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Compound Detail

CHEMBL803

CYTARABINE
💊 Approved Drug
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💊 Approved Drug
Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL803
Name CYTARABINE
Phase Approved
Structure Type MOL
InChI Key UHDGCWIWMRVCDJ-CCXZUQQUSA-N
Therapeutic ✓ Yes

Known Names

Alexan Alexan 100 Ara-c Ara-cytidine Arabinocytosine Arabinosyl cytosine Aracytidine Aracytin Aracytine Citarabina Cytarabine Cytarabine component of vyxeos +13 more
594
Targets
757
Activities
3
Assay Types
16
PK Parameters
20
Publications
25
Known Names
20
Indications
3
Mechanisms

Molecular Properties

243.2
MW (Da)
-2.56
ALogP
8
HBA
4
HBD
130.8
PSA (Ų)
0.45
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1969
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -arabine
USAN Year 1964

Extended Properties

Molecular Formula C9H13N3O5
MW 243.22
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 1.65

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓
RNA inhibitor INHIBITOR RNA ✓ ✓
DNA polymerase (alpha/delta/epsilon) inhibitor INHIBITOR DNA polymerase (alpha/delta/epsilon) ✓ ✓

Indications

Leukemia, Lymphoid Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Meningeal Carcinomatosis Meningeal Neoplasms Neoplasms Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Anemia, Refractory Anemia, Refractory, with Excess of Blasts Breast Neoplasms Graft vs Host Disease Histiocytosis, Langerhans-Cell Hodgkin Disease Hodgkin Disease Leukemia Leukemia, Basophilic, Acute

ATC Classification

L01BC01
cytarabine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

IC50 751 meas. best 9.4
EC50 5 meas. best 8.25
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L1210
CHEMBL386
 IC50 9.4 7.5477 0.4 13
CCRF-CEM
CHEMBL382
 IC50 9.0 7.3857 1.0 7
U-937
CHEMBL612794
 IC50 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
 IC50 8.43 7.06 3.7 3
MCF7
CHEMBL387
 IC50 8.4 6.245 4.0 8
P12-Ichikawa
CHEMBL614660
 IC50 8.26 8.26 5.5 1
CCRF-CEM
CHEMBL382
 EC50 8.25 8.25 5.6 1
SF-268
CHEMBL613977
 IC50 8.12 6.37 7.7 3
MOLT-4
CHEMBL614177
 IC50 8.0 7.0167 10.0 3
697
CHEMBL2366253
 IC50 7.97 7.97 10.6 1
ES1
CHEMBL2366146
 IC50 7.89 7.89 13.0 1
SMMC-7721
CHEMBL613831
 IC50 7.89 7.73 13.0 2
Jurkat E6.1
CHEMBL4296446
 IC50 7.75 7.75 18.0 1
Hepatitis C virus
CHEMBL379
 IC50 7.7 7.7 20.0 1
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 IC50 7.7 7.7 20.0 1
HEL
CHEMBL613888
 IC50 7.69 7.69 20.5 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.64 7.11 22.8 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.54 5.8727 29.0 11
CHP-212
CHEMBL1075423
 IC50 7.47 7.47 33.5 1
CTB-1
CHEMBL2366344
 IC50 7.46 7.46 34.4 1
A-427
CHEMBL614515
 IC50 7.46 7.46 34.5 1
MOLT-16
CHEMBL2366362
 IC50 7.44 7.44 36.1 1
COLO 320
CHEMBL614257
 IC50 7.4 7.4 40.0 1
BHT-101
CHEMBL1075398
 IC50 7.38 7.38 41.8 1
MC-IXC
CHEMBL1075495
 IC50 7.38 7.38 41.4 1
K5
CHEMBL2366152
 IC50 7.37 7.37 43.2 1
HL-60
CHEMBL383
 IC50 7.31 6.6438 49.0 8
NCI-H1703
CHEMBL1075522
 IC50 7.3 7.3 49.8 1
K562
CHEMBL385
 IC50 7.3 5.8125 50.0 8
A549
CHEMBL392
 IC50 7.3 5.96 49.7 8
MLMA
CHEMBL2366211
 IC50 7.26 7.26 55.5 1
LB2241-RCC
CHEMBL2366330
 IC50 7.26 7.26 55.3 1
P30-OHK
CHEMBL2366165
 IC50 7.25 7.25 56.5 1
RPMI 6410
CHEMBL614881
 IC50 7.22 7.22 60.0 1
HT-29
CHEMBL384
 IC50 7.18 6.315 66.0 2
J-RT3-T3-5
CHEMBL2366219
 IC50 7.17 7.17 68.4 1
NCI-H510A
CHEMBL2366332
 IC50 7.17 7.17 68.3 1
VA-ES-BJ
CHEMBL2366259
 IC50 7.14 7.14 71.7 1
T-24
CHEMBL614774
 IC50 7.11 7.11 78.6 1
NB69
CHEMBL1075510
 IC50 7.1 7.1 79.5 1
MEL-JUSO
CHEMBL1075501
 IC50 7.07 7.07 85.8 1
CTV-1
CHEMBL2366360
 IC50 7.07 7.07 84.7 1
SW982
CHEMBL2366238
 IC50 7.04 7.04 91.2 1
SNU1
CHEMBL614931
 IC50 7.01 7.01 96.8 1
HCT-116
CHEMBL394
 IC50 7.0 5.7757 100.0 7
NCI-H460
CHEMBL396
 IC50 7.0 6.01 100.0 2
GP5d
CHEMBL1075450
 IC50 6.99 6.99 102.0 1
SAS
CHEMBL1075569
 IC50 6.97 6.97 107.6 1
BFTC-905
CHEMBL1075396
 IC50 6.96 6.96 108.3 1
LB1047-RCC
CHEMBL2366136
 IC50 6.96 6.96 108.4 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5.0 nmol.hr/g Rattus norvegicus
AUC 46.0 nmol/g Mus musculus
AUC 19.2 nmol/g.hr Mus musculus
AUC 29429.62 ng.hr.mL-1 Mus musculus
CL 830.0 mL.min-1.g-1 Homo sapiens
CL 740.0 mL.min-1.g-1 Homo sapiens
CL 340.0 mL.min-1.g-1 Homo sapiens
CL 231400.0 mL.min-1.g-1 Homo sapiens
CL 228300.0 mL.min-1.g-1 Homo sapiens
CL 245100.0 mL.min-1.g-1 Homo sapiens
CL 169300.0 mL.min-1.g-1 Homo sapiens
CL 0.014 L/hr Homo sapiens
F 20.0 % Homo sapiens
T1/2 34.0 hr -
T1/2 0.2 hr Homo sapiens
T1/2 0.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L1210 IC50 = 0.4 nM 9.4 Cytotoxicity against deoxynucleoside analogue-sensitive mouse L1210 cells after ... 19674903
CCRF-CEM IC50 = 1.0 nM 9.0 Cytotoxicity against deoxynucleoside analogue-sensitive human CCRF-CEM cells aft... 19674903
U-937 IC50 = 2.0 nM 8.7 Cytotoxicity against human U937 cells assessed as reduction in cell viability me... 30954427
Unchecked IC50 = 3.7 nM 8.43 Compound was evaluated for its antiproliferative activity on human T-lymphocyte ... -
MCF7 IC50 = 4.0 nM 8.4 Cytotoxicity against deoxynucleoside analogue-sensitive human MCF7 cells after 3... 19674903
P12-Ichikawa IC50 = 5.537 nM 8.26 SANGER: Inhibition of human P12-ICHIKAWA cell growth in a cell viability assay. -
CCRF-CEM EC50 = 5.614 nM 8.25 Cytotoxicity against human CCRF-CEM cells after 48 hrs by cell titer-blue assay 19743858
CCRF-CEM IC50 = 6.0 nM 8.22 Cytotoxicity against human CCRF-CEM cells assessed as cell viability after 48 hr... 22582991
SF-268 IC50 = 7.68 nM 8.12 Cytotoxicity against human SF268 cells by MTT assay 19345581
MOLT-4 IC50 = 10.0 nM 8.0 Cytotoxicity against MOLT-4 human leukemic lymphoblastoid cell lines 6827546
L1210 IC50 = 10.0 nM 8.0 Inhibition of L1210 lymphoid leukemia cells 48 hr after administration (length o... 1527783
L1210 IC50 = 10.0 nM 8.0 Inhibition of L1210 lymphoid leukemia cells 72 hr after administration (length o... 1527783
697 IC50 = 10.6 nM 7.97 SANGER: Inhibition of human 697 cell growth in a cell viability assay. -
SMMC-7721 IC50 = 13.0 nM 7.89 Cytotoxicity against human SMMC7721 cells assessed as inhibition of cell prolife... 29886320
ES1 IC50 = 12.97 nM 7.89 SANGER: Inhibition of human ES1 cell growth in a cell viability assay. -
Jurkat E6.1 IC50 = 18.0 nM 7.75 Antiproliferative activity against human Jurkat E6-1 cells 30114661
CCRF-CEM IC50 = 20.0 nM 7.7 Cytotoxicity against CCRF-CEM human leukemic lymphoblastoid cell lines 6827546
Hepatitis C virus IC50 = 20.0 nM 7.7 Antiviral activity against Hepatitis C virus infected human 2209-23 cells by gen... 19055482
E3 ubiquitin-protein ligase Mdm2 IC50 = 20.0 nM 7.7 Inhibition of MDM2 (unknown origin) 30253242
HEL IC50 = 20.52 nM 7.69 SANGER: Inhibition of human HEL cell growth in a cell viability assay. -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 434
7057424 10.1021/jm00344a016 Mus musculus 60
3411602 10.1021/jm00117a020 Mus musculus 37
3761322 10.1021/jm00160a041 L1210 25
7452687 10.1021/jm00186a011 L1210 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
30954427 10.1016/j.bmcl.2019.03.044 U-937 14
3761322 10.1021/jm00160a041 P388 14
11356111 10.1021/jm0005149 Mus musculus 14
23230131 10.1124/dmd.112.048769 ADMET 13
92567 10.1021/jm00196a015 Mus musculus 12
1956046 10.1021/jm00115a017 Mus musculus 12
1652024 10.1021/jm00112a040 Mus musculus 12
3968680 10.1021/jm00380a004 Mus musculus 12
8510106 10.1021/jm00064a012 Mus musculus 12
118258 10.1021/jm00197a030 L1210 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
6827546 10.1021/jm00356a032 L1210 10
7143370 10.1021/jm00353a010 Mus musculus 10

Data from ChEMBL 36 via Core Engine