Tigecycline
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Also known as TigeciclinaTigecycline accordTygacilWAY-GAR-936TigecyclinSID144206463
Summary
Tigecycline (CHEMBL376140) is an approved small-molecule antibacterial drug (ATC J01AA12); indicated across 18 conditions including bacterial infectious disease and skin disease caused by bacterial infection.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01AA12
- Indications: 18 conditions
- Clinical trials: 59
- Chemistry: 585.6 Da · C29H39N5O8
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL376140 |
| Name | Tigecycline |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 54686904 |
| ChEBI | CHEBI:149836 |
| ATC | J01AA12 |
| Molecular formula | C29H39N5O8 |
| Molecular weight | 585.6 |
| InChIKey | SOVUOXKZCCAWOJ-HJYUBDRYSA-N |
SMILES: CC(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
IUPAC name: (4S,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
ChEBI definition: Tetracycline in which the hydroxy group at position 5 and the methyl group at position 6 are replaced by hydrogen, and with a dimethylamino substituent and an (N-tert-butylglycyl)amino substituent at positions 7 and 9, respectively. A glycylcycline antibiotic, it has activity against a broad range of Gram-positive and Gram-negative bacteria, including tetracycline-resistant organisms. It is used for the intravenous treatment of complicated skin and skin structure infections caused by susceptible organisms.
Pharmacological roles (ChEBI): antibacterial drug.
Also known as: Tigeciclina, Tigecycline, Tigecycline accord, Tygacil, WAY-GAR-936, tigecycline, Tigecyclin, TIGECYCLINE, SID144206463
Patent coverage: 3,960 distinct patent families (13,226 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 13,225 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Equilibrative nucleoside transporter 1, Muscarinic acetylcholine receptor M1, Prostaglandin G/H synthase 2, Adenosine receptor A3, Nuclear receptor subfamily 1 group I member 2, Prostaglandin G/H synthase 1.
Bioactivity
ChEMBL activities: 3 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| Q63921 | 6.8 | AC50 | 160 | nM | CHEMBL_ACT_25173914 |
| PTGS2 | 6.72 | AC50 | 189 | nM | CHEMBL_ACT_25165716 |
| NR1I2 | 5.62 | AC50 | 2390 | nM | CHEMBL_ACT_25187843 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
18 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| skin disease caused by bacterial infection | 4 | MONDO:0024295 | MONDO:0024295 |
| skin disorder caused by infection | 4 | MONDO:0024294 | MONDO:0024294 |
| skin disorder | 3 | MONDO:0005093 | EFO:0000701 |
| bacterial pneumonia | 3 | MONDO:0004652 | EFO:1001272 |
| staphylococcus aureus infection | 3 | MONDO:0005545 | EFO:0005681 |
| gram-negative bacterial infections | 3 | MONDO:0021678 | MONDO:0021678 |
| gram-positive bacterial infections | 3 | MONDO:0021679 | MONDO:0021679 |
| osteomyelitis | 3 | MONDO:0005246 | EFO:0003102 |
| bacterial infectious disease with sepsis | 2 | MONDO:0005229 | EFO:0003033 |
| lung disorder | 2 | MONDO:0005275 | EFO:0003818 |
| acute myeloid leukemia | 1 | MONDO:0018874 | EFO:0000222 |
| primary biliary cholangitis | 1 | MONDO:0005388 | EFO:1001486 |
| chronic kidney disease | 1 | MONDO:0005300 | EFO:0003884 |
4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 59.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 18 |
| Not specified | 18 |
| PHASE4 | 11 |
| PHASE2 | 5 |
| PHASE1 | 4 |
| PHASE2/PHASE3 | 2 |
| EARLY_PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06893835 | PHASE4 | ACTIVE_NOT_RECRUITING | Comparative Study of Clinical Outcomes and Safety Between Colistin and Tigecycline |
| NCT00195351 | PHASE4 | COMPLETED | Study Comparing Tigecycline Versus Ceftriaxone Sodium Plus Metronidazole in Complicated Intra-abdominal Infection |
| NCT00230971 | PHASE4 | COMPLETED | Study Comparing Tigecycline Versus Ceftriaxone Sodium Plus Metronidazole in Complicated Intra-abdominal Infection (cIAI) |
| NCT00368537 | PHASE4 | COMPLETED | Study Comparing the Safety and Efficacy of Tigecycline With Ampicillin-Sulbactam or Amoxicillin-Clavulanate to Treat Skin Infections |
| NCT00419991 | PHASE4 | COMPLETED | Open Label Non-comparative Clinical Trial of Tigecycline in Patients With Catheter Infection |
| NCT00488306 | PHASE4 | COMPLETED | Study Evaluating the Safety and Efficacy of Tigecycline in Hospitalized Patients With cIAI |
| NCT00488761 | PHASE4 | COMPLETED | Study Evaluating the Safety and Efficacy of Tigecycline in Hospitalized Patients With cSSSI |
| NCT01342731 | PHASE4 | UNKNOWN | Effectiveness and Safety of Tigecycline for Therapy of Infections Caused by Multi-Drug Resistant Acinetobacter Baumannii |
| NCT01560143 | PHASE4 | COMPLETED | Pharmacokinetics Of Tigecycline In Morbidly Obese Subjects |
| NCT01721408 | PHASE4 | COMPLETED | A Study To Determine The Efficacy And Safety Of Tigecycline Compared With Imipenem/Cliastatin to Treat Complicated Intra-Abdominal Infection |
| NCT04489459 | PHASE4 | UNKNOWN | Comparative Clinical Study Between Colistin-Tigecycline Combined Therapy Versus Colistin-Meropenem Combined Therapy in Treatment of Blood Stream Infections With Multidrug-Resistant Klebsiella Pneumoniae |
| NCT04310930 | PHASE2/PHASE3 | RECRUITING | Finding the Optimal Regimen for Mycobacterium Abscessus Treatment |
| NCT00079885 | PHASE3 | COMPLETED | Study Evaluating Tigecycline vs Levofloxacin in Hospitalized With Community-Acquired Pneumonia |
| NCT00079976 | PHASE3 | COMPLETED | Study Evaluating Tigecycline in Selected Serious Infections Caused by Vancomycin-Resistant Enterococcus (VRE) or Methicillin-Resistant Staphylococcus Aureus (MRSA) |
| NCT00079989 | PHASE3 | COMPLETED | Study Evaluating Tigecycline in Selected Serious Infections Due to Resistant Gram-Negative Organisms |
| NCT00080496 | PHASE3 | COMPLETED | Study Evaluating Tigecycline Versus Imipenem/Cilastatin in Hospital-Acquired Pneumonia |
| NCT00081575 | PHASE3 | COMPLETED | Study Comparing Tigecycline vs. Levofloxacin in Subjects Hospitalized With Community-Acquired Pneumonia |
| NCT00081744 | PHASE3 | COMPLETED | Study Comparing Tigecycline to Imipenem/Cilastatin in Complicated Intra-Abdominal Infections in Hospitalized Subjects |
| NCT00136201 | PHASE3 | COMPLETED | Study Comparing Tigecycline and Imipenem/Cilastatin in Chinese Subjects With Complicated Intra-Abdominal Infections |
| NCT00205816 | PHASE3 | COMPLETED | Study Evaluating Emergency-use Tigecycline in Subjects With Resistant Pathogens. |
| NCT00228410 | PHASE3 | COMPLETED | Study Comparing Tigecycline and Vancomycin With Aztreonam in Complicated Skin and Skin Structure Infections |
| NCT00366249 | PHASE3 | COMPLETED | Study Evaluating the Safety and Efficacy of a Once-daily Dose of Tigecycline vs Ertapenem in Diabetic Foot Infections (DFI) With a Substudy in Patients With Diabetic Foot Infections Complicated by Osteomyelitis. |
| NCT00575094 | PHASE3 | COMPLETED | Study Evaluating the Safety and Efficacy of Intravenous Tigecycline to Treat Hospitalized Japanese Subjects |
| NCT00911573 | PHASE3 | WITHDRAWN | Study Evaluating Tigecycline Versus Clindamycin Or Vancomycin On Complicated Skin And Skin Structure Infections Including Those Due To Methicillin-Resistant Staphylococcus Aureus (MRSA) In Pediatric Subjects |
| NCT00914888 | PHASE3 | WITHDRAWN | Study Evaluating Tigecycline Versus Ceftriaxone In Complicated Intra-Abdominal Infections & Community Acquired Pneumonia |
| NCT01483872 | PHASE3 | TERMINATED | Use of a Novel Catheter Lock Solution For Treatment of Hemodialysis Catheter Infections |
| NCT01602874 | PHASE3 | WITHDRAWN | Study Evaluating Tigecycline Versus Ceftriaxone In Complicated Intra-Abdominal Infections & Community Acquired Pneumonia |
| NCT01970371 | PHASE3 | COMPLETED | A Study of Plazomicin Compared With Colistin in Patients With Infection Due to Carbapenem-Resistant Enterobacteriaceae (CRE) |
| NCT02040818 | PHASE2/PHASE3 | WITHDRAWN | Treatment of Hemodialysis Catheter-Related Bacteremia |
| NCT04042077 | PHASE3 | TERMINATED | Delafloxacin IV and OS Administration Compared to Best Available Therapy in Patients With Surgical Site Infections |
| NCT06739382 | PHASE3 | COMPLETED | Management of Ventilation Acquired Pneumonia Caused by Pseudomonas and Acinetobacter Organisms in a Pediatric Center |
| NCT07485010 | PHASE2 | NOT_YET_RECRUITING | Testing a Novel Combination Treatment (Arm D) Versus Standard of Care for Intensive Phase Treatment for Mycobacterium Abscessus Pulmonary Disease in People With or Without Cystic Fibrosis in the Finding the Optimal Regimen for Mycobacterium Abscessus Treatment (FORMaT) Adaptive Platform Trial |
| NCT00488345 | PHASE2 | COMPLETED | Study Evaluating the Pharmacokinetics (PK), Safety, and Tolerability of Tigecycline in Patients 8 to 11 Years of Age |
| NCT00600600 | PHASE2 | COMPLETED | Tigecycline for Treatment of Rapidly Growing Mycobacteria |
| NCT00707239 | PHASE2 | TERMINATED | Study Evaluating Safety and Efficacy of Tigecycline Versus Imipenem/Cilastatin Subjects With Hospital-Acquired Pneumonia |
| NCT00719810 | PHASE2 | COMPLETED | Safety and Efficacy Study of a Fluoroquinolone to Treat Complicated Skin Infections |
| NCT00376324 | PHASE1 | COMPLETED | Study Evaluating the Pharmacokinetics of Tigecycline in Human Bone |
| NCT00406237 | PHASE1 | COMPLETED | Pharmacokinetic Study Of Tigecycline In Adult Subjects With Primary Biliary Cirrhosis |
| NCT01287793 | PHASE1 | COMPLETED | Study To Evaluate The Effect Of Single Intravenous Doses Of Tigecycline On QTc Intervals In Healthy Subjects |
| NCT01332786 | PHASE1 | COMPLETED | Safety Study Evaluating Intravenous Infusions of Tigecycline to Treat Acute Myeloid Leukemia |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).