FILOCICLOVIR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13N5O3
Molecular Weight	263.2526
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N=CN2\C=C3\CC3(CO)CO)C(=O)N1

InChI

InChIKey=KMUNHOKTIVSFRA-KXFIGUGUSA-N

InChI=1S/C11H13N5O3/c12-10-14-8-7(9(19)15-10)13-5-16(8)2-6-1-11(6,3-17)4-18/h2,5,17-18H,1,3-4H2,(H3,12,14,15,19)/b6-2-

HIDE SMILES / InChI

Description
Sources: https://www.microbiotix.com/programs | https://www.ncbi.nlm.nih.gov/pubmed/15561852

FILOCICLOVIR, also known as cyclopropavir, is a guanosine nucleoside analog. It is an antiviral drug ready for phase II clinical trials for the treatment of cytomegalovirus infection.

Originator

Approval Year

PubMed

Title	Date	PubMed
Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections.	2004 Dec	15561852
Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: second-generation methylenecyclopropane analogues of nucleosides.	2004 Jan 29	14736238
Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: synthesis and antiviral activity.	2005 Jan 13	15634003
In vitro activity and mechanism of action of methylenecyclopropane analogs of nucleosides against herpesvirus replication.	2005 Mar	15728900
Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays.	2009 Feb 26	19175319
Phosphonate analogues of cyclopropavir phosphates and their E-isomers. Synthesis and antiviral activity.	2009 Jun 1	19410465
Preclinical evaluation of GS-9160, a novel inhibitor of human immunodeficiency virus type 1 integrase.	2009 Mar	19104010
(Z)- and (E)-2-(1,2-dihydroxyethyl)methylenecyclopropane analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, absolute configuration, and antiviral activity.	2009 May 28	19397271
Synthesis and antiviral activities of methylenecyclopropane analogs with 6-alkoxy and 6-alkylthio substitutions that exhibit broad-spectrum antiviral activity against human herpesviruses.	2013 Aug	23669381

Patents

Sample Use Guides

In Vitro Use Guide

Filociclovir (cyclopropavir) is 10-fold more effective against human cytomegalovirus in vitro than ganciclovir (50% effective concentrations [EC50s]=0.46 and 4.1 uM, respectively) without any observed increase in cytotoxicity.

Name

Type

Language

FILOCICLOVIR

Official Name

English

CPV

Common Name

English

ZSM-162

Code

English

MBX-400

Code

English

ZSM-I 62

Code

English

ZSM-I62

Code

English

CYCLOPROPAVIR

Common Name

English

Filociclovir [WHO-DD]

Common Name

English

filociclovir [INN]

Common Name

English

(Z)-9-((2,2-BIS-(HYDROXYMETHYL)CYCLOPROPYLIDENE)METHYL)GUANINE

Systematic Name

English

FILOCICLOVIR [USAN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

319010