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Details

Stereochemistry EPIMERIC
Molecular Formula C35H64N5O8PS
Molecular Weight 745.95
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FOZIVUDINE TIDOXIL

SMILES

CCCCCCCCCCCCSCC(COP(O)(=O)OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])N2C=C(C)C(=O)NC2=O)OCCCCCCCCCC

InChI

InChIKey=IBHARWXWOCPXCR-WELGVCPWSA-N
InChI=1S/C35H64N5O8PS/c1-4-6-8-10-12-14-15-17-19-21-23-50-28-30(45-22-20-18-16-13-11-9-7-5-2)26-46-49(43,44)47-27-32-31(38-39-36)24-33(48-32)40-25-29(3)34(41)37-35(40)42/h25,30-33H,4-24,26-28H2,1-3H3,(H,43,44)(H,37,41,42)/t30?,31-,32+,33+/m0/s1

HIDE SMILES / InChI

Molecular Formula C35H64N5O8PS
Molecular Weight 745.95
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Fozivudine tidoxil is a thioether lipid–Zidovudine (ZDV) conjugate. After intake it is split intracellularly into the lipid moiety and ZDV-monophosphate, which is subsequently phosphorylated to the active metabolite ZDV-triphosphate. The rationale behind the development of fozivudine (FZD) was to take advantage of the high cleavage activity in mononuclear cells and other organs resulting in increased amounts of intracellular ZDV available for phosphorylation to the active metabolite, and a very low activity in red blood and stem cells, which should result in reduced haematologic toxicity. It is member of the family of nucleoside reverse transcriptase (RT) inhibitors. Fozivudine tidoxil has been in Phase II clinical trials for the treatment of HIV infection. There were three adverse events possibly related to fozivudine: urine abnormality, gastrointestinal pain and abnormal dreams.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
69.4 ng/mL
800 mg 1 times / day steady-state, oral
ZIDOVUDINE plasma
Homo sapiens
8.39 mg/L
800 mg 1 times / day steady-state, oral
FOZIVUDINE TIDOXIL plasma
Homo sapiens
30.03 ng/mL
200 mg 1 times / day steady-state, oral
ZIDOVUDINE plasma
Homo sapiens
70.54 ng/mL
400 mg 1 times / day steady-state, oral
ZIDOVUDINE plasma
Homo sapiens
4.14 mg/L
400 mg 1 times / day steady-state, oral
FOZIVUDINE TIDOXIL plasma
Homo sapiens
1.92 mg/L
200 mg 1 times / day steady-state, oral
FOZIVUDINE TIDOXIL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.1 h
800 mg 1 times / day steady-state, oral
ZIDOVUDINE plasma
Homo sapiens
4.4 h
800 mg 1 times / day steady-state, oral
FOZIVUDINE TIDOXIL plasma
Homo sapiens
7.1 h
200 mg 1 times / day steady-state, oral
ZIDOVUDINE plasma
Homo sapiens
6.1 h
400 mg 1 times / day steady-state, oral
ZIDOVUDINE plasma
Homo sapiens
4 h
400 mg 1 times / day steady-state, oral
FOZIVUDINE TIDOXIL plasma
Homo sapiens
3.5 h
200 mg 1 times / day steady-state, oral
FOZIVUDINE TIDOXIL plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
800 mg once daily or 600 mg twice daily or 1200 mg once daily over a period of 24 weeks.
Route of Administration: Oral
In Vitro Use Guide
Fozivudine showed dose-dependent inhibition of various HIV strains in vitro, with IC50 values of 0.02–0.2 uM/L (15–150 ng/mL).
Substance Class Chemical
Record UNII
687805287F
Record Status Validated (UNII)
Record Version