| Candidate ID: | R0217 |
| Source ID: | DB00618 |
| Source Type: | approved |
| Compound Type: |
small molecule
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| Compound Name: |
Demeclocycline
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| Synonyms: |
[4S-(4α,4aα,5aα,6β,12aα)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 6-demethyl-7-chlorotetracycline; 7-chloro-6-demethyltetracycline; Demeclocycline; Demethylchlortetracyclin; Demethylchlortetracycline; DMCT; DMCTC
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| Molecular Formula: |
C21H21ClN2O8
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| SMILES: |
[H][C@]12C[C@@]3([H])[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C(=O)C1=C([C@H]2O)C(Cl)=CC=C1O
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| Structure: |
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| DrugBank 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.
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| CAS Number: |
127-33-3
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| Molecular Weight: |
464.853
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| DrugBank 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.
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| DrugBank Pharmacology: |
Demeclocycline is a tetracycline antibiotic active against the following microorganisms: <i>Rickettsiae</i> (Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsial pox, tick fevers), <i>Mycoplasma pneumoniae</i> (PPLO, Eaton agent), agents of psittacosis and ornithosis, agents of lymphogranulomavenereum and granuloma inguinale, the spirochetal agent of relapsing fever (<i>Borrelia recurrentis</i>), <i>Haemophilus ducreyi</i> (chancroid), <i>Yersinia pestis</i>, <i>Pasteurella pestis</i> and <i>Pasteurella tularensis</i>, <i>Bartonella bacilliformis</i>, <i>Bacteroides species</i>, <i>Vibrio comma</i> and <i>Vibrio fetus</i>, and <i>Brucella species</i> (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 not a direct bactericidal agent; rather, it is a bacteriostatic drug that impairs bacterial growth. Because it is excreted more slowly than tetracycline, it maintains effective blood levels for longer periods of time.
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| DrugBank MoA: |
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.
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| Targets: |
30S ribosomal protein inhibitor; Vasopressin V2 receptor inhibitor
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| Inclusion Criteria: |
Indication associated
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