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

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H52N6O7
Molecular Weight 704.8555
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATAZANAVIR

SMILES

COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)(C)C

InChI

InChIKey=AXRYRYVKAWYZBR-GASGPIRDSA-N
InChI=1S/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1

HIDE SMILES / InChI

Molecular Formula C38H52N6O7
Molecular Weight 704.8555
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Atazanavir is the first once-daily protease inhibitor for the treatment of human immunodeficiency virus type 1 infection and should be used only in combination therapy, as part of a highly active antiretroviral therapy (HAART) regimen. In addition to being the most potent protease inhibitor in vitro, atazanavir has a distinct cross-resistance profile that does not confer resistance to other protease inhibitors. However, resistance to other protease inhibitors often confers clinically relevant resistance to atazanavir.

CNS Activity

Originator

Approval Year

Targets

Targets

Conditions
PubMed

PubMed

TitleDatePubMed
["Once daily" drugs simplify therapy. Rp. HAART once daily].
2003 Apr 28
[Antiretroviral therapy 2003. The current status].
2003 Apr 28
[New protease inhibitor against HIV. Viral load decreases--without lipid increase].
2003 Aug 21
The continuing evolution of HIV therapy.
2003 Dec
Gateways to clinical trials.
2003 Dec
[Are all boosted protease inhibitors the same? Previously treated patients profit too from lopinavir/r].
2003 Dec 11
Pharmacokinetics of amprenavir given once or twice a day when combined with atazanavir in heavily pre-treated HIV-positive patients.
2003 Dec 5
Dose-ranging, randomized, clinical trial of atazanavir with lamivudine and stavudine in antiretroviral-naive subjects: 48-week results.
2003 Dec 5
New anti-HIV protease inhibitors provide more treatment options.
2003 Nov
Atazanavir sulphate.
2003 Nov
Atazanavir (Reyataz) and emtricitabine (Emtriva) for HIV infection.
2003 Nov 10
Three new drugs approved by FDA.
2003 Nov-Dec
Atazanavir (Reyataz).
2003 Oct
Gateways to clinical trials.
2003 Oct
Releasing the true power of protease inhibitors.
2003 Oct
Meeting notes from the 2nd International AIDS Society Conference on HIV Pathogenesis and Treatment. Atazanavir in treatment-experienced patients.
2003 Sep
Boosted PIs: competition hots up.
2003 Sep
First once-daily protease inhibitor.
2003 Sep-Oct
Tenofovir disoproxil fumarate: clinical pharmacology and pharmacokinetics.
2004
Cross-resistance patterns among HIV protease inhibitors.
2004 Apr
[Atazanavir protects lipid metabolism. New PI with favorable metabolic profile].
2004 Apr 26
[Good experiences with saquinavir. Double boosting of protease inhibitors gains significance].
2004 Apr 26
[Interview with Professor Jürgen Rockstroh, director of the Bonn University Clinic. Atazanavir in general practice].
2004 Apr 26
[Long-term tolerance. Favorable lipid profile--favorable effect on development of lipodystrophy?].
2004 Apr 26
[Simplified HIV therapy. Atazanavir: the first protease inhibitor with once daily administration].
2004 Apr 26
Regression of lipodystrophy in HIV-infected patients under therapy with the new protease inhibitor atazanavir.
2004 Apr 9
Resistance to HIV protease inhibitors: mechanisms and clinical consequences.
2004 Aug
Comparison of once-daily atazanavir with efavirenz, each in combination with fixed-dose zidovudine and lamivudine, as initial therapy for patients infected with HIV.
2004 Aug 15
Boosted Reyataz: 48-week results.
2004 Jan-Feb
Atazanavir: a new protease inhibitor to treat HIV infection.
2004 Jul 1
Acute hepatic cytolysis in an HIV-infected patient taking atazanavir.
2004 Jul 23
Gateways to clinical trials.
2004 Jul-Aug
The influence of protease inhibitor resistance profiles on selection of HIV therapy in treatment-naive patients.
2004 Jun
Atazanavir: new option for treatment of HIV infection.
2004 Jun 1
Atazanavir enhances saquinavir hard-gel concentrations in a ritonavir-boosted once-daily regimen.
2004 Jun 18
Drug-induced liver injury associated with antiretroviral therapy that includes HIV-1 protease inhibitors.
2004 Mar 1
Atazanavir (Reyataz): new recommendations if combined with tenofovir (Viread) -- and warning on Viagra, Cialis, and Levitra.
2004 Mar 26
Optimizing dosing strategies for the combination of atazanavir plus saquinavir.
2004 Mar 5
Initial therapy for human immunodeficiency virus: broadening the options.
2004 Mar-Apr
New drugs of 2003.
2004 Mar-Apr
Kinetic and thermodynamic characterization of HIV-1 protease inhibitors.
2004 Mar-Apr
Gateways to clinical trials.
2004 May
Does atazanavir cause lipodystrophy?
2004 May
Identification of I50L as the signature atazanavir (ATV)-resistance mutation in treatment-naive HIV-1-infected patients receiving ATV-containing regimens.
2004 May 15
Simultaneous quantification of the new HIV protease inhibitors atazanavir and tipranavir in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2004 May 25
[New treatment options for HIV-infected patients].
2004 May 7
Atazanavir.
2004 Oct
Pseudoaneurysm of the femoral artery in a HIV-infected man.
2004 Oct
Determination of the new HIV-protease inhibitor atazanavir by liquid chromatography after solid-phase extraction.
2004 Oct 15
HIV-chemotherapy and -prophylaxis: new drugs, leads and approaches.
2004 Sep
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose of REYATAZ ((atazanavir sulfate) capsules) is 400 mg (two 200-mg capsules) once daily taken with food. When coadministered with efavirenz, it is recommended that REYATAZ 300 mg and ritonavir 100 mg be given with efavirenz 600 mg (all as a single daily dose with food). REYATAZ without ritonavir should not be coadministered with efavirenz. When coadministered with didanosine buffered formulations, 589 REYATAZ should be given (with food) 2 hours before or 1 hour after didanosine.
Route of Administration: Oral
In Vitro Use Guide
It was investigated the effect of atazanavir on P-glycoprotein (P-gp) expression and activity, as well as its inhibitory potency against CYP3A activity. Induction of P-gp activity and expression was studied using LS180V cells. P-gp inhibition was studied using both LS180V cells and Caco-2 cells. Extended (3-day) exposure of LS180V cells to 30 microM atazanavir caused a 2.5-fold increase in immunoreactive P-gp expression as well as a concentration-dependent decrease of intracellular Rh123 to a mean 45% (S.D. 5.2%) of control. Acute exposure (2 h) of LS180V cells to atazanavir increased intracellular Rh123 concentrations up to 300% of control at 100 microM atazanavir. At 30 microM and above, acute atazanavir exposure reversed P-gp induction caused by 3-day pretreatment with 10 microM ritonavir. P-gp inhibition was also observed in Caco-2 cells, causing an effect comparable to that observed for the known P-gp inhibitor verapamil (50% of control). In HLM, atazanavir was an inhibitor of triazolam hydroxylation, with inhibitory potency greatly increased by preincubation. IC50 values with and without preincubation were 0.31 microM (S.D. 0.13) and 5.7 microM (S.D. 4.1), respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:51:13 UTC 2019
Edited
by admin
on Mon Oct 21 19:51:13 UTC 2019
Record UNII
QZU4H47A3S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATAZANAVIR
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ATAZANAVIR [INN]
Common Name English
CGP-73547
Code English
BMS-232632
Code English
ATAZANAVIR [VANDF]
Common Name English
ATAZANAVIR [MI]
Common Name English
DIMETHYL (3S,8S,9S,12S)-9-BENZYL-3,12,DI-TERT-BUTYL-8-HYDROXY-4,11-DIOXO-6-(P-2-PYRIDYLBENZYL)-2,5,6,10,13-PENTAAZATETRADECANEDIOATE
Common Name English
2,5,6,10,13-PENTAAZATETRADECANEDIOIC ACID, 3-12-BIS(1,1-DIMETHYLETHYL)-8-HYDROXY-4,11-DIOXO-9-(PHENYLMETHYL)-6-((-4-(2-PYRIDINYL)PHENYL)METHYL)-, DIMETHYL ESTER, (3S,8S,9S,12S)-
Common Name English
ATAZANAVIR [WHO-DD]
Common Name English
ATAZANAVIR [HSDB]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AR15
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
WHO-VATC QJ05AE08
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
WHO-ATC J05AR23
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
NCI_THESAURUS C97366
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
LIVERTOX 69
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
NDF-RT N0000000246
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
WHO-ATC J05AE08
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
NDF-RT N0000175889
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
Code System Code Type Description
PUBCHEM
148192
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
MESH
C413408
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
CAS
198904-31-3
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
NDF-RT
N0000191269
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY UDP Glucuronosyltransferases Inhibitors [MoA]
WIKIPEDIA
ATAZANAVIR
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
LactMed
198904-31-3
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
EVMPD
SUB16398MIG
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
NCI_THESAURUS
C66872
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
NDF-RT
N0000182141
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
NDF-RT
N0000187062
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY Cytochrome P450 2C8 Inhibitors [MoA]
INN
8181
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
DRUG BANK
DB01072
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
MERCK INDEX
M2119
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY Merck Index
RXCUI
343047
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY RxNorm
HSDB
198904-31-3
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
EPA CompTox
198904-31-3
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
ChEMBL
CHEMBL1163
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY
NDF-RT
N0000190114
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
NDF-RT
N0000191272
Created by admin on Mon Oct 21 19:51:13 UTC 2019 , Edited by admin on Mon Oct 21 19:51:13 UTC 2019
PRIMARY UGT1A1 Inhibitors [MoA]
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
TARGET ORGANISM->INHIBITOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
substrate used: Cholyl-glycylamido-fluorescein (CGamF)
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC