 cell counts and HIV viral load measurements in HIV patients on HAART.
2001 Jul
The effect of fluconazole on ritonavir and saquinavir pharmacokinetics in HIV-1-infected individuals.
2001 Jun
Pharmacokinetic interaction between mefloquine and ritonavir in healthy volunteers.
2001 Jun
Effect of ritonavir/saquinavir on stereoselective pharmacokinetics of methadone: results of AIDS Clinical Trials Group (ACTG) 401.
2001 Jun 1
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.
2001 Jun 1
Vertical transmission of multidrug-resistant human immunodeficiency virus type 1 (HIV-1) and continued evolution of drug resistance in an HIV-1-infected infant.
2001 Jun 1
Simultaneous determination of the HIV-protease inhibitors indinavir, amprenavir, ritonavir, saquinavir and nelfinavir in human plasma by reversed-phase high-performance liquid chromatography.
2001 Jun 15
Treatment of tuberculosis in HIV-infected patients: safety and antiretroviral efficacy of the concomitant use of ritonavir and rifampin.
2001 Jun 15
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design.
2001 Jun 15
Analysis of human immunodeficiency virus type 1 drug resistance in children receiving nucleoside analogue reverse-transcriptase inhibitors plus nevirapine, nelfinavir, or ritonavir (Pediatric AIDS Clinical Trials Group 377).
2001 Jun 15
A comprehensive account on the role of efflux transporters in the gastrointestinal absorption of 13 commonly used substrate drugs in humans.
2001 Mar
The safety and antiviral effect of protease inhibitors in children.
2001 Mar
[HIV: a guide on management of seropositive patients].
2001 Mar 3
Lopinavir/ritonavir.
2001 Mar-Apr
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine.
2001 May
Secreted aspartic proteases of Candida albicans, Candida tropicalis, Candida parapsilosis and Candida lusitaniae. Inhibition with peptidomimetic inhibitors.
2001 May
P1/P1' modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays.
2001 May
A potential role for interleukin-7 in T-cell homeostasis.
2001 May 15
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.
2001 May 25
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment.
2001 May 25
Pharmacokinetics and safety of amprenavir and ritonavir following multiple-dose, co-administration to healthy volunteers.
2001 May 25
Clinical outcome among HIV-infected patients starting saquinavir hard gel compared to ritonavir or indinavir.
2001 May 25
Increased risk of lipodystrophy when nucleoside analogue reverse transcriptase inhibitors are included with protease inhibitors in the treatment of HIV-1 infection.
2001 May 4
[Effective in HIV: dual combination with indinavir and ritonavir].
2001 May 4
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography.
2001 May 5
Patents

Sample Use Guides

In Vivo Use Guide
600 mg twice-day with meals. Ritonavir should be started at no less than 300 mg twice daily and increased at 2 to 3 day intervals by 100 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
Ritonavir diminished the growth rate of Candida albicans as well as the activity of its secreted aspartyl proteinases (Saps) in a nitrogen-limited medium, yeast carbon base and bovine serum albumin (YCB-BSA). This inhibition occurred in a dose-dependent fashion; with 8 mg/l of ritonavir a partial growth inhibition (44%) was produced.
Name Type Language
RITONAVIR
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
NORVIR
Brand Name English
RITONAVIR [VANDF]
Common Name English
RITONAVIR [MI]
Common Name English
RITONAVIR [EP]
Common Name English
RITONAVIR [WHO-DD]
Common Name English
VIRITON
Brand Name English
EMPETUS
Brand Name English
RITONAVIR [INN]
Common Name English
RITONAVIR [USP]
Common Name English
ABBOTT-84538
Code English
VIEKIRAX COMPONENT RITONAVIR
Brand Name English
RITOVIR
Brand Name English
KALETRA COMPONENT RITONAVIR
Common Name English
RITONAVIR [HSDB]
Common Name English
NSC-693184
Code English
ABT-538
Code English
RITONAVIR COMPONENT OF VIEKIRAX
Brand Name English
RTV
Common Name English
RITONAVIR [EMA EPAR]
Common Name English
RITONAVIR [JAN]
Common Name English
RITONAVIR COMPONENT OF KALETRA
Common Name English
RITONAVIR [ORANGE BOOK]
Common Name English
RITONAVIRUM [WHO-IP LATIN]
Common Name English
A-84538
Code English
RITOMUNE
Brand Name English
RITONAVIR RELATED COMPOUNDS MIXTURE
USP-RS  
Common Name English
2,7,10,12-TETRAAZATRIDECANOIC ACID, 4-HYDROXY-12-METHYL-9-(1-METHYLETHYL)-13-(2-(1-METHYLETHYL)-4-THIAZOLYL)-8,11-DIOXO-3,6-BIS(PHENYLMETHYL)-, 5-THIAZOLYLMETHYL ESTER, (3S,4S,6S,9S)-
Systematic Name English
RITONAVIR [MART.]
Common Name English
2,4,7,12-TETRAAZATRIDECAN-13-OIC ACID, 10-HYDROXY-2-METHYL-5-(1-METHYLETHYL)-1-(2-(1-METHYLETHYL)-4-THIAZOLYL)-3,6-DIOXO-8,11-BIS(PHENYLMETHYL)-5-THIAZOLYLMETHYL ESTER (5S-(5R*,8R*,10R*,11R*))-
Common Name English
RITONAVIR RELATED COMPOUNDS MIXTURE [USP-RS]
Common Name English
RITONAVIR [WHO-IP]
Common Name English
VIEKIRAX
Brand Name English
5-THIAZOLYLMETHYL ((.ALPHA.S)-.ALPHA.-((1S,3S)-1-HYDROXY-3-((2S)-2-(3-((2-ISOPROPYL-4-THIAZOLYL)METHYL)-3-METHYLUREIDO)-3-METHYLBUTYRAMIDO)-4-PHENYLBUTYL)PHENETHYL)CARBAMATE
Common Name English
RITONAVIR [USAN]
Common Name English
Classification Tree Code System Code
LIVERTOX 853
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AR10
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AE03
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-VATC QJ05AE03
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
FDA ORPHAN DRUG 549816
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-VATC QJ05AR10
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AP52
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
EMA ASSESSMENT REPORTS LOPINAVIR (AUHTORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AX66
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
NCI_THESAURUS C97366
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
EMA ASSESSMENT REPORTS KALETRA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LPV/R)
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AR23
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AP53
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
NDF-RT N0000191001
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
FDA ORPHAN DRUG 509215
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
NDF-RT N0000175889
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
FDA ORPHAN DRUG 484715
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
NDF-RT N0000000246
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
EMA ASSESSMENT REPORTS VIEKIRAX (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
WHO-ATC J05AX67
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
EMA ASSESSMENT REPORTS NORVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
RITONAVIR
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Description: A white or almost white powder. Solubility: Practically insoluble in water, freely soluble in methanol R, sparingly soluble in acetone R and very slightly soluble in acetonitrile R. Category: Antiretroviral (Protease Inhibitor). Storage: Ritonavir should be kept in a well-closed container, protected from light. Additional information: Ritonavir may exhibit polymorphism. Requirements: Ritonavir contains not less than 98.5 % and not more than 101.0 % of C37H48N6O5S2, calculated with reference to the dried substance.
LactMed
155213-67-5
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
ChEMBL
CHEMBL163
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
INN
7449
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
EVMPD
SUB10342MIG
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
WIKIPEDIA
RITONAVIR
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
RXCUI
85762
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY RxNorm
NDF-RT
N0000182137
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
NDF-RT
N0000182141
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
NDF-RT
N0000187064
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
DRUG BANK
DB00503
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
MESH
D019438
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
NDF-RT
N0000185607
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 2C19 Inducers [MoA]
NDF-RT
N0000191266
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 1A2 Inducers [MoA]
NDF-RT
N0000190113
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
NDF-RT
N0000185507
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
EPA CompTox
155213-67-5
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
NDF-RT
N0000190117
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY UDP Glucuronosyltransferases Inducers [MoA]
NDF-RT
N0000190118
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 3A Inducers [MoA]
MERCK INDEX
M9636
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Merck Index
NDF-RT
N0000190114
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
PUBCHEM
392622
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
HSDB
155213-67-5
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
IUPHAR
8804
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
NCI_THESAURUS
C1609
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
CAS
155213-67-5
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY
NDF-RT
N0000185503
Created by admin on Mon Oct 21 19:47:06 UTC 2019 , Edited by admin on Mon Oct 21 19:47:06 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]