Demeclocycline hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-02574 |
| CAS | 64-73-3 |
| Molecular Weight | 501.31 |
| Molecular Formula | C21H22Cl2N2O8 |
| Purity | >98% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-02574 | 10 g | $176 | In stock |
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Add to cartDescription
Demethylchlorotetracycline is an antibiotic produced by Streptomyces viridifaciens and Str. aureofaciens S-604. It has antibacterial and anti-insect activity.
Specification
| Related CAS | 127-33-3 (free base) |
| Synonyms | Demethylchlortetracycline hydrochloride; Demethylchlorotetracycline hydrochloride |
| 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 |
| Canonical 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 |
| 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 |
| InChI Key | GUXHBMASAHGULD-SEYHBJAFSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | bacteria; parasites |
| Boiling Point | 795.9°C at 760 mmHg |
| Melting Point | 174-178°C (dec.) |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Good water solubility. |
Reference Reading
1. Demeclocycline Reduces the Growth of Human Brain Tumor-Initiating Cells: Direct Activity and Through Monocytes
Candice C Poon, Yibo Li, Susobhan Sarkar, V Wee Yong, Reza Mirzaei, Jianxiong Wang, Pinaki Bose, Khalil S Rawji, Mehul Kumar Front Immunol . 2020 Feb 21;11:272. doi: 10.3389/fimmu.2020.00272.
Myeloid cells that infiltrate into brain tumors are deactivated or exploited by the tumor cells. We previously demonstrated that compromised microglia, monocytes, and macrophages in malignant gliomas could be reactivated by amphotericin-B to contain the growth of brain tumorinitiating cells (BTICs). We identified meclocycline as another activator of microglia, so we sought to test whether its better-tolerated derivative, demeclocycline, also stimulates monocytes to restrict BTIC growth. Monocytes were selected for study as they would be exposed to demeclocycline in the circulation prior to entry into brain tumors to become macrophages. We found that demeclocycline increased the activity of monocytes in culture, as determined by tumor necrosis factor-α production and chemotactic capacity. The conditioned medium of demeclocycline-stimulated monocytes attenuated the growth of BTICs generated from human glioblastoma resections, as evaluated using neurosphere and alamarBlue assays, and cell counts. Demeclocycline also had direct effects in reducing BTIC growth. A global gene expression screen identified several genes, such as DNA damage inducible transcript 4, frizzled class receptor 5 and reactive oxygen species modulator 1, as potential regulators of demeclocycline-mediated BTIC growth reduction. Amongst several tetracycline derivatives, only demeclocycline directly reduced BTIC growth. In summary, we have identified demeclocycline as a novel inhibitor of the growth of BTICs, through direct effect and through indirect stimulation of monocytes. Demeclocycline is a candidate to reactivate compromised immune cells to improve the prognosis of patients with gliomas.
2. Evidence for the use of demeclocycline in the treatment of hyponatraemia secondary to SIADH: a systematic review
J Miell, C Jamookeeah, P Dhanjal Int J Clin Pract . 2015 Dec;69(12):1396-417. doi: 10.1111/ijcp.12713.
Aims:Hyponatraemia (HN) is the most common electrolyte balance disorder in clinical practice. Since the 1970s, demeclocycline has been used in some countries to treat chronic HN secondary to syndrome of inappropriate antidiuretic hormone secretion (SIADH). The precise mechanism of action of demeclocycline is unclear, but has been linked to the induction of nephrogenic diabetes insipidus. Furthermore, the safety profile of demeclocycline is variable with an inconsistent time to onset, and a potential for complications. There has been no systematic evaluation of the use of demeclocycline for the treatment of HN secondary to SIADH to date. A systematic literature review was performed to obtain an insight into the clinical safety and efficacy of demeclocycline for this condition.Methods:Embase(™) , MEDLINE(®) , MEDLINE(®) In-Process, and The Cochrane Library were searched on two occasions using MeSH terms combined with free-text terms. References were screened by two independent reviewers. Relevant publications were then extracted by two independent reviewers, with a third reviewer collating and finalising extractions.Results:The searches returned a total of 705 hits. 632 abstracts were screened after the removal of duplicates. Following screening, 35 full-length publications were reviewed. Of these, 17 were excluded, resulting in 18 studies deemed relevant for data extraction. Two were randomised controlled trials (RCTs), 16 were non-RCTs, and 10 were case reports.Discussion:Although most reports suggest that demeclocycline can address serum sodium levels in specific patients with HN, efficacy is variable, and may depend upon the underlying aetiology. Demeclocycline dose adjustments can be complex, and as its use in clinical practice is not well defined, it can differ between healthcare professionals.Conclusion:There is a lack of clinical and economic evidence supporting the use of demeclocycline for HN secondary to SIADH. Patients receiving demeclocycline for HN secondary to SIADH must be closely monitored.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
