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F7932

Sigma-Aldrich

Famciclovir

≥98% (HPLC)

Synonym(s):

2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetate ester, BRL 42810

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About This Item

Empirical Formula (Hill Notation):
C14H19N5O4
CAS Number:
104227-87-4
Molecular Weight:
321.33
MDL number:
MFCD00866964
UNSPSC Code:
12352200
PubChem Substance ID:
329799767
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

solubility

DMSO: ≥10 mg/mL

originator

Novartis

storage temp.

2-8°C

SMILES string

CC(=O)OCC(CCn1cnc2cnc(N)nc12)COC(C)=O

InChI

1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)

InChI key

GGXKWVWZWMLJEH-UHFFFAOYSA-N

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Application

Famciclovir is used in herpes virus infections and hepatitis B drug development research. It may be used as a reference compound. Famciclovir may be used to study the factors that control its conversion into penciclovir and other metabolites.

Biochem/physiol Actions

Famciclovir is an antiretroviral guanosine analog used to treat herpesvirus infections and hepatitis B. Famciclovir is rapidly converted to penciclovir. Viral thymidine kinase phosphorylates penciclovir to a monophosphate form that celular kinases convert in turn to penciclovir triphosphate. Penciclovir triphosphate competitively inhibits viral DNA polymerase and thus viral replication. Prolonged administration can lead to resistance; it is often manifested as selection of pre-existing resistant strains with mutations in the reverse transcriptase domain of the DNA polymerase gene.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Joshua T Schiffer et al.
The Journal of antimicrobial chemotherapy, 66(11), 2593-2600 (2011-08-26)
The presence of herpes simplex virus-2 (HSV-2) shedding episodes correlates with transmission to sexual partners and neonates, and some episodes correlate with disease manifestations. HSV-2-targeted guanosine analogues are effective when given on a prophylactic basis, but do not completely eliminate
Samira Mubareka et al.
Expert opinion on drug safety, 9(4), 643-658 (2010-05-01)
Famciclovir is the prodrug of penciclovir, a guanosine analogue that inhibits viruses of the alpha sub-family of the Herpesviridae, as well as hepatitis B virus. It is indicated for management of mucocutaneous herpes simplex virus disease and acute herpes zoster
Dene Simpson et al.
Drugs, 66(18), 2397-2416 (2006-12-22)
Famciclovir (Famvir) is the oral prodrug of penciclovir, an agent that has demonstrated antiviral activity against herpes simplex viruses, type 1 (HSV-1) and 2 (HSV-2) [which cause orolabial and/or genital herpes simplex], and against varicella zoster virus (VZV) [a reactivation
K S Gill et al.
Clinical pharmacokinetics, 31(1), 1-8 (1996-07-01)
Famciclovir is an oral prodrug of the antiherpesvirus nucleoside analogue, penciclovir. Following oral administration famciclovir undergoes extensive first pass metabolism to penciclovir and essentially no parent compound is recovered from plasma or urine. Penciclovir plasma concentrations reach a maximum less
Donald C Vinh et al.
Expert opinion on pharmacotherapy, 7(16), 2271-2286 (2006-10-25)
Herpes simplex virus is one of the most common causes of genital ulcer disease worldwide. Herpes simplex virus-2 is the more common cause of genital herpes, a chronic infection that is characterised by periodic reactivation, with the capacity to produce
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