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Compound Detail

CHEMBL105318

ALOVUDINE
🧪 Phase II
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🧪 Phase II
Cc1cn([C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL105318
Name ALOVUDINE
Phase Phase II
Structure Type MOL
InChI Key UXCAQJAQSWSNPQ-XLPZGREQSA-N

Known Names

Alovudina Alovudine CL 184,824 CL 184824 CL-184,824 CL-184824 MIV-310 MIV310 NSC-140025
10
Targets
25
Activities
3
Assay Types
0
PK Parameters
20
Publications
9
Known Names
1
Indications

Molecular Properties

244.2
MW (Da)
-0.54
ALogP
5
HBA
2
HBD
84.3
PSA (Ų)
0.73
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -vudine
USAN Year 1992

Extended Properties

Molecular Formula C10H13FN2O4
MW 244.22
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.51

Indications

HIV Infections

Activity Summary

EC50 18 meas. best 9.0
IC50 6 meas. best 8.7
Ki 1 meas. best 4.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CCRF-CEM
CHEMBL382
 EC50 9.0 9.0 1.0 1
MT4
CHEMBL388
 EC50 9.0 9.0 1.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.8 7.6517 1.6 6
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.7 7.9875 2.0 4
Human immunodeficiency virus 2
CHEMBL380
 EC50 8.49 6.8 3.2 3
L1210
CHEMBL386
 IC50 7.09 7.09 81.0 1
Unchecked
CHEMBL612545
 EC50 6.1 5.79 800.0 2
ADMET
CHEMBL612558
 EC50 6.0 6.0 1000.0 1
Human adenovirus 2
CHEMBL613715
 EC50 5.92 5.1933 1200.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.0 5.0 10000.0 1
Thymidylate kinase
CHEMBL2361
 Ki 4.55 4.55 28000.0 1
CCRF-CEM
CHEMBL382
 IC50 4.41 4.41 39000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CCRF-CEM EC50 = 1.0 nM 9.0 Tested for in vitro drug concentration which produces 50% survival of HIV-1 infe... 7932583
MT4 EC50 = 1.0 nM 9.0 Effective concentration achieving 50% protection of MT-4 cells against the cytop... 1697345
Human immunodeficiency virus 1 EC50 = 1.6 nM 8.8 Antiviral activity against HIV1 HE strain infected in CEM/0 cells assessed as in... 36099330
Human immunodeficiency virus 1 IC50 = 2.0 nM 8.7 Antiviral activity against wild type HIV1 clade B 94US3393IN clinical isolate in... 22352809
Human immunodeficiency virus 1 IC50 = 2.0 nM 8.7 Antiviral activity against wild type HIV1 clade C 98USMSC5016 clinical isolate i... 22352809
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against HIV-1 subtype B US/92/727 infected in PBMC assessed a... 22858097
Human immunodeficiency virus 2 EC50 = 3.2 nM 8.49 Antiviral activity against HIV2 ROD infected in CEM/0 cells assessed as inhibiti... 36099330
Human immunodeficiency virus 1 EC50 = 6.2 nM 8.21 Antiretroviral activity against HIV-1 3B infected in human CEM/0 cells expressin... 24751439
Human immunodeficiency virus 2 EC50 = 18.0 nM 7.75 Antiretroviral activity against HIV-2 ROD infected in human CEM/0 cells expressi... 24751439
Human immunodeficiency virus 1 EC50 = 20.0 nM 7.7 Antiviral activity against HIV-1 subtype 3B infected in CEM-SS cells assessed as... 22858097
Human immunodeficiency virus 1 IC50 = 26.0 nM 7.58 Antiviral activity against NNRTI-resistant HIV1 clade B A-17 clinical isolate in... 22352809
L1210 IC50 = 81.0 nM 7.09 Cytostatic activity against mouse L1210 cells assessed as inhibition of cell pro... 24751439
Human immunodeficiency virus 1 IC50 = 107.3 nM 6.97 Antiviral activity against multidrug-resistant HIV1 clade B 4775-5 clinical isol... 22352809
Human immunodeficiency virus 1 EC50 = 400.0 nM 6.4 Antiviral activity against HIV1 BaL infected in HeLa P4/R5 cells assessed as red... 22352809
Human immunodeficiency virus 1 EC50 = 800.0 nM 6.1 Antiviral activity against HIV1 3B infected in HeLa P4/R5 cells assessed as redu... 22352809
Unchecked EC50 = 800.0 nM 6.1 Inhibition of HIV1 3B dinucleoside reverse transcriptase infected in human P4R5 ... 28351588
ADMET EC50 = 1000.0 nM 6.0 Effective concentration required to inhibit 50% of HIV-1 in peripheral blood mon... 9341906
Human adenovirus 2 EC50 = 1200.0 nM 5.92 Antiviral activity against Adenovirus 2 infected in HEL cells assessed as inhibi... 29880251
Unchecked EC50 = 3300.0 nM 5.48 Inhibition of HIV1 BaL dinucleoside reverse transcriptase infected in human P4R5... 28351588
Human adenovirus 2 EC50 = 10000.0 nM 5.0 Antiviral activity against Human adenovirus 2 infected in HEL cells assessed as ... 27750154

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22352809 10.1021/jm201551m Human immunodeficiency virus 1 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3497272 10.1021/jm00391a003 MT4 7
22858097 10.1016/j.bmcl.2012.07.037 Human immunodeficiency virus 1 4
24751439 10.1016/j.bmcl.2014.03.092 Human immunodeficiency virus 2 3
8381182 10.1021/jm00055a006 Thymidine kinase, cytosolic 3
28351588 10.1016/j.bmcl.2017.03.031 Unchecked 3
3497272 10.1021/jm00391a003 ATH-8 cell line 2
3172142 10.1021/jm00118a033 MT4 2
9341906 10.1021/jm960694f ADMET 2
24751439 10.1016/j.bmcl.2014.03.092 CCRF-CEM 2
22858097 10.1016/j.bmcl.2012.07.037 ADMET 2
1697345 10.1021/jm00171a023 MT4 2
2754700 10.1021/jm00128a013 Human immunodeficiency virus type 1 reverse transcriptase 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
27742238 10.1016/j.bmcl.2016.09.071 NON-PROTEIN TARGET 2
1527788 10.1021/jm00096a011 MT4 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.1016/S0960-894X(01)81057-X T-cell line 2

Data from ChEMBL 36 via Core Engine