Declomycin

デメチルクロルテトラサイクリン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/09/17 09:56:34」(JST)

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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 Y 64-73-3 (HCl)
ATC code	D06AA01 J01AA01
PubChem	CID 5311063
DrugBank	DB00618
ChemSpider	10482117 Y
UNII	5R5W9ICI6O Y
KEGG	D03680 Y
ChEBI	CHEBI:4392 Y
ChEMBL	CHEMBL1591 Y
Chemical data
Formula	C21H21ClN2O8
Mol. mass	464.853 g/mol
SMILES CN(C)[C@@H]1C(\O)=C(\C(N)=O)C(=O)[C@@]2(O)C(/O)=C3/C(=O)c4c(O)ccc(Cl)c4[C@@H](O)[C@H]3C[C@@H]12
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 Y Key:FMTDIUIBLCQGJB-SEYHBJAFSA-N Y
Y (what is this?)  (verify)

Demeclocycline (marketed as Declomycin, Declostatin, and Ledermycin) is a tetracycline antibiotic derived from a strain of Streptomyces aureofaciens.

Uses

It is officially indicated for the treatment of various types of bacterial infections. It is used as an antibiotic iin the treatment of Lyme disease, acne, and bronchitis.^{[citation needed]} Resistance, though, is gradually becoming more common, and demeclocycline is now rarely used for infections.

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.

The use in SIADH actually relies on a side effect; demeclocycline induces nephrogenic diabetes insipidus (dehydration due to the inability to concentrate urine). The use of demeclocycline in SIADH was first reported in 1975, 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. Demeclocycline has since been the drug of choice for treating SIADH, although it may be superseded as vasopressin receptor antagonists, such as tolvaptan, become available.

Contraindications

Like 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.

Side effects and interactions

These are similar to those of other tetracyclines. Skin reactions with sunlight have been reported. 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 gastrointestinal tract. Demeclocycline should not be taken with food (particularly milk and other dairy products) or antacids.

Mechanism of action

As with related tetracycline antibiotics, demeclocycline acts by binding to the 30S and 50S ribosomal subunits, 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 is thought to block the binding of the hormone from its receptor.

References

UpToDate Contents

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• 1. 低ナトリウム血症の治療：抗利尿ホルモン不適合分泌（SIADH）症候群およびreset osmostat症候群 treatment of hyponatremia syndrome of inappropriate antidiuretic hormone secretion siadh and reset osmostat
• 2. テトラサイクリン tetracyclines
• 3. 肝硬変患者における低ナトリウム血症 hyponatremia in patients with cirrhosis
• 4. 腎性尿崩症の臨床症状および原因 clinical manifestations and causes of nephrogenic diabetes insipidus
• 5. 腎性骨異栄養症の骨生検および診断 bone biopsy and the diagnosis of renal osteodystrophy

English Journal

• Evidence for the use of demeclocycline in the treatment of hyponatraemia secondary to SIADH: a systematic review.

• Miell J1, Dhanjal P2, Jamookeeah C3.
• International journal of clinical practice.Int J Clin Pract.2015 Dec;69(12):1396-417. doi: 10.1111/ijcp.12713. Epub 2015 Aug 19.
• AIMS: Hyponatraemia (HN) is the most common electrolyte balance disorder in clinical practice. Since the 1970s, demeclocycline has been used in some countries to treat chronic HN secondary to syndrome of inappropriate antidiuretic hormone secretion (SIADH). The precise mechanism of action of demeclo
• PMID 26289137

• Demeclocycline as a contrast agent for detecting brain neoplasms using confocal microscopy.

• Wirth D1, Smith TW, Moser R, Yaroslavsky AN.
• Physics in medicine and biology.Phys Med Biol.2015 Apr 7;60(7):3003-11. doi: 10.1088/0031-9155/60/7/3003. Epub 2015 Mar 19.
• Complete resection of brain tumors improves life expectancy and quality. Thus, there is a strong need for high-resolution detection and microscopically controlled removal of brain neoplasms. The goal of this study was to test demeclocycline as a contrast enhancer for the intraoperative detection of
• PMID 25790138

• Factors affecting the rate of oxidation and resultant discolouration of tetracyclines contained in endodontic medicaments and irrigants.

• Bennett ZY1, Walsh LJ.
• International endodontic journal.Int Endod J.2015 Apr;48(4):373-9. doi: 10.1111/iej.12323. Epub 2014 Jul 11.
• AIM: To determine the effect of pH, oxygen levels and ions on tetracycline oxidation and resultant discolouration.METHODOLOGY: Solutions of demeclocycline hydrochloride or doxycycline hyclate were prepared and exposed to different pH conditions, pure oxygen or carbon dioxide, ascorbic acid or variou
• PMID 24889184

Japanese Journal

• 新抗生物質Declomycinの臨床使用経験

• 佐藤 彰一 [他]
• 産婦人科治療 3(5), ????, 1961-11
• NAID 40017827138

• 耳鼻科領域の各種急性感染症に対する新抗生物質Declomycinの使用経験例

• 高橋 宏明 [他]
• 耳鼻咽喉科臨床 53(11), ????, 1960-11
• NAID 40017867477

Related Pictures

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★リンクテーブル★

リンク元	「デメチルクロルテトラサイクリン」

「デメチルクロルテトラサイクリン」

　　[★]

英

demethylchlortetracycline DMCTC

ラ

demethylchlortetracyclinum

化

塩酸デメチルクロルテトラサイクリン demethylchlortetracycline hydrochloride

同

デメクロサイクリン demeclocycline

商

レダマイシン、Declomycin

関

テトラサイクリン系抗菌薬、SIADH

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デメクロサイクリン : 約 2,640 件
デメチルクロルテトラサイクリン : 約 7,710 件

特徴

• ADH antagonist; acts as a diuretic in SIADH

構造

• テトラサイクリン系抗菌薬