TIGECYCLINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2005)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J01AA12
UNII: 70JE2N95KR

Structure
InChI Key FPZLLRFZJZRHSY-HJYUBDRYSA-N
Smile CN(C)c1cc(NC(=O)CNC(C)(C)C)c(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C2=O
InChI
InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H39N5O8
Molecular Weight 585.66
AlogP 0.51
Hydrogen Bond Acceptor 11.0
Hydrogen Bond Donor 7.0
Number of Rotational Bond 6.0
Polar Surface Area 205.76
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 42.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial 70S ribosome inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Unclassified protein
- - - - 40

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Infections 4 D007239 ClinicalTrials
Staphylococcal Infections 3 D013203 ClinicalTrials
Diabetic Foot 3 D017719 ClinicalTrials
Skin Diseases 3 D012871 ClinicalTrials
Pneumonia, Bacterial 3 D018410 ClinicalTrials
Abdominal Abscess 3 D018784 ClinicalTrials
Gram-Negative Bacterial Infections 3 D016905 ClinicalTrials
Gram-Positive Bacterial Infections 3 D016908 ClinicalTrials
Osteomyelitis 3 D010019 ClinicalTrials
Bacteremia 2 D016470 ClinicalTrials
Liver Cirrhosis, Biliary 1 D008105 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Renal Insufficiency, Chronic 1 D051436 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 29.5
Gastrointestinal disorders Nausea 26.0
Gastrointestinal disorders Nausea 21.0
Gastrointestinal disorders Vomiting 19.7
Gastrointestinal disorders Vomiting 18.0
Gastrointestinal disorders Nausea 15.8
Gastrointestinal disorders Nausea 13.0
Gastrointestinal disorders Vomiting 13.0
Gastrointestinal disorders Diarrhoea 12.7
Gastrointestinal disorders Diarrhoea 12.0
Gastrointestinal disorders Diarrhoea 11.0
Gastrointestinal disorders Diarrhoea 10.8
Gastrointestinal disorders Vomiting 10.8
Investigations Body temperature increased 9.8
General disorders and administration site conditions Local reaction 9.1
General disorders and administration site conditions Local reaction 9.0
Gastrointestinal disorders Vomiting 9.0
Infections and infestations Infection 8.3
Investigations Body temperature increased 7.1
Nervous system disorders Headache 7.0
Infections and infestations Infection 7.0
Gastrointestinal disorders Abdominal pain 6.8
Gastrointestinal disorders Gastrointestinal pain 6.8
Nervous system disorders Headache 6.5
Blood and lymphatic system disorders Thrombocytosis 6.2
Blood and lymphatic system disorders Thrombocytosis 6.1
Gastrointestinal disorders Abdominal pain 6.0
Blood and lymphatic system disorders Anaemia 6.0
Gastrointestinal disorders Gastrointestinal pain 6.0
Nervous system disorders Headache 6.0
Nervous system disorders Headache 5.9
Gastrointestinal disorders Abdominal pain 5.7
Gastrointestinal disorders Gastrointestinal pain 5.7
Investigations Alanine aminotransferase increased 5.6
Vascular disorders Hypertension 5.6
Infections and infestations Infection 5.4
Investigations Alanine aminotransferase increased 5.0
Blood and lymphatic system disorders Anaemia 5.0
Investigations Aspartate aminotransferase increased 5.0
Hepatobiliary disorders Hypoproteinaemia 5.0
Infections and infestations Infection 5.0
Vascular disorders Hypertension 4.9
Blood and lymphatic system disorders Anaemia 4.8
Investigations Alanine aminotransferase increased 4.7
Hepatobiliary disorders Hypoproteinaemia 4.5
Investigations Aspartate aminotransferase increased 4.4
Investigations Aspartate aminotransferase increased 4.3
Blood and lymphatic system disorders Anaemia 4.2
Gastrointestinal disorders Constipation 4.1
Skin and subcutaneous tissue disorders Dermatitis 4.1
Skin and subcutaneous tissue disorders Pruritus 4.1
Skin and subcutaneous tissue disorders Rash 4.1
Gastrointestinal disorders Abdominal pain 4.0
Investigations Aspartate aminotransferase increased 4.0
Investigations Blood lactate dehydrogenase increased 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Vascular disorders Phlebitis 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Respiratory, thoracic and mediastinal disorders Cough 3.8
Vascular disorders Phlebitis 3.8
Respiratory, thoracic and mediastinal disorders Cough 3.7
Blood and lymphatic system disorders Leukocytosis 3.7
General disorders and administration site conditions Pain 3.7
Investigations Blood alkaline phosphatase increased 3.5
Investigations Blood lactate dehydrogenase increased 3.5
Cardiac disorders Dizziness 3.5
General disorders and administration site conditions Impaired healing 3.5
Nervous system disorders Insomnia 3.3
Cardiac disorders Oedema peripheral 3.3
Infections and infestations Abscess 3.2
Investigations Amylase increased 3.1
Investigations Amylase increased 3.0
General disorders and administration site conditions Asthenia 3.0
Investigations Blood alkaline phosphatase increased 3.0
Investigations Blood urea increased 3.0
Skin and subcutaneous tissue disorders Dermatitis 3.0
Cardiac disorders Dizziness 3.0
Hepatobiliary disorders Hypoproteinaemia 3.0
General disorders and administration site conditions Impaired healing 3.0
Vascular disorders Phlebitis 3.0
Skin and subcutaneous tissue disorders Rash 3.0
Gastrointestinal disorders Dyspepsia 2.9
Cardiac disorders Dyspnoea 2.9
Endocrine disorders Hyperglycaemia 2.9
Metabolism and nutrition disorders Hypokalaemia 2.9
General disorders and administration site conditions Pain 2.9
Gastrointestinal disorders Constipation 2.8
Cardiac disorders Dizziness 2.7
Cardiac disorders Dyspnoea 2.7
Infections and infestations Abscess 2.6
Investigations Blood alkaline phosphatase increased 2.6
General disorders and administration site conditions Impaired healing 2.6
Skin and subcutaneous tissue disorders Pruritus 2.6
General disorders and administration site conditions Asthenia 2.5
Blood and lymphatic system disorders Leukocytosis 2.5
Skin and subcutaneous tissue disorders Dermatitis 2.4
Skin and subcutaneous tissue disorders Rash 2.4
Musculoskeletal and connective tissue disorders Back pain 2.3
Blood and lymphatic system disorders Hyperbilirubinaemia 2.3
General disorders and administration site conditions Hyperhidrosis 2.3
Vascular disorders Hypotension 2.3
Nervous system disorders Insomnia 2.3
Investigations Blood urea increased 2.1
Metabolism and nutrition disorders Hypokalaemia 2.1
Infections and infestations Abscess 2.0
Investigations Amylase increased 2.0
General disorders and administration site conditions Asthenia 2.0
Gastrointestinal disorders Dyspepsia 2.0
Blood and lymphatic system disorders Hyperbilirubinaemia 2.0
Metabolism and nutrition disorders Hyponatraemia 2.0
General disorders and administration site conditions Impaired healing 2.0
Infections and infestations Pneumonia 2.0
Endocrine disorders Hyperglycaemia 1.8
Vascular disorders Phlebitis 1.8
General disorders and administration site conditions Asthenia 1.7
Vascular disorders Hypotension 1.7
Gastrointestinal disorders Dyspepsia 1.6
General disorders and administration site conditions Hyperhidrosis 1.6
Investigations Amylase increased 1.4
Gastrointestinal disorders Nausea 1.3
Musculoskeletal and connective tissue disorders Back pain 1.2
Gastrointestinal disorders Nausea 1.1
Gastrointestinal disorders Vomiting 1.1
Investigations Blood urea increased 1.0
Blood and lymphatic system disorders Hyperbilirubinaemia 1.0
Metabolism and nutrition disorders Hyponatraemia 1.0
Gastrointestinal disorders Nausea 1.0
Gastrointestinal disorders Vomiting 1.0
Blood and lymphatic system disorders Hyperbilirubinaemia 0.9
Investigations Blood urea increased 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.18
Infections and infestations
11.27
Blood and lymphatic system disorders
9.79
Investigations
9.26
Gastrointestinal disorders
8.19
Injury, poisoning and procedural complications
6.19
Vascular disorders
5.65
Hepatobiliary disorders
5.0
Skin and subcutaneous tissue disorders
4.14
Metabolism and nutrition disorders
4.01
Nervous system disorders
3.65
Respiratory, thoracic and mediastinal disorders
3.36
Immune system disorders
3.28
Renal and urinary disorders
3.11
Cardiac disorders
2.29

Cross References

Resources Reference
CAS NUMBER 220620-09-7
ChEBI 149836
ChEMBL CHEMBL376140
DrugBank DB00560
DrugCentral 2661
EPA CompTox DTXSID2048581
FDA SRS 70JE2N95KR
Human Metabolome Database HMDB0014700
Guide to Pharmacology 10929
KEGG C12012
SureChEMBL SCHEMBL101795
ZINC ZINC000014879972
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