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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H15N5O3
Molecular Weight 265.2689
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METACAVIR

SMILES

COc1c2c([nH]c(=N)n1)n(cn2)[C@@]3([H])CC[C@@]([H])(CO)O3

InChI

InChIKey=FJAOCNGVPLTSLD-NKWVEPMBSA-N
InChI=1S/C11H15N5O3/c1-18-10-8-9(14-11(12)15-10)16(5-13-8)7-3-2-6(4-17)19-7/h5-7,17H,2-4H2,1H3,(H2,12,14,15)/t6-,7+/m0/s1

HIDE SMILES / InChI

Molecular Formula C11H15N5O3
Molecular Weight 265.2689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Jun 26 13:31:07 UTC 2021
Edited
by admin
on Sat Jun 26 13:31:07 UTC 2021
Record UNII
W5EOS3V193
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METACAVIR
Common Name English
GUANOSINE, 2',3'-DIDEOXY-6-O-METHYL-
Systematic Name English
2',3'-DIDEOXY-6-O-METHYLGUANOSINE
Systematic Name English
PNA
Common Name English
((2S,5R)-5-(2-AMINO-6-METHOXY-PURIN-9-YL)TETRAHYDROFURAN-2-YL)METHANOL
Systematic Name English
Code System Code Type Description
PUBCHEM
10355487
Created by admin on Sat Jun 26 13:31:07 UTC 2021 , Edited by admin on Sat Jun 26 13:31:07 UTC 2021
PRIMARY
CAS
120503-45-9
Created by admin on Sat Jun 26 13:31:07 UTC 2021 , Edited by admin on Sat Jun 26 13:31:07 UTC 2021
PRIMARY
FDA UNII
W5EOS3V193
Created by admin on Sat Jun 26 13:31:07 UTC 2021 , Edited by admin on Sat Jun 26 13:31:07 UTC 2021
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Metacavir (PNA) is a novel synthetic nucleoside analog for oral administration with potent and specific antiviral activity against hepatitis B virus (HBV). We assessed the potential for mitochondrial toxicity of PNA in long-term cultures of HepG2 hepatoma cells by measuring mitochondrial function (through lactate secretion), levels of mitochondrial DNA (mtDNA), and the activities of respiratory-chain complexes I to IV. Exposure of HepG2 cells to PNA at concentrations up to 50 .MU.M for 15 days resulted in no deleterious effect on cell proliferation, levels of lactate or mtDNA, or enzyme activities of respiratory-chain complexes I to IV. In contrast, dideoxycytosine at 10 .MU.M and zidovudine at 50 .MU.M have significant effects on cell proliferation, levels of lactate and mtDNA, and enzyme activities of respiratory-chain complexes I to IV.