atazanavir Indications/Contra | FAERs | Orange Book | BioActivity |

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
0.30 g O

Approvals:

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

FDA Adverse Event Reporting System

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 2155.58 49.05 555 5142 22614 4610681
Maternal exposure during pregnancy 1213.68 49.05 332 5365 16761 4616534
Hyperbilirubinaemia 1074.17 49.05 233 5464 4318 4628977
Nephrolithiasis 1024.87 49.05 255 5442 8784 4624511
Abortion spontaneous 993.94 49.05 273 5424 13919 4619376
Exposure during pregnancy 942.50 49.05 318 5379 32653 4600642
Jaundice 749.24 49.05 213 5484 12261 4621034
Blood bilirubin increased 696.93 49.05 202 5495 12450 4620845
Premature baby 668.63 49.05 186 5511 9865 4623430
Renal colic 620.66 49.05 111 5586 691 4632604
Virologic failure 597.83 49.05 127 5570 2102 4631193
Lipodystrophy acquired 561.89 49.05 102 5595 698 4632597
Live birth 545.10 49.05 110 5587 1393 4631902
Drug interaction 503.45 49.05 245 5452 64263 4569032
Drug resistance 347.80 49.05 107 5590 8029 4625266
Abortion induced 347.60 49.05 92 5605 4005 4629290
Premature delivery 345.68 49.05 92 5605 4092 4629203
Immune reconstitution inflammatory syndrome 344.20 49.05 86 5611 2968 4630327
Stillbirth 326.23 49.05 76 5621 1938 4631357
Pregnancy 322.44 49.05 103 5594 8741 4624554
Caesarean section 291.57 49.05 84 5613 5014 4628281
Hepatitis 286.10 49.05 102 5595 12103 4621192
Acute kidney injury 265.84 49.05 166 5531 70265 4563030
Ocular icterus 255.64 49.05 58 5639 1309 4631986
Renal failure 245.45 49.05 131 5566 41238 4592057
Viral mutation identified 243.02 49.05 54 5643 1105 4632190
Foetal growth restriction 233.76 49.05 61 5636 2505 4630790
Low birth weight baby 206.79 49.05 56 5641 2654 4630641
Renal tubular disorder 201.65 49.05 49 5648 1499 4631796
Congenital naevus 198.95 49.05 30 5667 46 4633249
Calculus urinary 198.38 49.05 40 5657 501 4632794
Viral load increased 197.94 49.05 45 5652 1024 4632271
Cholelithiasis 191.93 49.05 71 5626 9331 4623964
Bilirubin conjugated increased 189.50 49.05 44 5653 1102 4632193
Normal newborn 184.89 49.05 47 5650 1735 4631560
Osteonecrosis 179.33 49.05 73 5624 12391 4620904
Ventricular septal defect 162.26 49.05 45 5652 2330 4630965
Mitochondrial toxicity 155.40 49.05 30 5667 295 4633000
Blood bilirubin unconjugated increased 147.09 49.05 29 5668 321 4632974
Alanine aminotransferase increased 138.19 49.05 79 5618 28294 4605001
Pyrexia 136.92 49.05 133 5564 107011 4526284
Foetal death 136.71 49.05 40 5657 2512 4630783
Pregnancy on contraceptive 136.68 49.05 27 5670 302 4632993
Nausea 132.56 49.05 166 5531 177167 4456128
Low set ears 128.97 49.05 24 5673 190 4633105
Osteoporosis 128.66 49.05 48 5649 6447 4626848
Patent ductus arteriosus 124.91 49.05 34 5663 1640 4631655
Rash 124.51 49.05 127 5570 108261 4525034
Dysphagia 118.73 49.05 69 5628 25462 4607833
Lipoatrophy 118.45 49.05 24 5673 308 4632987
Acoustic stimulation tests abnormal 117.81 49.05 19 5678 55 4633240
Cushing's syndrome 117.44 49.05 32 5665 1549 4631746
Proteinuria 116.84 49.05 45 5652 6591 4626704
Eyelid ptosis 114.17 49.05 33 5664 1984 4631311
Anaemia 112.88 49.05 100 5597 71460 4561835
Aspartate aminotransferase increased 109.64 49.05 65 5632 24873 4608422
Supernumerary nipple 106.70 49.05 16 5681 23 4633272
Cholestasis 105.74 49.05 44 5653 7876 4625419
Eosinophilia 104.09 49.05 42 5655 6951 4626344
Myocardial infarction 102.69 49.05 81 5616 49295 4584000
Trisomy 21 100.76 49.05 23 5674 532 4632763
Pancreatitis 100.48 49.05 54 5643 17124 4616171
Tubulointerstitial nephritis 98.89 49.05 39 5658 6080 4627215
Congenital anomaly 98.17 49.05 30 5667 2186 4631109
Treatment noncompliance 97.10 49.05 47 5650 11980 4621315
Renal impairment 95.87 49.05 60 5637 25278 4608017
Pre-eclampsia 93.78 49.05 27 5670 1600 4631695
Hepatic cirrhosis 92.19 49.05 36 5661 5466 4627829
Fanconi syndrome 91.95 49.05 22 5675 628 4632667
Polydactyly 91.02 49.05 21 5676 510 4632785
Transaminases increased 88.13 49.05 41 5656 9565 4623730
Premature rupture of membranes 87.06 49.05 23 5674 988 4632307
Trisomy 18 86.81 49.05 17 5680 181 4633114
Limb malformation 86.74 49.05 19 5678 362 4632933
Diarrhoea 86.51 49.05 124 5573 150061 4483234
Hydronephrosis 86.37 49.05 29 5668 2860 4630435
CD4 lymphocytes decreased 85.01 49.05 22 5675 871 4632424
Depression 83.86 49.05 71 5626 47662 4585633
Placental insufficiency 83.83 49.05 18 5679 311 4632984
Haematuria 82.13 49.05 43 5654 12927 4620368
Diabetes mellitus 80.35 49.05 45 5652 15456 4617839
CSF HIV escape syndrome 79.32 49.05 12 5685 19 4633276
Twin pregnancy 78.31 49.05 17 5680 310 4632985
Blood creatinine increased 78.11 49.05 54 5643 26846 4606449
Vomiting 78.09 49.05 105 5592 119594 4513701
Hepatic steatosis 77.77 49.05 33 5664 6195 4627100
Kaposi's sarcoma 76.13 49.05 22 5675 1320 4631975
Premature labour 76.06 49.05 25 5672 2307 4630988
Hepatomegaly 75.54 49.05 28 5669 3687 4629608
Pancytopenia 74.78 49.05 51 5646 24802 4608493
Hepatitis C 74.47 49.05 30 5667 4940 4628355
Weight decreased 73.85 49.05 70 5627 54394 4578901
Oligohydramnios 73.48 49.05 21 5676 1211 4632084
Foetal distress syndrome 71.10 49.05 19 5678 853 4632442
Gastrointestinal disorder 70.90 49.05 42 5655 16019 4617276
Placenta praevia 70.31 49.05 15 5682 251 4633044
Ureterolithiasis 69.76 49.05 18 5679 704 4632591
Left ventricular dilatation 69.29 49.05 13 5684 108 4633187
Gestational diabetes 69.02 49.05 21 5676 1507 4631788
Congenital central nervous system anomaly 68.15 49.05 16 5681 420 4632875
Toxic skin eruption 67.56 49.05 27 5670 4353 4628942
Breast disorder 67.33 49.05 16 5681 443 4632852
Small for dates baby 67.19 49.05 22 5675 2005 4631290
Hepatotoxicity 65.67 49.05 32 5665 8267 4625028
Nephropathy toxic 65.45 49.05 26 5671 4126 4629169
Liver disorder 65.10 49.05 37 5660 13061 4620234
Blood HIV RNA increased 64.52 49.05 15 5682 377 4632918
Fanconi syndrome acquired 64.30 49.05 17 5680 732 4632563
Nervous system disorder 63.84 49.05 29 5668 6402 4626893
Thrombocytopenia 62.19 49.05 60 5637 47613 4585682
Lymphadenopathy 61.67 49.05 33 5664 10359 4622936
Diplopia 60.61 49.05 28 5669 6423 4626872
Cytomegalovirus chorioretinitis 60.47 49.05 16 5681 691 4632604
Hyperlipidaemia 60.07 49.05 26 5671 5119 4628176
Hepatic enzyme increased 59.10 49.05 39 5658 17952 4615343
Blood creatine phosphokinase increased 57.68 49.05 36 5661 15063 4618232
Fatigue 57.17 49.05 101 5596 145465 4487830
Hypertriglyceridaemia 56.29 49.05 20 5677 2333 4630962
Maternal drugs affecting foetus 56.19 49.05 23 5674 3942 4629353
Blood triglycerides increased 55.99 49.05 25 5672 5300 4627995
Pruritus 55.58 49.05 69 5628 72503 4560792
Single umbilical artery 55.04 49.05 11 5686 131 4633164
Haemolytic anaemia 55.03 49.05 23 5674 4155 4629140
Treatment failure 54.72 49.05 34 5663 14113 4619182
Glycosuria 54.47 49.05 14 5683 539 4632756
Abdominal pain 54.07 49.05 62 5635 59962 4573333
Dermatitis exfoliative generalised 53.71 49.05 15 5682 795 4632500
HIV infection 53.24 49.05 14 5683 590 4632705
Congenital skin dimples 53.20 49.05 10 5687 84 4633211
Adverse event 52.97 49.05 35 5662 16137 4617158
Polyhydramnios 52.42 49.05 13 5684 432 4632863
Electrocardiogram QT prolonged 52.29 49.05 34 5663 15261 4618034
Depressed mood 52.23 49.05 28 5669 8816 4624479
Hypertension 51.81 49.05 56 5641 50742 4582553
Blood antidiuretic hormone increased 51.59 49.05 9 5688 47 4633248
Ultrasound antenatal screen abnormal 51.45 49.05 10 5687 102 4633193
Skull malformation 51.15 49.05 12 5685 314 4632981
Gastrointestinal tube insertion 51.13 49.05 15 5682 949 4632346
HIV-associated neurocognitive disorder 50.93 49.05 10 5687 108 4633187
Blood alkaline phosphatase increased 50.77 49.05 31 5666 12476 4620819
Umbilical cord abnormality 49.61 49.05 11 5686 222 4633073
Neuropathy peripheral 49.48 49.05 39 5658 23630 4609665
Pathogen resistance 49.20 49.05 19 5678 2797 4630498
Vanishing bile duct syndrome 49.13 49.05 12 5685 374 4632921

Pharmacologic Action:

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
ATC J05AR23 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)

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Prevention of HIV Infection after Exposure off-label use
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

Acid dissociation constants calculated using MoKa v3.0.0

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)

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)

None

Bioactivity Summary:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6875 CAPSULE 300 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16714-860 CAPSULE 150 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16714-861 CAPSULE 200 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16714-862 CAPSULE 300 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 51407-171 CAPSULE 150 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 51407-172 CAPSULE 200 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 51407-173 CAPSULE 300 mg ORAL ANDA 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 Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 60687-399 CAPSULE 300 mg ORAL ANDA 19 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65862-710 CAPSULE 100 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65862-711 CAPSULE 150 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65862-712 CAPSULE 200 mg ORAL ANDA 18 sections
Atazanavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65862-713 CAPSULE 300 mg ORAL ANDA 18 sections
REYATAZ HUMAN PRESCRIPTION DRUG LABEL 1 67296-1236 CAPSULE, GELATIN COATED 300 mg ORAL NDA 18 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 69097-443 CAPSULE, GELATIN COATED 100 mg ORAL ANDA 18 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 69097-444 CAPSULE, GELATIN COATED 150 mg ORAL ANDA 18 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 69097-445 CAPSULE, GELATIN COATED 200 mg ORAL ANDA 18 sections
ATAZANAVIR HUMAN PRESCRIPTION DRUG LABEL 1 69097-446 CAPSULE, GELATIN COATED 300 mg ORAL ANDA 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