Compound: zidovudine
SMILES: O=c1n(cc(C)c([nH]1)=O)[C@@H]2O[C@H](CO)[C@H](C2)N=[N+]=[N-]
InChIKey: HBOMLICNUCNMMY-XLPZGREQSA-N
Synonyms: zidovudine, Azidothymidine, 30516-87-1, 3'-Azido-3'-deoxythymidine, Retrovir, Thymidine, 3'-azido-3'-deoxy-, Zidovudinum, Compound S, Zidovudina, BW A509U, zidovudin, BWA509U, BW-A-509U, 3'-Deoxy-3'-azidothymidine, BW-A509U, DRG-0004, 3'-azt, DTXSID8020127, 3'-Azidothymidine, NSC 602670, 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione, 4B9XT59T7S, 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, CHEBI:10110, BW-A 509U, NSC-602670, DTXCID60127, AZT Antiviral, TRIZIVIR COMPONENT ZIDOVUDINE, AZT, Antiviral, 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione, AZT (Antiviral), Antiviral AZT, LAMIVUDINE/ZIDOVUDINE TEVA COMPONENT ZIDOVUDINE, BWA-509U, 3'-Azido-2',3'-Dideoxythymidine, 3' Azido 3' deoxythymidine, BWA 509U, 3' Azido 2',3' Dideoxythymidine, 1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl)-5-methylpyrimidine-2,4-dione, 1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl)-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, RefChem:6356, J05AF01, 623-849-4, NSC602670, AZT, ZIDOVUDINE [AZT], Trizivir, MFCD00006536, ZDV, 1-((2R,4S,5S)-4-AZIDO-5-(HYDROXYMETHYL)TETRAHYDROFURAN-2-YL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE, CHEMBL129, 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)thymine, MLS000028548, NCGC00023945-05, Zidovudinum [Latin], SMR000058351, Zidovudina [Spanish], 399024-19-2, Propolis+AZT, Retrovir(TM), AZT & Li & EPO, Retrovir (TN), CCRIS 105, Cpd S, Intron A & AZT, HSDB 6515, Racemic Liposomal AZT, Liposomal AZT-SN-1, Liposomal AZT-SN-3, Zidovudine+PRO 140, PC-SOD+AZT, AZT & srCD4, AZT & rIFN.alpha.2, AZT & rsT4, rIFN-beta seron & AZT, 3'-Azido-3'-deoxythymidine (AIDS), AZT & EPO, AZT & GM-CSF, AZT & HPA, AZT & sCD4, AZT & SST, zudovidine, UNII-4B9XT59T7S, Zidovir, AZT & Li & GM-CSF, AZT+PRO 140, Met-SDF-1.beta. & AZT, AZT & Li & IL-1, AZT & Li & IL-6, AZT & IL-1, AZT & IL-2, AZT & IL-6, AZT & Interferon-.alpha.-2, Retrovir;, Zidovudine RS, AZT & Concanavalin A (ConA), Zidovudine CRS, Apovir;, AZT & Lymphoblastoid Interferon, AZT & PM-19, Met-SDF-1.beta. & Zidovudine, 4lhm, 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 [AZT], AZT & rsCD4 & rIFN.alpha.A, 3'-azido-3'-deoxythymidine, AZT, DS-4152 & AZT, 1-((2R,4R,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione, 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione, 5-methyl-1-[rac-(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione, AZT & Colony-stimulating factor 2, AZT & NP (from PHCA or HSA), Zidovudine; 1-(3-Azido-2,3-dideoxy-ss-d-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione; Zidovudine (GR 63367X); BP Zidovudine and Lamivudine Impurity Standard, 3'-Azidothymidine;, Novo-AZT;, S2579, 3''-azido-thymidine, K7 [P Ti2 W10 O40], Zidovudine [USAN:USP:INN:BAN:JAN], Zidovudine & IFNL1, Zidovudine & IFNL2, Zidovudine & IFNL3, Zidovudine (Retrovir), Zidovudine (Standard), COMPOUND-S, Spectrum_001348, AZT & CD4(178)-PE 40, AZT & IFN.alpha., Zidovudine & IL-29, ZIDOVUDINE [MI], Zidovudine & IL-28A, Zidovudine & IL-28B, AZT, ZDV, ZIDOVUDINE [INN], ZIDOVUDINE [JAN], AZT & Interleukin 29, Opera_ID_1602, Prestwick3_000333, Spectrum2_000927, Spectrum3_001507, Spectrum4_000332, Spectrum5_001101, 3'azido-3'deoxythymidine, ZIDOVUDINE [HSDB], ZIDOVUDINE [IARC], ZIDOVUDINE [USAN], 3'-Azido-3'-deoxythymidine & Erythropoietin, 3'-Azido-3'-deoxythymidine & Sho-Saiko-To, Azidothymidine; Zidovudine, AZT & Interleukin 28A, AZT & Interleukin 28B, 3'-Azido-3'-deoxythymidine & Concanavalin A, 3'-Azido-3'-deoxythymidine & Interleukin-1, 3'-Azido-3'-deoxythymidine & Interleukin-2, 3'-Azido-3'-deoxythymidine & Interleukin-6, ZIDOVUDINE [VANDF], Epitope ID:768746, 3'-azido3'-deoxythymidine, AZT & IFNL1, AZT & IFNL2, AZT & IFNL3, ZIDOVUDINE [MART.], AZT & Interferon lambda-1, AZT & Interferon lambda-2, AZT & Interferon lambda-3, ZIDOVUDINE [USP-RS], ZIDOVUDINE [WHO-DD], ZIDOVUDINE [WHO-IP], 3''-Deoxy-3-azidothymidine, BSPBio_000365, BSPBio_003153, KBioGR_000703, KBioSS_001828, 3'-N3-ddT (AZT), MLS001055351, MLS001076358, MLS002153202, MLS002222249, Zidovudine & Interleukin 29, DivK1c_000524, SPECTRUM1502109, ZIDOVUDINE [EMA EPAR], 3'-deoxy-3'-azido-thymidine, SPBio_000834, Zidovudine & Interleukin 28A, Zidovudine & Interleukin 28B, 3'-Azido-3'-deoxythymidine;, AZT & IL-28A, AZT & IL-28B, BPBio1_000403, GTPL4825, orb1308679, orb3141292, Zidovudine (JP18/USP/INN), 3'-Azido-3'-deoxythymidine & Lithium & Erythropoietin, 3'-Azido-3'-deoxythymidine & Lithium & Interleukin-1, 3'-Azido-3'-deoxythymidine & Lithium & Interleukin-6, 3'-Azido-3'-deoxythymidine & Lymphoblastoid Interferon, SCHEMBL14615088, SN-1-dipalmitoylglycerophospho-AZT (in a lipid vesicle), SN-3-dipalmitoylglycerophospho-AZT (in a lipid vesicle), ZIDOVUDINE [EP IMPURITY], ZIDOVUDINE [ORANGE BOOK], AZT & IL-29, HMS501K06, KBio1_000524, KBio2_001828, KBio2_004396, KBio2_006964, KBio3_002653, racemic-dipalmitoylglycerophospho-AZT (in a lipid vesicle), ZIDOVUDINE [EP MONOGRAPH], 3''-Azido-3''-deoxy-thymidine, NINDS_000524, Zidovudine & Interferon lambda-1, Zidovudine & Interferon lambda-2, Zidovudine & Interferon lambda-3, HMS1921J20, HMS2090G11, HMS2092D06, HMS2096C07, HMS2234K17, HMS3259H17, HMS3713C07, Pharmakon1600-01502109, ZIDOVUDINE [USP MONOGRAPH], ZIDOVUDINUM [WHO-IP LATIN], 3'-azido-3'-deoxythymidine (azt), COMBIVIR COMPONENT ZIDOVUDINE, MSK10681, 3''azido-2''3''-dideoxythymidine, Tox21_110062, Tox21_110894, Tox21_202203, Tox21_300578, BBL033764, BDBM50002692, CCG-39924, EBC-13244, EBC-66074, HY-17413R, NSC758185, STK801891, AKOS005622576, AKOS015842610, Tox21_110062_1, 3''-azido-2'',3''-dideoxythymidine, DB00495, NC00666, NSC-758185, IDI1_000524, NCGC00014918-01, NCGC00023945-03, NCGC00023945-04, NCGC00023945-06, NCGC00023945-07, NCGC00023945-08, NCGC00023945-09, NCGC00023945-10, NCGC00023945-12, NCGC00023945-13, NCGC00023945-24, NCGC00023945-25, NCGC00178237-01, NCGC00178237-02, NCGC00254276-01, NCGC00259752-01, AS-13019, SY065461, SBI-0051731.P002, DB-225998, A2052, NS00000600, Propolis & Thymidine, 3'-azido-3'-deoxy-, SW198799-2, EN300-52518, 3'-Azido-3'-deoxythymidine, >=98% (HPLC), C07210, D00413, D88500, 3'-Azido-3'deoxythymidine & Interferon .alpha., 3'-Azido-3'-deoxythymidine, >=99.0% (HPLC), F358376, Q198504, SR-01000000098, SR-05000001587, SR-01000000098-3, SR-05000001587-1, BRD-K72903603-001-04-6, BRD-K72903603-001-14-5, BRD-K72903603-001-24-4, Z754931264, Zidovudine, European Pharmacopoeia (EP) Reference Standard, 3'-Azido-3'-deoxythymidine & Recombinant Interferon-.alpha.-2, Zidovudine, United States Pharmacopeia (USP) Reference Standard, 3'-Azido-3'-deoxythymidine & CD4-Pseudomonas exotoxin A hybrid, Beta interferon(rIFN-beta seron) & 3'-Azido-3'-deoxythymidine(AZT), Lecithinized superoxide dismutase & Thymidine, 3'-azido-3'-deoxy-, 3'-Azido-2',3'-dideoxythymidine & sCD4(soluble recombinant protein), Thymidine, 3'-azido-3'-deoxy- & PRO 140 (Anti-CCR5 monoclonal antibody), Zidovudine, Pharmaceutical Secondary Standard; Certified Reference Material, (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-(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), 3'-Azido-3'-deoxythymidine & Granulocyte-macrophage colony-stimulating factor, 3'-Azido-3'-deoxythymidine & Lithium & Granulocyte-macrophage colony-stimulating factor, 3'-Azido-3'deoxythymidine & Recombinant Soluble CD4 & Recombinant Interferon.alpha.A, 4-(4-Azido-5-hydroxy-tetrahydro-furan-2-yl)-5-methyl-3H-pyrazine-2,6-dione, Met-Stromal Cell-derived Factor-1.beta. (Human) & 3'-Azido-3'-deoxythymidine, 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,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-(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(3''-azido-2'',3''-dideoxythymidine), 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione(azidothymidine, AZT), 1-(4-Azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione(Zidovudine, AZT), 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
Theoretical properties:
molecular_formula: C10H13N5O4
molecular_weight: 267.24 g/mol
exact_mass: 267.09675391 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 3
heavy_atom_count: 19
topological_polar_surface_area: 93.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to beige, crystalline solid
color: White to beige, crystalline solid
odor: Odorless
melting_point: 223 to 234 °F (NTP, 1992)
solubility: 10 to 50 mg/mL at 63 °F (NTP, 1992)
vapor_pressure: 5.2X10-20 mm Hg @ 25 °C /Estimated/
Descriptions:
pubchem: Zidovudine (AZT) can cause cancer according to California Labor Code.
chebi: A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.
chembl: ZIDOVUDINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Zidovudine (ZDV), also known as azidothymidine (AZT), was the first antiretroviral medication used to prevent and treat HIV/AIDS. It is generally recommended for use in combination with other antiretrovirals. It may be used to prevent mother-to-child spread during birth or after a needlestick injury or other potential exposure. It is sold both by itself and together as lamivudine/zidovudine and abacavir/lamivudine/zidovudine. It can be used by mouth or by slow injection into a vein.
Common side effects include headaches, fever, and nausea. Serious side effects include liver problems, muscle damage, and high blood lactate levels. It is commonly used in pregnancy and appears to be safe for the fetus. ZDV is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class. It works by inhibiting the enzyme reverse transcriptase that HIV uses to make DNA and therefore decreases replication of the virus.
Zidovudine was first described in 1964. It was resynthesized from a public-domain formula by Burroughs Wellcome. It was approved in the United States in 1987 and was the first treatment for HIV. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.