demeclocycline

CHEBI:4392 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Tetracycline which lacks the methyl substituent at position 7 and in which the hydrogen para- to the phenolic hydroxy group is substituted by chlorine. Like tetracycline, it is an antibiotic, but being excreted more slowly, effective blood levels are maintained for longer. It is used (mainly as the hydrochloride) for the treatment of Lyme disease, acne and bronchitis, as well as for hyponatraemia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective. — 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	C21H21ClN2O8
Charge	0
Average mass	464.858 Da
Monoisotopic mass	464.09864 Da
Source	ChEBI
InChIKey	FMTDIUIBLCQGJB-SEYHBJAFSA-N

SMILES

[H][C@]12C[C@@]3([H])[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C(=O)c1c(O)ccc(Cl)c1[C@H]2O

InChI

InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1

Also called

demeclociclina (INN)— chebi
demeclocyclinum (INN)— chebi
(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (EXACT_SYNONYM)— chebi
6-demethyl-7-chlorotetracycline (EXACT_SYNONYM)— chebi
7-chloro-6-demethyltetracycline (EXACT_SYNONYM)— chebi
DMCT (EXACT_SYNONYM)— chebi
DMCTC (EXACT_SYNONYM)— chebi
Demeclocycline (EXACT_SYNONYM)— chebi
[4S-(4α,4aα,5aα,6β,12aα)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide (EXACT_SYNONYM)— chebi
demethylchlortetracycline (EXACT_SYNONYM)— chebi
declomycin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000667
beilstein:2230579
cas:127-33-3
chemspider:10482117
drugbank:DB00618
drugcentral:802
kegg.drug:D00290
kegg.drug:D03680
patent:FR1344645
patent:US2878289
patent:US3012946
patent:US3019172
patent:US3050446
patent:US3154476
wikipedia.en:Demeclocycline
chembl:CHEMBL1591
pubchem.compound:54680690

Activity roles

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

CHEBI:36047 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:3000667`	demeclocycline	`antibioticmech:aro-d4671f27d8`	2026-08-30
CHEBI	`CHEBI:4392`	demeclocycline	`antibioticmech:chebi-114c74722d`	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:3000667 (demeclocycline); database assertion, not a primary citation.)

Resistance mechanisms

12 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 10

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
tet(32)	ARO:3000196	not organism-specific	—	ARO:3000196 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(36)	ARO:3000197	not organism-specific	—	ARO:3000197 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(44)	ARO:3000556	not organism-specific	—	ARO:3000556 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(M)	ARO:3000186	not organism-specific	—	ARO:3000186 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(O)	ARO:3000190	not organism-specific	—	ARO:3000190 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(Q)	ARO:3000191	not organism-specific	—	ARO:3000191 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(S)	ARO:3000192	not organism-specific	—	ARO:3000192 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(T)	ARO:3000193	not organism-specific	—	ARO:3000193 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tet(W)	ARO:3000194	not organism-specific	—	ARO:3000194 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)
tetB(P)	ARO:3000195	not organism-specific	—	ARO:3000195 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
lmrP	ARO:3003969	not organism-specific	—	ARO:3003969 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000667 (demeclocycline); 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:3000667 (demeclocycline); 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.