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Compound Detail

CHEMBL1460

DIDANOSINE
💊 Approved Drug
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💊 Approved Drug
O=c1[nH]cnc2c1ncn2[C@H]1CC[C@@H](CO)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1460
Name DIDANOSINE
Phase Approved
Structure Type MOL
InChI Key BXZVVICBKDXVGW-NKWVEPMBSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1383

Known Names

(-)-didanosine BMY-40900 Ddi Didanosina Didanosine Didanosine system suitability mixture Didanosinum Dideoxyinosine (ddi) NSC-612049 Videx Videx ec
8
Targets
116
Activities
3
Assay Types
16
PK Parameters
20
Publications
11
Known Names
7
Indications
1
Mechanisms

Molecular Properties

236.2
MW (Da)
-0.21
ALogP
6
HBA
2
HBD
93.0
PSA (Ų)
0.75
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -nosine
USAN Year 1990

Extended Properties

Molecular Formula C10H12N4O3
MW 236.23
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness 0.68

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase ✓ ✓

Indications

HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome AIDS-Related Complex Tuberculosis AIDS Dementia Complex Lymphoma

ATC Classification

J05AF02
didanosine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
metabolic toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

EC50 77 meas. best 8.25
IC50 38 meas. best 7.0
Kd 1 meas. best 4.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.25 5.0674 5.6 61
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.0 5.48 100.0 17
ADMET
CHEMBL612558
 IC50 6.52 6.52 300.0 1
C8166
CHEMBL614533
 EC50 6.05 6.05 900.0 1
C8166
CHEMBL614533
 IC50 6.0 6.0 1000.0 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 5.64 4.737 2270.0 10
Human immunodeficiency virus 2
CHEMBL380
 IC50 5.57 5.46 2710.0 5
MT4
CHEMBL388
 IC50 5.57 4.7475 2710.0 8
CEM-V
CHEMBL614549
 EC50 5.55 5.55 2800.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 5.27 5.21 5370.0 2
MT4
CHEMBL388
 EC50 5.0 4.9625 10000.0 4
Albumin
CHEMBL3253
 Kd 4.36 4.36 44000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2100.0 ng.hr.mL-1 Rattus norvegicus
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 134.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.2 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 66.0 mL.min-1.kg-1 Rattus norvegicus
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Macaca
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 23.0 mL.min-1.kg-1 Canis lupus familiaris
Fu 0.95 - Homo sapiens
Fu 0.95 - Homo sapiens
MRT 1.2 hr Homo sapiens
T1/2 1.0 hr Rattus norvegicus
T1/2 1.4 hr Homo sapiens
T1/2 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 5.6 nM 8.25 Antiviral activity against HIV1 RF in human H9 cells assessed as inhibition of v... 11430019
Human immunodeficiency virus 1 EC50 = 5.6 nM 8.25 Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of v... 11430019
Human immunodeficiency virus 1 IC50 = 100.0 nM 7.0 Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of... 19596885
ADMET IC50 = 300.0 nM 6.52 Anti-HIV activity by using phytohemagglutininin-stimulated peripheral blood mono... 8648601
Human immunodeficiency virus 1 IC50 = 490.0 nM 6.31 Antiviral activity against HIV1 infected in human MT2 cells assessed as inhibiti... 19596885
Human immunodeficiency virus 1 IC50 = 760.0 nM 6.12 Antiviral activity against HIV-1 infected in PBMC (unknown origin) assessed as i... 37393791
C8166 EC50 = 900.0 nM 6.05 Compound was evaluated for the inhibition of p24 viral antigen production in C-8... -
C8166 IC50 = 1000.0 nM 6.0 Antiviral activity was evaluated by inhibition of HIV-1 replication in CD4+ lymp... -
Human immunodeficiency virus 1 IC50 = 1280.0 nM 5.89 Concentration required to inhibit HIV replication by 50% 1619614
Human immunodeficiency virus 1 EC50 = 2100.0 nM 5.68 Antiviral activity against HIV1 15104498
Human immunodeficiency virus 1 IC50 = 2300.0 nM 5.64 Antiviral activity against HIV1 infected in human HeLa P4/R5 cells assessed as i... 19596885
Human immunodeficiency virus 2 EC50 = 2270.0 nM 5.64 Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as prot... 25682562
Human immunodeficiency virus 1 EC50 = 2560.0 nM 5.59 Antiviral activity against HIV1 3B infected infected in human MT4 cells assessed... 25682562
Human immunodeficiency virus 2 IC50 = 2710.0 nM 5.57 Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as inhi... 20638854
MT4 IC50 = 2710.0 nM 5.57 Concentration required to protect the cell against HIV-2 strain ROD viral cytopa... 15149669
Human immunodeficiency virus 2 IC50 = 2710.0 nM 5.57 Antiviral activity against HIV2 ROD in MT4 cells after 4 days by MTT method 17095124
Human immunodeficiency virus 2 IC50 = 2710.0 nM 5.57 Antiviral activity against HIV2 ROD in human MT4 cells assessed as inhibition of... 17869386
Human immunodeficiency virus 2 IC50 = 2710.0 nM 5.57 Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as inhi... 18692274
CEM-V EC50 = 2800.0 nM 5.55 Inhibition of HIV-1 replication in CEM-V cells 9240351
Human immunodeficiency virus 1 IC50 = 3418.0 nM 5.47 Antiviral activity against wild type HIV-1 isolate infected in human PBMC cells ... -

Literature References

PubMed DOI Target Context # Activities
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 62
2106581 10.1021/jm00165a015 H9 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
18541728 10.1128/aac.00434-08 ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19596885 10.1128/aac.00392-09 Human immunodeficiency virus 1 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
19433557 10.1128/aac.00364-09 Rattus norvegicus 10
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
15920768 10.1002/jps.20373 ADMET 8
8426365 10.1021/jm00055a009 MT4 7
7707321 10.1021/jm00007a015 PBMC 6
17876005 10.1128/aac.00687-07 Human immunodeficiency virus 1 5
17470651 10.1128/aac.00039-07 ADMET 5
17470651 10.1128/aac.00039-07 H9c2 5
15658873 10.1021/jm049711o ADMET 5
19223644 10.1128/aac.01593-08 Human immunodeficiency virus 1 4
2033586 10.1021/jm00109a012 ATH-8 cell line 4
18426954 10.1124/dmd.108.020479 ADMET 4

Data from ChEMBL 36 via Core Engine