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Drug

D0128 | Zidovudine

Molecular Formula C10H13N5O4
Molecular Weight 267.24
Structure
State solid
Clearance * 0.65 +/- 0.29 L/hr/kg [HIV-infected, Birth to 14 Days of Age] * 1.14 +/- 0.24 L/hr/kg [HIV-infected, 14 Days to 3 Months of Age] * 1.85 +/- 0.47 L/hr/kg [HIV-infected, 3 Months to 12 Years of Age]. The transporters, ABCB1, ABCC4, ABCC5, and ABCG2 are involved with the clearance of zidovudine.
Volume of distribution Apparent volume of distribution, HIV-infected patients, IV administration = 1.6 ± 0.6 L/kg
Route of elimination As in adult patients, the major route of elimination was by metabolism to GZDV. After intravenous dosing, about 29% of the dose was excreted in the urine unchanged and about 45% of the dose was excreted as GZDV.
Protein binding 30-38%
Half life Elimination half life, HIV-infected patients, IV administration = 1.1 hours (range of 0.5 - 2.9 hours)
Absorption Rapid and nearly complete absorption from the gastrointestinal tract following oral administration; however, because of first-pass metabolism, systemic bioavailability of zidovudine capsules and solution is approximately 65% (range, 52 to 75%). Bioavailability in neonates up to 14 days of age is approximately 89%, and it decreases to approximately 61% and 65% in neonates over 14 days of age and children 3 months to 12 years, respectively. Administration with a high-fat meal may decrease the rate and extent of absorption.
Trade names Retrovir
Description nucleoside analogs ; nucleoside reverse transcriptase inhibitor (NRTI); dideoxynucleoside compound; potent inhibitor of HIV replication

J

J05AR05 Zidovudine, lamivudine and nevirapine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR04 Zidovudine, lamivudine and abacavir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AR01 Zidovudine and lamivudine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AF01 Zidovudine


[J05AF] Nucleoside and nucleotide reverse transcriptase inhibitors


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 416.1 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION > 800 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 242.0 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. increase EC20 36
ELECTRON TRANSPORT CHAIN Interfere 307
MITOCHONDRIAL FATTY ACID BETA OXIDATION 79μM 83 mice Lean mice vs Ob/ob mice Measurement of oxygen consumption in the presence of ADP (state 3) and the different substrates was carried out on the Mitologics screening platform EC20 227
SWELLING > 200 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36
ULTRASTRUCTURE abnormalize 307
ROS PRODUCTION Increase 307
MITOCHONDRIAL DNA METABOLIC PROCESS 194
MITOCHONDRIAL DNA METABOLIC PROCESS increase 307
MITOCHONDRIAL PROTEIN TRANSLATION decrease 307

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase > 800 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Cytochrome c oxidase Inhibition 307
Citrate synthase, mitochondrial Inhibition 307
DNA polymerase gamma 194
Mitochondrial thymidine kinase 2 human U2OS cell downregulate 196
deoxyguanosine kinase human U2OS cell downregulate 196
Reactive oxygen species increase 307
Cytochrome c > 200 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 96 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H341 (55.21%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H350 (54.17%): May cause cancer [Danger Carcinogenicity]


H351 (44.79%): Suspected of causing cancer [Warning Carcinogenicity]


H361 (55.21%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H372 (53.12%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P260, P264, P270, P281, P308+P313, P314, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H351: Suspected of causing cancer [Warning Carcinogenicity]


H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]


H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]


H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


 P201, P202, P260, P263, P264, P270, P281, P307+P311, P308+P313, P314, P321, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Acquired immunodeficiency syndrome

  • Autoimmune disorder

  • Disease progression

  • Immunodeficiency

  • Infection

  • Opportunistic infection

  • Pregnancy

  • Teratogenicity

  • Hepatomegaly (0.11)

  • Neutropenia (0.03)

  • Abdominal pain

  • Agranulocytosis

  • Anaemia

  • Asthenia

  • Body temperature increased

  • Breath sounds abnormal

  • Chest pain

  • Chills

  • Constipation

  • Cough

  • Decreased appetite

  • Dermatitis

  • Diarrhoea

  • Discomfort

  • Dizziness

  • Dysgeusia

  • Dyspepsia

  • Dyspnoea

  • Feeling abnormal

  • Gastrointestinal pain

  • Headache

  • Hyperhidrosis

  • Ill-defined disorder

  • Insomnia

  • Lymphadenopathy

  • Malaise

  • Mouth ulceration

  • Musculoskeletal discomfort

  • Myalgia

  • Nasopharyngitis

  • Nausea

  • Neuropathy peripheral

  • Paraesthesia

  • Pharyngitis

  • Rash

  • Rhinorrhoea

  • Somnolence

  • Splenomegaly

  • Stomatitis

  • Thrombocytopenia

  • Vomiting

  • Weight decreased

  • Wheezing

    • (AZT) 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (AZT)1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 1-((2R,4R,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
    1-((2R,4S,5S)-4-(diazoamino)-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 1-((2R,4S,5S)-4-AZIDO-5-(HYDROXYMETHYL)TETRAHYDROFURAN-2-YL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE 1-((2R,4S,5S)-4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
    1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 1-((2R,5S)-4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 1-((2S,4R,5R)-4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
    1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)thymine 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
    1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (AZT) 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (AzddThd, AZT) 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (N3ddThd)
    1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione [AZT] 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione(3''-azido-2'',3''-dideoxythymidine) 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione(AZT)
    1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione(Zidovudine, AZT) 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione(azidothymidine, AZT) 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
    1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
    146426-54-2 3′-Azido-3′-deoxythymidine 3''-Azido-3''-deoxy-thymidine
    3''-Deoxy-3-azidothymidine 3''-azido-2'',3''-dideoxythymidine 3''-azido-thymidine
    3''azido-2''3''-dideoxythymidine 3'-Azido-2',3'-Dideoxythymidine 3'-Azido-2',3'-dideoxythymidine & sCD4(soluble recombinant protein)
    3'-Azido-3'-deoxythymidine 3'-Azido-3'-deoxythymidine & CD4-Pseudomonas exotoxin A hybrid 3'-Azido-3'-deoxythymidine & Concanavalin A
    3'-Azido-3'-deoxythymidine & Erythropoietin 3'-Azido-3'-deoxythymidine & Granulocyte-macrophage colony-stimulating factor 3'-Azido-3'-deoxythymidine & Heteropolyoxotungstate PM-19
    3'-Azido-3'-deoxythymidine & Interleukin-1 3'-Azido-3'-deoxythymidine & Interleukin-2 3'-Azido-3'-deoxythymidine & Interleukin-6
    3'-Azido-3'-deoxythymidine & Lithium & Erythropoietin 3'-Azido-3'-deoxythymidine & Lithium & Granulocyte-macrophage colony-stimulating factor 3'-Azido-3'-deoxythymidine & Lithium & Interleukin-1
    3'-Azido-3'-deoxythymidine & Lithium & Interleukin-6 3'-Azido-3'-deoxythymidine & Lymphoblastoid Interferon 3'-Azido-3'-deoxythymidine & Recombinant Interferon-.alpha.-2
    3'-Azido-3'-deoxythymidine & Sho-Saiko-To 3'-Azido-3'-deoxythymidine (AIDS) 3'-Azido-3'-deoxythymidine, >=98% (HPLC)
    3'-Azido-3'-deoxythymidine, >=99.0% (HPLC) 3'-Azido-3'deoxythymidine & Interferon .alpha. 3'-Azido-3'deoxythymidine & Nanoparticles (from human serum albumin or polyhexylcyanoacrylate)
    3'-Azido-3'deoxythymidine & Recombinant Soluble CD4 & Recombinant Interferon.alpha.A 3'-Deoxy-3'-azidothymidine 3'-azido-3'-deoxythymidine, AZT
    3'-azido3'-deoxythymidine 3'-deoxy-3'-azido-thymidine 3'azido-3'deoxythymidine
    3-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)triaz-1-en-2-ium-1-ide 3-Azido-1,2,3-trideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-D-erythro- pentofuranuronic acid 3-Azido-3-deoxythymidine
    30516-87-1 399024-19-2 4-(4-Azido-5-hydroxy-tetrahydro-furan-2-yl)-5-methyl-3H-pyrazine-2,6-dione
    4B9XT59T7S 4lhm AB0012841
    AKOS005622576 AKOS015842610 ANW-26899
    AS-13019 AZT AZT & CD4(178)-PE 40
    AZT & Colony-stimulating factor 2 AZT & Concanavalin A (ConA) AZT & EPO
    AZT & GM-CSF AZT & HPA AZT & IFN.alpha.
    AZT & IFNL1 AZT & IFNL2 AZT & IFNL3
    AZT & IL-1 AZT & IL-2 AZT & IL-28A
    AZT & IL-28B AZT & IL-29 AZT & IL-6
    AZT & Interferon lambda-1 AZT & Interferon lambda-2 AZT & Interferon lambda-3
    AZT & Interferon-.alpha.-2 AZT & Interleukin 28A AZT & Interleukin 28B
    AZT & Interleukin 29 AZT & Li & EPO AZT & Li & GM-CSF
    AZT & Li & IL-1 AZT & Li & IL-6 AZT & Lymphoblastoid Interferon
    AZT & NP (from PHCA or HSA) AZT & PM-19 AZT & SST
    AZT & rIFN.alpha.2 AZT & rsCD4 & rIFN.alpha.A AZT & rsT4
    AZT & sCD4 AZT & srCD4 AZT (Antiviral)
    AZT Antiviral AZT TRANSPLACENTAL CARCINOGENESIS STUDY AZT+PRO 140
    AZT, Antiviral Azidothymidine Azidothymidine
    Azidothymidine;AZT;ZDV Aztec BBL033764
    BDBM50002692 BPBio1_000403 BRD-K72903603-001-04-6
    BRD-K72903603-001-14-5 BSPBio_000365 BSPBio_003153
    BW A509U BW-A 509U BW-A-509U
    BW-A509U BWA-509U BWA509U
    Beta interferon(rIFN-beta seron) & 3'-Azido-3'-deoxythymidine(AZT) C07210 CCG-39924
    CCRIS 105 CHEBI:10110 CHEMBL129
    CPD000058351 CTK4I2082 CZ0012
    Certified Reference Material Compound S Cpd S
    D00413 DB00495 DRG-0004
    DS-4152 & AZT DSSTox_CID_127 DSSTox_GSID_20127
    DSSTox_RID_75386 DTXSID8020127 DivK1c_000524
    EN300-52518 FT-0601543 GTPL4825
    HBOMLICNUCNMMY-XLPZGREQSA-N HMS1921J20 HMS2090G11
    HMS2092D06 HMS2096C07 HMS2234K17
    HMS3259H17 HMS3713C07 HMS501K06
    HSDB 6515 IDI1_000524 Interferon AD + 3'-azido-3'-deoxythymidine
    Intron A & AZT J-700147 J10271
    K7 [P Ti2 W10 O40] KBio1_000524 KBio2_001828
    KBio2_004396 KBio2_006964 KBio3_002653
    KBioGR_000703 KBioSS_001828 KS-00000WOF
    LS-1159 Lecithinized superoxide dismutase & Thymidine, 3'-azido-3'-deoxy- Liposomal AZT-SN-1
    Liposomal AZT-SN-3 MCULE-8664408343 MFCD00006536
    MLS000028548 MLS001055351 MLS001076358
    MLS002153202 MLS002222249 Met-SDF-1.beta. & AZT
    Met-SDF-1.beta. & Zidovudine Met-Stromal Cell-derived Factor-1.beta. (Human) & 3'-Azido-3'-deoxythymidine NC00666
    NCGC00014918-01 NCGC00023945-03 NCGC00023945-04
    NCGC00023945-05 NCGC00023945-06 NCGC00023945-07
    NCGC00023945-08 NCGC00023945-09 NCGC00023945-10
    NCGC00023945-12 NCGC00023945-13 NCGC00178237-01
    NCGC00178237-02 NCGC00254276-01 NCGC00259752-01
    NINDS_000524 NSC 602670 NSC-758185
    NSC758185 Opera_ID_1602 PC-SOD+AZT
    Pharmakon1600-01502109 Prestwick3_000333 Propolis & Thymidine, 3'-azido-3'-deoxy-
    Propolis+AZT Q198504 Racemic Liposomal AZT
    Retrovir Retrovir (TN) Retrovir(TM)
    S2579 SAM002548971 SBI-0051731.P002
    SCHEMBL14615088 SMR000058351 SN-1-dipalmitoylglycerophospho-AZT (in a lipid vesicle)
    SN-3-dipalmitoylglycerophospho-AZT (in a lipid vesicle) SPBio_000834 SPECTRUM1502109
    SR-01000000098 SR-01000000098-3 SR-05000001587
    SR-05000001587-1 STK801891 SW198799-2
    Spectrum2_000927 Spectrum3_001507 Spectrum4_000332
    Spectrum5_001101 Spectrum_001348 Sulfated polysaccharide-peptidoglycan DS-4152 & 3'-Azido-3'-deoxythymidine
    Thymidine, 3'-azido-3'-deoxy- Thymidine, 3'-azido-3'-deoxy- & PRO 140 (Anti-CCR5 monoclonal antibody) Tox21_110062
    Tox21_110062_1 Tox21_110894 Tox21_202203
    Tox21_300578 UNII-4B9XT59T7S W-5037
    Z1723414428 ZDV ZIDOVUDINE [AZT]
    ZINC3779042 ZVD Zidovudina
    Zidovudina [Spanish] Zidovudine Zidovudine & IFNL1
    Zidovudine & IFNL2 Zidovudine & IFNL3 Zidovudine & IL-28A
    Zidovudine & IL-28B Zidovudine & IL-29 Zidovudine & Interferon lambda-1
    Zidovudine & Interferon lambda-2 Zidovudine & Interferon lambda-3 Zidovudine & Interleukin 28A
    Zidovudine & Interleukin 28B Zidovudine & Interleukin 29 Zidovudine (JP17/USP/INN)
    Zidovudine (Retrovir) Zidovudine [USAN:INN:BAN:JAN] Zidovudine [USAN:USP:INN:BAN:JAN]
    Zidovudine+PRO 140 Zidovudine, European Pharmacopoeia (EP) Reference Standard Zidovudine, Pharmaceutical Secondary Standard
    Zidovudine, United States Pharmacopeia (USP) Reference Standard Zidovudinum Zidovudinum [Latin]
    rIFN-beta seron & AZT racemic-dipalmitoylglycerophospho-AZT (in a lipid vesicle) zidovudin
    zidovudine zudovidine

    DrugBank Name Zidovudine
    DrugBank DB00495
    CAS Number 146426-54-2, 25526-94-7, 30516-87-1, 399024-19-2
    PubChem Compound 35370
    KEGG Compound ID C07210
    KEGG Drug D00413
    PubChem.Substance 46508240
    ChEBI 10110
    PharmGKB PA451954
    ChemSpider 32555
    BindingDB 50002692.0
    TTD DAP000701
    Wikipedia Zidovudine
    HET AZZ
    DPD 1185

    1. Dykens et al. (2007)
    2. Chan et al. (2005)