Details of the Drug

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], [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

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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 [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 37.41868 micromolar/kg/day [8]
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 [9]
Water Solubility: The ability of drug to dissolve in water is measured as 25 mg/mL [4]

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

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	[10]
Human immunodeficiency virus Reverse transcriptase (HIV RT)	TT84ETX	POL_HV1B1	Inhibitor	[11]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic anion transporter 2 (SLC22A7)	DT0OC1Q	S22A7_HUMAN	Substrate	[12]
Organic anion transporter 4 (SLC22A11)	DT06JWZ	S22AB_HUMAN	Substrate	[12]
Multidrug resistance-associated protein 4 (ABCC4)	DTCSGPB	MRP4_HUMAN	Substrate	[13]
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[13]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[14]
Organic anion transporter 1 (SLC22A6)	DTQ23VB	S22A6_HUMAN	Substrate	[12]
Organic anion transporter 3 (SLC22A8)	DTVP67E	S22A8_HUMAN	Substrate	[12]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[15]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[16]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[17]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[18]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[17]
Cytochrome P450 2A6 (CYP2A6)	DEJVYAZ	CP2A6_HUMAN	Substrate	[17]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[17]
UDP-glucuronosyltransferase 2B7 (UGT2B7)_{Main DME}	DEB3CV1	UD2B7_HUMAN	Substrate	[19]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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]	[151]
Efavirenz	DMC0GSJ	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Efavirenz.	Human immunodeficiency virus disease [1C60-1C62]	[152]
Ritonavir	DMU764S	Minor	Increased metabolism of Zidovudine caused by Ritonavir mediated induction of UGT.	Human immunodeficiency virus disease [1C60-1C62]	[153]
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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]	[151]
Arn-509	DMT81LZ	Moderate	Accelerated clearance of Zidovudine due to the transporter induction by Arn-509.	Acute myeloid leukaemia [2A60]	[154]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[155]
Roflumilast	DMPGHY8	Moderate	Additive immunosuppressive effects by the combination of Zidovudine and Roflumilast.	Asthma [CA23]	[154]
Clarithromycin	DM4M1SG	Minor	Altered absorption of Zidovudine due to GI dynamics variation caused by Clarithromycin.	Bacterial infection [1A00-1C4Z]	[156]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Zidovudine and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[157]
Pentamidine	DMHZJCG	Moderate	Increased risk of nephrotoxicity by the combination of Zidovudine and Pentamidine.	Fungal infection [1F29-1F2F]	[151]
Amphotericin B	DMTAJQE	Moderate	Additive myelosuppressive effects by the combination of Zidovudine and Amphotericin B.	Fungal infection [1F29-1F2F]	[158]
Atovaquone	DMY4UMW	Minor	Decreased metabolism of Zidovudine caused by Atovaquone mediated inhibition of UGT.	Fungal infection [1F29-1F2F]	[159]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Zidovudine caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[160]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[161]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Zidovudine and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[162]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Zidovudine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[163]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Zidovudine and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[164]
Methotrexate	DM2TEOL	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Methotrexate.	Leukaemia [2A60-2B33]	[154]
Denosumab	DMNI0KO	Moderate	Additive myelosuppressive effects by the combination of Zidovudine and Denosumab.	Low bone mass disorder [FB83]	[165]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Zidovudine caused by PF-06463922 mediated induction of UGT.	Lung cancer [2C25]	[151]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[166]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Idelalisib.	Mature B-cell leukaemia [2A82]	[167]
Ethinyl estradiol	DMODJ40	Minor	Decreased metabolism of Zidovudine caused by Ethinyl estradiol mediated inhibition of UGT.	Menopausal disorder [GA30]	[168]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Zidovudine and Tecfidera.	Multiple sclerosis [8A40]	[169]
Siponimod	DM2R86O	Major	Additive immunosuppressive effects by the combination of Zidovudine and Siponimod.	Multiple sclerosis [8A40]	[151]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Zidovudine and Fingolimod.	Multiple sclerosis [8A40]	[170]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Zidovudine and Ocrelizumab.	Multiple sclerosis [8A40]	[171]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Zidovudine and Ozanimod.	Multiple sclerosis [8A40]	[154]
Rifabutin	DM1YBHK	Moderate	Increased metabolism of Zidovudine caused by Rifabutin mediated induction of CYP450 enzyme.	Mycobacterium infection [1B10-1B21]	[160]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive myelosuppressive effects by the combination of Zidovudine and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[172]
Orlistat	DMRJSP8	Moderate	Altered absorption of Zidovudine caused by Orlistat.	Obesity [5B80-5B81]	[173]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Zidovudine and Canakinumab.	Rheumatoid arthritis [FA20]	[174]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Zidovudine and Golimumab.	Rheumatoid arthritis [FA20]	[175]
Leflunomide	DMR8ONJ	Major	Additive myelosuppressive effects by the combination of Zidovudine and Leflunomide.	Rheumatoid arthritis [FA20]	[163]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[154]
Naltrexone	DMUL45H	Moderate	Increased risk of hepatotoxicity by the combination of Zidovudine and Naltrexone.	Substance abuse [6C40]	[176]
Azathioprine	DMMZSXQ	Moderate	Additive immunosuppressive effects by the combination of Zidovudine and Azathioprine.	Transplant rejection [NE84]	[151]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Zidovudine and Plazomicin.	Urinary tract infection [GC08]	[151]
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⏷ 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
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⏷ 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

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176	Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.