ZIDOVUDINE


Trade Names	RETROVIR ZIDOVUDINE
Synonyms	3'-azt AZT Azidothymidine BW A509U BW-A-509U BW-A509U BWA509U COMPOUND S COMPOUND-S NSC-602670 Retrovir Zidovudine Zidovudinum
Status
Molecule Category	Free-form
ATC	J05AF01
UNII	4B9XT59T7S
EPA CompTox	DTXSID8020127

Structure


InChI Key	HBOMLICNUCNMMY-XLPZGREQSA-N
Smiles	Cc1cn([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)c(=O)[nH]c1=O
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C10H13N5O4
Molecular Weight	267.25
AlogP	-0.2
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	3.0
Polar Surface Area	133.08
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	19.0

Pharmacology

Mechanism of Action	Action	Reference
Human immunodeficiency virus type 1 reverse transcriptase inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	2-38	3-50	5.4	-	0-96
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily	126	6-23	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	4.7-134.05
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	-	-	-	4.7

	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Avian myeloblastosis virus	-	430	-	-	-
Cricetulus griseus	-	-	-	-	95.75-134.05
Dengue virus	-	-	-	-	0
HIV-1 M:B_HXB2R	-	50	-	-	-
HIV-1 M:B_Lai	4-6.2	-	-	-	-
Homo sapiens	0.32-700	1-870	-	-	0-90
Human T-lymphotropic virus 1	-	-	-	-	100
Human immunodeficiency virus	2-20	2.5-10	-	-	98.1-100
Human immunodeficiency virus 1	0.004-890	0.3-250	5.4	-	0-100
Human immunodeficiency virus 2	2-56	0.2-200	-	-	-
Human immunodeficiency virus type 1	4.5	-	-	-	-
Human immunodeficiency virus type 1 (JRCSF ISOLATE)	0.96-170	-	-	-	-
Human immunodeficiency virus type 1 BH10	9	-	-	-	-
Human immunodeficiency virus type 2 (ISOLATE ROD)	1.6-490	1.7-40	-	-	-
Human immunodeficiency virus type 2 (isolate KR)	-	69	-	-	-
Influenza A virus (A/Bar-headed Goose/Qinghai/59/05(H5N1))	-	12	-	-	-
Influenza A virus (A/Viet Nam/1203/2004(H5N1))	-	11	-	-	-
Mus musculus	20-46	-	-	-	46-78
Porcine endogenous retrovirus	23	-	-	-	-
Rauscher murine leukemia virus	-	23	-	-	-
Simian immunodeficiency virus	11-12.2	0.5-10	-	-	-
West Nile virus	-	-	-	-	0
human immunodeficiency virus type IIIB	40	-	-	-	-
human immunodeficiency virus type i	100	-	-	-	-

Environmental Exposure

Environmental Exposure Map

Countries
South Africa

Cross References

Resources	Reference
ChEBI	10110
ChEMBL	CHEMBL129
DrugBank	DB00495
DrugCentral	2861
FDA SRS	4B9XT59T7S
Human Metabolome Database	HMDB0014638
Guide to Pharmacology	4825
KEGG	C07210
PDB	AZZ
PharmGKB	PA451954
PubChem	35370
SureChEMBL	SCHEMBL7409
ZINC	ZINC000003779042

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).