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tigecycline   Click here for help

GtoPdb Ligand ID: 10929

Synonyms: GAR-936 | GAR936 | TBG-MINO | Tygacil® | WAY-GAR-936
Approved drug
tigecycline is an approved drug (FDA (2005), EMA & UK (2006))
Compound class: Synthetic organic
Comment: Tigecycline is a first-in-class glycylcycline (tetracycline) antibacterial derived from minocycline [5,7]. It was designed to overcome efflux and ribosomal protection mechanisms of resistance that have emerged against the tetracycline class of compounds.

tigecycline is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 7
Rotatable bonds 8
Topological polar surface area 205.76
Molecular weight 585.28
XLogP 1.39
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C(Nc1cc(N(C)C)c2c(c1O)C(=C1[C@@H](C2)C[C@@H]2[C@@](C1=O)(O)C(=C(C(=O)[C@H]2N(C)C)C(=O)N)O)O)CNC(C)(C)C
Isomeric SMILES O=C(Nc1cc(N(C)C)c2c(c1O)C(=C1[C@@H](C2)C[C@@H]2[C@@](C1=O)(O)C(=C(C(=O)[C@H]2N(C)C)C(=O)N)O)O)CNC(C)(C)C
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/h10,12,14,21,31,36-37,40,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1
InChI Key SOVUOXKZCCAWOJ-HJYUBDRYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Bergeron J, Ammirati M, Danley D, James L, Norcia M, Retsema J, Strick CA, Su WG, Sutcliffe J, Wondrack L. (1996)
Glycylcyclines bind to the high-affinity tetracycline ribosomal binding site and evade Tet(M)- and Tet(O)-mediated ribosomal protection.
Antimicrob Agents Chemother, 40 (9): 2226-8. [PMID:8878615]
2. Bhavnani SM, Rubino CM, Ambrose PG, Babinchak TJ, Korth-Bradley JM, Drusano GL. (2010)
Impact of different factors on the probability of clinical response in tigecycline-treated patients with intra-abdominal infections.
Antimicrob Agents Chemother, 54 (3): 1207-12. [PMID:20038623]
3. Cercenado E, Marín M, Sánchez-Martínez M, Cuevas O, Martínez-Alarcón J, Bouza E. (2007)
In vitro activities of tigecycline and eight other antimicrobials against different Nocardia species identified by molecular methods.
Antimicrob Agents Chemother, 51 (3): 1102-4. [PMID:17194827]
4. Hajdu S, Holinka J, Reichmann S, Hirschl AM, Graninger W, Presterl E. (2010)
Increased temperature enhances the antimicrobial effects of daptomycin, vancomycin, tigecycline, fosfomycin, and cefamandole on staphylococcal biofilms.
Antimicrob Agents Chemother, 54 (10): 4078-84. [PMID:20679509]
5. Petersen PJ, Jacobus NV, Weiss WJ, Sum PE, Testa RT. (1999)
In vitro and in vivo antibacterial activities of a novel glycylcycline, the 9-t-butylglycylamido derivative of minocycline (GAR-936).
Antimicrob Agents Chemother, 43 (4): 738-44. [PMID:10103174]
6. Rose WE, Rybak MJ. (2006)
Tigecycline: first of a new class of antimicrobial agents.
Pharmacotherapy, 26 (8): 1099-110. [PMID:16863487]
7. Sum PE, Petersen P. (1999)
Synthesis and structure-activity relationship of novel glycylcycline derivatives leading to the discovery of GAR-936.
Bioorg Med Chem Lett, 9 (10): 1459-62. [PMID:10360756]
8. World Health Organization. Regional Office for Europe. 
Consideration of antibacterial medicines as part of the revisions to 2019 WHO Model List of Essential Medicines for adults (EML) and Model List of Essential Medicines for Children (EMLc): Section 6.2 Antibacterials including Access, Watch and Reserve Lists of antibiotics.
Accessed on 08/05/2026. Modified on 08/05/2026. https://iris.who.int/items/e2f730ae-f66f-44d6-bc24-164fe79164ec