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Compound Detail

CHEMBL1580

PENTOSTATIN
💊 Approved Drug
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💊 Approved Drug
OC[C@H]1O[C@@H](n2cnc3c2N=CNC[C@H]3O)C[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1580
Name PENTOSTATIN
Phase Approved
Structure Type MOL
InChI Key FPVKHBSQESCIEP-JQCXWYLXSA-N
Therapeutic ✓ Yes

Known Names

CI-825 Deoxycoformycin Nipent NSC-218321 PD 81565 PD-81565 Pentostatin Pentostatina Pentostatine YK-176
4
Targets
15
Activities
2
Assay Types
2
PK Parameters
20
Publications
10
Known Names
13
Indications
1
Mechanisms

Molecular Properties

268.3
MW (Da)
-1.18
ALogP
8
HBA
4
HBD
112.1
PSA (Ų)
0.54
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

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

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -stat-
USAN Year 1977

Extended Properties

Molecular Formula C11H16N4O4
MW 268.27
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 1.00

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Adenosine deaminase inhibitor INHIBITOR Adenosine deaminase ✓ ✓

Indications

Anemia Leukemia, Hairy Cell Neoplasms Neoplasms Graft vs Host Disease Leukemia, Lymphocytic, Chronic, B-Cell Bronchiolitis Obliterans Syndrome Leukemia Lymphoma Anemia, Aplastic Anemia, Sickle Cell Kidney Neoplasms Lymphoma, B-Cell

ATC Classification

L01XX08
pentostatin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

Ki 13 meas. best 11.0
IC50 2 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine deaminase
CHEMBL2966
 Ki 11.0 11.0 0.0 1
Adenosine deaminase
CHEMBL1910
 Ki 10.59 10.0925 0.0 4
Adenosine deaminase
CHEMBL4523370
 Ki 10.42 9.255 0.0 2
L1210
CHEMBL386
 IC50 6.6 6.16 250.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 9500.0 ng.hr.mL-1 Mus musculus
Cmax 45476.57 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine deaminase Ki = 0.01 nM 11.0 Binding affinity against Adenosine deaminase from calf intestinal mucosa was det... 11677121
Adenosine deaminase Ki = 0.026 nM 10.59 Inhibition of human erythrocytes ADA assessed as equilibrium dissociation consta... 30964283
Adenosine deaminase Ki = 0.033 nM 10.48 Inhibition constant against human adenosine deaminase was determined 12643924
Adenosine deaminase Ki = 0.038 nM 10.42 Inhibition of Plasmodium falciparum N-terminal thrombin cleavable His6-tagged AD... 30964283
Adenosine deaminase Ki = 0.1 nM 10.0 Compound was evaluated for the inhibition of adenosine deaminase 7310814
Adenosine deaminase Ki = 0.5 nM 9.3 Inhibition of human erythrocytes ADA assessed as reduction in formation of inosi... 30964283
Adenosine deaminase Ki = 8.2 nM 8.09 Inhibition of Plasmodium falciparum N-terminal thrombin cleavable His6-tagged AD... 30964283
L1210 IC50 = 250.0 nM 6.6 Compound was evaluated for the cytotoxicity against L1210 cells in presence of c... 3489838
L1210 IC50 = 1900.0 nM 5.72 Compound was evaluated for the cytotoxicity against L1210 cells in absence of co... 3489838

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30964283 10.1021/acs.jmedchem.9b00182 Adenosine deaminase 4
15139750 10.1021/jm0499559 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
25462277 10.1016/j.ejmech.2014.10.080 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
16033254 10.1021/jm050413g Mus musculus 2
3489838 10.1021/jm00160a046 L1210 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
12643924 10.1016/s0960-894x(03)00026-x Mus musculus 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2

Data from ChEMBL 36 via Core Engine