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didanosine videx dideoxyinosine	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	55 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	38 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
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
MRTD (Maximum Recommended Therapeutic Daily Dose)	24.19 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
CL (Clearance)	11 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.40 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.95 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.77 L/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

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

FDA Adverse Event Reporting System (Female)

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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

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FDA Adverse Event Reporting System (Male)

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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

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FDA Adverse Event Reporting System (Geriatric)

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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

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FDA Adverse Event Reporting System (Pediatric)

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Pharmacologic Action:

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Source	Code	Description
ATC	J05AF02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Nucleoside and nucleotide reverse transcriptase inhibitors
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
FDA EPC	N0000175462	Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
FDA EXT	N0000175459	Nucleoside Analog
FDA MoA	N0000009947	Nucleoside Reverse Transcriptase Inhibitors
MeSH PA	D019380	Anti-HIV Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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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

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🐶 Veterinary Drug Use

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🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.94	acidic
pKa2	12.68	acidic
pKa3	1.93	Basic
pKa4	0.76	Basic

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Orange Book patent data (new drug applications)

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Orange Book exclusivity data (new drug applications)

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Bioactivity Summary:

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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

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External reference:

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ID	Source
2DI	PDB_CHEM_ID
003604	NDDF
135398739	PUBCHEM_CID
152494	RXNORM
19194001	SNOMEDCT_US
387105006	SNOMEDCT_US
4020118	VUID
4020118	VANDF
4588	MMSL
4833	IUPHAR_LIGAND_ID

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Pharmaceutical products:

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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

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