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

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

tetracycline antibioticARO:3000050

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:26895 CHEBI:26895
ARO:3000050 ARO:3000050

Chemical structure

Computed structure properties
Molecular formula	C22H24N2O8
Charge	0
Average mass	444.44 Da
Monoisotopic mass	444.15327 Da
Source	ChEBI
InChIKey	JBIWCJUYHHGXTC-AKNGSSGZSA-N

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

Equivalent identifiers for this same structure in other resources.

ARO:0000069
cas:564-25-0
chemspider:10469369
drugbank:DB00254
drugcentral:961
hmdb:HMDB0014399
kegg.compound:C06973
kegg.drug:D07876
knapsack:C00017127
lipidmaps:LMPK07000001
metacyc.compound:CPD-19256
patent:US3019260
patent:US3200149
pdb-ccd:DXT
reaxys:3041790
vsdb:1840
wikipedia.en:Doxycycline
chembl:CHEMBL1200699
pubchem.compound:54671203

Activity roles

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

CHEBI:36047 CHEBI:36047
CHEBI:38068 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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:0000069`	doxycycline	`antibioticmech:aro-854cc68fcb`	2026-08-30
CHEBI	`CHEBI:50845`	doxycycline	`antibioticmech:chebi-7394cb23df`	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:0000069 (doxycycline); database assertion, not a primary citation.)

Resistance mechanisms

15 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_TARGET_PROTECTION 12

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
poxtA	ARO:3004470	not organism-specific	—	ARO:3004470 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(32)	ARO:3000196	not organism-specific	—	ARO:3000196 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(36)	ARO:3000197	not organism-specific	—	ARO:3000197 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(44)	ARO:3000556	not organism-specific	—	ARO:3000556 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(61)	ARO:3004576	not organism-specific	—	ARO:3004576 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(M)	ARO:3000186	not organism-specific	—	ARO:3000186 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(O)	ARO:3000190	not organism-specific	—	ARO:3000190 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(Q)	ARO:3000191	not organism-specific	—	ARO:3000191 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(S)	ARO:3000192	not organism-specific	—	ARO:3000192 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(T)	ARO:3000193	not organism-specific	—	ARO:3000193 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(W)	ARO:3000194	not organism-specific	—	ARO:3000194 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tetB(P)	ARO:3000195	not organism-specific	—	ARO:3000195 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
tet(63)	ARO:3007493	not organism-specific	—	ARO:3007493 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)
tet(64)	ARO:3007494	not organism-specific	—	ARO:3007494 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000069 (doxycycline); database assertion, not a primary citation.)

ANTIBIOTIC_INACTIVATION 1

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:0000069 (doxycycline); 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

Provenance

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