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

Molecular Formula	C11H13N5O3
Molecular Weight	263.2526
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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
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
Fluorinated methylenecyclopropane analogues of nucleosides. Synthesis and antiviral activity of (Z)- and (E)-9-{[(2-fluoromethyl-2-hydroxymethyl)-cyclopropylidene]methyl}adenine and -guanine.	2008 Mar 1	18082410
Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays.	2009 Feb 26	19175319
Preclinical evaluation of GS-9160, a novel inhibitor of human immunodeficiency virus type 1 integrase.	2009 Mar	19104010
Cytomegalovirus UL97 mutations affecting cyclopropavir and ganciclovir susceptibility.	2011 Jan	21041510
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:11:03 GMT 2023` Edited by `admin` on `Sat Dec 16 02:11:03 GMT 2023`
Record UNII	EAO0TD9B13
Record Status	`Validated (UNII)`
Record Version

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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