didanosine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals 869 69655-05-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • didanosine
  • videx
  • dideoxyinosine
A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.
  • Molecular weight: 236.23
  • Formula: C10H12N4O3
  • CLOGP: -1.92
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 88.74
  • ALOGS: -1.56
  • ROTB: 2

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
0.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 27.30 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 55 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 24.19 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 38 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.77 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 11 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.95 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 9, 1991 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
Pregnancy 444.76 32.35 143 4031 26994 46654894
Viral mutation identified 280.93 32.35 58 4116 1841 46680047
Foetal exposure during pregnancy 224.14 32.35 89 4085 30658 46651230
Portal hypertension 219.91 32.35 53 4121 3430 46678458
Exposure during pregnancy 213.93 32.35 128 4046 108084 46573804
Drug resistance 194.89 32.35 69 4105 17299 46664589
Lactic acidosis 162.86 32.35 73 4101 33836 46648052
Caesarean section 160.15 32.35 59 4115 16544 46665344
Abortion induced 155.14 32.35 51 4123 10209 46671679
Lipodystrophy acquired 154.37 32.35 34 4140 1471 46680417
Abortion spontaneous 142.35 32.35 72 4102 43574 46638314
Stillbirth 130.09 32.35 40 4134 6451 46675437
Hypertriglyceridaemia 122.19 32.35 37 4137 5667 46676221
Virologic failure 103.03 32.35 26 4148 2029 46679859
Blood lactic acid increased 97.20 32.35 31 4143 5626 46676262
Pathogen resistance 95.11 32.35 31 4143 6029 46675859
Premature rupture of membranes 79.13 32.35 25 4149 4398 46677490
Premature baby 77.42 32.35 36 4138 18076 46663812
Live birth 71.98 32.35 29 4145 10301 46671587
Retinoblastoma 71.03 32.35 12 4162 121 46681767
Pancreatitis 69.15 32.35 45 4129 43582 46638306
Premature delivery 67.76 32.35 35 4139 22034 46659854
Foetal death 65.97 32.35 26 4148 8717 46673171
Immune reconstitution inflammatory syndrome 65.09 32.35 23 4151 5702 46676186
Normal newborn 64.03 32.35 23 4151 5978 46675910
Mitochondrial toxicity 59.54 32.35 12 4162 335 46681553
Varices oesophageal 59.12 32.35 18 4156 2801 46679087
Amniotic cavity infection 49.73 32.35 13 4161 1165 46680723
Retinal toxicity 46.06 32.35 12 4162 1061 46680827
Nodular regenerative hyperplasia 44.26 32.35 9 4165 263 46681625
Ventricular septal defect 41.30 32.35 15 4159 4019 46677869
CD4 lymphocytes decreased 41.24 32.35 12 4162 1598 46680290
Pregnancy on contraceptive 40.93 32.35 11 4163 1096 46680792
Portal vein thrombosis 40.24 32.35 13 4161 2454 46679434
Non-cirrhotic portal hypertension 39.73 32.35 7 4167 92 46681796
Maternal drugs affecting foetus 36.74 32.35 15 4159 5503 46676385
Lipase increased 36.43 32.35 17 4157 8586 46673302
Maternal exposure during pregnancy 35.91 32.35 45 4129 102504 46579384
Hypophosphataemia 35.73 32.35 16 4158 7351 46674537
Viral load increased 34.12 32.35 10 4164 1365 46680523
Hyperlactacidaemia 33.40 32.35 11 4163 2204 46679684
Neutropenia neonatal 33.25 32.35 6 4168 91 46681797
Fanconi syndrome acquired 32.89 32.35 9 4165 960 46680928

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
Lipodystrophy acquired 829.69 21.09 196 8750 3364 29940168
Mitochondrial toxicity 667.89 21.09 154 8792 2360 29941172
Eyelid ptosis 543.29 21.09 151 8795 5037 29938495
Diplopia 303.27 21.09 124 8822 13648 29929884
Progressive external ophthalmoplegia 296.12 21.09 70 8876 1196 29942336
Portal hypertension 264.67 21.09 81 8865 3792 29939740
Pinealoblastoma 205.31 21.09 37 8909 141 29943391
Foetal exposure during pregnancy 190.40 21.09 125 8821 36746 29906786
Lipoatrophy 187.68 21.09 42 8904 555 29942977
Hepatic fibrosis 159.02 21.09 54 8892 3526 29940006
Retinal toxicity 141.57 21.09 31 8915 368 29943164
Virologic failure 140.79 21.09 48 8898 3171 29940361
Lactic acidosis 139.96 21.09 97 8849 31116 29912416
Drug resistance 138.58 21.09 82 8864 20051 29923481
Viral mutation identified 130.06 21.09 43 8903 2583 29940949
Blood lactic acid increased 126.51 21.09 52 8894 5778 29937754
Nodular regenerative hyperplasia 117.03 21.09 30 8916 724 29942808
Hypertriglyceridaemia 113.18 21.09 53 8893 8045 29935487
Hyperlactacidaemia 106.73 21.09 37 8909 2569 29940963
Ophthalmoplegia 100.76 21.09 30 8916 1274 29942258
Pathogen resistance 90.37 21.09 46 8900 8364 29935168
Fanconi syndrome 87.63 21.09 29 8917 1746 29941786
Varices oesophageal 81.94 21.09 33 8913 3476 29940056
Pancreatitis 80.79 21.09 75 8871 36415 29907117
Extraocular muscle paresis 79.64 21.09 20 8926 443 29943089
HIV infection 77.36 21.09 26 8920 1642 29941890
Fanconi syndrome acquired 75.21 21.09 27 8919 2076 29941456
Drug-induced liver injury 74.55 21.09 57 8889 21217 29922315
Mitochondrial cytopathy 72.52 21.09 16 8930 197 29943335
Hyperlipidaemia 71.29 21.09 47 8899 13860 29929672
Pregnancy 66.00 21.09 15 8931 213 29943319
Hepatic cirrhosis 65.32 21.09 47 8899 15952 29927580
Osteonecrosis 64.96 21.09 47 8899 16088 29927444
Oesophageal varices haemorrhage 62.07 21.09 26 8920 3025 29940507
CD4 lymphocytes decreased 60.82 21.09 23 8923 2047 29941485
Facial wasting 59.54 21.09 13 8933 152 29943380
Ascites 59.41 21.09 63 8883 35858 29907674
Exposure during pregnancy 56.65 21.09 35 8911 9226 29934306
Immune reconstitution inflammatory syndrome 54.67 21.09 34 8912 9067 29934465
Optic nerve neoplasm 51.58 21.09 9 8937 27 29943505
Renal tubular disorder 49.78 21.09 26 8920 4980 29938552
Gynaecomastia 49.66 21.09 31 8915 8320 29935212
Cachexia 48.27 21.09 28 8918 6583 29936949
Mitochondrial myopathy 47.96 21.09 11 8935 163 29943369
Pancreatitis acute 47.76 21.09 48 8898 25647 29917885
Kaposi's sarcoma 47.58 21.09 16 8930 1012 29942520
Viral load increased 47.16 21.09 21 8925 2833 29940699
Congenital neoplasm 45.85 21.09 8 8938 24 29943508
Blood antidiuretic hormone increased 44.19 21.09 9 8937 73 29943459
Hepatomegaly 42.11 21.09 30 8916 10017 29933515
Lipase increased 41.27 21.09 28 8918 8648 29934884
Portal hypertensive gastropathy 39.60 21.09 12 8934 541 29942991
Off label use 38.98 21.09 13 8933 249277 29694255
Amylase increased 38.09 21.09 23 8923 5818 29937714
Post streptococcal glomerulonephritis 36.50 21.09 7 8939 40 29943492
Cholestasis 36.42 21.09 41 8905 24909 29918623
Premature baby 36.31 21.09 34 8912 16657 29926875
Dyslipidaemia 35.93 21.09 22 8924 5705 29937827
HIV wasting syndrome 35.57 21.09 8 8938 108 29943424
Jaundice 35.36 21.09 46 8900 32440 29911092
Fall 35.23 21.09 6 8940 181866 29761666
Foetal distress syndrome 32.73 21.09 12 8934 979 29942553
Acquired immunodeficiency syndrome 31.92 21.09 10 8936 504 29943028
Aspartate aminotransferase increased 31.76 21.09 63 8883 63359 29880173
Blood triglycerides increased 31.35 21.09 29 8917 13988 29929544
Oesophageal candidiasis 31.18 21.09 18 8928 4192 29939340
Fat tissue increased 31.03 21.09 9 8937 348 29943184
Pneumonia 30.56 21.09 33 8913 334273 29609259
Hepatic steatosis 30.02 21.09 29 8917 14764 29928768
Hepatitis B 29.84 21.09 20 8926 6052 29937480
Neonatal disorder 29.80 21.09 11 8935 915 29942617
Gamma-glutamyltransferase increased 29.54 21.09 40 8906 29310 29914222
Glycosuria 29.47 21.09 12 8934 1299 29942233
Vanishing bile duct syndrome 29.35 21.09 10 8936 658 29942874
Pneumococcal sepsis 29.05 21.09 10 8936 679 29942853
Death 28.71 21.09 39 8907 357244 29586288
Splenomegaly 28.44 21.09 27 8919 13453 29930079
Drug interaction 28.17 21.09 126 8820 199442 29744090
Dysphagia 28.00 21.09 56 8890 56642 29886890
Liver disorder 27.65 21.09 39 8907 29683 29913849
Drug ineffective 26.50 21.09 38 8908 340349 29603183
Hypophosphataemia 26.49 21.09 21 8925 8224 29935308
Portal vein thrombosis 26.16 21.09 15 8931 3449 29940083
Hypothalamic pituitary adrenal axis suppression 25.91 21.09 7 8939 208 29943324
Nephropathy toxic 25.73 21.09 23 8923 10616 29932916
Multiple-drug resistance 25.65 21.09 14 8932 2927 29940605
Ocular icterus 25.11 21.09 14 8932 3050 29940482
Hyperbilirubinaemia 24.99 21.09 28 8918 16914 29926618
Retinal degeneration 24.41 21.09 7 8939 260 29943272
Aplasia cutis congenita 23.59 21.09 6 8940 140 29943392
Mammoplasty 23.46 21.09 4 8942 10 29943522
Hepatitis 23.30 21.09 31 8915 22325 29921207
Dyspnoea 23.28 21.09 40 8906 333255 29610277
Blood phosphorus decreased 22.71 21.09 13 8933 2979 29940553
Renal tubular acidosis 22.62 21.09 11 8935 1811 29941721
Musculoskeletal toxicity 22.06 21.09 5 8941 70 29943462
Blood insulin increased 21.97 21.09 7 8939 373 29943159
Weight decreased 21.80 21.09 96 8850 150825 29792707
Lymphadenopathy 21.23 21.09 31 8915 24345 29919187

Pharmacologic Action:

SourceCodeDescription
ATC J05AF02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleoside and nucleotide reverse transcriptase inhibitors
FDA MoA N0000009947 Nucleoside Reverse Transcriptase Inhibitors
FDA EXT N0000175459 Nucleoside Analog
FDA EPC N0000175462 Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D009676 Noxae
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
MeSH PA D018894 Reverse Transcriptase Inhibitors
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:53756 reverse transcriptase inhibitor
CHEBI has role CHEBI:63090 purine-nucleoside phosphorylase 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
Metabolic alkalosis contraindication 1388004
Anuria contraindication 2472002 DOID:2983
Hypophosphatemia contraindication 4996001
Hypocalcemia contraindication 5291005
Alcoholism contraindication 7200002
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Constipation contraindication 14760008 DOID:2089
Pulmonary edema contraindication 19242006 DOID:11396
Retinal disorder contraindication 29555009 DOID:5679
Sarcoidosis contraindication 31541009 DOID:11335
Dehydration contraindication 34095006
Portal hypertension contraindication 34742003 DOID:10762
Hyperuricemia contraindication 35885006 DOID:1920
Hypertensive disorder contraindication 38341003 DOID:10763
Hypernatremia contraindication 39355002
Fecal impaction contraindication 44635007
Chronic heart failure contraindication 48447003
Acute nephropathy contraindication 58574008
Diarrhea contraindication 62315008
Optic neuritis contraindication 66760008 DOID:1210
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Hemorrhoids contraindication 70153002 DOID:9746
Diabetes mellitus contraindication 73211009 DOID:9351
Pancreatitis contraindication 75694006 DOID:4989
Oliguria contraindication 83128009
Kidney disease contraindication 90708001 DOID:557
Lactic acidosis contraindication 91273001 DOID:3650
Kidney stone contraindication 95570007
Gastrointestinal obstruction contraindication 126765001
Steatosis of liver contraindication 197321007
Impaired renal function disorder contraindication 197663003
Osteolysis contraindication 203522001
Myocardial dysfunction contraindication 233928007
Disease of liver contraindication 235856003 DOID:409
Chronic diarrhea contraindication 236071009
Aluminum intoxication contraindication 236546003
Peripheral edema contraindication 271809000
Peripheral nerve disease contraindication 302226006
Hypertriglyceridemia contraindication 302870006
Familial hyperkalemic periodic paralysis contraindication 304737009 DOID:14451
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Azotemia contraindication 445009001
Smokes tobacco daily contraindication 449868002
Severe dehydration contraindication 450316000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.94 acidic
pKa2 12.68 acidic
pKa3 1.93 Basic
pKa4 0.76 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
Reverse transcriptase/RNaseH Enzyme INHIBITOR IC50 5.21 WOMBAT-PK CHEMBL

External reference:

IDSource
4020118 VUID
N0000148104 NUI
D00296 KEGG_DRUG
4020118 VANDF
C0012133 UMLSCUI
CHEBI:490877 CHEBI
2DI PDB_CHEM_ID
CHEMBL1460 ChEMBL_ID
DB00900 DRUGBANK_ID
D016049 MESH_DESCRIPTOR_UI
135398739 PUBCHEM_CID
4833 IUPHAR_LIGAND_ID
6664 INN_ID
K3GDH6OH08 UNII
152494 RXNORM
4588 MMSL
63947 MMSL
854 MMSL
d00078 MMSL
003604 NDDF
19194001 SNOMEDCT_US
387105006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
VIDEX EC HUMAN PRESCRIPTION DRUG LABEL 1 0087-6671 CAPSULE, DELAYED RELEASE 125 mg ORAL NDA 28 sections
VIDEX EC HUMAN PRESCRIPTION DRUG LABEL 1 0087-6672 CAPSULE, DELAYED RELEASE 200 mg ORAL NDA 28 sections
VIDEX EC HUMAN PRESCRIPTION DRUG LABEL 1 0087-6673 CAPSULE, DELAYED RELEASE 250 mg ORAL NDA 28 sections
VIDEX EC HUMAN PRESCRIPTION DRUG LABEL 1 0087-6674 CAPSULE, DELAYED RELEASE 400 mg ORAL NDA 28 sections
Didanosine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0236 CAPSULE, DELAYED RELEASE PELLETS 250 mg ORAL ANDA 27 sections
Didanosine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0353 CAPSULE, DELAYED RELEASE PELLETS 400 mg ORAL ANDA 27 sections
Didanosine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5464 CAPSULE, DELAYED RELEASE PELLETS 250 mg ORAL ANDA 28 sections