demeclocycline

• CAT Number: M132189
• CAS Number: 127-33-3
• Molecular Formula: C21H21ClN2O8
• Molecular Weight: 464.855
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• InChI: InChI=1S/C21H21ClN2O8/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/h3-4,6-7,14-15,25-27,30,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
• InChIKey: GUXHBMASAHGULD-SEYHBJAFSA-N
• SMILES: CN(C)C1C2CC3C(C4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O

Demeclocycline (INN, BAN) (brand names Declomycin, Declostatin, Ledermycin, Bioterciclin, Deganol, Deteclo), also known as demeclocycline hydrochloride (USAN) (brand names Detravis, Meciclin, Mexocine, Clortetrin), is a semisynthetic tetracycline antibiotic which was derived from a strain of Streptomyces aureofaciens. Demeclocycline binds to bacterial 30S ribosomal subunit and prevents binding of aminoacyl-tRNA to the mRNA-ribosome complex, thereby inhibiting protein synthesis. Demeclocycline also inhibits the effect of vasopressin on the renal tubules, thereby causing diuresis. (Source: https://en.wikipedia.org/wiki/Demeclocycline).

Reference

1:Evidence for the use of demeclocycline in the treatment of hyponatraemia secondary to SIADH: a systematic review. Miell J, Dhanjal P, Jamookeeah C.Int J Clin Pract. 2015 Dec;69(12):1396-417. doi: 10.1111/ijcp.12713. Epub 2015 Aug 19. Review. PMID: 26289137 Free PMC Article2:Demeclocycline as a contrast agent for detecting brain neoplasms using confocal microscopy. Wirth D, Smith TW, Moser R, Yaroslavsky AN.Phys Med Biol. 2015 Apr 7;60(7):3003-11. doi: 10.1088/0031-9155/60/7/3003. Epub 2015 Mar 19. PMID: 25790138 3:Comparative evaluation of methylene blue and demeclocycline for enhancing optical contrast of gliomas in optical images. Wirth D, Snuderl M, Curry W, Yaroslavsky A.J Biomed Opt. 2014 Sep;19(9):90504. doi: 10.1117/1.JBO.19.9.090504. PMID: 25239672 4:Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Kortenoeven ML, Sinke AP, Hadrup N, Trimpert C, Wetzels JF, Fenton RA, Deen PM.Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18. doi: 10.1152/ajprenal.00723.2012. Epub 2013 Oct 23. PMID: 24154696 Free Article5:Studies of the interaction between demeclocycline and human serum albumin by multi-spectroscopic and molecular docking methods. Dong C, Ma S, Liu Y.Spectrochim Acta A Mol Biomol Spectrosc. 2013 Feb 15;103:179-86. doi: 10.1016/j.saa.2012.10.050. Epub 2012 Nov 7. PMID: 23261611 6:Root discolouration following short-term application of steroid medicaments containing clindamycin, doxycycline or demeclocycline. Chen BK, George R, Walsh LJ.Aust Endod J. 2012 Dec;38(3):124-8. doi: 10.1111/aej.12000. Epub 2012 Nov 2. PMID: 23211072 7:Development and validation of a reversed-phase liquid chromatographic method for analysis of demeclocycline and related impurities. Kahsay G, Maxa J, Van Schepdael A, Hoogmartens J, Adams E.J Sep Sci. 2012 Jun;35(10-11):1310-8. doi: 10.1002/jssc.201101071. PMID: 22733511 8:Preparation of aqueous two-phase systems composed of two pH-response polymers and liquid-liquid extraction of demeclocycline. Yan B, Cao X.J Chromatogr A. 2012 Jul 6;1245:39-45. doi: 10.1016/j.chroma.2012.05.045. Epub 2012 May 17. PMID: 22658298 9:A prospective clinical trial on the influence of a triamcinolone/demeclocycline and a calcium hydroxide based temporary cement on pain perception. Willershausen B, Willershausen I, Ehlers V, Azaripour A, Briseño B.Head Face Med. 2012 Mar 13;8:9. doi: 10.1186/1746-160X-8-9. PMID: 22414157 Free PMC Article10:Preparation and characterization of demeclocycline liposomal formulations and assessment of their intraocular pressure-lowering effects. Afouna MI, Khattab IS, Reddy IK.Cutan Ocul Toxicol. 2005;24(2):111-24. PMID: 17040889