AntibioticMech

tigecycline

CHEBI:149836 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

glycylcyclineARO:0000042

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC29H39N5O8
Charge0
Average mass585.658 Da
Monoisotopic mass585.27986 Da
SourceChEBI
InChIKeyFPZLLRFZJZRHSY-HJYUBDRYSA-N

SMILES

[H][C@@]12Cc3c(N(C)C)cc(NC(=O)CNC(C)(C)C)c(O)c3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2

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

Also called

Cross-references

Equivalent identifiers for this same structure in other resources.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
SourceNative IDLabelMinted CURIEVersion
ARO ARO:0000030 tigecycline antibioticmech:aro-ba2bb436ff 2026-08-30
CHEBI CHEBI:149836 tigecycline antibioticmech:chebi-4917944044 2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

antibiotic sensitive 16S rRNA NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000755

CARD/ARO database assertion; target organism, strain, and assay are not specified. 16S rRNA is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

Mechanism summary

Clinical status
APPROVED

Resistance mechanisms

11 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_EFFLUX 8
ANTIBIOTIC_EFFLUX
DeterminantARO IDOrganismGene familiesEvidence
Acinetobacter baumannii AbuO ARO:3004578 not organism-specific —
  • ARO:3004578 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
AcrAB-TolC ARO:3000384 not organism-specific —
  • ARO:3000384 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
AdeABC ARO:3000770 not organism-specific —
  • ARO:3000770 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
Enterobacter cloacae acrA ARO:3004042 not organism-specific —
  • ARO:3004042 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
Klebsiella pneumoniae acrR with mutation conferring multidrug antibiotic resistance ARO:3003373 not organism-specific —
  • ARO:3003373 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
Klebsiella pneumoniae ramR mutants ARO:3003380 not organism-specific —
  • ARO:3003380 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
mepA ARO:3000026 not organism-specific —
  • ARO:3000026 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
oqxAB ARO:3003921 not organism-specific —
  • ARO:3003921 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
ANTIBIOTIC_INACTIVATION 3
ANTIBIOTIC_INACTIVATION
DeterminantARO IDOrganismGene familiesEvidence
tet(X) ARO:3000205 not organism-specific —
  • ARO:3000205 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
tet(X3) ARO:3004719 not organism-specific —
  • ARO:3004719 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)
tet(X4) ARO:3004720 not organism-specific —
  • ARO:3004720 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (ARO, CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.