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Methacycline

Catalog No. DB00931 Name DrugBank
CAS Number 914-00-1 Website http://www.ualberta.ca/
M. F. C22H22N2O8 Telephone (780) 492-3111
M. W. 442.41868 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 807

SYNONYMS

IUPAC name
(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-1,2,3,4,4a,5,5a,6,11,12a-decahydrotetracene-2-carboxamide
IUPAC Traditional name
(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-4,4a,5,5a-tetrahydro-2H-tetracene-2-carboxamide
Brand Name
Rondomycin
Synonyms
Methacyclin
Metacycline

DATABASE IDS

CAS Number 914-00-1

PROPERTIES

Hydrophobicity(logP) -0.3
Solubility 7.55 mg/mL at 21 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A broad-spectrum semisynthetic antibiotic related to tetracycline but excreted more slowly and maintaining effective blood levels for a more extended period. [PubChem]
Indication For the treatment of acute bacterial exacerbations of chronic bronchitis
Pharmacology Methacycline is a tetracycline antibiotic. Similar to other tetracyclines, it has a wide spectrum of antimicrobial action. It is active against most Gram-positive bacteria (pneumococci, streptococci, staphylococci) and Gram-negative bacteria (E. coli, salmonella, shigella, etc.), and towards agents causing onithosis, psittacosis, trachoma, and some Protozoa. Like other tetracyclines, the general usefulness of methacycline has been reduced with the onset of bacterial resistance.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption 58% absorbed
Half Life 14 hours
Protein Binding 75-78% protein bound
References
Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [Pubmed]
Li J, Chen L, Wang X, Jin H, Ding L, Zhang K, Zhang H: Determination of tetracyclines residues in honey by on-line solid-phase extraction high-performance liquid chromatography. Talanta. 2008 Jun 15;75(5):1245-52. Epub 2008 Jan 20. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. Pubmed
  • Li J, Chen L, Wang X, Jin H, Ding L, Zhang K, Zhang H: Determination of tetracyclines residues in honey by on-line solid-phase extraction high-performance liquid chromatography. Talanta. 2008 Jun 15;75(5):1245-52. Epub 2008 Jan 20. Pubmed