Demeclocycline

Demeclocycline
Demeclocycline
Systematic (IUPAC) name
(2E,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-1,2,3,4,4a,5,5a,6,12,12a-decahydrotetracene-1,3,12-trione
Clinical data
Trade names Declomycin
AHFS/Drugs.com monograph
MedlinePlus a682103
Pregnancy cat. D(US)
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 60–80%
Protein binding 41–50%
Metabolism Hepatic
Half-life 10–17 hours
Excretion Renal
Identifiers
CAS number 127-33-3 YesY
64-73-3 (HCl)
ATC code D06AA01 J01AA01
PubChem CID 5311063
DrugBank APRD00272
ChemSpider 10482117 YesY
UNII 5R5W9ICI6O YesY
KEGG D03680 YesY
ChEBI CHEBI:4392 YesY
ChEMBL CHEMBL1591 YesY
Chemical data
Formula C21H21ClN2O8 
Mol. mass 464.853 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Demeclocycline (marketed as Declomycin, Declostatin and Ledermycin) is a tetracycline antibiotic.

It is derived from a strain of Streptomyces aureofaciens.[1]

Contents

Uses

In infections

It is officially indicated for the treatment of various types of bacterial infections.[2]

Its use as an antibiotic is particularly in Lyme disease, acne and bronchitis.[citation needed]

Resistance is gradually becoming more common, and demeclocycline is now rarely used for infections.

In SIADH

It is widely used (though off-label in many countries) in the treatment of hyponatremia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) when fluid restriction alone has been ineffective.[3]

The use in SIADH actually relies on a side effect; demeclocycline induces nephrogenic diabetes insipidus (dehydration due to the inability to concentrate urine).[3] The use of demeclocycline in SIADH was first reported in 1975,[4] and, in 1978, a larger study found it to be more effective and better tolerated than lithium carbonate, the only available treatment at the time.[5] Demeclocycline has since been the drug of choice for treating SIADH, although it may be superseded as vasopressin receptor antagonists, such as tolvaptan, become available.[5]

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.[6]

Side effects and interactions

These are similar to those of other tetracyclines. Skin reactions with sunlight have been reported.[5] Demeclocycline is unique in that it is the only tetracycline known to cause nephrogenic diabetes insipidus.

Tetracyclines bind to cations such as calcium, iron (when given orally), and magnesium, rendering them insoluble and inabsorbable for the GI tract. Demeclocycline should not be taken with food (particularly milk and other dairy products) or antacids.[6]

Mechanism of action

As with related tetracycline antibiotics, demeclocycline acts by binding to the 30S- and 50S-RNA, which impairs protein synthesis by bacteria. It is bacteriostatic (it impairs bacterial growth but does not kill bacteria directly).

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.[7]

References

  1. ^ "demeclocycline" at Dorland's Medical Dictionary
  2. ^ "DailyMed: About DailyMed". http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=673. Retrieved 2008-12-20. 
  3. ^ a b Goh KP (May 2004). "Management of hyponatremia". American Family Physician 69 (10): 2387–94. PMID 15168958. http://www.aafp.org/afp/20040515/2387.html. 
  4. ^ Cherrill DA, Stote RM, Birge JR, Singer I (November 1975). "Demeclocycline treatment in the syndrome of inappropriate antidiuretic hormone secretion". Annals of Internal Medicine 83 (5): 654–6. PMID 173218. 
  5. ^ a b c Tolstoi LG (2002). "A brief review of drug-induced syndrome of inappropriate secretion of antidiuretic hormone". Medscape Pharmacotherapy 4 (1). http://www.medscape.com/viewarticle/420687_print.  Retrieved on October 27, 2008.
  6. ^ a b Lexi-Comp (August 2008). "Demeclocycline". The Merck Manual Professional. http://www.merck.com/mmpe/lexicomp/demeclocycline.html.  Retrieved on October 27, 2008.
  7. ^ De Troyer A, Demanet JC (1975). "Correction of antidiuresis by demeclocycline". N Engl J Med 293 (18): 915–8. doi:10.1056/NEJM197510302931809. PMID 170519. 



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Look at other dictionaries:

  • Demeclocycline — См. Демеклоциклин (Источник: «Словарь терминов микробиологии») …   Словарь микробиологии

  • demeclocycline — A broad spectrum antibiotic that is more slowly excreted and more stable in acid and alkali than are other forms of the tetracyclines; available as the hydrochloride. * * * de·mec·lo·cy·cline .dem ə klō sī .klēn n a broad spectrum tetracycline… …   Medical dictionary

  • demeclocycline — n. a tetracycline antibiotic that is active against a wide range of bacteria and is used to treat various infections. It is also used to treat syndrome of inappropriate secretion of antidiuretic hormone. Demeclocycline is administered by mouth;… …   The new mediacal dictionary

  • demeclocycline hydrochloride — [USP] the monohydrochloride salt of demeclocycline, administered orally as an antibiotic. It is also used orally as a diuretic in the treatment of syndrome of inappropriate antidiuretic hormone (SIADH) …   Medical dictionary

  • demeclocycline — /dem euh kloh suy kleen/, n. Pharm. a broad spectrum antibiotic, C21H21ClN2O8, derived from a mutant strain of the bacterium Streptomyces aureofaciens: used against a wide range of susceptible microorganisms. [contr. and rearrangement of 7 chloro …   Universalium

  • demeclocycline — noun A tetracycline antibiotic derived from a strain of Streptomyces aureofaciens …   Wiktionary

  • demeclocycline — /dem euh kloh suy kleen/, n. Pharm. a broad spectrum antibiotic, C21H21ClN2O8, derived from a mutant strain of the bacterium Streptomyces aureofaciens: used against a wide range of susceptible microorganisms. [contr. and rearrangement of 7 chloro …   Useful english dictionary

  • demeclocycline hydrochloride — noun tetracycline antibacterial (trade name Declomycin) effective in the treatment of some bacterial and rickettsial and other infections • Syn: ↑Declomycin • Usage Domain: ↑trade name (for: ↑Declomycin) • Hypernyms: ↑ …   Useful english dictionary

  • Демеклоциклин (Demeclocycline) — антибиотик; активен против широкого диапазона бактерий; применяется для лечения различных инфекций. Назначается внутрь; характерные побочные эффекты: тошнота, понос, а также симптомы, вызванные размножением микроорганизмов, нечувствительных к… …   Медицинские термины

  • ДЕМЕКЛОЦИКЛИН — (demeclocycline) антибиотик; активен против широкого диапазона бактерий; применяется для лечения различных инфекций. Назначается внутрь; характерные побочные эффекты: тошнота, понос, а также симптомы, вызванные размножением микроорганизмов,… …   Толковый словарь по медицине

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