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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O4
Molecular Weight 267.2413
Optical Activity ( + )
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZIDOVUDINE

SMILES

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

InChI

InChIKey=HBOMLICNUCNMMY-XLPZGREQSA-N
InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H13N5O4
Molecular Weight 267.2413
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zidovudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated. Zidovudine, a structural analog of thymidine, is a prodrug that must be phosphorylated to its active 5′-triphosphate metabolite, zidovudine triphosphate (ZDV-TP). It inhibits the activity of HIV-1 reverse transcriptase (RT) via DNA chain termination after incorporation of the nucleotide analogue. It competes with the natural substrate dGTP and incorporates itself into viral DNA. It is also a weak inhibitor of cellular DNA polymerase α and γ. Zidovudine is used in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections. Zidovudine is marketed as Retrovir.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
22.0 µM [IC50]
0.01 µM [EC50]
24.0 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
In vitro anti-hepatitis B virus activities of 5"-O-myristoyl analogue derivatives of 3"-fluoro-2",3"-dideoxythymidine (FLT) and 3"-azido-2",3"-dideoxythymidine (AZT).
1998 Sep-Dec
New series of mixed pronucleotides. Synthesis and anti-HIV activities of mononucleoside phenyl SATE phosphotriesters.
1999 Apr-May
Synthesis and anti-HIV activity of some S-acyl-2-thioethyl (SATE) phosphoramidate derivatives of 3'-azido-2',3'-dideoxythymidine.
1999 Apr-May
Anti-HIV pronucleotides: SATE versus phenyl as a protecting group of AZT phosphoramidate derivatives.
1999 Apr-May
Antiviral nucleoside drug delivery via amino acid phosphoramidates.
1999 Apr-May
Antiviral activity and resistance profile of phosphazid--a novel prodrug of AZT.
1999 Apr-May
Anti-HIV-1 activities of 1,3-dioxolane guanine and 2,6-diaminopurine dioxolane.
1999 Apr-May
Long-term effects of prenatal 3'-azido-3'-deoxythymidine (AZT) exposure on intermale aggressive behaviour of mice.
1999 Aug
Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides.
1999 Aug
A new point mutation (P157S) in the reverse transcriptase of human immunodeficiency virus type 1 confers low-level resistance to (-)-beta-2',3'-dideoxy-3'-thiacytidine.
1999 Aug
Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide.
1999 Aug
Synthesis and anti-HIV activity of 1,1,3-trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazines (TTDs): a new family of HIV-1 specific non-nucleoside reverse transcriptase inhibitors.
1999 Dec
Charge modification of plasma and milk proteins results in antiviral active compounds.
1999 Dec
N'-[2-(2-thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1.
1999 Dec 20
Inhibition of beta-globin gene expression by 3'-azido-3'-deoxythymidine in human erythroid progenitor cells.
1999 Dec 31
Zidovudine (AZT) induced alterations in mitochondrial biogenesis in rat striated muscles.
1999 Jan
Relation of peripheral neuropathy to HIV treatment in four randomized clinical trials including didanosine.
1999 Jul
Biological evaluation of proanthocyanidin dimers and related polyphenols.
1999 Jul
Zidovudine-induced experimental myopathy: dual mechanism of mitochondrial damage.
1999 Jul 1
Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents.
1999 Jul 15
Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'alpha-C-branched-chain sugar pyrimidine nucleosides.
1999 Jul 29
A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody.
1999 Jun
Characterization of human immunodeficiency virus type 1 strains resistant to the non-nucleoside reverse transcriptase inhibitor RD4-2217.
1999 Nov
Resistance of the human immunodeficiency virus to the inhibitory action of negatively charged albumins on virus binding to CD4.
1999 Nov 20
Synthesis and anti-retroviral activity of O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) phosphoramidate derivatives.
1999 Oct
Synthesis of 2',3'-dideoxy-2'-fluoro-L-threo-pentofuranosyl nucleosides as potential antiviral agents.
1999 Oct
In vitro induction of human immunodeficiency virus type 1 variants resistant to phosphoralaninate prodrugs of Z-methylenecyclopropane nucleoside analogues.
1999 Oct
Mechanism of action and in vitro activity of 1',3'-dioxolanylpurine nucleoside analogues against sensitive and drug-resistant human immunodeficiency virus type 1 variants.
1999 Oct
Genotoxicity of 3'-azido-3'-deoxythymidine in the human lymphoblastoid cell line, TK6: relationships between DNA incorporation, mutant frequency, and spectrum of deletion mutations in HPRT.
1999 Oct 19
Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus.
1999 Sep
Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents.
1999 Sep
N-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1.
1999 Sep 20
The anti-HIV pseudopeptide HB-19 forms a complex with the cell-surface-expressed nucleolin independent of heparan sulfate proteoglycans.
1999 Sep 24
Persistent mitochondrial dysfunction and perinatal exposure to antiretroviral nucleoside analogues.
1999 Sep 25
Prophylactic contraceptives for HIV/AIDS.
1999 Sep-Oct
Synthesis and biological activity of N-acylphenothiazines.
2000 Apr
Antiviral properties of a series of 1,6-naphthyridine and 7, 8-dihydroisoquinoline derivatives exhibiting potent activity against human cytomegalovirus.
2000 Apr
Cardiac dysfunction occurs in the HIV-1 transgenic mouse treated with zidovudine.
2000 Feb
Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.
2000 Jan
Antioxidant function of phenethyl-5-bromo-pyridyl thiourea compounds with potent anti-HIV activity.
2000 Jan 3
Cytochrome c oxidase deficiency in the muscle of patients with zidovudine myopathy is segmental and affects both mitochondrial DNA- and nuclear DNA-encoded subunits.
2000 Jul
In vitro selection of mutations in the human immunodeficiency virus type 1 reverse transcriptase that decrease susceptibility to (-)-beta-D-dioxolane-guanosine and suppress resistance to 3'-azido-3'-deoxythymidine.
2000 Jul
Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients.
2000 Jun 10
'Double-Drugs'--a new class of prodrug form of an HIV protease inhibitor conjugated with a reverse transcriptase inhibitor by a spontaneously cleavable linker.
2000 Jun 5
Structure-activity relationship studies on potential non-nucleoside DABO-like inhibitors of HIV-1 reverse transcriptase.
2000 Mar
Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release.
2000 Mar
Variable sensitivity of CCR5-tropic human immunodeficiency virus type 1 isolates to inhibition by RANTES analogs.
2000 May
3'-azido-3'-deoxythimidine (AZT) is glucuronidated by human UDP-glucuronosyltransferase 2B7 (UGT2B7).
2000 May
Fetal mitochondrial heart and skeletal muscle damage in Erythrocebus patas monkeys exposed in utero to 3'-azido-3'-deoxythymidine.
2000 May 1
Anti-human immunodeficiency virus activity of novel aminoglycoside-arginine conjugates at early stages of infection.
2000 May 1
Patents

Sample Use Guides

In Vivo Use Guide
Treatment of HIV-1 infection: Adults: 600 mg/day in divided doses with other antiretroviral agents. Pediatric patients (6 weeks to <18 years of age): Dosage should be calculated based on body weight not to exceed adult dose.
Route of Administration: Oral
In Vitro Use Guide
The antiviral activity of CD8(+) cells from 2 LTSs was inhibited by 5 uM of zidovudine.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:46:01 UTC 2019
Edited
by admin
on Mon Oct 21 19:46:01 UTC 2019
Record UNII
4B9XT59T7S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZIDOVUDINE
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
BW-A509U
Code English
AZIDOTHYMIDINE
Systematic Name English
3'-DEOXY-3'-AZIDOTHYMIDINE
Systematic Name English
THYMIDINE, 3'-AZIDO-3'-DEOXY-
Systematic Name English
ZDV
Common Name English
ZIDOVUDINE [MI]
Common Name English
COMBIVIR COMPONENT ZIDOVUDINE
Common Name English
ZIDOVUDINE [USP-RS]
Common Name English
AZT
Common Name English
ZIDOVUDINE COMPONENT OF TRIZIVIR
Brand Name English
TRIZIVIR COMPONENT ZIDOVUDINE
Brand Name English
ZIDOVUDINE [IARC]
Common Name English
ZIDOVUDINE [WHO-DD]
Common Name English
ZIDOVUDINE COMPONENT OF LAMIVUDINE/ZIDOVUDINE TEVA
Brand Name English
ZIDOVUDINE COMPONENT OF COMBIVIR
Common Name English
ZIDOVUDINE [EP]
Common Name English
ZIDOVUDINE [USAN]
Common Name English
ZIDOVUDINE [JAN]
Common Name English
COMPOUND S
Code English
ZIDOVUDINE [EMA EPAR]
Common Name English
ZIDOVUDINE [ORANGE BOOK]
Common Name English
ZIDOVUDINE [USP]
Common Name English
ZIDOVUDINE [VANDF]
Common Name English
RETROVIR
Brand Name English
3'-AZIDO-3'-DEOXYTHYMIDINE
Systematic Name English
ZIDOVUDINE [MART.]
Common Name English
3'-AZT
Common Name English
ZIDOVUDINE [WHO-IP]
Common Name English
3'-AZIDOTHYMIDINE
Systematic Name English
ZIDOVUDINE [HSDB]
Common Name English
ZIDOVUDINE [INN]
Common Name English
BW-A-509U
Code English
COMPOUND-S
Code English
NSC-602670
Code English
ZIDOVUDINUM [WHO-IP LATIN]
Common Name English
LAMIVUDINE/ZIDOVUDINE TEVA COMPONENT ZIDOVUDINE
Brand Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS COMBIVIR (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
FDA ORPHAN DRUG 8185
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-VATC QJ05AR04
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-ATC J05AR05
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-ATC J05AF01
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NDF-RT N0000175462
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-VATC QJ05AR01
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-ATC J05AR04
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NCI_THESAURUS C1557
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NCI_THESAURUS C97452
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NDF-RT N0000009947
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
EMA ASSESSMENT REPORTS LAMIVUDINE/ZIDOVUDINE TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-ATC J05AR01
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-VATC QJ05AR05
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
WHO-VATC QJ05AF01
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
LIVERTOX 1047
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
ZIDOVUDINE
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY Description: A white or brownish powder. Solubility: Soluble in ethanol (~750 g/l) TS, sparingly soluble in water. Category: Antiretroviral (Nucleoside Reverse Transcriptase Inhibitor). Storage: Zidovudine should be kept in a tightly closed container, protected from light. Additional information: Zidovudine may exhibit polymorphism. Definition: Zidovudine contains not less than 97.0% and not more than 103.0% of C10H13N5O4, calculated with reference to the dried substance.
NCI_THESAURUS
C947
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
INN
6118
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
CAS
30516-87-1
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
MESH
D015215
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
IUPHAR
4825
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
RXCUI
11413
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY RxNorm
LactMed
30516-87-1
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
DRUG BANK
DB00495
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
EPA CompTox
30516-87-1
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
EVMPD
SUB00153MIG
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
MERCK INDEX
M11592
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
ZIDOVUDINE
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
ChEMBL
CHEMBL129
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
PUBCHEM
35370
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
HSDB
30516-87-1
Created by admin on Mon Oct 21 19:46:01 UTC 2019 , Edited by admin on Mon Oct 21 19:46:01 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TARGET ORGANISM->INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TRANSPORTER -> NON-SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> NON-SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
AMOUNT FORMED FOLLOWING ADMINISTRATION
MINOR
METABOLITE TOXIC -> PARENT
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
Related Record Type Details
IMPURITY -> PARENT
The impurity peaks are eluted at the following relative retention times with reference to zidovudine (retention time about 12 to 13 minutes): impurity C (thymine) about 0.3. The test is not valid unless the resolution factor between the peaks due to zidovudine and impurity B is at least 2. In the chromatogram obtained with solution (1): - the area of any peak corresponding to impurity C, when multiplied by a correction factor of 0.6, is not greater than four times the area of the principal peak in the chromatogram obtained with solution (2) (2.0%).
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
The impurity peaks are eluted at the following relative retention times with reference to zidovudine (retention time about 12 to 13 minutes): impurity B about 1.2. The test is not valid unless the resolution factor between the peaks due to zidovudine and impurity B is at least 2. In the chromatogram obtained with solution (1):- the area of any peak corresponding to impurity B, is not greater than twice the area of the principal peak in the chromatogram obtained with solution (2) (1.0%).
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
The impurity peaks are eluted at the following relative retention times with reference to zidovudine (retention time about 12 to 13 minutes): impurity A (stavudine) about 0.4;. The test is not valid unless the resolution factor between the peaks due to zidovudine and impurity B is at least 2. In the chromatogram obtained with solution (1):- the area of any peak corresponding to impurity A, when multiplied by a correction factor of 0.9, is not greater than the area of the principal peak in the chromatogram obtained with solution (2) (0.5%).
IMPURITY -> PARENT
IMPURITY -> PARENT
Not Specified
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Population
PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC Population
PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Population
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Populations
PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC Population
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Population
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Polpulation
PHARMACOKINETIC