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didanosine videx dideoxyinosine	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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	387.31	109.08	101	1334	29476	50574213
Viral mutation identified	342.77	109.08	56	1379	1573	50602116
Foetal exposure during pregnancy	331.83	109.08	88	1347	27271	50576418
Drug resistance	234.14	109.08	62	1373	18927	50584762
Caesarean section	173.38	109.08	47	1388	15592	50588097
Abortion induced	122.02	109.08	32	1403	9312	50594377
Pathogen resistance	122.01	109.08	29	1406	5660	50598029

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	723.42	63.98	136	2278	2958	29569155
Mitochondrial toxicity	685.22	63.98	125	2289	2286	29569827
Eyelid ptosis	612.72	63.98	129	2285	5057	29567056
Diplopia	432.60	63.98	117	2297	13401	29558712
Foetal exposure during pregnancy	349.64	63.98	123	2291	33744	29538369
Progressive external ophthalmoplegia	326.69	63.98	61	2353	1256	29570857
Pinealoblastoma	252.45	63.98	37	2377	146	29571967
Virologic failure	192.62	63.98	45	2369	2802	29569311
Viral mutation identified	187.87	63.98	43	2371	2445	29569668
Hepatic fibrosis	176.41	63.98	43	2371	3209	29568904
Retinal toxicity	161.03	63.98	28	2386	376	29571737
Pathogen resistance	145.90	63.98	45	2369	8071	29564042
Ophthalmoplegia	137.34	63.98	31	2383	1651	29570462
Drug-induced liver injury	136.43	63.98	55	2359	21600	29550513
Drug resistance	119.63	63.98	50	2364	21490	29550623
Mitochondrial myopathy	80.34	63.98	14	2400	190	29571923
Dysphagia	77.94	63.98	51	2363	54875	29517238
Congenital neoplasm	70.30	63.98	10	2404	30	29572083

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	818.57	62.14	145	2951	3882	64491754
Mitochondrial toxicity	764.06	62.14	129	2967	2577	64493059
Eyelid ptosis	585.02	62.14	126	2970	9399	64486237
Viral mutation identified	512.98	62.14	95	3001	3251	64492385
Diplopia	409.79	62.14	116	2980	26649	64468987
Progressive external ophthalmoplegia	358.40	62.14	61	3035	1266	64494370
Drug resistance	311.61	62.14	100	2996	35002	64460634
Pregnancy	272.46	62.14	80	3016	20785	64474851
Foetal exposure during pregnancy	250.69	62.14	55	3041	4421	64491215
Virologic failure	247.33	62.14	52	3044	3414	64492222
Pathogen resistance	231.22	62.14	63	3033	12480	64483156
Retinal toxicity	230.89	62.14	42	3054	1288	64494348
Hepatic fibrosis	186.40	62.14	45	3051	5507	64490129
Drug-induced liver injury	135.58	62.14	59	3037	47584	64448052
Ophthalmoplegia	133.59	62.14	30	3066	2672	64492964
Caesarean section	128.61	62.14	39	3057	11235	64484401
Abortion induced	98.83	62.14	28	3068	6360	64489276
Mitochondrial myopathy	82.88	62.14	14	3082	275	64495361
Premature delivery	80.03	62.14	31	3065	18558	64477078
Pinealoblastoma	77.59	62.14	11	3085	62	64495574
Dysphagia	76.30	62.14	53	3043	106759	64388877
Retinoblastoma	74.81	62.14	11	3085	83	64495553
Portal hypertension	72.97	62.14	22	3074	6197	64489439
Live birth	71.61	62.14	25	3071	11179	64484457
Multiple-drug resistance	67.77	62.14	21	3075	6481	64489155
Stillbirth	65.69	62.14	18	3078	3615	64492021
Lactic acidosis	64.88	62.14	39	3057	61371	64434265
Dyslipidaemia	64.40	62.14	22	3074	9220	64486416
Strongyloidiasis	63.80	62.14	17	3079	3073	64492563

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
6664	INN_ID
4833	IUPHAR_LIGAND_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