doxycycline

CHEBI:50845 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Tetracycline in which the 5β-hydrogen is replaced by a hydroxy group, while the 6α-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis. — ChEBI

Classification

tetracycline antibioticARO:3000050

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:26895
• tetracycline antibiotic ARO:3000050

Chemical structure

SMILES

[H][C@@]12C(=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]3([H])[C@H]1O)C(=O)c1c(O)cccc1[C@@H]2C

InChI

InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

Also called

• Jenacyclin (BRAND_NAME)— chebi
• Supracyclin (BRAND_NAME)— chebi
• Vibramycin (BRAND_NAME)— chebi
• doxiciclina (INN)— chebi
• doxycyclinum (INN)— chebi
• (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (EXACT_SYNONYM)— chebi
• (4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE (EXACT_SYNONYM)— chebi
• 5-hydroxy-α-6-deoxytetracycline (EXACT_SYNONYM)— chebi
• 6α-deoxy-5-oxytetracycline (EXACT_SYNONYM)— chebi
• Doxycyclin (EXACT_SYNONYM)— chebi
• Doxycycline (EXACT_SYNONYM)— chebi
• doxycycline (anhydrous) (EXACT_SYNONYM)— chebi
• Azudoxat (EXACT_SYNONYM)— aro
• Deoxymykoin (EXACT_SYNONYM)— aro
• Doxiciclina (EXACT_SYNONYM)— aro
• Doxitard (EXACT_SYNONYM)— aro
• Doxycyclinum (EXACT_SYNONYM)— aro
• Doxytetracycline (EXACT_SYNONYM)— aro
• Vibramycine (EXACT_SYNONYM)— aro
• Vibravenos (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.

• doxycyclineARO:0000069
• cas:564-25-0
• chemspider:10469369
• hmdb:HMDB0014399
• kegg.compound:C06973
• lipidmaps:LMPK07000001
• metacyc.compound:CPD-19256
• pdb-ccd:DXT
• reaxys:3041790
• vsdb:1840
• chembl:CHEMBL1200699
• pubchem.compound:54671203

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.

• drugbank:DB00254
• drugcentral:961
• kegg.drug:D07876

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

• patent:US3019260
• patent:US3200149
• wikipedia.en:Doxycycline

Activity roles

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

• antibacterial drug CHEBI:36047
• antimalarial CHEBI:38068

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.

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:0000069 (doxycycline); database assertion, not a primary citation.)

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

1 observations · Browse all observations · Complete record (JSON.gz)

Resistance mechanisms

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

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 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank doxycycline-resistant Enterococcus faecium isolate MIC observation.

7. STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted

   Structured BioSample accessions on 1 activity_spectrum observation(s) where evidence notes already named exactly one accession.

Provenance

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

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