GANCICLOVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (1989)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: J05AB06
UNII: P9G3CKZ4P5

Structure
InChI Key IRSCQMHQWWYFCW-UHFFFAOYSA-N
Smile Nc1nc(O)c2ncn(COC(CO)CO)c2n1
InChI
InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H13N5O4
Molecular Weight 255.23
AlogP -1.56
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 5.0
Polar Surface Area 139.54
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 18.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human herpesvirus 1 DNA polymerase inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- - 15849 - 17
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 11

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Cytomegalovirus Retinitis 4 D017726 ClinicalTrials
Cytomegalovirus Infections 3 D003586 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Conjunctivitis 3 D003231 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Carcinoma, Hepatocellular 2 D006528 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials
Neuroblastoma 1 D009447 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Mesothelioma 1 D008654 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Eye disorders Vision blurred 60.0
Gastrointestinal disorders Diarrhoea 41.0
Investigations Body temperature increased 35.9
Investigations Body temperature increased 35.3
Investigations Body temperature increased 31.0
Gastrointestinal disorders Diarrhoea 31.0
Gastrointestinal disorders Diarrhoea 30.0
Gastrointestinal disorders Nausea 30.0
Immune system disorders Transplant rejection 30.0
Gastrointestinal disorders Diarrhoea 29.0
Nervous system disorders Tremor 28.0
Nervous system disorders Headache 27.0
Gastrointestinal disorders Diarrhoea 26.5
Gastrointestinal disorders Diarrhoea 26.0
Blood and lymphatic system disorders Neutropenia 25.7
Nervous system disorders Tremor 25.0
Gastrointestinal disorders Diarrhoea 24.4
Immune system disorders Transplant rejection 24.0
Gastrointestinal disorders Nausea 23.0
Nervous system disorders Headache 22.0
Gastrointestinal disorders Nausea 21.8
Gastrointestinal disorders Vomiting 21.0
Eye disorders Eye irritation 20.0
Vascular disorders Hypertension 20.0
Nervous system disorders Insomnia 20.0
Blood and lymphatic system disorders Anaemia 19.7
Nervous system disorders Headache 18.7
Nervous system disorders Headache 18.0
Vascular disorders Hypertension 18.0
Infections and infestations Infection 18.0
Nervous system disorders Tremor 17.0
Blood and lymphatic system disorders Anaemia 16.8
Respiratory, thoracic and mediastinal disorders Cough 16.0
Nervous system disorders Headache 16.0
Nervous system disorders Insomnia 16.0
Gastrointestinal disorders Vomiting 16.0
Respiratory, thoracic and mediastinal disorders Cough 15.1
Gastrointestinal disorders Abdominal pain 15.0
Gastrointestinal disorders Gastrointestinal pain 15.0
Vascular disorders Hypertension 15.0
Eye disorders Retinal detachment 15.0
Investigations Body temperature increased 14.0
Renal and urinary disorders Renal failure 14.0
Renal and urinary disorders Renal impairment 14.0
Gastrointestinal disorders Vomiting 14.0
Investigations Body temperature increased 13.0
Vascular disorders Hypertension 13.0
Gastrointestinal disorders Vomiting 12.6
Investigations Body temperature increased 12.0
Vascular disorders Hypertension 12.0
Renal and urinary disorders Renal failure 12.0
Nervous system disorders Tremor 12.0
Blood and lymphatic system disorders Neutropenia 11.8
Gastrointestinal disorders Nausea 11.0
Nervous system disorders Headache 10.0
Gastrointestinal disorders Abdominal pain 9.0
Investigations Body temperature increased 9.0
Gastrointestinal disorders Gastrointestinal pain 9.0
Nervous system disorders Neuropathy peripheral 9.0
General disorders and administration site conditions Oedema 9.0
Immune system disorders Transplant rejection 9.0
General disorders and administration site conditions Injection site infection 8.0
Nervous system disorders Paraesthesia 8.0
Gastrointestinal disorders Abdominal pain 7.6
Gastrointestinal disorders Gastrointestinal pain 7.6
Infections and infestations Pneumocystis jirovecii pneumonia 7.3
Nervous system disorders Insomnia 7.0
Nervous system disorders Neuropathy peripheral 7.0
Blood and lymphatic system disorders Thrombocytopenia 6.6
Infections and infestations Sepsis 6.1
Nervous system disorders Headache 6.0
Nervous system disorders Insomnia 6.0
Immune system disorders Transplant rejection 6.0
Gastrointestinal disorders Vomiting 6.0
Infections and infestations Sepsis 5.8
Nervous system disorders Confusional state 5.0
Eye disorders Conjunctival hyperaemia 5.0
General disorders and administration site conditions Feeling abnormal 5.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 5.0
Eye disorders Punctate keratitis 5.0
Blood and lymphatic system disorders Thrombocytopenia 5.0
General disorders and administration site conditions Decreased appetite 4.9
General disorders and administration site conditions Pain 4.6
Investigations Blood alkaline phosphatase increased 4.4
Cardiac disorders Chest pain 4.4
Investigations Blood alkaline phosphatase increased 4.2
Respiratory, thoracic and mediastinal disorders Productive cough 3.6
Cardiac disorders Chest pain 3.4
Infections and infestations Sepsis 3.4
Respiratory, thoracic and mediastinal disorders Sinus congestion 3.4
Investigations Blood creatinine increased 3.2
Investigations Blood culture positive 3.2
Nervous system disorders Hypoaesthesia 3.2
Blood and lymphatic system disorders Leukopenia 3.2
Skin and subcutaneous tissue disorders Pruritus 3.2
Gastrointestinal disorders Vomiting 3.0
Blood and lymphatic system disorders Lymphadenopathy 2.9
Gastrointestinal disorders Dysphagia 2.7
General disorders and administration site conditions Pain 2.5
Infections and infestations Pneumocystis jirovecii pneumonia 2.5
Respiratory, thoracic and mediastinal disorders Productive cough 2.5
Skin and subcutaneous tissue disorders Pruritus 2.5
Respiratory, thoracic and mediastinal disorders Sinus congestion 2.5
Psychiatric disorders Anxiety 2.4
Musculoskeletal and connective tissue disorders Arthralgia 2.4
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.4
General disorders and administration site conditions Injection site inflammation 2.2
Gastrointestinal disorders Oesophageal candidiasis 2.2
Psychiatric disorders Anxiety 1.7
Musculoskeletal and connective tissue disorders Arthralgia 1.7
Investigations Blood creatinine increased 1.7
Investigations Blood culture positive 1.7
Gastrointestinal disorders Diarrhoea 1.7
Gastrointestinal disorders Dysphagia 1.7
Gastrointestinal disorders Flatulence 1.7
Nervous system disorders Hypoaesthesia 1.7
Blood and lymphatic system disorders Lymphadenopathy 1.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.7
Gastrointestinal disorders Oesophageal candidiasis 1.7
General disorders and administration site conditions Asthenia 0.8
General disorders and administration site conditions Discomfort 0.8
General disorders and administration site conditions Feeling abnormal 0.8
General disorders and administration site conditions Ill-defined disorder 0.8
General disorders and administration site conditions Injection site infection 0.8
Blood and lymphatic system disorders Leukopenia 0.8
General disorders and administration site conditions Malaise 0.8

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
20.26
Eye disorders
19.6
Nervous system disorders
14.32
Injury, poisoning and procedural complications
9.03
Blood and lymphatic system disorders
6.39
Infections and infestations
5.29
Vascular disorders
4.41
Hepatobiliary disorders
3.52
Investigations
2.64
Skin and subcutaneous tissue disorders
2.42

Cross References

Resources Reference
CAS NUMBER 82410-32-0
ChEBI 465284
ChEMBL CHEMBL182
DrugBank DB01004
DrugCentral 1277
EPA CompTox DTXSID8041032
FDA SRS P9G3CKZ4P5
Human Metabolome Database HMDB0015139
PDB GA2
PharmGKB PA449733
PubChem 135398740
SureChEMBL SCHEMBL3033
ZINC ZINC000000001505
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