6-Demethyl-7-chlorotetracycline;6-Demethylchlorotetracycline;7-Chloro-6-demethyltetracycline;Bioterciclin;Clortetrin;Declomycin;Deganol;Demeclociclina [INN-Spanish];Demeclocycline [USAN:BAN];Demeclocycline HCL;Demeclocycline hydrochloride;Demeclocyclinum [INN-Latin];Demeclor;Demethylchlorotetracycline;Demethylchlortetracyclin;Demethylchlortetracycline;Demethylchlortetracycline hydrochloride;Demethylchlortetracyclinum;Demetraclin;Diuciclin;DMCT;DMCT (antibiotic);Elkamicina;Ledermycin;Ledermycin hydrochloride;Methylchlorotetracycline;Mexocine;Novotriclina;Perciclina;Sumaclina;Tri-demethylchlortetracycline;

A tetracycline analog having a 7-chloro and a 6-methyl. Because it is excreted more slowly than tetracycline, it maintains effective blood levels for longer periods of time. [PubChem]

• Abbott laboratories pharmaceutical products div
• Alpharma us pharmaceuticals division
• Amneal pharmaceutical
• Barr laboratories inc
• Convenant pharma inc
• Elkins sinn div ah robins co inc
• Heather drug co inc
• Impax laboratories inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• John j ferrante
• Laboratorios atral sarl
• Lederle laboratories div american cyanamid co
• Mm mast and co
• Mutual pharmaceutical co inc
• Mylan pharmaceuticals inc
• Private formulations inc
• Proter laboratory spa
• Purepac pharmaceutical co
• Roxane laboratories inc
• Sandoz inc
• Stiefel laboratories inc
• Superpharm corp
• Valeant pharmaceuticals international
• Warner chilcott inc
• Watson laboratories inc
• West ward pharmaceutical corp
• Wyeth ayerst laboratories

Synthesis Reference	Not Available
General Reference	De Troyer A, Demanet JC: Correction of antidiuresis by demeclocycline. N Engl J Med. 1975 Oct 30;293(18):915-8. Pubmed

Form	Route	Strength
Tablet	Oral

Unit description	Cost	Unit
Declomycin 300 mg tablet	22.29 USD	tablet
Demeclocycline 300 mg tablet	17.06 USD	tablet
Declomycin 150 mg tablet	12.31 USD	tablet
Demeclocycline 150 mg tablet	9.42 USD	tablet

Type	small molecule

Classes

Tetracyclines

Substructures

Tetracyclines Hydroxy Compounds Benzyl Alcohols and Derivatives Naphthalenes Phenols and Derivatives Amino Ketones Phenylpropenes Benzene and Derivatives Aryl Halides Halobenzenes Aliphatic and Aryl Amines Alcohols and Polyols Aromatic compounds Cinnamaldehydes Ketenes and Derivatives Phenyl Esters Enols Ketones

antibacterials 抗细菌;

Indication	Used primarily to treat Lyme disease, acne, and bronchitis. Also indicated (but rarely used) to treat urinary tract infections, gum disease, malaria, and other bacterial infections such as gonorrhea and chlamydia. 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.
Pharmacodynamics	Demeclocycline is a tetracycline antibiotic active against the following microorganisms: Rickettsiae (Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsial pox, tick fevers), Mycoplasma pneumoniae (PPLO, Eaton agent), agents of psittacosis and ornithosis, agents of lymphogranulomavenereum and granuloma inguinale, the spirochetal agent of relapsing fever (Borrelia recurrentis), Haemophilus ducreyi (chancroid), Yersinia pestis, Pasteurella pestis and Pasteurella tularensis, Bartonella bacilliformis, Bacteroides species, Vibrio comma and Vibrio fetus, and Brucella species (in conjunction with streptomycin). Demeclocycline inhibits cell growth by inhibiting translation. Demeclocycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane. Demeclocycline is bacteriostatic (it impairs bacterial growth but does not kill bacteria directly). Because it is excreted more slowly than tetracycline, it maintains effective blood levels for longer periods of time.
Mechanism of action	Demeclocycline inhibits cell growth by inhibiting translation. It binds (reversibly) to the 30S and 50S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome, which impairs protein synthesis by bacteria. The binding is reversible in nature. 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.
Absorption	Tetracyclines are readily absorbed.
Volume of distribution	Not Available
Protein binding	41-50%
Metabolism	Hepatic
Route of elimination	Demeclocycline hydrochloride, like other tetracyclines, is concentrated in the liver and excreted into the bile where it is found in much higher concentrations than in the blood. Following a single 150 mg dose of demeclocycline hydrochloride in normal volunteers, 44% (n = 8) was excreted in urine and 13% and 46%, respectively, were excreted in feces in two patients within 96 hours as active drug.
Half life	10-17 hours
Clearance	Renal cl=35 mL/min/1.73 m2
Toxicity	Oral, rat: LD50 = 2372 mg/kg
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Pathway Name SMPDB ID Demeclocycline Pathway SMP00290

Properties
State	solid
Melting point	220-223 oC
Experimental Properties	Property Value Source water solubility 1520 mg/L PhysProp logP 0.2 PhysProp logS -2.52 [ADME Research, USCD] PhysProp
Predicted Properties	Property Value Source water solubility 5.30e-01 g/l ALOGPS logP -0.07 ALOGPS logP -0.02 ChemAxon Molconvert logS -2.94 ALOGPS pKa 7.45 ChemAxon Molconvert hydrogen acceptor count 10 ChemAxon Molconvert hydrogen donor count 6 ChemAxon Molconvert polar surface area 181.62 ChemAxon Molconvert rotatable bond count 1 ChemAxon Molconvert refractivity 123.34 ChemAxon Molconvert polarizability 43.75 ChemAxon Molconvert

Drug	Interaction
Acenocoumarol	The tetracycline, demeclocycline, may increase the anticoagulant effect of acenocoumarol.
Acitretin	Increased risk of intracranial hypertension
Aluminium	Formation of non-absorbable complexes
Amoxicillin	Possible antagonism of action
Ampicillin	Possible antagonism of action
Anisindione	The tetracycline, demeclocycline, may increase the anticoagulant effect of anisindione.
Attapulgite	Formation of non-absorbable complexes
Azlocillin	Possible antagonism of action
Aztreonam	Possible antagonism of action
Bacampicillin	Possible antagonism of action
Calcium	Formation of non-absorbable complexes
Carbenicillin	Possible antagonism of action
Clavulanate	Possible antagonism of action
Cloxacillin	Possible antagonism of action
Cyclacillin	Possible antagonism of action
Dicloxacillin	Possible antagonism of action
Dicumarol	The tetracycline, demeclocycline, may increase the anticoagulant effect of dicumarol.
Ethinyl Estradiol	This anti-infectious agent could decrease the effect of the oral contraceptive
Etretinate	Increased risk of intracranial hypertension
Flucloxacillin	Possible antagonism of action
Hetacillin	Possible antagonism of action
Iron	Formation of non-absorbable complexes
Iron Dextran	Formation of non-absorbable complexes
Isotretinoin	Increased risk of intracranial hypertension
Magnesium	Formation of non-absorbable complexes
Magnesium oxide	Formation of non-absorbable complexes
Mestranol	This anti-infectious agent could decrease the effect of the oral contraceptive
Methoxyflurane	The tetracycline, demeclocycline, may increase the renal toxicity of methoxyflurane.
Meticillin	Possible antagonism of action
Mezlocillin	Possible antagonism of action
Nafcillin	Possible antagonism of action
Oxacillin	Possible antagonism of action
Penicillin G	Possible antagonism of action
Penicillin V	Possible antagonism of action
Piperacillin	Possible antagonism of action
Pivampicillin	Possible antagonism of action
Pivmecillinam	Possible antagonism of action
Tazobactam	Possible antagonism of action
Ticarcillin	Demeclocycline may reduce the effect of Ticarcillin by inhibiting bacterial growth. Ticarcillin exerts its effects on actively growing bacteria. To achieve synergism, Ticarcillin should be administered at least 2 hours prior to using Demeclocycline.
Tretinoin	Demeclocycline may increase the adverse effects of oral Tretinoin. Increased risk of pseudotumour cerebri. Concurrent therapy should be avoided.
Warfarin	The tetracycline, demeclocycline, may increase the anticoagulant effect of warfarin.
Zinc	Formation of non-absorbable complexes

• Avoid milk and multivalent ions.
• Take on an empty stomach.