tigecycline
Trade name: tygacil
Approved
Jun 15, 2005
Tigecycline (INN) is an antibiotic used to treat a number of bacterial infections. It is a first in class glycylcycline that is administered intravenously. For the treatment of infections caused by susceptible strains of the designated microorganisms in the following conditions: Complicated skin and skin structure infections caused by Escherichia coli, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus agalactiae, Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Streptococcus pyogenes and Bacteroides fragilis. Complicated intra-abdominal infections caused by Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Klebsiella oxytoca, Klebsiella pneumoniae, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Bacteroides fragilis, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides vulgatus, Clostridium perfringens, and Peptostreptococcus micros. Tigecycline, a glycylcycline, inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. Tigecycline carries a glycylamido moiety attached to the 9-position of minocycline. The substitution pattern is not present in any naturally occurring or semisynthetic tetracycline and imparts certain microbiologic properties to tigecycline. In general, tigecycline is considered bacteriostatic; however, TYGACIL has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila. In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterials. — NCATS
Clinical trial activity
49 trials · 48 clinical orgs · 14 marketing orgs
Earliest trial started Apr 1, 2002 (NCT00600600)
Timeline
2000s
2010s
- May 27, 2015
Sandoz — Marketing Organization
- May 27, 2015
Novartis — Marketing Organization
- Dec 1, 2016
Fresenius — NDA Secondary Org
- Jan 18, 2018
Accord Research — NDA Secondary Org
- Aug 2, 2018
Amneal Pharmaceuticals — NDA Secondary Org
- Aug 2, 2018
Amneal Pharmaceuticals — Marketing Organization
- Dec 21, 2018
Apotex — Marketing Organization
- Jun 11, 2019
Aurobindo Pharma — Marketing Organization
- Jun 11, 2019
Eugia Pharma — Marketing Organization
- Oct 18, 2019
Xellia Pharmaceuticals — Marketing Organization
- Oct 18, 2019
Novo Nordisk — Marketing Organization
2020s
- May 13, 2021
Eu Yan Sang — Marketing Organization
- May 13, 2021
Meitheal — Marketing Organization
Indications
Approved for
Studied for
- Abdominal Abscess · Phase 4
- Abdominal Injuries · Phase 3
- Abscess · Phase 2
- Appendicitis · Phase 4
- Bacteremia · Phase 4
- Bacterial Infections · Phase 4
- Blood-Borne Infections · Phase 3
- Catheter-Related Infections · Phase 4
- Cholecystitis · Phase 4
- Community-Acquired Infections · Phase 3
- Cross Infection · Phase 4
- Dermatology · Phase 2
- Diabetic Foot · Phase 3
- Diverticulitis · Phase 4
- Gram-Negative Bacterial Infections · Phase 3
- Gram-Positive Bacterial Infections · Phase 3
- Healthcare-Associated Pneumonia · Phase 3
- Healthy Volunteers · Phase 1
- Hematologic Neoplasms · Phase 4
- Intraabdominal Infections · Phase 4
- Kidney Failure, Chronic · Phase 1
- Klebsiella pneumoniae · Phase 4
- Leukemia · Phase 4
- Leukemia, Myeloid, Acute · Phase 1
- Liver Cirrhosis, Biliary · Phase 1
- Lung Diseases · Phase 2/Phase 3
- Lymphoma · Phase 4
- Methicillin Resistance · Phase 3
- Multiple Myeloma · Phase 4
- Myelodysplastic Syndromes · Phase 4
- Obesity · Phase 4
- Osteomyelitis · Phase 3
- Peritonitis · Phase 4
- Pneumonia, Bacterial · Phase 3
- Pneumonia, Ventilator-Associated · Phase 3
- Pyelonephritis · Phase 3
- Skin Diseases · Phase 3
- Skin Diseases, Bacterial · Phase 4
- Skin Diseases, Infectious · Phase 4
- Staphylococcal Infections · Phase 4
- Staphylococcal Skin Infections · Phase 2
- Stem Cell Transplantation · Phase 4
- Surgical Wound Infection · Phase 3
- Urinary Tract Infections · Phase 3
- Vancomycin Resistance · Phase 3
Mechanism of action
- Bacterial 70S ribosomeINHIBITOR
Bacterial 70S ribosome inhibitor
16s RRNA
- 30S ribosomal protein S2 (rpsB) ↗
- 50S ribosomal protein L4 (rplD) ↗
- 30S ribosomal protein S15 (rpsO) ↗
- 30S ribosomal protein S16 (rpsP) ↗
- 30S ribosomal protein S17 (rpsQ) ↗
- 30S ribosomal protein S18 (rpsR) ↗
- 30S ribosomal protein S19 (rpsS) ↗
- 30S ribosomal protein S20 (rpsT) ↗
- 30S ribosomal protein S21 (rpsU) ↗
- 30S ribosomal protein S3 (rpsC) ↗
- 30S ribosomal protein S4 (rpsD) ↗
- 30S ribosomal protein S5 (rpsE) ↗
- 30S ribosomal protein S6 (rpsF) ↗
- 30S ribosomal protein S7 (rpsG) ↗
- 30S ribosomal protein S8 (rpsH) ↗
- 30S ribosomal protein S9 (rpsI) ↗
- 50S ribosomal protein L35 (rpmI) ↗
- 50S ribosomal protein L36 2 (ykgO) ↗
- 50S ribosomal protein L36 (rpmJ) ↗
- 50S ribosomal protein L3 (rplC) ↗
- 50S ribosomal protein L5 (rplE) ↗
- 50S ribosomal protein L6 (rplF) ↗
- 50S ribosomal protein L7/L12 (rplL) ↗
- 30S ribosomal protein S1 (rpsA) ↗
- 30S ribosomal protein S10 (rpsJ) ↗
- 30S ribosomal protein S11 (rpsK) ↗
- 30S ribosomal protein S12 (rpsL) ↗
- 30S ribosomal protein S13 (rpsM) ↗
- 30S ribosomal protein S14 (rpsN) ↗
- 50S ribosomal protein L10 (rplJ) ↗
- 50S ribosomal protein L11 (rplK) ↗
- 50S ribosomal protein L13 (rplM) ↗
- 50S ribosomal protein L14 (rplN) ↗
- 50S ribosomal protein L15 (rplO) ↗
- 50S ribosomal protein L16 (rplP) ↗
- 50S ribosomal protein L17 (rplQ) ↗
- 50S ribosomal protein L18 (rplR) ↗
- 50S ribosomal protein L19 (rplS) ↗
- 50S ribosomal protein L1 (rplA) ↗
- 50S ribosomal protein L20 (rplT) ↗
- 50S ribosomal protein L21 (rplU) ↗
- 50S ribosomal protein L22 (rplV) ↗
- 50S ribosomal protein L23 (rplW) ↗
- 50S ribosomal protein L24 (rplX) ↗
- 50S ribosomal protein L25 (rplY) ↗
- 50S ribosomal protein L27 (rpmA) ↗
- 50S ribosomal protein L28 (rpmB) ↗
- 50S ribosomal protein L29 (rpmC) ↗
- 50S ribosomal protein L2 (rplB) ↗
- 50S ribosomal protein L30 (rpmD) ↗
- 50S ribosomal protein L31 type B (ykgM) ↗
- 50S ribosomal protein L31 (rpmE) ↗
- 50S ribosomal protein L32 (rpmF) ↗
- 50S ribosomal protein L33 (rpmG) ↗
- 50S ribosomal protein L34 (rpmH) ↗
Approval history
- approvedPriority reviewJun 15, 2005
Chemistry & pharmacology
SMILES
CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(O)=C(NC(=O)CNC(C)(C)C)C=C4N(C)C- Mol. weight
- 585.6487 g/mol
- Lipinski Ro5
- 3 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Prescription Only
Oral
No
Parenteral
Yes
Topical
No
Sources
- WikipediaGlycopeptide ↗
- NCATS70JE2N95KR ↗
- ChEMBLCHEMBL376140 ↗
- WikipediaTigecycline ↗
Also known as
- (4s,4as,5ar,12as)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
- (4s,4as,5ar,12as)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
- 9-(tert-butylglycylamido)minocycline
- gar 936
- gar-936
- glycopeptide
- glycopeptide
- glycylcycline
- tbg-mino
- tigeciclina
- tigeciclina
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecycline
- tigecyclinum
- tigecyclinum
- tygacil
- tygacil
- tygacil
- tygacil
- tygacil
- tygacil
- way-gar-936
- way-gar-936
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07089186 | Phase 3 | Apr 12, 2025 | Qilu Pharmaceutical Co., Ltd. |
| NCT06893835 | Phase 4 | Dec 1, 2024 | Beni Suef University |
| NCT07258225 | Phase 4 | Apr 1, 2024 | Government of Egypt |
| NCT06739382 | Phase 3 | Jan 1, 2021 | Beni Suef University, Cairo University |
| NCT03962920 | N/A | May 1, 2020 | University of Copenhagen |
| NCT04310930 | Phase 2/Phase 3 (Phase 3) | Mar 31, 2020 | Cystic Fibrosis Foundation, Erasmus University Rotterdam, Government of Australia, Griffith University, James Cook University Hospital, Middlesbrough, UK, Monash University, Murdoch University, Newcastle University, South Australian Health and Medical Research Institute, University of Copenhagen, University of Manitoba, University of Melbourne, University of Paris, University of Queensland |
| NCT04208763 | N/A | Dec 20, 2019 | Institute of Liver and Biliary Sciences, India |
| NCT04489459 | Phase 4 | Sep 21, 2019 | Al Azhar University |
| NCT04042077 | Phase 3 | Aug 31, 2019 | Hospital Agostino Gemelli, Menarini Group |
| NCT03950544 | Early Phase 1 (Phase 1) | Jan 1, 2019 | Huazhong University of Science and Technology |
| NCT02800785 | N/A | May 1, 2016 | Cancer Research Network, University of California, Los Angeles, University of Washington |
| NCT01970371 | Phase 3 | Sep 1, 2014 | Achaogen, Inc., Department of Health and Human Services |
| NCT02191475 | Phase 2/Phase 3 (Phase 3) | May 1, 2014 | Nanjing Medical University, Tianjin Medical University, Zhejiang Hisun Pharmaceutical Co. Ltd. |
| NCT02040818 | Phase 2/Phase 3 (Phase 3) | Nov 1, 2013 | National Institutes of Health (NIH), University of California, San Diego |
| NCT01721408 | Phase 4 | Nov 1, 2012 | Pfizer |
| NCT01592032 | Phase 4 | May 1, 2012 | Clinica Universidad de Navarra |
| NCT01483872 | Phase 3 | Mar 1, 2012 | University of California, San Diego |
| NCT01560143 | Phase 4 | Mar 1, 2012 | Pfizer, University of Michigan |
| NCT00911573 | Phase 3 | Aug 1, 2011 | Pfizer |
| NCT01342731 | Phase 4 | Jul 1, 2011 | Mahidol University, Siriraj Hospital |
Organizations
Research & Development (48)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Pfizer | For profit | 27 | 25 | 5 | 2002 |
| Wyeth | For profit | 20 | 0 | 4 | 2002 |
| Beni Suef University | Academic/Hospital | 2 | 2 | 2 | 2021 |
| University of California, Los Angeles | Academic/Hospital | 2 | 0 | 2 | 2011 |
| University of California, San Diego | Academic/Hospital | 2 | 2 | 1 | 2012 |
| University of Copenhagen | Academic/Hospital | 2 | 1 | 2 | 2020 |
| Achaogen, Inc. | For profit | 1 | 1 | 1 | 2014 |
| Al Azhar University | Academic/Hospital | 1 | 1 | 1 | 2019 |
| Baylor University | Academic/Hospital | 1 | 1 | 1 | 2006 |
| Cairo University | Academic/Hospital | 1 | 0 | 1 | 2021 |
| Cancer Research Network | Academic/Hospital | 1 | 0 | 1 | 2016 |
| Clinica Universidad de Navarra | Academic/Hospital | 1 | 1 | 1 | 2012 |
| Cornell University | Academic/Hospital | 1 | 0 | 1 | 2011 |
| CPL Associates | For profit | 1 | 1 | 1 | 2007 |
| Cystic Fibrosis Foundation | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Department of Health and Human Services | Government | 1 | 0 | 1 | 2014 |
| Erasmus University Rotterdam | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Government of Australia | Government | 1 | 0 | 1 | 2020 |
| Government of Egypt | Government | 1 | 1 | 1 | 2024 |
| Griffith University | Academic/Hospital | 1 | 0 | 1 | 2020 |
Marketing (17)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Accord Research | For profit | NDA2 | Jan 18, 2018 |
| Amneal Pharmaceuticals | For profit | NDA2 | Aug 2, 2018 |
| Amneal Pharmaceuticals | For profit | MKTG | Aug 2, 2018 |
| Apotex | For profit | MKTG | Dec 21, 2018 |
| Apotex | For profit | SYN | Dec 21, 2018 |
| Aurobindo Pharma | For profit | MKTG | Jun 11, 2019 |
| Eu Yan Sang | For profit | MKTG | May 13, 2021 |
| Eugia Pharma | For profit | MKTG | Jun 11, 2019 |
| Fresenius | For profit | NDA2 | Dec 1, 2016 |
| Meitheal | For profit | MKTG | May 13, 2021 |
| Novartis | For profit | MKTG | May 27, 2015 |
| Novo Nordisk | For profit | MKTG | Oct 18, 2019 |
| Pfizer | For profit | NDA2 | Jun 15, 2005 |
| Sandoz | For profit | SYN | May 27, 2015 |
| Sandoz | For profit | MKTG | May 27, 2015 |
| Wyeth | For profit | NDA | Jun 15, 2005 |
| Xellia Pharmaceuticals | For profit | MKTG | Oct 18, 2019 |