FAMCICLOVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (1994)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: J05AB09
UNII: QIC03ANI02

Structure
InChI Key GGXKWVWZWMLJEH-UHFFFAOYSA-N
Smile CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O
InChI
InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H19N5O4
Molecular Weight 321.34
AlogP 0.54
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 122.22
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 23.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human herpesvirus 1 DNA polymerase inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 68

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Meniere Disease 3 D008575 ClinicalTrials
Herpes Simplex 3 D006561 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache
Nervous system disorders Headache 39.3
Nervous system disorders Headache 37.7
Infections and infestations Upper respiratory tract infection 31.8
Infections and infestations Upper respiratory tract infection
Infections and infestations Infection
Infections and infestations Infection 24.7
Nervous system disorders Headache 22.7
Infections and infestations Sinusitis 19.5
Nervous system disorders Headache 18.2
Nervous system disorders Headache
Nervous system disorders Headache 15.9
Infections and infestations Sinusitis
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Pharyngitis
Nervous system disorders Headache 13.5
Nervous system disorders Headache 13.3
Gastrointestinal disorders Nausea 12.5
Musculoskeletal and connective tissue disorders Back pain 12.3
Gastrointestinal disorders Nausea
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Pharyngitis 11.0
Nervous system disorders Headache 9.69
Gastrointestinal disorders Diarrhoea
Nervous system disorders Headache
Gastrointestinal disorders Nausea
Nervous system disorders Headache 9.1
Gastrointestinal disorders Diarrhoea 9.0
Nervous system disorders Headache 8.7
Gastrointestinal disorders Nausea 8.7
Nervous system disorders Headache 8.5
Gastrointestinal disorders Nausea 8.4
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 7.9
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 7.9
Gastrointestinal disorders Diarrhoea 7.7
Reproductive system and breast disorders Dysmenorrhoea 7.6
Nervous system disorders Headache 7.27
Gastrointestinal disorders Nausea 7.2
Nervous system disorders Headache 7.1
Nervous system disorders Headache
Nervous system disorders Headache
Nervous system disorders Headache
Reproductive system and breast disorders Dysmenorrhoea
Nervous system disorders Headache 5.5
Nervous system disorders Headache 5.42
Nervous system disorders Headache
Nervous system disorders Headache 5.3
Gastrointestinal disorders Dyspepsia 5.2
Gastrointestinal disorders Diarrhoea 4.91
Gastrointestinal disorders Diarrhoea 4.9
Gastrointestinal disorders Nausea 4.9
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia 4.8
Gastrointestinal disorders Diarrhoea
General disorders and administration site conditions Fatigue 4.8
Gastrointestinal disorders Flatulence 4.8
Gastrointestinal disorders Gastrointestinal pain
Nervous system disorders Headache
Gastrointestinal disorders Vomiting 4.8
Gastrointestinal disorders Diarrhoea 4.7
Gastrointestinal disorders Nausea 4.6
Gastrointestinal disorders Nausea
General disorders and administration site conditions Asthenia 4.4
General disorders and administration site conditions Fatigue 4.4
Gastrointestinal disorders Nausea 4.3
Gastrointestinal disorders Nausea 4.26
Gastrointestinal disorders Nausea
Nervous system disorders Headache
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Pruritus 3.7
Gastrointestinal disorders Nausea 3.61
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain 3.5
Gastrointestinal disorders Gastrointestinal pain 3.5
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Vomiting
Skin and subcutaneous tissue disorders Dermatitis 3.3
Skin and subcutaneous tissue disorders Rash 3.3
Gastrointestinal disorders Vomiting 3.3
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Dyspepsia
Metabolism and nutrition disorders Enzyme abnormality
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Nausea
Blood and lymphatic system disorders Neutropenia 3.2
Cardiac disorders Dizziness
Nervous system disorders Migraine 3.1
Gastrointestinal disorders Vomiting 3.1
Gastrointestinal disorders Diarrhoea 3.09
Gastrointestinal disorders Nausea 2.88
Skin and subcutaneous tissue disorders Pruritus
Nervous system disorders Somnolence
Infections and infestations Nasopharyngitis 2.64
Nervous system disorders Paraesthesia 2.6
General disorders and administration site conditions Asthenia 2.51
General disorders and administration site conditions Fatigue 2.51
Gastrointestinal disorders Nausea 2.5
Gastrointestinal disorders Nausea 2.45
Gastrointestinal disorders Abdominal pain upper 2.41
Cardiac disorders Dizziness 2.41
Gastrointestinal disorders Abdominal pain 2.4
Gastrointestinal disorders Gastrointestinal pain 2.4
Gastrointestinal disorders Abdominal pain 2.3
Gastrointestinal disorders Diarrhoea 2.3
Cardiac disorders Dizziness 2.3
Gastrointestinal disorders Gastrointestinal pain 2.3
Gastrointestinal disorders Nausea 2.27
Metabolism and nutrition disorders Enzyme abnormality 2.2
Gastrointestinal disorders Nausea 2.2
Skin and subcutaneous tissue disorders Pruritus 2.2
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Vomiting 2.1
General disorders and administration site conditions Asthenia 2.0
Investigations Blood creatine phosphokinase increased 2.0
Gastrointestinal disorders Dyspepsia 2.0
General disorders and administration site conditions Fatigue 2.0
Cardiac disorders Dizziness 1.93
Cardiac disorders Dizziness 1.92
Reproductive system and breast disorders Dysmenorrhoea 1.84
Nervous system disorders Insomnia 1.84
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.84
Gastrointestinal disorders Diarrhoea 1.8
Reproductive system and breast disorders Dysmenorrhoea 1.8
Gastrointestinal disorders Diarrhoea 1.76
General disorders and administration site conditions Asthenia 1.73
General disorders and administration site conditions Fatigue 1.73
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.6
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 1.6
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 1.6
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Gastrointestinal pain
Blood and lymphatic system disorders Hyperbilirubinaemia
Skin and subcutaneous tissue disorders Rash
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal pain 1.5
General disorders and administration site conditions Asthenia 1.5
Gastrointestinal disorders Diarrhoea 1.5
Cardiac disorders Dizziness
Cardiac disorders Dizziness 1.5
General disorders and administration site conditions Fatigue 1.5
Gastrointestinal disorders Flatulence 1.5
Gastrointestinal disorders Gastrointestinal pain 1.5
Gastrointestinal disorders Nausea 1.5
Blood and lymphatic system disorders Neutropenia
General disorders and administration site conditions Chills
General disorders and administration site conditions Decreased appetite
Investigations Gamma-glutamyltransferase increased
Investigations Hepatic enzyme increased
Infections and infestations Herpes zoster
Ear and labyrinth disorders Tinnitus
Gastrointestinal disorders Diarrhoea 1.36
Infections and infestations Nasopharyngitis 1.36
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 1.3
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 1.3
Gastrointestinal disorders Dyspepsia 1.3
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 1.3
Blood and lymphatic system disorders Hyperbilirubinaemia 1.3
Blood and lymphatic system disorders Leukopenia 1.3
Gastrointestinal disorders Abdominal discomfort 1.23
Psychiatric disorders Anxiety 1.23
Musculoskeletal and connective tissue disorders Back pain 1.23
Gastrointestinal disorders Dry mouth 1.23
Cardiac disorders Palpitations 1.23
Gastrointestinal disorders Vomiting 1.23
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 1.2
General disorders and administration site conditions Asthenia 1.2
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Fatigue 1.2
Infections and infestations Fungal infection 1.2
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 1.2
Nervous system disorders Insomnia 1.2
Infections and infestations Nasopharyngitis 1.2
Skin and subcutaneous tissue disorders Pruritus 1.2
Nervous system disorders Somnolence 1.2
Gastrointestinal disorders Vomiting 1.2
Gastrointestinal disorders Abdominal pain 1.1
Investigations Body temperature increased 1.1
Gastrointestinal disorders Flatulence 1.1
Gastrointestinal disorders Gastrointestinal pain 1.1
Nervous system disorders Somnolence
Gastrointestinal disorders Vomiting 1.1
Gastrointestinal disorders Constipation 1.0
General disorders and administration site conditions Hyperhidrosis 1.0
Gastrointestinal disorders Abdominal pain 0.967
Gastrointestinal disorders Gastrointestinal pain 0.967
Gastrointestinal disorders Abdominal pain 0.9
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrointestinal pain 0.9
Blood and lymphatic system disorders Leukopenia
Nervous system disorders Paraesthesia 0.9
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea
Infections and infestations Nasopharyngitis
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 0.7
Investigations Blood creatine phosphokinase increased 0.7
Skin and subcutaneous tissue disorders Dermatitis
Cardiac disorders Dizziness
Reproductive system and breast disorders Dysmenorrhoea
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 0.7
Gastrointestinal disorders Flatulence
Nervous system disorders Migraine
Nervous system disorders Migraine 0.7
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Rash
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 0.7
Gastrointestinal disorders Abdominal pain upper 0.613
Gastrointestinal disorders Abdominal discomfort 0.602
Musculoskeletal and connective tissue disorders Back pain 0.602
Reproductive system and breast disorders Dysmenorrhoea 0.602
Respiratory, thoracic and mediastinal disorders Laryngeal pain 0.602
Gastrointestinal disorders Vomiting 0.602
General disorders and administration site conditions Asthenia 0.6
General disorders and administration site conditions Chills 0.6
Reproductive system and breast disorders Dysmenorrhoea
General disorders and administration site conditions Fatigue 0.6
Gastrointestinal disorders Flatulence 0.6
Investigations Gamma-glutamyltransferase increased 0.6
Nervous system disorders Migraine
Nervous system disorders Migraine 0.6
Skin and subcutaneous tissue disorders Pruritus
Nervous system disorders Somnolence 0.6
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Decreased appetite 0.5
Infections and infestations Herpes zoster 0.5
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia
Skin and subcutaneous tissue disorders Dermatitis 0.4
Reproductive system and breast disorders Dysmenorrhoea 0.4
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrointestinal pain
Skin and subcutaneous tissue disorders Rash 0.4
Gastrointestinal disorders Dry mouth 0.3
Gastrointestinal disorders Abdominal pain 0.2
Gastrointestinal disorders Flatulence 0.2
Gastrointestinal disorders Gastrointestinal pain 0.2
Investigations Hepatic enzyme increased 0.2
Nervous system disorders Migraine 0.2
Blood and lymphatic system disorders Anaemia 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
18.91
General disorders and administration site conditions
13.96
Psychiatric disorders
9.74
Gastrointestinal disorders
7.1
Infections and infestations
5.53
Skin and subcutaneous tissue disorders
5.53
Injury, poisoning and procedural complications
4.21
Respiratory, thoracic and mediastinal disorders
4.21
Vascular disorders
4.21
Investigations
3.88
Cardiac disorders
3.72
Immune system disorders
3.39
Eye disorders
3.22
Renal and urinary disorders
3.14
Musculoskeletal and connective tissue disorders
2.73

Cross References

Resources Reference
CAS NUMBER 104227-87-4
ChEBI 4974
ChEMBL CHEMBL880
DrugBank DB00426
DrugCentral 1128
EPA CompTox DTXSID0023038
FDA SRS QIC03ANI02
Human Metabolome Database HMDB0014570
PharmGKB PA449585
PubChem 3324
SureChEMBL SCHEMBL2949
ZINC ZINC000001530635
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