ZIDOVUDINE

Search structure
Trade Names:
Synonyms:
AZT
Status: Approved (1987)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: J05AF01
UNII: 4B9XT59T7S

Structure
InChI Key HBOMLICNUCNMMY-XLPZGREQSA-N
Smile 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

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
2-24900 3-21430 5 - 0-96
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily
126 6-23 - - -
Enzyme Transferase
- 12500 - 28000-28000 -
Secreted protein
- - 44000 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 10-134
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 5

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 4 D015658 ClinicalTrials
Tuberculosis 3 D014376 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Pregnancy 3 D011247 ClinicalTrials
Pneumonia, Pneumocystis 3 D011020 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
AIDS Dementia Complex 3 D015526 ClinicalTrials
AIDS-Related Complex 3 D000386 ClinicalTrials
Diarrhea 3 D003967 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Paraparesis, Tropical Spastic 2 D015493 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Liver Cirrhosis, Biliary 2 D008105 ClinicalTrials
Castleman Disease 2 D005871 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 2 D015459 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Infections 2 D007239 ClinicalTrials
Severe Combined Immunodeficiency 1 D016511 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 63.0
Nervous system disorders Headache 62.5
Gastrointestinal disorders Nausea 61.0
Nervous system disorders Headache 58.0
Gastrointestinal disorders Nausea 57.3
General disorders and administration site conditions Discomfort 55.6
General disorders and administration site conditions Feeling abnormal 55.6
General disorders and administration site conditions Ill-defined disorder 55.6
General disorders and administration site conditions Malaise 55.6
General disorders and administration site conditions Discomfort 53.2
General disorders and administration site conditions Feeling abnormal 53.2
General disorders and administration site conditions Ill-defined disorder 53.2
General disorders and administration site conditions Malaise 53.2
General disorders and administration site conditions Discomfort 53.0
General disorders and administration site conditions Feeling abnormal 53.0
Nervous system disorders Headache
General disorders and administration site conditions Ill-defined disorder 53.0
General disorders and administration site conditions Malaise 53.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea 51.4
Gastrointestinal disorders Nausea 51.0
Gastrointestinal disorders Nausea 46.0
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Ill-defined disorder
General disorders and administration site conditions Malaise
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Ill-defined disorder
General disorders and administration site conditions Malaise
Nervous system disorders Headache 42.0
Gastrointestinal disorders Nausea
Nervous system disorders Headache
Gastrointestinal disorders Nausea 36.2
Investigations Body temperature increased 32.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea
Gastrointestinal disorders Mouth ulceration 27.7
Gastrointestinal disorders Stomatitis 27.7
Nervous system disorders Neuropathy peripheral 25.5
Investigations Body temperature increased 25.0
Gastrointestinal disorders Vomiting 25.0
Gastrointestinal disorders Abdominal pain 21.3
Gastrointestinal disorders Gastrointestinal pain 21.3
Cardiac disorders Dizziness 20.8
General disorders and administration site conditions Decreased appetite 20.1
General disorders and administration site conditions Decreased appetite 20.0
Gastrointestinal disorders Gastrointestinal pain 20.0
General disorders and administration site conditions Decreased appetite 19.3
Gastrointestinal disorders Gastrointestinal pain
Respiratory, thoracic and mediastinal disorders Cough 18.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Nausea
Cardiac disorders Dizziness 17.9
Gastrointestinal disorders Vomiting 17.2
Skin and subcutaneous tissue disorders Dermatitis 17.0
Skin and subcutaneous tissue disorders Rash 17.0
Gastrointestinal disorders Vomiting 17.0
Gastrointestinal disorders Vomiting 16.4
Investigations Body temperature increased 16.0
Cardiac disorders Dizziness
Respiratory, thoracic and mediastinal disorders Cough 15.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Investigations Body temperature increased 14.9
Gastrointestinal disorders Diarrhoea 14.9
Gastrointestinal disorders Vomiting 14.9
Skin and subcutaneous tissue disorders Dermatitis 14.0
Skin and subcutaneous tissue disorders Rash 14.0
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Decreased appetite 12.8
Investigations Body temperature increased
Skin and subcutaneous tissue disorders Dermatitis 12.0
Gastrointestinal disorders Diarrhoea 12.0
Skin and subcutaneous tissue disorders Rash 12.0
Gastrointestinal disorders Stomatitis 12.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 11.0
Hepatobiliary disorders Hepatomegaly 11.0
Blood and lymphatic system disorders Lymphadenopathy 11.0
Infections and infestations Nasopharyngitis 11.0
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 11.0
Gastrointestinal disorders Diarrhoea 10.6
General disorders and administration site conditions Decreased appetite
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Asthenia 9.0
Investigations Breath sounds abnormal 9.0
Blood and lymphatic system disorders Lymphadenopathy 9.0
Nervous system disorders Somnolence
Respiratory, thoracic and mediastinal disorders Wheezing 9.0
General disorders and administration site conditions Asthenia 8.6
Gastrointestinal disorders Abdominal pain 8.51
General disorders and administration site conditions Chills 8.51
Gastrointestinal disorders Gastrointestinal pain 8.51
Gastrointestinal disorders Nausea 8.51
Gastrointestinal disorders Pharyngitis 8.51
Nervous system disorders Headache 8.5
Gastrointestinal disorders Constipation 8.1
General disorders and administration site conditions Decreased appetite
Gastrointestinal disorders Diarrhoea 8.0
General disorders and administration site conditions Discomfort 8.0
Gastrointestinal disorders Dysgeusia
General disorders and administration site conditions Feeling abnormal 8.0
General disorders and administration site conditions Ill-defined disorder 8.0
General disorders and administration site conditions Malaise 8.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 8.0
Musculoskeletal and connective tissue disorders Myalgia 8.0
Infections and infestations Nasopharyngitis 8.0
Gastrointestinal disorders Nausea 8.0
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 8.0
Nervous system disorders Somnolence 8.0
Blood and lymphatic system disorders Splenomegaly 8.0
Gastrointestinal disorders Vomiting 8.0
Investigations Breath sounds abnormal 7.0
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Ill-defined disorder
General disorders and administration site conditions Malaise
Gastrointestinal disorders Nausea 7.0
Gastrointestinal disorders Vomiting 7.0
Respiratory, thoracic and mediastinal disorders Wheezing 7.0
Gastrointestinal disorders Constipation 6.4
Cardiac disorders Chest pain 6.38
General disorders and administration site conditions Decreased appetite 6.38
Investigations Weight decreased 6.38
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Constipation 6.0
Gastrointestinal disorders Diarrhoea 6.0
Cardiac disorders Dizziness 6.0
Gastrointestinal disorders Dyspepsia 6.0
Nervous system disorders Paraesthesia 6.0
Gastrointestinal disorders Stomatitis 6.0
Gastrointestinal disorders Vomiting 6.0
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Dysgeusia 5.0
Gastrointestinal disorders Dyspepsia 5.0
Cardiac disorders Dyspnoea 5.0
General disorders and administration site conditions Hyperhidrosis 5.0
Nervous system disorders Insomnia 5.0
Blood and lymphatic system disorders Splenomegaly 5.0
Gastrointestinal disorders Mouth ulceration 4.26
Nervous system disorders Neuropathy peripheral 4.26
Gastrointestinal disorders Stomatitis 4.26
Investigations Weight decreased 4.26
Gastrointestinal disorders Constipation
Cardiac disorders Dizziness
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Hyperhidrosis
Nervous system disorders Neuropathy peripheral 4.0
Gastrointestinal disorders Constipation
Cardiac disorders Dyspnoea
Blood and lymphatic system disorders Neutropenia 3.0
Nervous system disorders Paraesthesia
Blood and lymphatic system disorders Thrombocytopenia 3.0
Gastrointestinal disorders Vomiting
Investigations Body temperature increased 2.13
Cardiac disorders Chest pain 2.13
General disorders and administration site conditions Chills 2.13
Gastrointestinal disorders Pharyngitis 2.13
Gastrointestinal disorders Vomiting 2.13
Gastrointestinal disorders Pharyngitis 2.1
Blood and lymphatic system disorders Agranulocytosis
Blood and lymphatic system disorders Agranulocytosis 2.0
Blood and lymphatic system disorders Anaemia 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Blood and lymphatic system disorders Agranulocytosis 1.8
Blood and lymphatic system disorders Agranulocytosis
Blood and lymphatic system disorders Anaemia 1.1
Blood and lymphatic system disorders Anaemia
Blood and lymphatic system disorders Anaemia 1.0
Gastrointestinal disorders Dyspepsia
Nervous system disorders Insomnia
Blood and lymphatic system disorders Thrombocytopenia
Blood and lymphatic system disorders Thrombocytopenia
Blood and lymphatic system disorders Anaemia

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Pregnancy, puerperium and perinatal conditions
13.69
Injury, poisoning and procedural complications
10.0
General disorders and administration site conditions
7.63
Nervous system disorders
7.36
Congenital, familial and genetic disorders
6.45
Gastrointestinal disorders
5.28
Investigations
4.94
Blood and lymphatic system disorders
4.79
Metabolism and nutrition disorders
4.6
Infections and infestations
4.41
Skin and subcutaneous tissue disorders
3.35
Vascular disorders
3.05
Musculoskeletal and connective tissue disorders
2.96
Cardiac disorders
2.9
Hepatobiliary disorders
2.88
Renal and urinary disorders
2.55
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.16
Immune system disorders
2.08
Respiratory, thoracic and mediastinal disorders
2.08
Psychiatric disorders
2.04

Cross References

Resources Reference
CAS NUMBER 30516-87-1
ChEBI 10110
ChEMBL CHEMBL129
DrugBank DB00495
DrugCentral 2861
EPA CompTox DTXSID8020127
FDA SRS 4B9XT59T7S
Human Metabolome Database HMDB0014638
Guide to Pharmacology 4825
KEGG C07210
PDB AZZ
PharmGKB PA451954
PubChem 35370
SureChEMBL SCHEMBL7409
ZINC ZINC000003779042
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