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didanosine videx dideoxyinosine	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	-0.991		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	9.141		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	1.690	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	1.377	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	89	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	92.210	%	High	1
herg	hERG pIC50	3.626	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	1.197	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	3.192	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	85.170	%	High	1
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	2.938		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	2.254		High	1
mppb	Mouse plasma protein binding (% unbound)	92.630		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	2.559		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pppb	Pig plasma protein binding (% unbound)	93.680	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	1.517	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	95.450	%	High	1
rppb	Rat plasma protein binding (% unbound)	85.650	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	883.080	uM	High	1

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
Viral mutation identified	393.06	104.02	61	1568	1964	90624854
Pregnancy	358.35	104.02	101	1528	61946	90564872
Foetal exposure during pregnancy	336.67	104.02	89	1540	42886	90583932
Drug resistance	257.02	104.02	67	1562	30382	90596436
Retinal toxicity	196.58	104.02	32	1597	1390	90625428
Caesarean section	186.52	104.02	47	1582	18530	90608288
Pathogen resistance	140.97	104.02	32	1597	8083	90618735
Abortion induced	133.86	104.02	33	1596	11855	90614963
Stillbirth	132.79	104.02	30	1599	7413	90619405
Virologic failure	110.72	104.02	21	1608	2203	90624615
Premature rupture of membranes	107.84	104.02	24	1605	5534	90621284
Premature delivery	107.10	104.02	36	1593	38726	90588092

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	838.19	52.77	153	2832	3297	42615053
Mitochondrial toxicity	739.74	52.77	132	2853	2483	42615867
Eyelid ptosis	673.88	52.77	142	2843	6519	42611831
Diplopia	443.00	52.77	126	2859	20190	42598160
Progressive external ophthalmoplegia	377.19	52.77	68	2917	1343	42617007
Foetal exposure during pregnancy	330.95	52.77	124	2861	47187	42571163
Pinealoblastoma	265.23	52.77	38	2947	149	42618201
Viral mutation identified	251.68	52.77	56	2929	3275	42615075
Virologic failure	246.89	52.77	57	2928	3937	42614413
Retinal toxicity	218.95	52.77	37	2948	490	42617860
Pathogen resistance	195.97	52.77	59	2926	11391	42606959
Hepatic fibrosis	175.36	52.77	45	2940	4827	42613523
Ophthalmoplegia	166.19	52.77	37	2948	2163	42616187
Drug resistance	126.49	52.77	57	2928	34191	42584159
Drug-induced liver injury	123.52	52.77	58	2927	38215	42580135
Portal hypertension	91.95	52.77	27	2958	4760	42613590
Dysphagia	86.21	52.77	57	2928	72662	42545688
Mitochondrial myopathy	82.40	52.77	14	2971	191	42618159
Congenital neoplasm	71.82	52.77	10	2975	30	42618320
Blood lactic acid increased	70.50	52.77	25	2960	8014	42610336
Strongyloidiasis	59.99	52.77	18	2967	3413	42614937
Dyslipidaemia	59.43	52.77	23	2962	9395	42608955
Optic nerve neoplasm	56.51	52.77	8	2977	28	42618322
Premature baby	56.38	52.77	29	2956	23124	42595226
Multiple-drug resistance	53.85	52.77	20	2965	7302	42611048
Retinopathy	53.33	52.77	15	2970	2266	42616084

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	973.74	64.04	162	3495	4362	110581280
Mitochondrial toxicity	838.35	64.04	136	3521	3109	110582533
Eyelid ptosis	663.89	64.04	139	3518	13188	110572454
Viral mutation identified	627.08	64.04	111	3546	4308	110581334
Diplopia	441.29	64.04	125	3532	41769	110543873
Progressive external ophthalmoplegia	427.59	64.04	68	3589	1352	110584290
Retinal toxicity	417.02	64.04	68	3589	1591	110584051
Drug resistance	350.26	64.04	112	3545	56262	110529380
Virologic failure	324.69	64.04	65	3592	4887	110580755
Pathogen resistance	305.14	64.04	78	3579	17594	110568048
Foetal exposure during pregnancy	253.58	64.04	57	3600	7448	110578194
Pregnancy	231.18	64.04	80	3577	50987	110534655
Hepatic fibrosis	201.83	64.04	48	3609	8018	110577624
Ophthalmoplegia	170.42	64.04	36	3621	3514	110582128
Caesarean section	135.09	64.04	39	3618	13778	110571864
Retinopathy	129.94	64.04	30	3627	4399	110581243
Portal hypertension	119.43	64.04	32	3625	8605	110577037
Drug-induced liver injury	115.60	64.04	63	3594	120004	110465638
Abortion induced	107.52	64.04	29	3628	7990	110577652
Multiple-drug resistance	101.64	64.04	31	3626	13204	110572438
Drug interaction	92.02	64.04	97	3560	500086	110085556
Dysphagia	91.17	64.04	59	3598	153541	110432101
Dyslipidaemia	87.82	64.04	29	3628	15936	110569706
Mitochondrial myopathy	81.77	64.04	14	3643	440	110585202
Pinealoblastoma	81.69	64.04	11	3646	62	110585580
Retinoblastoma	79.14	64.04	11	3646	81	110585561
Premature delivery	76.19	64.04	31	3626	30601	110555041
Stillbirth	69.47	64.04	18	3639	4246	110581396
Strongyloidiasis	66.68	64.04	18	3639	4968	110580674

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
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000963	Antimetabolites
MeSH PA	D000998	Antiviral Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D018894	Reverse Transcriptase Inhibitors
MeSH PA	D019380	Anti-HIV Agents
MeSH PA	D019384	Nucleic Acid Synthesis Inhibitors
CHEBI has role	CHEBI:22587	antiviral agent
CHEBI has role	CHEBI:33231	antitubercular agent
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:36044	antiviral drug
CHEBI has role	CHEBI:53756	HIV-1 reverse transcriptase inhibitor
CHEBI has role	CHEBI:63090	EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
CHEBI has role	CHEBI:64946	anti-HIV agent
CHEBI has role	CHEBI:176497	geroprotector

Related Drugs by ATC class:

J05AF Nucleoside and nucleotide reverse transcriptase inhibitors 12 drugs

abacavir adefovir dipivoxil clevudine emtricitabine entecavir lamivudine stavudine telbivudine tenofovir alafenamide tenofovir disoproxil zalcitabine zidovudine

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