QuickView for Demeclocycline (compound)

Summary
General Info

PubChem

PubChem Compound 2983

Name:	Demeclocycline
PubChem Compound ID:	2983
Description:	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.
Molecular formula:	C₂₁H₂₁ClN₂O₈
Molecular weight:	464.853 g/mol

DrugBank

Identification

Name:	Demeclocycline
Name (isomeric):	DB00618
Drug Type:	small molecule
Description:	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.
Brand:	6-Demethyl-7-chlorotetracycline, Mexocine, Demeclocycline hydrochloride, Demeclociclina [INN-Spanish], Demethylchlortetracycline, Sumaclina, Demeclocycline HCL, Ledermycin hydrochloride, Novotriclina, Methylchlorotetracycline, Bioterciclin, Clortetrin, Demethylchlortetracyclinum, DMCT, DMCT (antibiotic), Deganol, Tri-demethylchlortetracycline, Demethylchlorotetracycline, Perciclina, Demetraclin, Demeclocyclinum [INN-Latin], Declomycin, Ledermycin, Demeclocycline [USAN:BAN], Elkamicina, Demeclor, Demethylchlortetracyclin, Demethylchlortetracycline hydrochloride, 6-Demethylchlorotetracycline, Diuciclin, 7-Chloro-6-demethyltetracycline
Category:	Anti-Bacterial Agents, Tetracyclines
CAS number:	127-33-3

Pharmacology

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.
Pharmacology:	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 ... show more » 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. show less «
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 ant... show more » 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. show less «
Absorption:	Tetracyclines are readily absorbed.
Protein binding:	41-50%
Biotransformation:	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

Interactions

Food interaction:

Avoid milk and multivalent ions.

Take on an empty stomach.

Drug interaction:

Flucloxacillin	Possible antagonism of action
Tazobactam	Possible antagonism of action
Hetacillin	Possible antagonism of action
Isotretinoin	Increased risk of intracranial hypertension
Iron	Formation of non-absorbable complexes

Flucloxacillin	Possible antagonism of action
Tazobactam	Possible antagonism of action
Hetacillin	Possible antagonism of action
Isotretinoin	Increased risk of intracranial hypertension
Iron	Formation of non-absorbable complexes
Penicillin G	Possible antagonism of action
Calcium	Formation of non-absorbable complexes
Magnesium oxide	Formation of non-absorbable complexes
Zinc	Formation of non-absorbable complexes
Piperacillin	Possible antagonism of action
Oxacillin	Possible antagonism of action
Pivampicillin	Possible antagonism of action
Magnesium	Formation of non-absorbable complexes
Etretinate	Increased risk of intracranial hypertension
Mezlocillin	Possible antagonism of action
Bacampicillin	Possible antagonism of action
Tretinoin	Demeclocycline may increase the adverse effects of oral Tretinoin. Increased risk of pseudotumour cerebri. Concurrent therapy should be avoided.
Methoxyflurane	The tetracycline, demeclocycline, may increase the renal toxicity of methoxyflurane.
Calcium Chloride	Calcium salts such as calcium chloride may decrease the serum concentration of tetracycline derivatives such as demeclocycline. In general, the coadministration of oral calcium salts and oral tetracycline derivatives should be avoided. Interactions may be able to be minimized by administering oral calcium preparations several hours before or after the dose of the oral tetracycline derivatives. Even with dose separation, therapy may still be compromised. Monitor for decreased therapeutic effect of oral tetracycline derivatives.
Nafcillin	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.
Penicillin V	Possible antagonism of action
Cloxacillin	Possible antagonism of action
Ethinyl Estradiol	This anti-infectious agent could decrease the effect of the oral contraceptive
Attapulgite	Formation of non-absorbable complexes
Aluminium	Formation of non-absorbable complexes
Anisindione	The tetracycline, demeclocycline, may increase the anticoagulant effect of anisindione.
Dicumarol	The tetracycline, demeclocycline, may increase the anticoagulant effect of dicumarol.
Carbenicillin	Possible antagonism of action
Acenocoumarol	The tetracycline, demeclocycline, may increase the anticoagulant effect of acenocoumarol.
Ampicillin	Possible antagonism of action
Pivmecillinam	Possible antagonism of action
Cyclacillin	Possible antagonism of action
Mestranol	This anti-infectious agent could decrease the effect of the oral contraceptive
Aztreonam	Possible antagonism of action
Meticillin	Possible antagonism of action
Warfarin	The tetracycline, demeclocycline, may increase the anticoagulant effect of warfarin.
Calcium Acetate	Calcium salts such as calcium acetate may decrease the serum concentration of tetracycline derivatives such as demeoclocycline. In general, the coadministration of oral calcium salts and oral tetracycline derivatives should be avoided. Interactions may be able to be minimized by administering oral calcium preparations several hours before or after the dose of the oral tetracycline derivatives. Even with dose separation, therapy may still be compromised. Monitor for decreased therapeutic effect of oral tetracycline derivatives.
Colesevelam	Bile acid sequestrants such as colesevelam may decrease the absorption of Tetracycline Derivatives. Monitor for decreased therapeutic effects of tetracycline derivatives if coadministered with a bile acid sequestrant. If these agents are used concomitantly, separate doses 2 or more hours to minimize the interaction. The manufacturer of colesevelam suggests that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
Amoxicillin	Possible antagonism of action
Acitretin	Increased risk of intracranial hypertension
Iron Dextran	Formation of non-absorbable complexes
Dicloxacillin	Possible antagonism of action
Azlocillin	Possible antagonism of action
Bexarotene	Tetracycline derivatives like demeclocycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Clavulanate	Possible antagonism of action

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Targets

30S ribosomal protein S9

30S ribosomal protein S4