Article: Demeclocycline

Demeclocycline
Systematic (IUPAC) name
2-(amino-hydroxy-methylidene)- 7-chloro-4-dimethylamino- 6,10,11,12a-tetrahydroxy-4, 4a,5,5a,6,12a- hexahydrotetracene-1,3,12-trione
Identifiers
CAS number	127-33-3
ATC code	D06AA01 J01AA01
PubChem	5311063
DrugBank	APRD00272
Chemical data
Formula	C21H21ClN2O8
Mol. weight	464.853 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	41-50%
Metabolism	Hepatic
Half life	10-17 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	Oral 150 mg/300 mg

Demeclocycline (marketed as Declomycin®, Declostatin® and Ledermycin®) is a member of the tetracycline antibiotics group used in various types of bacterial infections. One of its other registered uses is the treatment of hyponatremia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective. It is derived from the Streptomyces aureofaciens fungal strain.

Mode of action

Its use as an antibiotic is particularly in Lyme disease, acne and bronchitis. Resistance is gradually becoming more common. As with related tetracycline antibiotics, demeclocycline acts by binding to the 30S- and 50S-RNA, which impairs protein synthesis by bacteria. It is therefore bacteriostatic (it impairs bacterial growth but does not kill bacteria directly). Demeclocycline is rarely used for infections.

The use in SIADH actually relies on a side-effect of tetracycline antibiotics; many may cause diabetes insipidus (dehydration due to the inability to concentrate urine). It is not completely understood why demeclocycline impairs the action of antidiuretic hormone, but it is thought that it blocks the binding of the hormone to its receptor.

Side-effects and interactions

These are similar to other tetracyclines. Hypersensitivity may occur. Skin reactions with sunlight have been reported.

Contraindications

As other tetracyclines, demeclocycline is contraindicated in children and pregnant or nursing women. All members of this class interfere with bone development and may discolour teeth.