atazanavir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
0.30 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 7 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 8.11 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 64 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

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

FDA Adverse Event Reporting System (Female)

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
Maternal exposure during pregnancy 1382.73 72.45 321 1680 14542 2341542
Abortion spontaneous 1081.79 72.45 259 1742 13186 2342898
Foetal exposure during pregnancy 1009.32 72.45 207 1794 5045 2351039
Exposure during pregnancy 743.74 72.45 220 1781 24999 2331085
Live birth 598.29 72.45 107 1894 1184 2354900
Premature baby 383.69 72.45 86 1915 3118 2352966
Pregnancy 375.93 72.45 101 1900 7848 2348236
Abortion induced 361.53 72.45 83 1918 3353 2352731
Stillbirth 335.29 72.45 67 1934 1374 2354710
Caesarean section 331.78 72.45 80 1921 4001 2352083
Hyperbilirubinaemia 330.46 72.45 67 1934 1482 2354602
Premature delivery 297.76 72.45 70 1931 3130 2352954
Normal newborn 194.67 72.45 42 1959 1258 2354826
Foetal growth restriction 188.67 72.45 40 1961 1100 2354984
Nephrolithiasis 182.93 72.45 51 1950 4492 2351592
Jaundice 182.05 72.45 53 1948 5455 2350629
Pregnancy on contraceptive 151.07 72.45 27 1974 291 2355793
Congenital naevus 147.31 72.45 20 1981 20 2356064
Hepatitis 141.00 72.45 45 1956 6292 2349792
Blood bilirubin increased 139.99 72.45 43 1958 5302 2350782
Foetal death 137.32 72.45 34 1967 1878 2354206
Renal colic 133.00 72.45 24 1977 274 2355810
Ventricular septal defect 120.17 72.45 26 1975 786 2355298
Low set ears 119.60 72.45 18 1983 56 2356028
Acoustic stimulation tests abnormal 105.78 72.45 15 1986 26 2356058
Pre-eclampsia 104.23 72.45 26 1975 1478 2354606
Supernumerary nipple 100.51 72.45 13 1988 5 2356079
Viral mutation identified 97.35 72.45 18 1983 237 2355847
Patent ductus arteriosus 96.47 72.45 21 1980 653 2355431
Virologic failure 95.29 72.45 18 1983 268 2355816
Lipodystrophy acquired 94.49 72.45 18 1983 281 2355803
Drug resistance 94.36 72.45 27 1974 2597 2353487
Immune reconstitution inflammatory syndrome 93.72 72.45 23 1978 1221 2354863
Eosinophilia 91.05 72.45 27 1974 2943 2353141
Premature rupture of membranes 90.28 72.45 21 1980 885 2355199
Twin pregnancy 89.26 72.45 17 1984 265 2355819
Drug interaction 88.19 72.45 50 1951 29113 2326971
Low birth weight baby 86.77 72.45 20 1981 809 2355275
Premature labour 86.28 72.45 24 1977 2082 2354002
Placental insufficiency 84.46 72.45 16 1985 242 2355842
Oligohydramnios 83.85 72.45 20 1981 940 2355144
Gestational diabetes 81.39 72.45 21 1980 1366 2354718
Placenta praevia 79.11 72.45 15 1986 228 2355856
Polydactyly 76.52 72.45 13 1988 101 2355983
Renal failure 75.68 72.45 38 1963 17311 2338773

FDA Adverse Event Reporting System (Male)

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
Nephrolithiasis 772.93 43.08 183 2477 3809 1740312
Hyperbilirubinaemia 630.45 43.08 140 2520 2147 1741974
Foetal exposure during pregnancy 603.09 43.08 165 2495 6194 1737927
Jaundice 490.35 43.08 139 2521 5923 1738198
Renal colic 475.18 43.08 85 2575 377 1743744
Lipodystrophy acquired 425.79 43.08 75 2585 298 1743823
Blood bilirubin increased 372.26 43.08 113 2547 6097 1738024
Drug interaction 253.47 43.08 129 2531 27829 1716292
Immune reconstitution inflammatory syndrome 216.99 43.08 55 2605 1494 1742627
Acute kidney injury 186.71 43.08 114 2546 34830 1709291
Ocular icterus 181.85 43.08 40 2620 574 1743547
Cholelithiasis 169.67 43.08 53 2607 3112 1741009
Renal tubular disorder 162.56 43.08 39 2621 836 1743285
Premature baby 160.76 43.08 50 2610 2892 1741229
Renal failure 154.07 43.08 83 2577 19934 1724187
Hepatitis 146.36 43.08 53 2607 4902 1739219
Osteonecrosis 146.14 43.08 50 2610 3912 1740209
Calculus urinary 144.07 43.08 29 2631 262 1743859
Mitochondrial toxicity 142.03 43.08 27 2633 175 1743946
Nausea 136.32 43.08 109 2551 51087 1693034
Alanine aminotransferase increased 132.44 43.08 64 2596 12214 1731907
Eyelid ptosis 117.23 43.08 29 2631 708 1743413
Lipoatrophy 117.17 43.08 21 2639 93 1744028
Depression 95.30 43.08 57 2603 16612 1727509
Aspartate aminotransferase increased 95.02 43.08 49 2611 10707 1733414
Viral load increased 92.97 43.08 23 2637 561 1743560
Renal impairment 91.55 43.08 50 2610 12264 1731857
Drug resistance 89.53 43.08 33 2627 3197 1740924
Hepatic cirrhosis 84.35 43.08 30 2630 2623 1741498
Hydronephrosis 82.47 43.08 25 2635 1320 1742801
Dysphagia 80.32 43.08 43 2617 10125 1733996
Kaposi's sarcoma 79.33 43.08 22 2638 845 1743276
Pancreatitis 78.98 43.08 38 2622 7149 1736972
Diarrhoea 76.77 43.08 81 2579 53771 1690350
Pyrexia 75.56 43.08 75 2585 46325 1697796
Proteinuria 74.93 43.08 28 2632 2816 1741305
Osteoporosis 74.78 43.08 24 2636 1531 1742590
Myocardial infarction 74.37 43.08 59 2601 27115 1717006
Diplopia 73.96 43.08 27 2633 2543 1741578
Ureterolithiasis 70.99 43.08 17 2643 360 1743761
Blood bilirubin unconjugated increased 70.68 43.08 15 2645 179 1743942
Tubulointerstitial nephritis 70.26 43.08 27 2633 2931 1741190
Fatigue 68.13 43.08 74 2586 50707 1693414
Weight decreased 67.85 43.08 52 2608 22701 1721420
Hepatic steatosis 62.85 43.08 24 2636 2560 1741561
Depressed mood 62.71 43.08 25 2635 2991 1741130
Haematuria 62.57 43.08 33 2627 7527 1736594
Diabetes mellitus 62.46 43.08 32 2628 6876 1737245
Vomiting 62.41 43.08 62 2598 38253 1705868
Fanconi syndrome 62.26 43.08 15 2645 326 1743795
Anaemia 62.04 43.08 55 2605 29402 1714719
Hepatomegaly 61.01 43.08 21 2639 1664 1742457
Exposure during pregnancy 60.84 43.08 24 2636 2793 1741328
Nephropathy toxic 60.44 43.08 21 2639 1711 1742410
Hyperlipidaemia 58.91 43.08 22 2638 2207 1741914
Blood creatinine increased 57.89 43.08 39 2621 13907 1730214
Rash 56.42 43.08 59 2601 38634 1705487
Vanishing bile duct syndrome 56.25 43.08 12 2648 147 1743974
Thrombocytopenia 55.64 43.08 45 2615 21204 1722917
Lymphadenopathy 55.23 43.08 25 2635 4089 1740032
Virologic failure 54.72 43.08 14 2646 392 1743729
Cushing's syndrome 53.75 43.08 15 2645 589 1743532
Blood antidiuretic hormone increased 53.19 43.08 9 2651 26 1744095
Fanconi syndrome acquired 52.69 43.08 14 2646 456 1743665
Pruritus 52.14 43.08 45 2615 23177 1720944
Hypertension 50.51 43.08 41 2619 19407 1724714
Myositis 50.45 43.08 18 2642 1585 1742536
Abdominal pain 48.96 43.08 42 2618 21448 1722673
Enanthema 48.82 43.08 10 2650 99 1744022
Heterotaxia 47.84 43.08 8 2652 21 1744100
Neonatal hyponatraemia 47.84 43.08 8 2652 21 1744100
Liver disorder 47.75 43.08 25 2635 5611 1738510
Hepatitis C 47.30 43.08 20 2640 2776 1741345
Blood creatine phosphokinase increased 47.20 43.08 29 2631 8827 1735294
Wrong dose 45.76 43.08 9 2651 71 1744050
Ventricular septal defect 45.71 43.08 14 2646 764 1743357
Cholestasis 45.20 43.08 21 2639 3644 1740477
Hypertriglyceridaemia 43.50 43.08 15 2645 1194 1742927

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