CLOFARABINE

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Search structure


Trade Names	CLOFARABINE CLOLAR
Synonyms	Clofarabine Clolar Evoltra NSC-759857
Status
Molecule Category	UNKNOWN
ATC	L01BB06
UNII	762RDY0Y2H
EPA CompTox	DTXSID5046437


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	WDDPHFBMKLOVOX-AYQXTPAHSA-N
Smiles	Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F
InChI	InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C10H11ClFN5O3
Molecular Weight	303.68
AlogP	-0.35
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	2.0
Polar Surface Area	119.31
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	20.0

Pharmacology

Mechanism of Action	Action	Reference
DNA inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 2 Phosphodiesterase 2A	-	3120	-	-	32

Assay Description	Organism	Bioactivity	Reference
Compound was tested for cytotoxicity against CCRF-CEM cell lines	Homo sapiens	50.0 nM
Compound was tested for cytotoxicity against HEp-2 cell lines	Homo sapiens	12.0 nM
Compound was tested for cytotoxicity against K562 cell lines	Homo sapiens	3.0 nM
Compound was tested for cytotoxicity against L1210 cell lines	Mus musculus	230.0 nM
Cytostatic activity against human HL60 cells after 48 hrs by MTT assay	Homo sapiens	100.0 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory)	None	1.0 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory)	None	5.16 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory)	None	1.0 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory)	None	163.6 nM
PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory)	None	1.0 nM
Inhibition of recombinant human PDE2A catalytic domain (580 to 919 residues) expressed in Escherichia coli BL21 (Codonplus) at 1 uM using [3H]cGMP as substrate after 15 mins by liquid scintillation counting method relative to control	Homo sapiens	32.13 %
Cytotoxicity against human CCRF-CEM cells assessed as decrease in cell viability after 72 hrs by MTT assay	Homo sapiens	44.0 nM
Cytotoxicity against human Granta cells assessed as decrease in cell viability after 72 hrs by MTT assay	Homo sapiens	17.0 nM
Cytotoxicity against human RL cells assessed as decrease in cell viability after 72 hrs by MTT assay	Homo sapiens	380.0 nM
Cytotoxicity against human HL60 cells assessed as decrease in cell viability after 72 hrs by MTT assay	Homo sapiens	40.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-0.68 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.64 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	25.0 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.22 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.83 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.39 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.04 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.04 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.83 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.39 %

Cross References

Resources	Reference
ChEBI	681569
ChEMBL	CHEMBL1750
DrugBank	DB00631
DrugCentral	691
FDA SRS	762RDY0Y2H
Human Metabolome Database	HMDB0014769
Guide to Pharmacology	6802
PDB	CFB
PharmGKB	PA164754863
PubChem	119182
SureChEMBL	SCHEMBL9040
ZINC	ZINC000003798247

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).