Synonym
Declostatin; Ledermycin; Bioterciclin; Deganol; Deteclo; Demeclocycline; Ledermycin; Declomycin; Demeclociclina; Demeclocyclinum; DMCTC; Detravis; Meciclin; Mexocine; Clortetrin
IUPAC/Chemical Name
(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
InChi Key
FMTDIUIBLCQGJB-SEYHBJAFSA-N
InChi Code
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/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
SMILES Code
O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])C[C@]3([H])[C@H](O)C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4Cl)N
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Demeclocycline is a tetracycline antibiotic used to treat a wide variety of susceptible bacterial infections.
In vitro activity:
Because earlier results suggest that demeclocycline alone reduced BTIC growth, it was sought to investigate its direct role further. BTICs were subjected to different concentrations of demeclocycline and found that 5 and 10 μM decreased sphere formation and cell number (Figures 3A,B). Notably, demeclocycline at 10 μM concentration had selective efficacy on BTICs as it was without obvious toxicity to non-transformed CNS cells such as microtubule associated protein-2 (MAP-2) labeled neurons (Figures 3D,E). As the above experiments involved the treatment of freshly dissociated BTIC lines with demeclocycline to determine whether the medication reduced sphere formation and other indices of BTIC growth, it was next addressed whether demeclocycline affected BTIC spheres that were already well-formed. It was found that when demeclocycline (10 μM) was added to growing spheres 3 days after their formation from singly dissociated cells, the drug still reduced the further growth of spheres of the BT025 and BT048 lines (Figures 3F–H). Overall, the results suggest that demeclocycline can control BTIC growth in two ways: using monocytes as an intermediary, and directly by affecting the proliferation and sphere-forming capacity of BTICs.
Reference: Front Immunol. 2020; 11: 272. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7047330/
In vivo activity:
Immunoblot analysis revealed a significant 75% reduction in AQP2 (aquaporin) abundance in the inner medulla of rats treated with demeclocycline compared with control rats (Fig. 10A). However, demeclocycline treatment led to significant 2.5- and 2.0-fold increases in AQP2 abundance in the outer medulla and cortex, respectively (Fig. 10, B and C). In kidney sections from control rats, immunostaining with a total AQP2 antibody demonstrated clear labeling of the apical and basolateral plasma membrane of inner medullary collecting duct cells (Fig. 11, A and C). In comparison, in kidney sections from demeclocycline-treated rats, AQP2 labeling intensity was clearly reduced (Fig. 11B). In addition, the cellular distribution of AQP2 was different in demeclocycline-treated rats; AQP2 was less prominent at the apical and basolateral plasma membrane, and greater numbers of AQP2-positive intracellular vesicles were observed (Fig. 11D). Immunohistochemistry using an antibody against pS256 AQP2 showed a large decrease in labeling intensity in demeclocycline-treated rats compared with control rats (Fig. 11, E and F, for the inner medulla). Additionally, immunoblot analysis revealed that AC5/6 abundance was 50% reduced in the inner medulla of demeclocycline-treated rats (Fig. 12A).
Reference: Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18. https://pubmed.ncbi.nlm.nih.gov/24154696/
|
Solvent |
mg/mL |
mM |
| Solubility |
| H2O |
1.5 |
3.23 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
464.85
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Kortenoeven ML, Sinke AP, Hadrup N, Trimpert C, Wetzels JF, Fenton RA, Deen PM. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18. doi: 10.1152/ajprenal.00723.2012. Epub 2013 Oct 23. PMID: 24154696. 2. Sarkar S, Li Y, Mirzaei R, Rawji KS, Poon CC, Wang J, Kumar M, Bose P, Yong VW. Demeclocycline Reduces the Growth of Human Brain Tumor-Initiating Cells: Direct Activity and Through Monocytes. Front Immunol. 2020 Feb 21;11:272. doi: 10.3389/fimmu.2020.00272. PMID: 32153581; PMCID: PMC7047330.
3. Jiang SX, Lertvorachon J, Hou ST, Konishi Y, Webster J, Mealing G, Brunette E, Tauskela J, Preston E. Chlortetracycline and demeclocycline inhibit calpains and protect mouse neurons against glutamate toxicity and cerebral ischemia. J Biol Chem. 2005 Oct 7;280(40):33811-8. doi: 10.1074/jbc.M503113200. Epub 2005 Aug 9. PMID: 16091365.
In vitro protocol:
1. Kortenoeven ML, Sinke AP, Hadrup N, Trimpert C, Wetzels JF, Fenton RA, Deen PM. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18. doi: 10.1152/ajprenal.00723.2012. Epub 2013 Oct 23. PMID: 24154696. 2. Sarkar S, Li Y, Mirzaei R, Rawji KS, Poon CC, Wang J, Kumar M, Bose P, Yong VW. Demeclocycline Reduces the Growth of Human Brain Tumor-Initiating Cells: Direct Activity and Through Monocytes. Front Immunol. 2020 Feb 21;11:272. doi: 10.3389/fimmu.2020.00272. PMID: 32153581; PMCID: PMC7047330.
In vivo protocol:
1. Jiang SX, Lertvorachon J, Hou ST, Konishi Y, Webster J, Mealing G, Brunette E, Tauskela J, Preston E. Chlortetracycline and demeclocycline inhibit calpains and protect mouse neurons against glutamate toxicity and cerebral ischemia. J Biol Chem. 2005 Oct 7;280(40):33811-8. doi: 10.1074/jbc.M503113200. Epub 2005 Aug 9. PMID: 16091365.
2. Kortenoeven ML, Sinke AP, Hadrup N, Trimpert C, Wetzels JF, Fenton RA, Deen PM. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18. doi: 10.1152/ajprenal.00723.2012. Epub 2013 Oct 23. PMID: 24154696.
1: Miell J, Dhanjal P, Jamookeeah C. Evidence for the use of demeclocycline in the treatment of hyponatraemia secondary to SIADH: a systematic review. Int J Clin Pract. 2015 Dec;69(12):1396-417. doi: 10.1111/ijcp.12713. Epub 2015 Aug 19. Review. PubMed PMID: 26289137.
2: Wirth D, Smith TW, Moser R, Yaroslavsky AN. Demeclocycline as a contrast agent for detecting brain neoplasms using confocal microscopy. Phys Med Biol. 2015 Apr 7;60(7):3003-11. doi: 10.1088/0031-9155/60/7/3003. Epub 2015 Mar 19. PubMed PMID: 25790138.
3: Wirth D, Snuderl M, Curry W, Yaroslavsky A. Comparative evaluation of methylene blue and demeclocycline for enhancing optical contrast of gliomas in optical images. J Biomed Opt. 2014 Sep;19(9):90504. doi: 10.1117/1.JBO.19.9.090504. PubMed PMID: 25239672.
4: Kortenoeven ML, Sinke AP, Hadrup N, Trimpert C, Wetzels JF, Fenton RA, Deen PM. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1705-18. doi: 10.1152/ajprenal.00723.2012. Epub 2013 Oct 23. PubMed PMID: 24154696.
5: Dong C, Ma S, Liu Y. Studies of the interaction between demeclocycline and human serum albumin by multi-spectroscopic and molecular docking methods. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Feb 15;103:179-86. doi: 10.1016/j.saa.2012.10.050. Epub 2012 Nov 7. PubMed PMID: 23261611.
6: Chen BK, George R, Walsh LJ. Root discolouration following short-term application of steroid medicaments containing clindamycin, doxycycline or demeclocycline. Aust Endod J. 2012 Dec;38(3):124-8. doi: 10.1111/aej.12000. Epub 2012 Nov 2. PubMed PMID: 23211072.
7: Kahsay G, Maxa J, Van Schepdael A, Hoogmartens J, Adams E. Development and validation of a reversed-phase liquid chromatographic method for analysis of demeclocycline and related impurities. J Sep Sci. 2012 Jun;35(10-11):1310-8. doi: 10.1002/jssc.201101071. PubMed PMID: 22733511.
8: Yan B, Cao X. Preparation of aqueous two-phase systems composed of two pH-response polymers and liquid-liquid extraction of demeclocycline. J Chromatogr A. 2012 Jul 6;1245:39-45. doi: 10.1016/j.chroma.2012.05.045. Epub 2012 May 17. PubMed PMID: 22658298.
9: Willershausen B, Willershausen I, Ehlers V, Azaripour A, Briseño B. A prospective clinical trial on the influence of a triamcinolone/demeclocycline and a calcium hydroxide based temporary cement on pain perception. Head Face Med. 2012 Mar 13;8:9. doi: 10.1186/1746-160X-8-9. PubMed PMID: 22414157; PubMed Central PMCID: PMC3341180.
10: Afouna MI, Khattab IS, Reddy IK. Preparation and characterization of demeclocycline liposomal formulations and assessment of their intraocular pressure-lowering effects. Cutan Ocul Toxicol. 2005;24(2):111-24. PubMed PMID: 17040889.
