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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N5O7P
Molecular Weight 347.2216
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZIDOVUDINE MONOPHOSPHATE

SMILES

Cc1cn([C@@]2([H])C[C@@]([H])([C@@]([H])(COP(=O)(O)O)O2)N=[N+]=[N-])c(=O)nc1O

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 347.2216
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
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

PubMed

PubMed

TitleDatePubMed
Phase I/II trial with fozivudine tidoxil (BM 21.1290): a 7 day randomized, placebo-controlled dose-escalating trial.
1997 Dec
Mitochondrial DNA depletion in rat liver induced by fosalvudine tidoxil, a novel nucleoside reverse transcriptase inhibitor prodrug.
2009 Jul
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 Jun 26 06:41:15 UTC 2021
Edited
by admin
on Sat Jun 26 06:41:15 UTC 2021
Record UNII
97YMU05VPJ
Record Status Validated (UNII)
Record Version
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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
EPA CompTox
29706-85-2
Created by admin on Sat Jun 26 06:41:15 UTC 2021 , Edited by admin on Sat Jun 26 06:41:15 UTC 2021
PRIMARY
DRUG BANK
DB03666
Created by admin on Sat Jun 26 06:41:15 UTC 2021 , Edited by admin on Sat Jun 26 06:41:15 UTC 2021
PRIMARY
PUBCHEM
65374
Created by admin on Sat Jun 26 06:41:15 UTC 2021 , Edited by admin on Sat Jun 26 06:41:15 UTC 2021
PRIMARY
CAS
29706-85-2
Created by admin on Sat Jun 26 06:41:15 UTC 2021 , Edited by admin on Sat Jun 26 06:41:15 UTC 2021
PRIMARY
FDA UNII
97YMU05VPJ
Created by admin on Sat Jun 26 06:41:15 UTC 2021 , Edited by admin on Sat Jun 26 06:41:15 UTC 2021
PRIMARY
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