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Compound Detail

CHEMBL788

IDOXURIDINE
💊 Approved Drug
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💊 Approved Drug
O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1I
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL788
Name IDOXURIDINE
Phase Approved
Structure Type MOL
InChI Key XQFRJNBWHJMXHO-RRKCRQDMSA-N
Therapeutic ✓ Yes

Known Names

5-IUDR 5IUDR ALLERGAN-211 ALLERGAN211 Dendrid Herplex Idox Idoxuridina Idoxuridine Idoxuridinum Joddeoxiuridin Kerecid +5 more
11
Targets
38
Activities
3
Assay Types
2
PK Parameters
20
Publications
17
Known Names
3
Indications
1
Mechanisms

Molecular Properties

354.1
MW (Da)
-1.22
ALogP
6
HBA
3
HBD
104.5
PSA (Ų)
0.58
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1963
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -uridine
USAN Year 1962

Extended Properties

Molecular Formula C9H11IN2O5
MW 354.10
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.91

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Eye Infections Virus Diseases Leukemia

ATC Classification

D06BB01
idoxuridine
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
J05AB02
idoxuridine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE
S01AD01
idoxuridine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

EC50 22 meas. best 6.4
IC50 9 meas. best 6.17
Ki 7 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thymidine kinase, cytosolic
CHEMBL2883
 Ki 7.05 7.05 90.0 1
Unchecked
CHEMBL612545
 Ki 7.05 6.875 90.0 2
Human alphaherpesvirus 1
CHEMBL377
 Ki 6.4 6.07 400.0 2
Cowpox virus
CHEMBL612672
 EC50 6.4 5.3763 400.0 8
Unchecked
CHEMBL612545
 IC50 6.17 6.17 680.6 1
Vaccinia virus
CHEMBL613493
 EC50 6.0 5.3657 1000.0 7
Thymidine kinase
CHEMBL1075062
 IC50 5.82 5.82 1500.0 1
Cowpox virus
CHEMBL612672
 IC50 5.7 5.7 2000.0 1
Human alphaherpesvirus 2
CHEMBL370
 EC50 5.62 4.865 2400.0 2
L5178Y
CHEMBL614720
 IC50 5.62 5.4125 2400.0 4
Human alphaherpesvirus 1
CHEMBL377
 EC50 5.55 5.55 2800.0 1
Human alphaherpesvirus 2
CHEMBL370
 Ki 5.4 5.4 3980.0 1
Vaccinia virus
CHEMBL613493
 IC50 5.22 5.22 6000.0 1
Macacine alphaherpesvirus 1
CHEMBL3301403
 EC50 5.07 5.01 8500.0 2
Ramos
CHEMBL614629
 EC50 4.32 4.32 47900.0 1
Jurkat
CHEMBL397
 EC50 4.1 4.1 79700.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.24 hr Mus musculus
T1/2 22.6 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 90.0 nM 7.05 Inhibition constant against HSV-1 TK 14584954
Thymidine kinase, cytosolic Ki = 90.0 nM 7.05 Binding affinity constant against HSV-1 thymidine kinase 14584954
Unchecked Ki = 200.0 nM 6.7 Competitive inhibition of HSV-1 pyrimidine deoxythymidine kinase using 2-[14C]de... 214555
Human alphaherpesvirus 1 Ki = 400.0 nM 6.4 Kinetic inhibition constant against herpes simplex virus type I pyrimidine deoxy... 6244411
Cowpox virus EC50 = 400.0 nM 6.4 Antiviral activity against TK+ cowpox virus delta crmA in HFF cells 16821766
Unchecked IC50 = 680.6 nM 6.17 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Vaccinia virus EC50 = 1000.0 nM 6.0 Antiviral activity against cidofovir-resistant Vaccinia virus 15A harboring DNA ... 19029322
Cowpox virus EC50 = 1100.0 nM 5.96 Antiviral activity against TK+ Cowpox virus Delta crmA in HFF cells after 48 hrs... 17325220
Thymidine kinase IC50 = 1500.0 nM 5.82 Inhibition of Herpes B virus recombinant thymidine kinase-mediated [3H]TdR phosp... 17438061
Cowpox virus EC50 = 1800.0 nM 5.75 Antiviral activity against Cowpox virus Brighton in HFF cells after 1 hr by plaq... 17325220
Human alphaherpesvirus 1 Ki = 1840.0 nM 5.74 Binding affinity against HSV-1(KOS) 2989522
Cowpox virus EC50 = 2000.0 nM 5.7 Antiviral activity against cowpox virus in HFF cells by plaque reduction assay 16821766
Cowpox virus IC50 = 2000.0 nM 5.7 Antiviral activity against Cowpox virus 19112024
Cowpox virus EC50 = 2200.0 nM 5.66 Antiviral activity against thymidine kinase positive Cowpox virus harboring delt... 19029322
Vaccinia virus EC50 = 2400.0 nM 5.62 Antiviral activity against ST-246-resistant Vaccinia virus VV911 harboring DNA p... 19029322
Human alphaherpesvirus 2 EC50 = 2400.0 nM 5.62 Antiviral activity against HSV2 MS infected in HFF after 3 days by plaque reduct... 19770274
L5178Y IC50 = 2400.0 nM 5.62 In vitro growth inhibition of FdUrd resistant L5178Y-Resistant murine leukemia c... 11101356
Human alphaherpesvirus 1 EC50 = 2800.0 nM 5.55 Antiviral activity against Herpes simplex virus 1 F infected in african green mo... 17438061
Vaccinia virus EC50 = 2800.0 nM 5.55 Antiviral activity against Vaccinia virus WR infected in HFF assessed as reducti... 19029322
L5178Y IC50 = 3800.0 nM 5.42 In vitro growth inhibition of L5178Y-Parental murine leukemia cells 11101356

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2547072 10.1021/jm00128a029 Oryctolagus cuniculus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7877148 10.1021/jm00005a010 E6SM 11
3027341 10.1021/jm00385a026 Oryctolagus cuniculus 9
6300403 10.1021/jm00358a029 Oryctolagus cuniculus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3039140 10.1021/jm00391a036 NON-PROTEIN TARGET 7
2989522 10.1021/jm00145a010 Human alphaherpesvirus 1 7
7877148 10.1021/jm00005a010 HEL 7
2842506 10.1021/jm00117a026 Human alphaherpesvirus 1 6
6267280 10.1021/jm00136a007 PRK 6
6245212 10.1021/jm00177a008 Oryctolagus cuniculus 5
3037079 10.1021/jm00390a013 Vero 5
218006 10.1021/jm00187a005 Human alphaherpesvirus 1 5
6302254 10.1021/jm00359a008 PRK 5
7932543 10.1021/jm00045a025 NON-PROTEIN TARGET 5
3037079 10.1021/jm00390a013 HEp-2 5
19029322 10.1128/aac.01257-08 Vaccinia virus 5
11101356 10.1021/jm000975u L5178Y 4

Data from ChEMBL 36 via Core Engine