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.

Label unavailable CHEBI:139592
Label unavailable CHEBI:26895
glycylcycline ARO:0000042

Chemical structure

Computed structure properties
Molecular formula	C29H39N5O8
Charge	0
Average mass	585.658 Da
Monoisotopic mass	585.27986 Da
Source	ChEBI
InChIKey	FPZLLRFZJZRHSY-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

(4S,4aS,5aR,12aS)-9-[(N-tert-butylglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (EXACT_SYNONYM)— chebi
(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 (EXACT_SYNONYM)— chebi
Tygacil (EXACT_SYNONYM)— aro

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Activity roles

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

antibacterial drug CHEBI:36047

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
Source	Native ID	Label	Minted CURIE	Version
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).

ARO:3000755 (CARD/ARO asserts targeted_by_antibiotic ARO:0000030 (tigecycline); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

11 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_EFFLUX 8

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
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
Determinant	ARO ID	Organism	Gene families	Evidence
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

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

Explore across X-Mech: MediaIngredientMech (tigecycline) · CultureMech · NaturalProductMech · PathwayMech · TraitMech