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

Stem definition	Drug id	CAS RN
antivirals	869	69655-05-6

Description:

Molecule	Description
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didanosine videx dideoxyinosine	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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

Molecule

Description

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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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:

Dose	Unit	Route
0.40	g	O

ADMET properties:

Property	Value	Reference
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:

Date	Agency	Company	Orphan
Oct. 9, 1991	FDA	BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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|

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Reverse transcriptase/RNaseH	Enzyme		Q72549_9HIV1	INHIBITOR	IC50	5.21		WOMBAT-PK	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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