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didanosine videx dideoxyinosine	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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

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