atazanavir indications/contra

Stem definitionDrug idCAS RN
HIV protease inhibitors 254 198904-31-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • BMS-232632
  • atazanavir
  • reyataz
  • atazanavir sulphate
  • atazanavir sulfate
An azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.
  • Molecular weight: 704.87
  • Formula: C38H52N6O7
  • CLOGP: 5.92
  • LIPINSKI: 3
  • HAC: 13
  • HDO: 5
  • TPSA: 171.22
  • ALOGS: -5.33
  • ROTB: 18

Drug dosage:

DoseUnitRoute
0.30 g O

Approvals:

DateAgencyCompanyOrphan
March 2, 2004 EMA
June 20, 2003 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System

scroll-->
MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Foetal exposure during pregnancy 1495.93 44.03 390 4367 15161 3365941
Maternal exposure during pregnancy 967.00 44.03 254 4503 10017 3371085
Nephrolithiasis 919.77 44.03 225 4532 6611 3374491
Hyperbilirubinaemia 906.12 44.03 194 4563 3077 3378025
Abortion spontaneous 841.28 44.03 230 4527 10555 3370547
Exposure during pregnancy 746.66 44.03 261 4496 27302 3353800
Jaundice 688.63 44.03 194 4563 9913 3371189
Blood bilirubin increased 667.61 44.03 191 4566 10318 3370784
Renal colic 590.14 44.03 105 4652 572 3380530
Premature baby 552.09 44.03 152 4605 7101 3374001
Live birth 491.91 44.03 95 4662 858 3380244
Virologic failure 446.98 44.03 93 4664 1261 3379841
Lipodystrophy acquired 389.35 44.03 71 4686 452 3380650
Abortion induced 316.08 44.03 85 4672 3606 3377496
Pregnancy 309.03 44.03 99 4658 7781 3373321
Drug interaction 287.82 44.03 156 4601 46656 3334446
Immune reconstitution inflammatory syndrome 284.16 44.03 71 4686 2242 3378860
Acute kidney injury 270.93 44.03 153 4604 49530 3331572
Caesarean section 267.61 44.03 78 4679 4448 3376654
Premature delivery 258.96 44.03 67 4690 2438 3378664
Stillbirth 258.17 44.03 61 4696 1514 3379588
Ocular icterus 249.98 44.03 56 4701 1089 3380013
Hepatitis 232.07 44.03 84 4673 9541 3371561
Renal failure 213.93 44.03 114 4643 32826 3348276
Calculus urinary 192.06 44.03 38 4719 391 3380711
Drug resistance 184.34 44.03 59 4698 4604 3376498
Viral load increased 184.06 44.03 41 4716 775 3380327
Osteonecrosis 165.58 44.03 68 4689 10831 3370271
Normal newborn 154.35 44.03 40 4717 1461 3379641
Blood bilirubin unconjugated increased 143.13 44.03 28 4729 270 3380832

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC J05AE08 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
ATC J05AR15 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D017320 HIV Protease Inhibitors
MeSH PA D011480 Protease Inhibitors
CHEBI has role CHEBI:36044 antiviral drug
FDA EPC N0000175889 Protease Inhibitor
FDA MoA N0000191272 UGT1A1 Inhibitors
FDA MoA N0000191269 UDP Glucuronosyltransferases Inhibitors
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
FDA MoA N0000190114 Cytochrome P450 3A Inhibitors
FDA MoA N0000187062 Cytochrome P450 2C8 Inhibitors

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Hyperbilirubinemia contraindication 14783006 DOID:2741
Hepatic failure contraindication 59927004
Chronic type B viral hepatitis contraindication 61977001
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Hemophilia contraindication 90935002
Lactic acidosis contraindication 91273001 DOID:3650
Kidney stone contraindication 95570007
Chronic hepatitis C contraindication 128302006
Liver function tests abnormal contraindication 166603001
Atrioventricular block contraindication 233917008 DOID:0050820
Disease of liver contraindication 235856003 DOID:409
Breastfeeding (mother) contraindication 413712001
Prevention of HIV Infection after Exposure off-label use

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.91 acidic
pKa2 11.57 acidic
pKa3 4.94 Basic
pKa4 1.0 Basic

Orange Book patent data (new drug applications)

scroll-->
Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 300MG BASE EVOTAZ BRISTOL-MYERS SQUIBB N206353 Jan. 29, 2015 RX TABLET ORAL 8148374 Sept. 3, 2029 TREATMENT OF HIV INFECTION USING A COMPOSITION CONTAINING A PHARMACOKINETIC ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENASE

Orange Book exclusivity data (new drug applications)

scroll-->
Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 100MG BASE ATAZANAVIR SULFATE TEVA PHARMS USA A091673 April 22, 2014 RX CAPSULE ORAL June 25, 2018 PATENT CHALLENGE
EQ 150MG BASE ATAZANAVIR SULFATE TEVA PHARMS USA A091673 April 22, 2014 RX CAPSULE ORAL June 25, 2018 PATENT CHALLENGE
EQ 200MG BASE ATAZANAVIR SULFATE TEVA PHARMS USA A091673 April 22, 2014 RX CAPSULE ORAL June 25, 2018 PATENT CHALLENGE
EQ 300MG BASE ATAZANAVIR SULFATE TEVA PHARMS USA A091673 April 22, 2014 RX CAPSULE ORAL June 25, 2018 PATENT CHALLENGE
EQ 50MG BASE/PACKET REYATAZ BRISTOL MYERS SQUIBB N206352 June 2, 2014 RX POWDER ORAL Sept. 24, 2018 NEW PATIENT POPULATION
EQ 50MG BASE/PACKET REYATAZ BRISTOL MYERS SQUIBB N206352 June 2, 2014 RX POWDER ORAL March 24, 2019 PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 1A2 Enzyme Ki 4.92 WOMBAT-PK
Cytochrome P450 2C9 Enzyme Ki 4.92 WOMBAT-PK
Cytochrome P450 3A4 Enzyme Ki 5.63 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 4.17 CHEMBL
UDP-glucuronosyltransferase 1-1 Enzyme Ki 5.72 WOMBAT-PK
Pol polyprotein Enzyme INHIBITOR Ki 9.62 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein Ki 8.58 WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme IC50 7.59 CHEMBL
Protease Enzyme IC50 8.40 CHEMBL

External reference:

scroll-->
IDSource
4024316 VUID
N0000022320 NUI
C1145759 UMLSCUI
D01276 KEGG_DRUG
4MT4VIE29P UNII
229975-97-7 SECONDARY_CAS_RN
DB01072 DRUGBANK_ID
343047 RXNORM
d04882 MMSL
413591007 SNOMEDCT_US
413592000 SNOMEDCT_US
4024316 VANDF
N0000022320 NDFRT
000306 NDDF
CHEMBL1163 ChEMBL_ID
CHEMBL1200678 ChEMBL_ID
148192 PUBCHEM_CID
8181 INN_ID
D000069446 MESH_DESCRIPTOR_UI
CHEBI:37924 CHEBI
DR7 PDB_CHEM_ID

Pharmaceutical products:

scroll-->
ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 0003-3622 CAPSULE, GELATIN COATED 300 mg ORAL NDA 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 0003-3624 CAPSULE, GELATIN COATED 150 mg ORAL NDA 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 0003-3631 CAPSULE, GELATIN COATED 200 mg ORAL NDA 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 0003-3638 POWDER 50 mg ORAL NDA 19 sections
EVOTAZ HUMAN PRESCRIPTION DRUG LABEL 2 0003-3641 TABLET 300 mg ORAL NDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0093-5526 CAPSULE 150 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0093-5527 CAPSULE 200 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0093-5528 CAPSULE 300 mg ORAL ANDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 50090-1007 CAPSULE, GELATIN COATED 300 mg ORAL NDA 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 50090-1581 CAPSULE, GELATIN COATED 200 mg ORAL NDA 19 sections
EVOTAZ HUMAN PRESCRIPTION DRUG LABEL 2 50090-1724 TABLET 300 mg ORAL NDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 54868-4854 CAPSULE, GELATIN COATED 200 mg ORAL NDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 54868-4857 CAPSULE, GELATIN COATED 150 mg ORAL NDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 54868-5838 CAPSULE, GELATIN COATED 300 mg ORAL NDA 18 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 59762-0408 CAPSULE, GELATIN COATED 150 mg ORAL NDA authorized generic 19 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 59762-0409 CAPSULE, GELATIN COATED 200 mg ORAL NDA authorized generic 19 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 59762-0410 CAPSULE, GELATIN COATED 300 mg ORAL NDA authorized generic 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 67296-1236 CAPSULE, GELATIN COATED 300 mg ORAL NDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 69189-3624 CAPSULE, GELATIN COATED 150 mg ORAL NDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 69189-3631 CAPSULE, GELATIN COATED 200 mg ORAL NDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 70518-0469 CAPSULE, GELATIN COATED 300 mg ORAL NDA 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 70518-0688 CAPSULE, GELATIN COATED 150 mg ORAL NDA 19 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 70518-0725 CAPSULE, GELATIN COATED 200 mg ORAL NDA 19 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 70518-0946 CAPSULE 300 mg ORAL ANDA 18 sections