U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N5O7P
Molecular Weight 347.2212
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZIDOVUDINE MONOPHOSPHATE

SMILES

CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O

InChI

InChIKey=OIFWQOKDSPDILA-XLPZGREQSA-N
InChI=1S/C10H14N5O7P/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(22-8)4-21-23(18,19)20/h3,6-8H,2,4H2,1H3,(H,12,16,17)(H2,18,19,20)/t6-,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H14N5O7P
Molecular Weight 347.2212
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
30.03 ng/mL
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ZIDOVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
69.4 ng/mL
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ZIDOVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
70.54 ng/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ZIDOVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.92 mg/L
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FOZIVUDINE TIDOXIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.14 mg/L
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FOZIVUDINE TIDOXIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8.39 mg/L
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FOZIVUDINE TIDOXIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.1 h
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ZIDOVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7.1 h
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ZIDOVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.1 h
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ZIDOVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.5 h
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FOZIVUDINE TIDOXIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4 h
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FOZIVUDINE TIDOXIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.4 h
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FOZIVUDINE TIDOXIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Phase II placebo-controlled trial of fozivudine tidoxil for HIV infection: pharmacokinetics, tolerability, and efficacy.
2000 Mar 1
Fozivudine: BM 211290, fozivudine tidoxil, FZT, HDP 990002, W 09726867.
2004
Fozivudine tidoxil as single-agent therapy decreases plasma and cell-associated viremia during acute feline immunodeficiency virus infection.
2011 May-Jun
Administration of Fozivudine tidoxil as a single-agent therapeutic during acute feline immunodeficiency virus infection does not alter chronic infection.
2012 Jun
Virological efficacy of 24-week fozivudine-based regimen in ART-naive patients from Tanzania and Côte d'Ivoire.
2017 Feb 20
Patents

Sample Use Guides

800 mg once daily or 600 mg twice daily or 1200 mg once daily over a period of 24 weeks.
Route of Administration: Oral
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
Created
by admin
on Sat Dec 16 01:56:57 UTC 2023
Edited
by admin
on Sat Dec 16 01:56:57 UTC 2023
Record UNII
97YMU05VPJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZIDOVUDINE MONOPHOSPHATE
Common Name English
AZT-MP
Common Name English
AZIDOTHYMIDINE MONOPHOSPHATE
Systematic Name English
3'-AZIDO-3'-DEOXYTHYMIDINE 5'-PHOSPHATE
Systematic Name English
5'-THYMIDYLIC ACID, 3'-AZIDO-3'-DEOXY-
Common Name English
AZT 5'-MONOPHOSPHATE
Common Name English
Code System Code Type Description
DRUG BANK
DB03666
Created by admin on Sat Dec 16 01:56:57 UTC 2023 , Edited by admin on Sat Dec 16 01:56:57 UTC 2023
PRIMARY
PUBCHEM
65374
Created by admin on Sat Dec 16 01:56:57 UTC 2023 , Edited by admin on Sat Dec 16 01:56:57 UTC 2023
PRIMARY
CAS
29706-85-2
Created by admin on Sat Dec 16 01:56:57 UTC 2023 , Edited by admin on Sat Dec 16 01:56:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID30183855
Created by admin on Sat Dec 16 01:56:57 UTC 2023 , Edited by admin on Sat Dec 16 01:56:57 UTC 2023
PRIMARY
FDA UNII
97YMU05VPJ
Created by admin on Sat Dec 16 01:56:57 UTC 2023 , Edited by admin on Sat Dec 16 01:56:57 UTC 2023
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
PARENT -> METABOLITE ACTIVE
METABOLITE ACTIVE -> PARENT