ALAMIFOVIR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H20F6N5O5PS
Molecular Weight	575.422
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(SC2=NC(N)=NC3=C2N=CN3CCOCP(=O)(OCC(F)(F)F)OCC(F)(F)F)C=C1

InChI

InChIKey=VDBGPMJFHCJMOL-UHFFFAOYSA-N

InChI=1S/C19H20F6N5O5PS/c1-32-12-2-4-13(5-3-12)37-16-14-15(28-17(26)29-16)30(10-27-14)6-7-33-11-36(31,34-8-18(20,21)22)35-9-19(23,24)25/h2-5,10H,6-9,11H2,1H3,(H2,26,28,29)

HIDE SMILES / InChI

Molecular Formula	C19H20F6N5O5PS
Molecular Weight	575.422
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800015117 | https://www.ncbi.nlm.nih.gov/pubmed/15855501

Alamifovir is a novel antiviral agent which was under development with Mitsubishi Pharma Corporation in Japan as a potential treatment for hepatitis B (HBV). Alamifovir and its hydrolyzed derivatives have shown preclinical efficacy activity against wild-type and lamivudine-resistant hepatitis B virus. The effective concentration of alamifovir required to reduce replication by 50% (EC50) for the wild-type was 0.027 uM, which is approximately 20 times less than lamivudine, and the EC50 for the lamivudine-resistant mutants was 2.6 to 3.3 uM. The mechanism of action of alamifovir appears to be via the inhibition of the protein priming reaction and the packaging reaction, thereby decreasing HBV replication. Alamifovir`s development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
The treatment of chronic hepatitis B: Focus on adefovir-like antivirals.	2008-08	19209262
Cross-resistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV.	2005	16152756
Safety and efficacy of alamifovir in patients with chronic hepatitis B virus infection.	2004-11	15519660
The mechanisms of action of antivirals against hepatitis B virus infection.	2003-05	12697634
Antiviral activities of MCC-478, a novel and specific inhibitor of hepatitis B virus.	2002-09	12183240
Novel nucleoside analogue MCC-478 (LY582563) is effective against wild-type or lamivudine-resistant hepatitis B virus.	2002-08	12121939
2-Amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) esters as novel HBV-specific antiviral reagents.	2002-07-04	12086499
The mitochondrial permeability transition contributes to acute ethanol-induced apoptosis in rat hepatocytes.	2001-08	11481617

Patents

Sample Use Guides

In Vivo Use Guide

Two studies were conducted to examine the single- and multiple-dose alamifovir pharmacokinetics after oral administration in healthy males. In study 1, subjects were given single doses (0.2 to 80 mg), with a subset receiving 20 mg in a fed state. Study 2 subjects were dosed with 2.5 to 15 mg twice daily for 15 days.

Route of Administration: Oral

In Vitro Use Guide

The effective concentration of alamifovir required to reduce HBV replication by 50% (EC50) for the wild-type was 0.027 uM, which is approximately 20 times less than lamivudine, and the EC50 for the lamivudine-resistant mutants was 2.6 to 3.3 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:43:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:43:46 GMT 2025`
Record UNII	0N739K2A8A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALAMIFOVIR

Official Name

English

LY-582563

Preferred Name

English

PHOSPHONIC ACID, ((2-(2-AMINO-6-((4-METHOXYPHENYL)THIO)-9H-PURIN-9-YL)ETHOXY)METHYL)-, BIS(2,2,2-TRIFLUOROETHYL) ESTER

Systematic Name

English

alamifovir [INN]

Common Name

English

BIS(2,2,2-TRIFLUOROETHYL) ((2-(2-AMINO-6-((4-METHOXYPHENYL)SULFANYL)-9H-PURIN-9-YL)ETHOXY)METHYL)PHOSPHONATE

Systematic Name

English

MCC-478

Code

English

PHOSPHONIC ACID, P-((2-(2-AMINO-6-((4-METHOXYPHENYL)THIO)-9H-PURIN-9-YL)ETHOXY)METHYL)-, BIS(2,2,2-TRIFLUOROETHYL) ESTER

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281