METACAVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=C2N=CN([C@H]3CC[C@@H](CO)O3)C2=NC(N)=N1

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	265.2685
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical
Record UNII	W5EOS3V193
Record Status	`Validated (UNII)`
Record Version

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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

Official Name

English

((2S,5R)-5-(2-AMINO-6-METHOXY-PURIN-9-YL)TETRAHYDROFURAN-2-YL)METHANOL

Systematic Name

English

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Code System

Code

Type

Description

PUBCHEM

10355487

PRIMARY

CAS

120503-45-9

PRIMARY

FDA UNII

W5EOS3V193

PRIMARY

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Related Record

Type

Details


					77H9EM77P7

HEPATITIS B VIRUS

TARGET ORGANISM->INHIBITOR

Amount:

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Related Record

Type

Details


					W5EOS3V193

METACAVIR

ACTIVE MOIETY

Comments:

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.

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