adefovir dipivoxil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals 88 142340-99-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • adefovir dipivoxil
  • hepsera
  • preveon
inhibitor of African swine fever virus
  • Molecular weight: 501.48
  • Formula: C20H32N5O8P
  • CLOGP: 1.40
  • LIPINSKI: 2
  • HAC: 13
  • HDO: 1
  • TPSA: 166.98
  • ALOGS: -2.90
  • ROTB: 15

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.40 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 45 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.43 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 12 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 6, 2003 EMA
Sept. 20, 2002 FDA GILEAD

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
Osteomalacia 621.17 59.87 86 1598 571 46683807
Fanconi syndrome acquired 418.08 59.87 64 1620 905 46683473
Hypophosphataemia 344.48 59.87 74 1610 7293 46677085
Drug resistance 197.16 59.87 56 1628 17312 46667066
Osteoporosis 146.74 59.87 55 1629 40553 46643825
Fanconi syndrome 146.39 59.87 26 1658 934 46683444
Bone pain 139.04 59.87 55 1629 46835 46637543
Blood phosphorus decreased 126.07 59.87 29 1655 3851 46680527
Renal tubular disorder 110.62 59.87 24 1660 2441 46681937
Hepatitis B DNULL increased 91.11 59.87 14 1670 200 46684178
Viral load increased 82.37 59.87 17 1667 1358 46683020
Hypophosphataemic osteomalacia 81.33 59.87 12 1672 128 46684250
Hypouricaemia 71.78 59.87 11 1673 154 46684224
Viral mutation identified 65.97 59.87 15 1669 1884 46682494
Blood alkaline phosphatase increased 63.01 59.87 30 1654 39579 46644799
Aminoaciduria 62.33 59.87 10 1674 191 46684187
Pathogen resistance 61.71 59.87 18 1666 6042 46678336

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
Osteomalacia 1647.20 51.20 257 5009 651 29946561
Hypophosphataemia 911.27 51.20 224 5042 8021 29939191
Fanconi syndrome acquired 795.77 51.20 157 5109 1946 29945266
Drug resistance 425.15 51.20 152 5114 19981 29927231
Osteoporosis 407.54 51.20 126 5140 10537 29936675
Blood phosphorus decreased 363.79 51.20 88 5178 2904 29944308
Fanconi syndrome 342.50 51.20 76 5190 1699 29945513
Bone pain 292.79 51.20 114 5152 18912 29928300
Viral mutation identified 252.48 51.20 64 5202 2562 29944650
Hepatitis B DNULL increased 227.45 51.20 44 5222 483 29946729
Hypophosphataemic osteomalacia 218.37 51.20 34 5232 82 29947130
Multiple fractures 201.86 51.20 47 5219 1307 29945905
Bone density decreased 169.22 51.20 43 5223 1735 29945477
Hypouricaemia 165.55 51.20 30 5236 223 29946989
Blood alkaline phosphatase increased 164.39 51.20 89 5177 31398 29915814
Urine phosphorus increased 156.29 51.20 23 5243 31 29947181
Viral load increased 149.06 51.20 43 5223 2811 29944401
Renal tubular disorder 145.04 51.20 48 5218 4958 29942254
Blood creatinine increased 118.53 51.20 110 5156 91265 29855947
Hepatic cancer 99.68 51.20 39 5227 6509 29940703
Renal impairment 97.04 51.20 95 5171 84089 29863123
Glucose urine present 96.00 51.20 24 5242 904 29946308
Glycosuria 92.45 51.20 25 5241 1286 29945926
Gait disturbance 89.18 51.20 86 5180 74691 29872521
Hepatitis B reactivation 89.00 51.20 29 5237 2848 29944364
Aminoaciduria 88.74 51.20 16 5250 115 29947097
Proteinuria 87.95 51.20 47 5219 16098 29931114
Arthralgia 85.74 51.20 112 5154 135679 29811533
Renal tubular dysfunction 82.05 51.20 18 5248 379 29946833
Renal glycosuria 82.04 51.20 12 5254 15 29947197
Urine phosphorus decreased 81.66 51.20 13 5253 38 29947174
Pathogen resistance 80.52 51.20 36 5230 8374 29938838
Hepatitis B 77.97 51.20 32 5234 6040 29941172
Bone marrow oedema 67.28 51.20 16 5250 487 29946725
Genotype drug resistance test positive 65.74 51.20 20 5246 1569 29945643
Urine calcium increased 64.24 51.20 10 5256 24 29947188
Blood uric acid decreased 63.27 51.20 14 5252 307 29946905
Protein urine present 60.74 51.20 25 5241 4750 29942462
Alanine aminotransferase increased 55.90 51.20 67 5199 74209 29873003

Pharmacologic Action:

SourceCodeDescription
ATC J05AF08 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleoside and nucleotide reverse transcriptase inhibitors
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:49103 drug metabolites
CHEBI has role CHEBI:50909 agente nefrotoxico
CHEBI has role CHEBI:53756 reverse transcriptase inhibitor
CHEBI has role CHEBI:59517 dna synthesis inhibitors
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
MeSH PA D018894 Reverse Transcriptase Inhibitors
FDA EPC N0000175656 Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor
FDA EXT N0000175459 Nucleoside Analog
FDA MoA N0000009947 Nucleoside Reverse Transcriptase Inhibitors
CHEBI has role CHEBI:50266 prodrugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chronic type B viral hepatitis indication 61977001
Kidney disease contraindication 90708001 DOID:557
Lactic acidosis contraindication 91273001 DOID:3650
Steatosis of liver contraindication 197321007
Toxic nephropathy contraindication 236514003
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
Drug Resistance to Anti-retroviral Therapy contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.73 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase subunit gamma-1 Enzyme WOMBAT-PK
Protein P Polyprotein INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
U6Q8Z01514 UNII
4021357 VUID
N0000179520 NUI
106941-25-7 SECONDARY_CAS_RN
C0540694 UMLSCUI
C0050175 UMLSCUI
CHEBI:31175 CHEBI
CHEBI:2469 CHEBI
CHEMBL922 ChEMBL_ID
60871 PUBCHEM_CID
DB00718 DRUGBANK_ID
CHEMBL484 ChEMBL_ID
C106812 MESH_SUPPLEMENTAL_RECORD_UI
C053001 MESH_SUPPLEMENTAL_RECORD_UI
7313 INN_ID
6GQP90I798 UNII
60172 PUBCHEM_CID
DB13868 DRUGBANK_ID
141400 RXNORM
16958 MMSL
205746 MMSL
44701 MMSL
d04814 MMSL
009376 NDDF
009377 NDDF
409114008 SNOMEDCT_US
412072006 SNOMEDCT_US
412073001 SNOMEDCT_US
4021357 VANDF
4024286 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ADEFOVIR DIPIVOXIL HUMAN PRESCRIPTION DRUG LABEL 1 42794-003 TABLET 10 mg ORAL ANDA 19 sections
Hepsera HUMAN PRESCRIPTION DRUG LABEL 1 46014-0501 TABLET 10 mg ORAL NDA 32 sections
Adefovir dipivoxil HUMAN PRESCRIPTION DRUG LABEL 1 60505-3947 TABLET 10 mg ORAL ANDA 29 sections
Hepsera HUMAN PRESCRIPTION DRUG LABEL 1 61958-0501 TABLET 10 mg ORAL NDA 29 sections