didanosine 🐶 Veterinary Use | 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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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: -1.12
  • 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 µM/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 380.86 99.24 101 1437 36735 63450749
Viral mutation identified 374.51 99.24 60 1478 1750 63485734
Foetal exposure during pregnancy 336.61 99.24 89 1449 31873 63455611
Drug resistance 251.28 99.24 66 1472 22867 63464617
Caesarean section 176.69 99.24 47 1491 16985 63470499
Pathogen resistance 133.72 99.24 31 1507 6367 63481117
Abortion induced 128.98 99.24 33 1505 10209 63477275
Premature delivery 105.30 99.24 36 1502 30245 63457239
Premature rupture of membranes 103.28 99.24 24 1514 4969 63482515
Stillbirth 101.11 99.24 25 1513 6725 63480759

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 791.48 59.09 147 2525 3197 34951062
Mitochondrial toxicity 743.96 59.09 135 2537 2564 34951695
Eyelid ptosis 664.87 59.09 139 2533 5627 34948632
Diplopia 460.42 59.09 127 2545 16716 34937543
Progressive external ophthalmoplegia 363.75 59.09 67 2605 1368 34952891
Foetal exposure during pregnancy 346.87 59.09 124 2548 37977 34916282
Pinealoblastoma 261.53 59.09 38 2634 151 34954108
Viral mutation identified 253.57 59.09 56 2616 2898 34951361
Virologic failure 233.73 59.09 54 2618 3426 34950833
Pathogen resistance 188.75 59.09 56 2616 9426 34944833
Hepatic fibrosis 173.99 59.09 45 2627 4562 34949697
Retinal toxicity 167.22 59.09 29 2643 411 34953848
Ophthalmoplegia 158.46 59.09 35 2637 1805 34952454
Drug resistance 137.02 59.09 57 2615 25870 34928389
Drug-induced liver injury 131.18 59.09 57 2615 28775 34925484
Mitochondrial myopathy 81.18 59.09 14 2658 191 34954068
Portal hypertension 80.76 59.09 24 2648 4038 34950221
Dysphagia 79.85 59.09 53 2619 62328 34891931
Congenital neoplasm 70.95 59.09 10 2662 30 34954229
Strongyloidiasis 62.63 59.09 18 2654 2693 34951566

FDA Adverse Event Reporting System (Geriatric)

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 898.44 61.02 156 3263 4169 79736800
Mitochondrial toxicity 829.77 61.02 139 3280 2975 79737994
Eyelid ptosis 636.99 61.02 136 3283 10908 79730061
Viral mutation identified 606.93 61.02 110 3309 3748 79737221
Diplopia 441.61 61.02 126 3293 33340 79707629
Progressive external ophthalmoplegia 401.79 61.02 67 3352 1378 79739591
Drug resistance 349.48 61.02 111 3308 42102 79698867
Virologic failure 283.54 61.02 59 3360 4132 79736837
Pathogen resistance 281.89 61.02 74 3345 14268 79726701
Pregnancy 261.36 61.02 80 3339 26771 79714198
Foetal exposure during pregnancy 253.60 61.02 57 3362 5733 79735236
Retinal toxicity 246.28 61.02 44 3375 1367 79739602
Hepatic fibrosis 199.41 61.02 49 3370 7231 79733738
Ophthalmoplegia 156.93 61.02 34 3385 2878 79738091
Drug-induced liver injury 132.63 61.02 62 3357 66055 79674914
Caesarean section 128.85 61.02 39 3380 12496 79728473
Retinopathy 115.73 61.02 28 3391 3863 79737106
Abortion induced 103.53 61.02 29 3390 7080 79733889
Multiple-drug resistance 84.50 61.02 26 3393 8782 79732187
Mitochondrial myopathy 84.08 61.02 14 3405 283 79740686
Dysphagia 79.94 61.02 55 3364 122081 79618888
Pinealoblastoma 78.83 61.02 11 3408 62 79740907
Portal hypertension 76.83 61.02 23 3396 7085 79733884
Premature delivery 76.40 61.02 31 3388 23436 79717533
Retinoblastoma 75.94 61.02 11 3408 84 79740885
Dyslipidaemia 73.45 61.02 25 3394 11608 79729361
Strongyloidiasis 66.44 61.02 18 3401 3880 79737089
Stillbirth 66.18 61.02 18 3401 3937 79737032
Lactic acidosis 64.03 61.02 39 3380 70320 79670649
Live birth 61.83 61.02 25 3394 18719 79722250
Optic nerve neoplasm 61.38 61.02 8 3411 24 79740945

FDA Adverse Event Reporting System (Pediatric)

None

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
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:36044 antiviral drugs
CHEBI has role CHEBI:53756 reverse transcriptase inhibitors
CHEBI has role CHEBI:63090 purine-nucleoside phosphorylase inhibitors
CHEBI has role CHEBI:176497 geroprotectors
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

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
152494 RXNORM
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
4588 MMSL
63947 MMSL
854 MMSL
d00078 MMSL
003604 NDDF
19194001 SNOMEDCT_US
387105006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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