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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 of ALAMIFOVIR

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

Description

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

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.