didanosine ๐Ÿถ 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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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 ยตM/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 383.22 105.10 101 1386 32932 56257648
Viral mutation identified 372.63 105.10 60 1427 1654 56288926
Foetal exposure during pregnancy 333.42 105.10 91 1396 33732 56256848
Drug resistance 252.87 105.10 66 1421 20476 56270104
Caesarean section 175.33 105.10 47 1440 16044 56274536
Pathogen resistance 133.04 105.10 31 1456 5969 56284611
Abortion induced 128.13 105.10 33 1454 9612 56280968
Premature delivery 106.23 105.10 36 1451 27024 56263556

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 771.11 60 145 2472 3119 31691608
Mitochondrial toxicity 733.59 60 134 2483 2439 31692288
Eyelid ptosis 656.17 60 138 2479 5317 31689410
Diplopia 467.87 60 126 2491 14036 31680691
Progressive external ophthalmoplegia 347.79 60 65 2552 1329 31693398
Foetal exposure during pregnancy 343.76 60 128 2489 40748 31653979
Pinealoblastoma 259.01 60 38 2579 149 31694578
Viral mutation identified 220.09 60 50 2567 2719 31692008
Virologic failure 213.44 60 50 2567 3115 31691612
Hepatic fibrosis 168.42 60 43 2574 3831 31690896
Pathogen resistance 167.60 60 51 2566 8650 31686077
Retinal toxicity 158.83 60 28 2589 404 31694323
Ophthalmoplegia 157.17 60 35 2582 1733 31692994
Drug resistance 131.54 60 55 2562 23398 31671329
Drug-induced liver injury 129.52 60 55 2562 24308 31670419
Portal hypertension 80.99 60 24 2593 3701 31691026
Mitochondrial myopathy 80.11 60 14 2603 191 31694536
Dysphagia 79.92 60 53 2564 57623 31637104
Congenital neoplasm 70.18 60 10 2607 30 31694697

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 876.18 59.20 154 3150 4062 70921078
Mitochondrial toxicity 820.79 59.20 138 3166 2772 70922368
Eyelid ptosis 632.22 59.20 135 3169 9967 70915173
Viral mutation identified 578.84 59.20 106 3198 3516 70921624
Diplopia 448.33 59.20 125 3179 28022 70897118
Progressive external ophthalmoplegia 384.31 59.20 65 3239 1339 70923801
Drug resistance 343.11 59.20 109 3195 38081 70887059
Virologic failure 272.08 59.20 57 3247 3793 70921347
Pathogen resistance 267.13 59.20 71 3233 13208 70911932
Foetal exposure during pregnancy 266.61 59.20 60 3244 5585 70919555
Pregnancy 264.43 59.20 80 3224 23701 70901439
Retinal toxicity 231.32 59.20 42 3262 1314 70923826
Hepatic fibrosis 182.30 59.20 45 3259 6222 70918918
Ophthalmoplegia 155.28 59.20 34 3270 2781 70922359
Caesarean section 128.63 59.20 39 3265 11568 70913572
Drug-induced liver injury 127.98 59.20 59 3245 56054 70869086
Abortion induced 103.18 59.20 29 3275 6596 70918544
Multiple-drug resistance 87.00 59.20 26 3278 7329 70917811
Mitochondrial myopathy 83.20 59.20 14 3290 277 70924863
Dysphagia 79.77 59.20 55 3249 112779 70812361
Pinealoblastoma 77.92 59.20 11 3293 62 70925078
Premature delivery 76.82 59.20 31 3273 21273 70903867
Retinoblastoma 73.31 59.20 11 3293 100 70925040
Portal hypertension 72.69 59.20 22 3282 6470 70918670
Live birth 67.29 59.20 25 3279 13754 70911386
Stillbirth 65.40 59.20 18 3286 3787 70921353
Lactic acidosis 63.88 59.20 39 3265 64985 70860155
Dyslipidaemia 63.65 59.20 22 3282 9838 70915302
Strongyloidiasis 61.17 59.20 17 3287 3706 70921434
Abortion spontaneous 60.77 59.20 28 3276 26451 70898689
Optic nerve neoplasm 60.72 59.20 8 3296 24 70925116
Treatment failure 59.42 59.20 51 3253 144091 70781049

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ 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