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Compound Detail

CHEMBL467

HYDROXYUREA
💊 Approved Drug
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💊 Approved Drug

Basic Information

ChEMBL ID CHEMBL467
Name HYDROXYUREA
Phase Approved
Structure Type MOL
InChI Key VSNHCAURESNICA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Droxia Hidroxicarbamida Hydrea Hydroxycarbamide Hydroxyurea NSC-32065 Siklos SQ 1089 SQ-1089 Xromi
10
Targets
28
Activities
3
Assay Types
8
PK Parameters
20
Publications
10
Known Names
20
Indications
1
Mechanisms

Molecular Properties

76.0
MW (Da)
-0.96
ALogP
2
HBA
3
HBD
75.3
PSA (Ų)
0.26
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1967
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1965

Extended Properties

Molecular Formula CH4N2O2
MW 76.05
Aromatic Rings 0
Heavy Atoms 5
NP-Likeness -0.32

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ribonucleoside-diphosphate reductase RR1 inhibitor INHIBITOR Ribonucleoside-diphosphate reductase RR1 ✓ ✓

Indications

Anemia, Sickle Cell Carcinoma, Squamous Cell Carcinoma, Squamous Cell Leukemia, Myelogenous, Chronic, BCR-ABL Positive Melanoma Neoplasms Astrocytoma Carcinoma Glioblastoma Hematologic Diseases Hemochromatosis Hemoglobinopathies HIV Infections Laryngeal Neoplasms Leukemia Leukemia, Promyelocytic, Acute Mouth Neoplasms Myelodysplastic Syndromes Myeloproliferative Disorders Paranasal Sinus Neoplasms

ATC Classification

L01XX05
hydroxycarbamide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
infectious disease
Country: United States

Activity Summary

IC50 23 meas. best 4.67
Ki 4 meas. best 4.64
EC50 1 meas. best 4.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L1210
CHEMBL386
 IC50 4.67 4.2767 21379.6 3
Carbonic anhydrase 9
CHEMBL3594
 Ki 4.64 4.64 23000.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.59 4.59 25800.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 4.55 4.55 28000.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 4.51 4.51 31000.0 1
P388
CHEMBL389
 IC50 4.5 4.5 32000.0 1
Unchecked
CHEMBL612545
 IC50 4.43 4.3233 37150.0 3
Urease subunit alpha/Urease subunit beta
CHEMBL3885651
 IC50 4.0 4.0 100000.0 1
Vero
CHEMBL391
 IC50 4.0 4.0 100000.0 1
Toxoplasma gondii
CHEMBL612888
 IC50 4.0 4.0 100000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 1.5 mL.min-1.kg-1 Homo sapiens
Fu 1.0 - Homo sapiens
Fu 1.0 - Homo sapiens
MRT 4.8 hr Homo sapiens
T1/2 3.4 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L1210 IC50 = 21379.62 nM 4.67 Concentration required for 50% inhibition of cell growth (L1210 Leukemia) 2991520
Carbonic anhydrase 9 Ki = 23000.0 nM 4.64 Inhibition of human CA9 16759856
Human immunodeficiency virus 1 EC50 = 25800.0 nM 4.59 Potentiation of 5-Aza-C-induced antiviral activity against VSV-G pseudotyped HIV... 27117260
Carbonic anhydrase 2 Ki = 28000.0 nM 4.55 Inhibition of human CA2 16759856
Carbonic anhydrase 5A, mitochondrial Ki = 31000.0 nM 4.51 Inhibition of human CA5a 16759856
P388 IC50 = 32000.0 nM 4.5 Antiproliferative activity of compound expressed as concentration that inhibits ... 2709372
Unchecked IC50 = 37150.0 nM 4.43 Inhibition of [14C]-cytidine incorporation into DNA in Burkitt''s lymphoma cells 11405653
Unchecked IC50 = 37200.0 nM 4.43 Inhibition of ribonucleotide reductase (unknown origin) 24712764
Unchecked IC50 = 77500.0 nM 4.11 Inhibition of urease (unknown origin) using urea as substrate preincubated for 3... 38516598
L1210 IC50 = 82000.0 nM 4.09 Activity against lymphocytic murine leukemia cell line L1210 using MTS/PES micro... 11784145
L1210 IC50 = 85000.0 nM 4.07 Antiproliferative activity of compound expressed as concentration that inhibits ... 2709372
Vero IC50 = 100000.0 nM 4.0 Compound tested on vero cells infected with Toxoplasma gondii after 24 h 15863319
Toxoplasma gondii IC50 = 100000.0 nM 4.0 Compound tested on intracellular parasites Toxoplasma gondii in vero cells after... 15863319
Toxoplasma gondii IC50 = 100000.0 nM 4.0 Inhibition of intracellular parasite Toxoplasma gondii 17905587
Urease subunit alpha/Urease subunit beta IC50 = 100000.0 nM 4.0 Inhibition of Helicobacter pylori urease 35305460

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 409
18694950 10.1128/aac.00124-08 Leishmania mexicana 31
27117260 10.1016/j.bmc.2016.03.052 Unchecked 25
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
32496057 10.1021/acs.jnatprod.0c00115 K562 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32496057 10.1021/acs.jnatprod.0c00115 K562-Lucena 1 11
33109398 10.1016/j.ejmech.2020.112938 Mus musculus 8
20070106 10.1021/jm901371v Homo sapiens 8
11405653 10.1021/jm000979z Unchecked 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17905587 10.1016/j.bmc.2007.09.025 Toxoplasma gondii 7
1800632 10.1021/np50077a010 NON-PROTEIN TARGET 5
2666666 10.1021/jm00128a032 HeLa 4
22889416 10.1021/jm300602n Mus musculus 4
20541294 10.1016/j.ejmech.2010.05.017 Toxoplasma gondii 4
12904079 10.1021/jm0301538 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
6319702 10.1021/jm00368a024 L1210 3

Data from ChEMBL 36 via Core Engine