Famciclovir

FCV · Famvir · famcyclovir · Oravir · FaMtrex · FaMcivir · BRL-42810 · Amciclovir

식별자 및 물리적 특성

CAS No.	104227-87-4
분자식	C14H19N5O4
평균 분자량	321.33 g/mol
단동위원소 질량	321.14370409 g/mol
SMILES	CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O
InChIKey	GGXKWVWZWMLJEH-UHFFFAOYSA-N
PubChem CID	3324
ChEMBL	CHEMBL880
ChEBI	CHEBI:4974
EC No.	630-411-6
DTXSID	DTXSID0023038

화학 및 물리적 성질

XLogP	0
극성 표면적	122
수소 결합 공여자 수	1
수소 결합 수용자 수	8
회전 가능 결합 수	9
무거운 원자 수	23
형식 전하	0
복잡도	404
의약품	PharmaceuticalsPharmaceuticals -> Listed in ZINC15
LogP(분배 계수)	0.60.32
Color/Form	White shiny plates from ethyl acetate-hexane
용해도	Solubility in water (25 °C): > 25% w/v initiallyrapidly precipitates as sparingly soluble monohydrate (2-3% w/v)Freely soluble in acetone, methanolsparingly soluble in ethanol, isopropanol1.32e+00 g/LDMSO: ≥10mg/mL
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntiviral AgentsFDA approved drugs -> Active ingredient
Decomposition	When heated to decomposition material emits toxic fumes of /nitrogen oxides/.
녹는점	102-104 °C102 - 104 °C102-104°C
Physical Description	Solid
Collision Cross Section	167.77 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]168.4 Å² [M+H]+ [CCS Type: TW
끓는 점	550.2±60.0 °C(Predicted)
밀도	1.40±0.1 g/cm3(Predicted)
저장 조건	2-8°C
pKa(산도 계수)	4.00±0.10(Predicted)
물리적 상태	고체
색상	흰색에서 황백색까지
헨리 상수	1.0×108 mol/(m3Pa) at 25℃, HSDB (2015)
InChI	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)
InChIKey	GGXKWVWZWMLJEH-UHFFFAOYSA-N
SMILES	C(OC(=O)C)C(CCN1C2C(N=C1)=CN=C(N)N=2)COC(=O)C

화학적 성질

Off-White Powder

안전 및 규제

GHS 분류	DangerH319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P203, P264+P265, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
화재 가능성	This material is assumed to be combustible.
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including famciclovir, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Toxic Combustion Products	Emits toxic fumes under fire conditions.
Hazard Classes and Categories	Eye Irrit. 2 (50%)
Skin, Eye, and Respiratory Irritations	If breathed in, move person into fresh air. If not breathing, give artificial respiration.In case of skin contact, wash off with soap and plenty of water.In case of eye contact, flush eyes with water as a precaution.If swallowed, never give anything by mouth to an unconscious person. Rinse mouth with water.
소화 절차	Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
보관 조건	Store Famvir at room temperature between 59 deg and 86 °F (15 deg to 30 °C).Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.Recommended storage temperature: 2 - 8 °C
정리 방법	Wear approved respiratory protection, chemically compatible gloves, and protective clothing. Wipe up spillage or collect spillage using a high-efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.

용도

개요

Famciclovir, an effective oral prodrug of the antiviral penciclovir, was launched in the UK and shortly after in the U.S.A. for the treatment of shingles (herpes zoster). As the diacetyl ester of the 6-deoxy- penciclovir, famciclovir has significantly improved oral absorption. It is converted to penciclovir in vivo with a bioavailability of 41 % in rats. Penciclovir is phosphorylated, and hence activated onty in herpesvirus infected cells. This stable metabolite, penciclovir-triphosphate, is a strong inhibitor of herpesvirus DNA polymerases and of viral DNA synthesis with long lasting effects. The high selectivity of famciclovir/penciclovir to herpes family of viruses and their rather low toxicity may make this agent superior to other existing drugs.

용도

sterol absorption inhibitor. Famciclovir (Famvir) a synthetic acyclic purine analog derived from guanine. It is the diacetyl ester (prodrug) of penciclovir, which exhibits no antiviral activity until hydrolyzed to penciclovir and its active metabolites. It is indicated for the management of acute herpes zoster infections. It has been shown to relieve acute symptoms as well as to shorten the duration of postherpetic neuralgia. It is also used for the treatment or suppression of recurrent episodes of genital herpes in immunocompetent patients and in the treatment of recurrent herpes simplex types 1 and 2 infections in patients with human immunodeficiency virus.

일반 설명

Famciclovir is a diacetyl prodrug of penciclovir.As a prodrug,it lacks antiviral activity. Penciclovir, 9-[4-hydroxy-3-hydroxymethylbut-1-yl] guanine, is an acyclic guanine nucleoside analog. The structure is similar to that of acyclovir,except in penciclovir, a side chain oxygen has beenreplaced by a carbon atom and an extra hydroxymethylgroup is present.VSV-infected cells, penciclovir is first phosphorylated byviral thymidine kinase41 and then further elaborated to thetriphosphate by host cell kinases. Penciclovir triphosphate isa competitive inhibitor of viral DNA polymerase. The pharmacokineticparameters of penciclovir are quite different fromthose of acyclovir. Although penciclovir triphosphate is about100-fold less potent in inhibiting viral DNA polymerase thanacyclovir triphosphate, it is present in the tissues for longerperiods and in much higher concentrations than acyclovir.