Demeclocycline (hydrochloride)

Demeclocycline is a broad-spectrum tetracycline antibiotic produced by S. aureofaciens. It has antimicrobial activity against ~3,200 pathogenic Gram-positive and Gram-negative bacteria in vitro that is 2-fold greater than that of tetracycline (Cay-14328). The bactericidal action of demeclocycline is comparable to that of chlortetracycline but the duration of action is longer due to its resistance to degradation by acids or alkalis. It is effective against S. pyogenes and K. pneumoniae infections in vivo when administered orally or subcutaneously in mice. Demeclocycline decreases aquaporin 2 (AQP2) water channel gene transcription and protein abundance in mpkCCD murine collecting duct cells in a dose-dependent manner. It also increases urine volume, decreases urine osmolity, and increases fractional excretion of water in a rat model of hyponatremia. Formulations containing demeclocycline have been used to treat hyponatremia due to syndrome of inappropriate antidiuretic hormone secretion (SIADH) and as endodontic antibiotics to prevent infection following root canal procedures.Formal Name: (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide, monohydrochloride. CAS Number: 64-73-3. Synonyms: Demethylchlortetracycline, Demethyltetracycline. Molecular Formula: C21H21ClN2O8 . HCl. Formula Weight: 501.3. Purity: >90%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 1.4 mg/mL, DMSO: 1 mg/mL, PBS (pH 7.2): 3.3 mg/mL. lambdamax: 229, 266, 369 nm. SMILES: O[C@H](C1=C(C2=O)C(O)=CC=C1Cl)[C@]3([H])C2=C(O)[C@@](C(C(C(N)=O)=C(O)[C@H]4N(C)C)=O)(O)[C@@]4([H])C3.Cl. InChi Code: InChI=1S/C21H21ClN2O8.ClH/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31,/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31),1H/t6-,7-,14-,15-,21-,/m0./s1. InChi Key: GVSJQNRGSCOSNJ-KBHRXELFSA-N.