PRIMAQUINE PHOSPHATE

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Search structure


Trade Names	PRIMAQUINE PRIMAQUINE PHOSPHATE
Synonyms	Malquine NSC-149765 Primachine phosphate Primaquine Primaquine Phosphate Primaquine diphosphate Primaquine phosphate Primaquini diphosphas WR 2975
Status
Molecule Category	Salt-form
UNII	H0982HF78B
EPA CompTox	DTXSID6045248
Parent Compound:	PRIMAQUINE


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

Structure


InChI Key	GJOHLWZHWQUKAU-UHFFFAOYSA-N
Smiles	COc1cc(NC(C)CCCN)c2ncccc2c1.O=P(O)(O)O.O=P(O)(O)O
InChI	InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;21-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2(H3,1,2,3,4)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C15H27N3O9P2
Molecular Weight	455.34
AlogP	2.78
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	6.0
Polar Surface Area	60.17
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	19.0

Assay Description	Organism	Bioactivity	Reference
HARVARD: Inhibition of blood stage Plasmodium falciparum Dd2 infection	Plasmodium falciparum	794.0 nM
Cytotoxicity against rat L6 cells after 70 hrs by Alamar Blue-based assay	Rattus norvegicus	27.1 ug.mL-1
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	2.56 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	11.33 %
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	-0.14 %		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	-0.14 %

Cross References

Resources	Reference
ChEMBL	CHEMBL43128
FDA SRS	H0982HF78B
PubChem	6135
SureChEMBL	SCHEMBL41096

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).