Demeclocycline

Summary

Demeclocycline (CHEMBL1591) is an approved small-molecule antibacterial drug (ATC D06AA01); indicated across 2 conditions including bacterial infectious disease and osteomyelitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D06AA01 (+1 more)
• Indications: 2 conditions
• Clinical trials: 4
• Chemistry: 464.9 Da · C21H21ClN2O8

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1591
Name	Demeclocycline
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	54680690
ChEBI	CHEBI:4392
ATC	D06AA01, J01AA01
Molecular formula	C21H21ClN2O8
Molecular weight	464.9
InChIKey	GUXHBMASAHGULD-SEYHBJAFSA-N

SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3[C@@H](C4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O

IUPAC name: (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide

ChEBI definition: 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.

Pharmacological roles (ChEBI): antibacterial drug, geroprotector, aquaretic.

Also known as: Demeclociclina, Demeclocycline, Demethylchlortetracycline, SID90341625, demeclocycline, DEMECLOCYCLINE, DEMECLOCYCLINE HYDROCHLORIDE

Parent form; salt/anhydrous children: CHEMBL1200474

Patent coverage: 5,346 distinct patent families (20,295 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 20,020 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: Alpha-ketoglutarate-dependent dioxygenase FTO, Androgen receptor, Nuclear receptor subfamily 1 group I member 2.

Bioactivity

ChEMBL activities: 3 potent at pChembl ≥ 5 of 3 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
FTO	5.86	IC50	1390	nM	CHEMBL_ACT_24989146
P15207	5.58	AC50	2600	nM	CHEMBL_ACT_25187208
NR1I2	5.29	AC50	5100	nM	CHEMBL_ACT_25187885

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
osteomyelitis	0	MONDO:0005246	EFO:0003102

Clinical trials

Total trials: 4.

Phase distribution

Phase	Trials
PHASE4	2
PHASE1	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01753856	PHASE4	COMPLETED	Effects of Teriparatide or Denosumab on Bone in Postmenopausal Women With Osteoporosis
NCT02576652	PHASE4	COMPLETED	Bone Histomorphometry in Postmenopausal Men and Women With Osteoarthritis Undergoing Total Hip Replacement
NCT02740933	PHASE1	UNKNOWN	Demeclocycline Fluorescence for Intraoperative Delineation Brain Tumors
NCT00873808	Not specified	WITHDRAWN	S0307A, Long-Term Bone Quality in Women With Breast Cancer Enrolled on Clinical Trial SWOG-S0307

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).