Demeclocycline

Title: Demeclocycline
CAS Registry Number: 127-33-3
CAS Name: [4S-(4a,4aa,5aa,6b,12aa)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide
Additional Names: 7-chloro-6-demethyltetracycline; demethylchlortetracycline (obsolete)
Manufacturers' Codes: RP-10192
Trademarks: Bioterciclin; Declomycin (Wyeth); Deganol; Ledermycin (Wyeth); Periciclina
Molecular Formula: C21H21ClN2O8
Molecular Weight: 464.85
Percent Composition: C 54.26%, H 4.55%, Cl 7.63%, N 6.03%, O 27.53%
Literature References: Antibiotic related to tetracycline produced by Streptomyces aureofaciens. Prepn: McCormick et al., J. Am. Chem. Soc. 79, 4561 (1957); US 2878289 (1959 to Am. Cyanamid). Improved fermentation processes: Szumski, US 3012946; Goodman, Matrishin, US 3019172; Goodman, US 3050446 (1961, 1962, 1962 all to Am. Cyanamid); FR 1344645 (1963 to Merck & Co.); Neidleman, US 3154476 (1964 to Olin Mathieson). Abs config: Dobrynin et al., Tetrahedron Lett. 1962, 901. Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Derivative Type: Sesquihydrate
Properties: mp 174-178° (dec). [a]D25 -258° (c = 0.5 in 0.1N H2SO4). Solubilities: Marsh, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967).
Melting point: mp 174-178° (dec)
Optical Rotation: [a]D25 -258° (c = 0.5 in 0.1N H2SO4)
Derivative Type: Hydrochloride
CAS Registry Number: 64-73-3
Trademarks: Clortetrin (Fargal); Demetraciclina (Bios); Detravis (Vis); Meciclin (Citobios); Mexocine (Specia)
Properties: LD50 orally in rats: 2372 mg/kg (Goldenthal).
Toxicity data: LD50 orally in rats: 2372 mg/kg (Goldenthal)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Tetracyclines.
Demecolcine Demeton Demexiptiline Denatonium Benzoate Dendrotoxins

Demeclocycline
Demeclocycline.png
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 YesY
64-73-3 (HCl)
ATC code D06AA01 J01AA01
PubChem CID 5311063
DrugBank DB00618
ChemSpider 10482117 YesY
UNII 5R5W9ICI6O YesY
KEGG D03680 YesY
ChEBI CHEBI:4392 YesY
ChEMBL CHEMBL1591 YesY
Chemical data
Formula C21H21ClN2O8 
Mol. mass 464.853 g/mol
 YesY (what is this?)  (verify)

Demeclocycline (marketed as Declomycin, Declostatin, and Ledermycin) is a tetracycline antibiotic derived from a strain of Streptomyces aureofaciens.[1]