General Information of Drug (ID: DM4KI7O)

Drug Name
Zidovudine
Synonyms
zidovudine; Azidothymidine; 30516-87-1; 3'-Azido-3'-deoxythymidine; Retrovir; AZT; Zidovudinum; Compound S; Thymidine, 3'-azido-3'-deoxy-; ZIDOVUDINE [AZT]; zidovudin; BW A509U; Zidovudinum [Latin]; Zidovudina [Spanish]; BWA509U; DRG-0004; 3'-Azido-2',3'-Dideoxythymidine; ZDV; UNII-4B9XT59T7S; 3'-Deoxy-3'-azidothymidine; CCRIS 105; Aztec; BW-A509U; BW-A-509U; HSDB 6515; 3'-Azido-3'-deoxythymidine (AIDS); CHEMBL129; NSC 602670; BW-A 509U; MLS000028548; 4B9XT59T7S; AZT; Antiviral; Azidodeoxythymidine; ZVD; Zidovudin; Zidovudina; AZT Antiviral; AZT TRANSPLACENTAL CARCINOGENESIS STUDY; Antiviral AZT; Cpd S; Racemic Liposomal AZT; Zidovudine EP III; BWA 509U; K7 [P Ti2 W10 O40]; AZT & EPO; AZT & HPA; AZT & Lymphoblastoid Interferon; AZT & SST; AZT & rsT4; AZT & sCD4; AZT & srCD4; AZT (Antiviral); AZT+PRO 140; AZT, Antiviral; Apo-Zidovudine; BWA-509U; Intron A & AZT; Novo-Azt; Propolis+AZT; Retrovir (TN); Retrovir(TM); Retrovis (TN); Zidovudine+PRO 140; AZT & Colony-stimulating factor 2; AZT & Concanavalin A (ConA); AZT & GM-CSF; AZT & IFN-alpha; AZT & IL-1; AZT & IL-2; AZT & IL-6; AZT & Li & EPO; AZT & NP (from PHCA or HSA); AZT & PM-19; DS-4152 & AZT; Liposomal AZT-SN-1; Liposomal AZT-SN-3; PC-SOD+AZT;RIFN-beta seron & AZT; AZT & CD4(178)-PE 40; AZT & Li & GM-CSF; AZT & Li & IL-1; AZT & Li & IL-6; AZT & rIFNalpha2; Racemic-dipalmitoylglycerophospho-AZT (in a lipid vesicle); Zidovudine (JAN/USP/INN); Zidovudine [USAN:INN:BAN:JAN]; AZT & rsCD4 & rIFNalphaA; SN-1-dipalmitoylglycerophospho-AZT (in a lipid vesicle); SN-3-dipalmitoylglycerophospho-AZT (in a lipid vesicle); AZT & Interferon-alpha-2; Met-SDF-1beta & AZT; Met-SDF-1beta & Zidovudine; Interferon AD + 3'-azido-3'-deoxythymidine; 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)thymine; 3′-Azido-3′-deoxythymidine; 3' Azido 2',3' Dideoxythymidine; 3' Azido 3' deoxythymidine; 3'-Azido-3'-deoxythymidine & Concanavalin A; 3'-Azido-3'-deoxythymidine & Erythropoietin; 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 & Interleukin-1; 3'-Azido-3'-deoxythymidine & Lithium & Interleukin-6; 3'-Azido-3'-deoxythymidine & Lymphoblastoid Interferon; 3'-Azido-3'-deoxythymidine & Sho-Saiko-To; 3'-Azido-3'deoxythymidine & Interferon-alpha; 3'-Azidothymidine; 3'-azido-3'-deoxythymidine, AZT; 3-Azido-3-deoxythymidine; Dendrigen; CTCE-0422
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Approved [1]
Diarrhea ME05.1 Investigative [2]
Nephropathy GC2Z Investigative [2]
Virus infection 1A24-1D9Z Investigative [3]
Therapeutic Class
Anti-HIV Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 267.24
Logarithm of the Partition Coefficient (xlogp) 0
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Bioavailability
63% of drug becomes completely available to its intended biological destination(s) [5]
Clearance
The drug present in the plasma can be removed from the body at the rate of 25 mL/min/kg [6]
Elimination
2.8% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.1 hours [6]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 37.41868 micromolar/kg/day [7]
Unbound Fraction
The unbound fraction of drug in plasma is 0.8% [6]
Vd
The volume of distribution (Vd) of drug is 1.6 +/- 0.6 L/kg []
Water Solubility
The ability of drug to dissolve in water is measured as 25 mg/mL [4]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Cell death Not Available CDKN2A OTBOQ73Y [8]
Cell death Not Available HRAS OTFYE6AJ [8]
Cell-mediated cytotoxicity Not Available SDS OT5WTJ2M [8]
Cell-mediated cytotoxicity Not Available COX4I1 OTU0FC24 [8]
Cytogenetic abnormality Not Available POLRMT OT5Q8ZUJ [8]
Hematopoiesis impaired Not Available IL3 OT0CQ35N [8]
Metabolic disorder Not Available SLC25A5? OT1XIBMN [8]
Mitochondrial toxicity Not Available MT-CO1 OTG3O9BN [8]
Mitochondrial toxicity Not Available rep OTMJ5H6Y [8]
Mitochondrial toxicity Not Available NRF1 OTOXWNV8 [8]
Mitochondrial toxicity Not Available CYB5R3 OTUGT3G8 [8]
⏷ Show the Full List of 11 ADR Information of This Drug
Chemical Identifiers
Formula
C10H13N5O4
IUPAC Name
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Canonical SMILES
CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
InChI
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
InChIKey
HBOMLICNUCNMMY-XLPZGREQSA-N
Cross-matching ID
PubChem CID
35370
ChEBI ID
CHEBI:10110
CAS Number
30516-87-1
DrugBank ID
DB00495
TTD ID
D01XYJ
VARIDT ID
DR00296
INTEDE ID
DR1729
ACDINA ID
D00739
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fms-like tyrosine kinase 3 (FLT-3) TTGJCWZ FLT3_HUMAN Binder [9]
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [10]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporter 2 (SLC22A7) DT0OC1Q S22A7_HUMAN Substrate [11]
Organic anion transporter 4 (SLC22A11) DT06JWZ S22AB_HUMAN Substrate [11]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [12]
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [12]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [13]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [11]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [11]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [14]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [15]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [16]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [17]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [16]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [16]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [16]
UDP-glucuronosyltransferase 2B7 (UGT2B7)
Main DME
DEB3CV1 UD2B7_HUMAN Substrate [18]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
11-beta-hydroxysteroid dehydrogenase 1 (HSD11B1) OTO7FJA9 DHI1_HUMAN Gene/Protein Processing [19]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [20]
ABC-type oligopeptide transporter ABCB9 (ABCB9) OTSOBOL5 ABCB9_HUMAN Gene/Protein Processing [21]
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Gene/Protein Processing [19]
Acetyl-CoA carboxylase 2 (ACACB) OT96UIP1 ACACB_HUMAN Gene/Protein Processing [19]
Acyl carrier protein, mitochondrial (NDUFAB1) OTF906UR ACPM_HUMAN Gene/Protein Processing [22]
Adenine phosphoribosyltransferase (APRT) OT5ZUKVF APT_HUMAN Gene/Protein Processing [23]
Adenosine 3'-phospho 5'-phosphosulfate transporter 2 (SLC35B3) OTBDPI8I S35B3_HUMAN Gene/Protein Processing [21]
Adenosine deaminase (ADA) OTOX2872 ADA_HUMAN Gene/Protein Processing [24]
Adiponectin (ADIPOQ) OTNX23LE ADIPO_HUMAN Gene/Protein Processing [25]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Human immunodeficiency virus infection
ICD Disease Classification 1C62
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Fms-like tyrosine kinase 3 (FLT-3) DTT FLT3 2.11E-01 -0.05 -0.16
Organic anion transporter 3 (SLC22A8) DTP OAT3 5.19E-01 -8.88E-03 -2.08E-02
P-glycoprotein 1 (ABCB1) DTP P-GP 9.39E-02 1.07E-01 2.80E-01
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 8.54E-01 1.24E-02 7.20E-02
Organic anion transporter 1 (SLC22A6) DTP OAT1 7.18E-01 -4.56E-02 -1.42E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 9.45E-01 -5.34E-02 -9.01E-02
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 3.73E-06 2.82E-01 7.01E-01
Organic anion transporter 2 (SLC22A7) DTP OAT2 5.96E-02 -5.09E-02 -3.48E-01
Organic anion transporter 4 (SLC22A11) DTP OAT4 4.61E-04 -7.04E-02 -3.49E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 1.10E-01 -5.91E-02 -3.60E-01
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 1.82E-04 -1.35E-01 -5.84E-01
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 2.02E-01 -2.49E-02 -1.81E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 2.40E-01 -3.31E-02 -1.97E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 1.90E-01 -9.81E-03 -5.96E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Zidovudine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Cobicistat DM6L4H2 Moderate Decreased metabolism of Zidovudine caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [26]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [27]
Ritonavir DMU764S Minor Increased metabolism of Zidovudine caused by Ritonavir mediated induction of UGT. Human immunodeficiency virus disease [1C60-1C62] [28]
Coadministration of a Drug Treating the Disease Different from Zidovudine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [26]
Arn-509 DMT81LZ Moderate Accelerated clearance of Zidovudine due to the transporter induction by Arn-509. Acute myeloid leukaemia [2A60] [29]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [30]
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Zidovudine and Roflumilast. Asthma [CA23] [29]
Clarithromycin DM4M1SG Minor Altered absorption of Zidovudine due to GI dynamics variation caused by Clarithromycin. Bacterial infection [1A00-1C4Z] [31]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Zidovudine and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [32]
Pentamidine DMHZJCG Moderate Increased risk of nephrotoxicity by the combination of Zidovudine and Pentamidine. Fungal infection [1F29-1F2F] [26]
Amphotericin B DMTAJQE Moderate Additive myelosuppressive effects by the combination of Zidovudine and Amphotericin B. Fungal infection [1F29-1F2F] [33]
Atovaquone DMY4UMW Minor Decreased metabolism of Zidovudine caused by Atovaquone mediated inhibition of UGT. Fungal infection [1F29-1F2F] [34]
Rifapentine DMCHV4I Moderate Increased metabolism of Zidovudine caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [35]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Brentuximab vedotin. Hodgkin lymphoma [2B30] [36]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Zidovudine and Mipomersen. Hyper-lipoproteinaemia [5C80] [37]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Zidovudine and Teriflunomide. Hyper-lipoproteinaemia [5C80] [38]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Zidovudine and BMS-201038. Hyper-lipoproteinaemia [5C80] [39]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Methotrexate. Leukaemia [2A60-2B33] [29]
Denosumab DMNI0KO Moderate Additive myelosuppressive effects by the combination of Zidovudine and Denosumab. Low bone mass disorder [FB83] [40]
PF-06463922 DMKM7EW Moderate Increased metabolism of Zidovudine caused by PF-06463922 mediated induction of UGT. Lung cancer [2C25] [26]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [41]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Idelalisib. Mature B-cell leukaemia [2A82] [42]
Ethinyl estradiol DMODJ40 Minor Decreased metabolism of Zidovudine caused by Ethinyl estradiol mediated inhibition of UGT. Menopausal disorder [GA30] [43]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Zidovudine and Tecfidera. Multiple sclerosis [8A40] [44]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Zidovudine and Siponimod. Multiple sclerosis [8A40] [26]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Zidovudine and Fingolimod. Multiple sclerosis [8A40] [45]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Zidovudine and Ocrelizumab. Multiple sclerosis [8A40] [46]
Ozanimod DMT6AM2 Major Additive immunosuppressive effects by the combination of Zidovudine and Ozanimod. Multiple sclerosis [8A40] [29]
Rifabutin DM1YBHK Moderate Increased metabolism of Zidovudine caused by Rifabutin mediated induction of CYP450 enzyme. Mycobacterium infection [1B10-1B21] [35]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive myelosuppressive effects by the combination of Zidovudine and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [47]
Orlistat DMRJSP8 Moderate Altered absorption of Zidovudine caused by Orlistat. Obesity [5B80-5B81] [48]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Zidovudine and Canakinumab. Rheumatoid arthritis [FA20] [49]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Zidovudine and Golimumab. Rheumatoid arthritis [FA20] [50]
Leflunomide DMR8ONJ Major Additive myelosuppressive effects by the combination of Zidovudine and Leflunomide. Rheumatoid arthritis [FA20] [38]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [29]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Zidovudine and Naltrexone. Substance abuse [6C40] [51]
Azathioprine DMMZSXQ Moderate Additive immunosuppressive effects by the combination of Zidovudine and Azathioprine. Transplant rejection [NE84] [26]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Zidovudine and Plazomicin. Urinary tract infection [GC08] [26]
⏷ Show the Full List of 35 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
FD&C blue no. 1 E00263 19700 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Ferrosoferric oxide E00231 14789 Colorant
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 3350 E00652 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Potassium hydroxide E00233 14797 Alkalizing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin E00637 Not Available Other agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Triacetin E00080 5541 Humectant; Plasticizing agent; Solvent
⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Zidovudine 100 mg capsule 100 mg Oral Capsule Oral
Zidovudine 300 mg tablet 300 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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42 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
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44 Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
45 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
46 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
47 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
48 MHRA. Medicines and Healthcare Products Regulatory Agency "Orlistat: theoretical interaction with antiretroviral HIV medicines.".
49 Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
50 Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
51 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.