VALACYCLOVIR HYDROCHLORIDE

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Trade Names	VALACYCLOVIR HYDROCHLORIDE VALTREX
Synonyms	256-U-87 HYDROCHLORIDE 256U87 HYDROCHLORIDE BW-256 BW-256U87 NSC-759101 Valaciclovir (as hydrochloride) Valaciclovir hydrochloride Valacyclovir hcl Valacyclovir hydrochloride Valtrex
Status
Molecule Category	Salt-form
UNII	G447S0T1VC
EPA CompTox	DTXSID2044210
Parent Compound:	VALACYCLOVIR


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

Structure


InChI Key	ZCDDBUOENGJMLV-QRPNPIFTSA-N
Smiles	CC(C)[C@H](N)C(=O)OCCOCn1cnc2c(=O)nc(N)[nH]c21.Cl
InChI	InChI=1S/C13H20N6O4.ClH/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20;/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20);1H/t8-;/m0./s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C13H21ClN6O4
Molecular Weight	360.8
AlogP	-0.8
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	7.0
Polar Surface Area	151.14
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Human herpesvirus 1 DNA polymerase inhibitor	INHIBITOR	FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	69

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	68.57 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	80.91 %
Drug uptake in wild type mouse jejunum at 0.01 to 50 mM by nonlinear Michaelis-Menten equation analysis	Mus musculus	3.0 10'-5 cm/s
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	12.39 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	2.88 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	6.23 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	17.42 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	7.25 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	3.14 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-5.07 %
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	-3.85 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-4.848 %
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	0.13 %		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	0.13 %

Cross References

Resources	Reference
ChEBI	9919
ChEMBL	CHEMBL1201110
FDA SRS	G447S0T1VC
Guide to Pharmacology	4824
KEGG	C07184
PubChem	135398741
SureChEMBL	SCHEMBL40830
ZINC	ZINC01530713

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).