LAMIVUDINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1995)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J05AF05
UNII: 2T8Q726O95

Structure
InChI Key JTEGQNOMFQHVDC-NKWVEPMBSA-N
Smile Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1
InChI
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H11N3O3S
Molecular Weight 229.26
AlogP -0.59
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 90.37
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 15.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
42 - - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 54200 - - -
Secreted protein
- - 44000 - -
Structural protein
- - - - 18-94

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 4 D015658 FDA
Hepatitis B, Chronic 4 D019694 ClinicalTrials
Liver Cirrhosis 3 D008103 ClinicalTrials
Diarrhea 3 D003967 ClinicalTrials
AIDS-Associated Nephropathy 3 D016263 ClinicalTrials
Tuberculosis 3 D014376 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Paraparesis, Tropical Spastic 2 D015493 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials

Related Entries

MCS

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Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 46.0
Nervous system disorders Headache 42.0
Nervous system disorders Headache
Nervous system disorders Headache 35.1
Nervous system disorders Headache 33.7
Investigations Body temperature increased 32.0
Investigations Body temperature increased 31.8
Gastrointestinal disorders Nausea 29.0
Nervous system disorders Headache 28.9
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Fatigue
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 27.0
General disorders and administration site conditions Asthenia 26.0
General disorders and administration site conditions Discomfort 26.0
General disorders and administration site conditions Fatigue 26.0
General disorders and administration site conditions Feeling abnormal 26.0
General disorders and administration site conditions Ill-defined disorder 26.0
General disorders and administration site conditions Malaise 26.0
General disorders and administration site conditions Asthenia 25.0
Investigations Body temperature increased 25.0
General disorders and administration site conditions Discomfort 25.0
General disorders and administration site conditions Fatigue 25.0
General disorders and administration site conditions Feeling abnormal 25.0
General disorders and administration site conditions Ill-defined disorder 25.0
Infections and infestations Infection 25.0
General disorders and administration site conditions Malaise 25.0
General disorders and administration site conditions Asthenia 24.6
General disorders and administration site conditions Discomfort 24.6
General disorders and administration site conditions Fatigue 24.6
General disorders and administration site conditions Feeling abnormal 24.6
General disorders and administration site conditions Ill-defined disorder 24.6
General disorders and administration site conditions Malaise 24.6
Nervous system disorders Neuropathy peripheral 23.3
General disorders and administration site conditions Asthenia 23.0
General disorders and administration site conditions Discomfort 23.0
General disorders and administration site conditions Fatigue 23.0
General disorders and administration site conditions Feeling abnormal 23.0
General disorders and administration site conditions Ill-defined disorder 23.0
General disorders and administration site conditions Malaise 23.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 22.1
General disorders and administration site conditions Pain 22.1
Gastrointestinal disorders Diarrhoea 22.0
Nervous system disorders Headache 22.0
Nervous system disorders Headache 21.2
Nervous system disorders Headache
Infections and infestations Infection
Infections and infestations Viral infection 20.9
Nervous system disorders Headache 20.8
Infections and infestations Respiratory tract infection 20.5
Gastrointestinal disorders Gastrointestinal pain 20.0
General disorders and administration site conditions Asthenia 19.0
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Respiratory tract infection 19.0
Infections and infestations Respiratory tract infection 18.1
General disorders and administration site conditions Asthenia
Respiratory, thoracic and mediastinal disorders Cough 18.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal discomfort 17.4
General disorders and administration site conditions Pain 17.4
Gastrointestinal disorders Abdominal discomfort
Gastrointestinal disorders Gastrointestinal pain 17.0
Gastrointestinal disorders Nausea
General disorders and administration site conditions Pain
Infections and infestations Respiratory tract infection
Gastrointestinal disorders Vomiting
Investigations Body temperature increased 16.0
Gastrointestinal disorders Nausea 16.0
Gastrointestinal disorders Vomiting 16.0
Gastrointestinal disorders Abdominal discomfort 15.0
Respiratory, thoracic and mediastinal disorders Cough 15.0
Gastrointestinal disorders Gastrointestinal pain
General disorders and administration site conditions Pain 15.0
Gastrointestinal disorders Nausea 14.5
Gastrointestinal disorders Vomiting 14.5
Respiratory, thoracic and mediastinal disorders Cough 14.4
Skin and subcutaneous tissue disorders Dermatitis 14.0
Gastrointestinal disorders Diarrhoea 14.0
General disorders and administration site conditions Discomfort 14.0
Gastrointestinal disorders Gastrointestinal infection 14.0
General disorders and administration site conditions Pain 14.0
Skin and subcutaneous tissue disorders Rash 14.0
Gastrointestinal disorders Nausea 13.9
Gastrointestinal disorders Vomiting 13.9
Gastrointestinal disorders Abdominal discomfort 13.8
Gastrointestinal disorders Diarrhoea 13.8
General disorders and administration site conditions Pain 13.8
Skin and subcutaneous tissue disorders Dermatitis 13.6
Skin and subcutaneous tissue disorders Rash 13.6
Musculoskeletal and connective tissue disorders Musculoskeletal pain 13.5
General disorders and administration site conditions Pain 13.5
Respiratory, thoracic and mediastinal disorders Cough 13.0
Gastrointestinal disorders Oropharyngeal discomfort 13.0
Gastrointestinal disorders Oropharyngeal pain 13.0
Infections and infestations Infection 12.8
Gastrointestinal disorders Diarrhoea 12.5
Nervous system disorders Neuropathy peripheral 12.4
Investigations Body temperature increased
Investigations Body temperature increased 12.0
General disorders and administration site conditions Chills 12.0
Skin and subcutaneous tissue disorders Dermatitis 12.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 12.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 12.0
Gastrointestinal disorders Nausea 12.0
General disorders and administration site conditions Pain 12.0
Skin and subcutaneous tissue disorders Rash 12.0
Gastrointestinal disorders Stomatitis 12.0
Gastrointestinal disorders Vomiting 12.0
Gastrointestinal disorders Stomatitis 11.9
Respiratory, thoracic and mediastinal disorders Cough 11.8
General disorders and administration site conditions Discomfort 11.8
Infections and infestations Infection 11.8
General disorders and administration site conditions Pain 11.8
Skin and subcutaneous tissue disorders Acne 11.6
General disorders and administration site conditions Discomfort 11.6
Infections and infestations Folliculitis 11.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 11.6
Musculoskeletal and connective tissue disorders Myalgia 11.6
General disorders and administration site conditions Pain 11.6
Psychiatric disorders Sleep disorder 11.6
Blood and lymphatic system disorders Lymphadenopathy 11.4
Gastrointestinal disorders Abdominal discomfort 11.3
Infections and infestations Infection 11.3
General disorders and administration site conditions Pain 11.3
Gastrointestinal disorders Abdominal pain 11.0
General disorders and administration site conditions Decreased appetite 11.0
Gastrointestinal disorders Gastrointestinal pain 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
Infections and infestations Infection 10.8
Psychiatric disorders Sleep disorder 10.8
Hepatobiliary disorders Hepatomegaly 10.6
Infections and infestations Nasopharyngitis 10.6
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 10.6
Cardiac disorders Dizziness 10.4
Infections and infestations Infection 10.4
Infections and infestations Bronchitis 10.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 10.0
Nervous system disorders Neuropathy peripheral 10.0
Infections and infestations Infection 9.76
Respiratory, thoracic and mediastinal disorders Cough 9.72
Musculoskeletal and connective tissue disorders Musculoskeletal pain 9.72
General disorders and administration site conditions Discomfort 9.6
Infections and infestations Infection 9.6
Musculoskeletal and connective tissue disorders Musculoskeletal pain 9.6
General disorders and administration site conditions Pain 9.6
Cardiac disorders Dizziness 9.3
General disorders and administration site conditions Discomfort 9.2
General disorders and administration site conditions Pain 9.2
Gastrointestinal disorders Abdominal discomfort 9.1
General disorders and administration site conditions Pain 9.1
Investigations Blood creatine phosphokinase increased 9.0
Investigations Breath sounds abnormal 9.0
Blood and lymphatic system disorders Lymphadenopathy 9.0
Respiratory, thoracic and mediastinal disorders Wheezing 9.0
Investigations Breath sounds abnormal 8.9
Respiratory, thoracic and mediastinal disorders Wheezing 8.9
Nervous system disorders Neuropathy peripheral 8.5
Gastrointestinal disorders Abdominal discomfort 8.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 8.4
Musculoskeletal and connective tissue disorders Myalgia 8.4
General disorders and administration site conditions Pain 8.4
Gastrointestinal disorders Abdominal discomfort
General disorders and administration site conditions Discomfort 8.33
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 8.33
Gastrointestinal disorders Abdominal discomfort 8.1
General disorders and administration site conditions Pain 8.1
Psychiatric disorders Sleep disorder 8.1
General disorders and administration site conditions Asthenia 8.0
General disorders and administration site conditions Decreased appetite
Gastrointestinal disorders Diarrhoea 8.0
General disorders and administration site conditions Discomfort 8.0
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
Infections and infestations Nasopharyngitis 8.0
Gastrointestinal disorders Nausea 8.0
Blood and lymphatic system disorders Neutropenia 8.0
Gastrointestinal disorders Oropharyngeal discomfort
Gastrointestinal disorders Oropharyngeal pain
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 8.0
Blood and lymphatic system disorders Splenomegaly 8.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 8.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 7.74
Psychiatric disorders Sleep disorder 7.64
Blood and lymphatic system disorders Splenomegaly 7.63
General disorders and administration site conditions Hyperhidrosis 7.6
Infections and infestations Viral infection 7.6
Gastrointestinal disorders Gastrointestinal infection 7.5
Cardiac disorders Dizziness 7.41
Infections and infestations Infection 7.4
Gastrointestinal disorders Abdominal discomfort 7.2
General disorders and administration site conditions Pain 7.2
Infections and infestations Sinusitis 7.2
Investigations Breath sounds abnormal 7.0
General disorders and administration site conditions Decreased appetite 7.0
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Feeling abnormal
Infections and infestations Fungal skin infection 7.0
General disorders and administration site conditions Hyperhidrosis 7.0
General disorders and administration site conditions Ill-defined disorder
Infections and infestations Infection 7.0
Nervous system disorders Insomnia 7.0
General disorders and administration site conditions Malaise
Gastrointestinal disorders Nausea 7.0
Blood and lymphatic system disorders Neutropenia 7.0
Psychiatric disorders Sleep disorder 7.0
Infections and infestations Viral skin infection 7.0
Gastrointestinal disorders Vomiting 7.0
Respiratory, thoracic and mediastinal disorders Wheezing 7.0
Cardiac disorders Dizziness 6.94
Infections and infestations Infection 6.9
Skin and subcutaneous tissue disorders Acne 6.8
Infections and infestations Folliculitis 6.8
Infections and infestations Sinusitis 6.8
Gastrointestinal disorders Nausea 6.78
Gastrointestinal disorders Vomiting 6.78
Psychiatric disorders Sleep disorder 6.73
Infections and infestations Viral infection 6.6
Infections and infestations Sinusitis 6.5
Gastrointestinal disorders Gastrointestinal infection 6.4
Gastrointestinal disorders Diarrhoea 6.36
General disorders and administration site conditions Hyperhidrosis 6.3
Infections and infestations Fungal skin infection 6.1
Investigations Body temperature increased 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Gastrointestinal disorders Diarrhoea 6.0
General disorders and administration site conditions Discomfort 6.0
Cardiac disorders Dizziness 6.0
General disorders and administration site conditions Feeling abnormal 6.0
General disorders and administration site conditions Ill-defined disorder 6.0
General disorders and administration site conditions Malaise 6.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 6.0
Musculoskeletal and connective tissue disorders Myalgia 6.0
Blood and lymphatic system disorders Neutropenia 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Gastrointestinal disorders Stomatitis 6.0
Gastrointestinal disorders Vomiting 6.0
Gastrointestinal disorders Abdominal discomfort 5.8
Infections and infestations Bronchitis 5.8
General disorders and administration site conditions Pain 5.8
Nervous system disorders Headache 5.76
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.7
Musculoskeletal and connective tissue disorders Myalgia 5.7
Infections and infestations Fungal skin infection 5.6
Respiratory, thoracic and mediastinal disorders Respiration abnormal 5.6
Respiratory, thoracic and mediastinal disorders Respiratory disorder 5.6
Nervous system disorders Headache
Gastrointestinal disorders Abdominal discomfort 5.2
Gastrointestinal disorders Gastrointestinal infection 5.2
General disorders and administration site conditions Inflammation 5.2
General disorders and administration site conditions Pain 5.2
Infections and infestations Viral skin infection 5.2
Musculoskeletal and connective tissue disorders Arthralgia 5.0
Investigations Blood creatine phosphokinase increased
Gastrointestinal disorders Diarrhoea 5.0
Gastrointestinal disorders Dyspepsia 5.0
Nervous system disorders Headache 5.0
General disorders and administration site conditions Hyperhidrosis 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Blood and lymphatic system disorders Neutropenia 5.0
Gastrointestinal disorders Vomiting 5.0
Infections and infestations Bronchitis 4.8
Infections and infestations Bronchitis 4.7
Infections and infestations Sinusitis 4.7
Infections and infestations Viral skin infection 4.7
Infections and infestations Viral infection 4.3
Gastrointestinal disorders Abdominal discomfort 4.19
General disorders and administration site conditions Pain 4.19
Investigations Liver function test abnormal
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Abdominal discomfort 4.1
Infections and infestations Fungal skin infection 4.1
General disorders and administration site conditions Pain 4.1
Respiratory, thoracic and mediastinal disorders Respiration abnormal 4.1
Respiratory, thoracic and mediastinal disorders Respiratory disorder 4.1
Blood and lymphatic system disorders Anaemia 4.0
Investigations Body temperature increased
Psychiatric disorders Depression 4.0
Cardiac disorders Dizziness 4.0
Gastrointestinal disorders Dyspepsia
Dysthymic disorder 4.0
Gastrointestinal disorders Flatulence 4.0
General disorders and administration site conditions Hyperhidrosis
Psychiatric disorders Sleep disorder 4.0
Skin and subcutaneous tissue disorders Acne 3.9
Cardiac disorders Dizziness 3.9
Infections and infestations Folliculitis 3.9
General disorders and administration site conditions Inflammation 3.8
General disorders and administration site conditions Asthenia 3.66
General disorders and administration site conditions Discomfort 3.66
General disorders and administration site conditions Fatigue 3.66
General disorders and administration site conditions Feeling abnormal 3.66
General disorders and administration site conditions Ill-defined disorder 3.66
Investigations Liver function test abnormal 3.66
General disorders and administration site conditions Malaise 3.66
Skin and subcutaneous tissue disorders Acne 3.5
Infections and infestations Folliculitis 3.5
General disorders and administration site conditions Inflammation 3.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.5
Musculoskeletal and connective tissue disorders Myalgia 3.5
Respiratory, thoracic and mediastinal disorders Respiration abnormal 3.5
Respiratory, thoracic and mediastinal disorders Respiratory disorder 3.5
Infections and infestations Viral skin infection 3.5
Skin and subcutaneous tissue disorders Dermatitis 3.14
Gastrointestinal disorders Nausea 3.14
Skin and subcutaneous tissue disorders Rash 3.14
Gastrointestinal disorders Vomiting 3.14
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Fatigue
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
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal distension 3.0
Gastrointestinal disorders Abdominal pain 3.0
Blood and lymphatic system disorders Anaemia 3.0
Gastrointestinal disorders Diarrhoea
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
Blood and lymphatic system disorders Neutropenia 3.0
General disorders and administration site conditions Pain 3.0
Blood and lymphatic system disorders Thrombocytopenia 3.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Diarrhoea 2.62
Gastrointestinal disorders Pharyngitis 2.09
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Skin and subcutaneous tissue disorders Rash
Blood and lymphatic system disorders Anaemia 2.0
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Dry mouth 2.0
Gastrointestinal disorders Dyspepsia 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
Gastrointestinal disorders Nausea 2.0
General disorders and administration site conditions Pain 2.0
Respiratory, thoracic and mediastinal disorders Respiration abnormal 2.0
Respiratory, thoracic and mediastinal disorders Respiratory disorder 2.0
General disorders and administration site conditions Inflammation 1.7
Psychiatric disorders Affective disorder 1.0
Blood and lymphatic system disorders Anaemia 1.0
General disorders and administration site conditions Asthenia 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
General disorders and administration site conditions Fatigue 1.0
Nervous system disorders Headache
General disorders and administration site conditions Hyperhidrosis 1.0
Gastrointestinal disorders Mouth ulceration 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Gastrointestinal disorders Stomatitis 1.0
Blood and lymphatic system disorders Thrombocytopenia 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.58
Investigations
8.32
Infections and infestations
7.08
Injury, poisoning and procedural complications
7.08
Nervous system disorders
6.0
Metabolism and nutrition disorders
5.64
Hepatobiliary disorders
5.58
Renal and urinary disorders
5.22
Pregnancy, puerperium and perinatal conditions
4.84
Musculoskeletal and connective tissue disorders
4.37
Gastrointestinal disorders
4.2
Skin and subcutaneous tissue disorders
3.7
Respiratory, thoracic and mediastinal disorders
3.27
Vascular disorders
3.23
Psychiatric disorders
2.92
Blood and lymphatic system disorders
2.69
Immune system disorders
2.59
Congenital, familial and genetic disorders
2.53
Cardiac disorders
2.38

Cross References

Resources Reference
CAS NUMBER 134678-17-4
ChEBI 63577
ChEMBL CHEMBL141
DrugBank DB00709
DrugCentral 1539
FDA SRS 2T8Q726O95
Human Metabolome Database HMDB0014847
KEGG C07065
PDB 3TC
PharmGKB PA450163
PubChem 60825
SureChEMBL SCHEMBL109675
ZINC ZINC000000012346
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