Demeclocycline HCl | CAS#64-73-3 | protein translation inhibitor | calpain inhibitor

Demeclocycline HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540101

CAS#: 64-73-3 (HCl)

Description: Demeclocycline HCl is a protein translation inhibitor and potential calpain inhibitor used to treat bacteria infections. It also decreases expression of aquaporin 2 (AQP@) and adenylate cyclase 5/6 to prevent hyponatremia in SIADH and suppresses glutamate-induced neuronal death in models of cerebral ischemia.

Chemical Structure

Demeclocycline HCl

CAS# 64-73-3 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540101
Name: Demeclocycline HCl
CAS#: 64-73-3 (HCl)
Chemical Formula: C21H22Cl2N2O8
Exact Mass: 500.08
Molecular Weight: 501.310
Elemental Analysis: C, 50.31; H, 4.42; Cl, 14.14; N, 5.59; O, 25.53

Price and Availability

Size	Price	Availability
100mg	USD 250	2 Weeks
500mg	USD 450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 127-33-3 (free base) 64-73-3 (HCl) 13215-10-6 (hydrate) 17146-81-5 (calcium)

Synonym: Demeclocycline HCl; Detravis; Ledermycin

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 hydrochloride

InChi Key: GVSJQNRGSCOSNJ-KBHRXELFSA-N

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

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.[H]Cl

Appearance: Solid powder

Purity: >95% (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

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

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Product Data:

Product Data

Instruction:

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Biological target:	Demeclocycline hydrochloride is a tetracycline antibiotic; is an antibiotic in the treatment of Lyme disease, acne, and bronchitis.
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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	67.0	133.65
	H2O	30.0	59.84

Preparing Stock Solutions

The following data is based on the product molecular weight 501.31 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.

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1: Peri A, Giuliani C. Management of euvolemic hyponatremia attributed to SIADH in the hospital setting. Minerva Endocrinol. 2014 Mar;39(1):33-41. Review. PubMed PMID: 24513602.

2: Cervellin G, Lippi G. How we define hyponatraemia? Eur J Clin Invest. 2015 Nov;45(11):1219. doi: 10.1111/eci.12516. Epub 2015 Sep 2. PubMed PMID: 26259932.

3: Fatori Popovic S, Lübbers HT, von Mandach U. [Pregnancy and lactation: antibiotics. mouthwashes and pastes or ointments. Swiss Dent J. 2016;126(6):598-9. French. PubMed PMID: 27377565.

4: ROLA A. [Ledermycin syrup for infants]. J Med (Oporto). 1961 Sep 2;46:11-2. Portuguese. PubMed PMID: 13742905.

5: Nakazawa S, Oka S, Otaka T, Sato H, Chikoaka H. [Clinical study on demethylchlortetracycline (Ledermycin) dry syrup in pediatrics]. Jpn J Antibiot. 1969 Jun;22(3):197-9. Japanese. PubMed PMID: 4980821.

6: Nolting S. [Treatment of syphilis with demethyltetracycline (Ledermycin)]. Med Klin. 1966 Dec 23;61(51):2043-4. German. PubMed PMID: 4968161.

7: FENNER O. [Demethylchlortetracycline (ledermycin). Comparative bacteriological research]. Med Welt. 1960 Aug 20;33-34:1672-9. German. PubMed PMID: 13822177.

8: 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.

9: ROECKL H. [1st experiences with demethylchlortetracyclin (Ledermycin) in dermatology]. Munch Med Wochenschr. 1961 Feb 3;103:266-8. German. PubMed PMID: 13742664.

10: WILSON JR. Demethylchlortetracycline (Ledermycin). Med Press. 1961 Jun 14;245:539-42. PubMed PMID: 13785682.

11: Yamada N, Yoshioka H, Nambu H, Itagaki M. [Therapeutic results of demethylchlortetracycline (Ledermycin) dry syrup administration in acute infections in children]. Jpn J Antibiot. 1969 Jun;22(3):203-5. Japanese. PubMed PMID: 4980481.

12: Lindsay R, Zhou H, Cosman F, Nieves J, Dempster D. Double and quadruple tetracycline labeling of bone: impact of the label itself. J Bone Miner Res. 2013 Jan;28(1):222-3. doi: 10.1002/jbmr.1818. PubMed PMID: 23255455.

13: Beumer HM. Double-blind trial with sulfamethoxazole plus trimethoprim (Bactrim) versus demethyl-chlortetracycline (Ledermycin) in chronic respiratory tract infections. Respiration. 1972;29(3):257-69. PubMed PMID: 4626854.

14: KOPP H. [Therapy of gonorrhea. 3 patient groups treated with 0.3 and 0.2 mega-units of procaine penicilin with Ledermycin]. Ugeskr Laeger. 1961 Jun 2;123:767-70. Danish. PubMed PMID: 13753077.

15: EYME P. [Demethylchlortetracycline/Ledermycin (DMCTC). Clinico-therapeutic results]. Med Welt. 1960 Oct 29;44:2528-9. German. PubMed PMID: 13697717.

16: KLASSEN FJ, OBERHOFFER G, VORLAENDER KO. [Clinical results of treatment of bacterial infections with demethyl-chloretetracycline (DMCT, Ledermycin)]. Munch Med Wochenschr. 1963 Jun 7;105:1216-21. German. PubMed PMID: 14033285.

17: BIETTI GB, LANZIERI M. [Preliminary trials on the activity exercised by an antibiotic with delayed elimination (demethylchlortetracycline-ledermycin) in the intermittent treatment of trachoma]. Rev Int Trach. 1961;38:409-15. French. PubMed PMID: 13869096.

18: 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.

19: Nagao Y. [The clinical and experimental use of demethylchlortetracycline (Ledermycin) in oral surgery]. Shikwa Gakuho. 1965 Aug;65(8):70-5. Japanese. PubMed PMID: 4953208.

20: Nagamatsu K, Saeki Y, Wagatsuma Y, Shishido T, Togashi T. [Clinical use of demethylchlortetracycline (Ledermycin) dry syrup in respiratory infections in children]. Jpn J Antibiot. 1969 Jun;22(3):210-2. Japanese. PubMed PMID: 4980483.

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