Demeclocycline
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| Category | Antibiotics |
| Catalog number | BBF-03477 |
| CAS | 127-33-3 |
| Molecular Weight | 464.85 |
| Molecular Formula | C21H21ClN2O8 |
| Purity | >98% by HPLC |
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Description
It is produced by the strain of Streptomuces aureofaciens var. 38-2-14. It shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis.
Specification
| Related CAS | 17146-81-5 (calcium salt) 64-73-3 (hydrochloride) |
| Synonyms | Demethylchlortetracycline; 6-Demethylchlotetracycline; DMCT; 7-Chloro-6-demethyltetracycline; Ledermycin; RP 10192; Antibiotic 38-2-14 A; Novotriclina; Perciclina; Sumaclina |
| Storage | Store at-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 to orange solid |
| Boiling Point | 787.1±60.0°C (Predicted) |
| Melting Point | 220-223°C |
| Density | 1.8±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
| LogP | 0.2 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Demeclocycline is a tetracycline antibiotic. Tetracyclines target the 28S small subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result tetracyclines are cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. The likely target of most tetracyclines is the 12S rRNA molecule in the mitochondrial ribosome, which is analogous to the 16S rRNA in bacterial ribosomes. |
| Toxicity | LD50 = 2372 mg/kg (Oral, rat). |
Reference Reading
1.Persistent syndrome of inappropriate antidiuretic hormone secretion following traumatic brain injury.
Dick M1, Catford SR2, Kumareswaran K3, Hamblin PS3, Topliss DJ3. Endocrinol Diabetes Metab Case Rep. 2015;2015:150070. doi: 10.1530/EDM-15-0070. Epub 2015 Aug 27.
The syndrome of inappropriate antidiuretic hormone secretion (SIADH) can occur following traumatic brain injury (TBI), but is usually transient. There are very few case reports describing chronic SIADH and all resolved within 12 months, except for one case complicated by meningo-encephalitis. Persistent symptomatic hyponatremia due to chronic SIADH was present for 4 years following a TBI in a previously well 32-year-old man. Hyponatremia consistent with SIADH initially occurred in the immediate period following a high-speed motorbike accident in 2010. There were associated complications of post-traumatic amnesia and mild cognitive deficits. Normalization of serum sodium was achieved initially with fluid restriction. However, this was not sustained and he subsequently required a permanent 1.2 l restriction to maintain near normal sodium levels. Multiple episodes of acute symptomatic hyponatremia requiring hospitalization occurred over the following years when he repeatedly stopped the fluid restriction.
2.Factors affecting the rate of oxidation and resultant discolouration of tetracyclines contained in endodontic medicaments and irrigants.
Bennett ZY1, Walsh LJ. Int Endod J. 2015 Apr;48(4):373-9. doi: 10.1111/iej.12323. Epub 2014 Jul 11.
AIM: To determine the effect of pH, oxygen levels and ions on tetracycline oxidation and resultant discolouration.
3.Effect of magnesium dose on amount of pharmaceuticals in struvite recovered from urine.
Kemacheevakul P1, Chuangchote S2, Otani S3, Matsuda T3, Shimizu Y3. Water Sci Technol. 2015;72(7):1102-10. doi: 10.2166/wst.2015.313.
Phosphorus (P) recovery was carried out through struvite precipitation from urines. Human urine, however, contains not only high nutrients for plants, such as P and nitrogen, but also pharmaceuticals and hormones. In this work, effects of magnesium (Mg) dose (in terms of Mg:P ratio) on P recovery efficiency and pharmaceutical amounts contained in struvite were investigated. Batch-scale experiments of synthetic and human urines revealed that struvite precipitation formed more X-shaped crystals with an increased molar ratio of Mg:P, while the amount of pharmaceuticals (tetracycline, demeclocycline, and oxytetracycline) in struvite decreased with an increased molar ratio of Mg:P. The lowest pharmaceutical amounts in struvite were found at the Mg:P ratio of 2:1 from both samples. Moreover, the maximum P recovery efficiency, quantity and purity of struvite were found in the range of 1.21 to 2:1. It indicated that the molar ratio of Mg:P has a significant impact on struvite precipitation in terms of pharmaceutical amounts in struvite; morphology, quantity and purity of struvite; and P recovery.
4.pH-dependent spectroscopy of tetracycline and its analogs.
Mojica ER1, Nguyen E, Rozov M, Bright FV. J Fluoresc. 2014 Jul;24(4):1183-98. doi: 10.1007/s10895-014-1399-7. Epub 2014 May 9.
Tetracyclines (TCs), broad spectrum antibiotics widely used in the prevention and treatment of infectious diseases, are amphoteric molecules containing several ionizable functional groups that exist predominantly as zwitterions at a given pH value. TCs are reported to undergo a wide variety of reactions at different pH values i.e. TCs form to anhydrotetracyclines at low pH, 4-epitetracyclines at pH 3-5 and isotetracyclines at high pH values. The pH-dependent absorbance and emission properties of tetracycline and its 10 analogs (4-epitetracycline, doxycyline, oxytetracycline, chlortetracycline, 4-epichlortetracycline, isochlortetracycline, methacycline, rolitetracycline, minocycline, and demeclocycline) were investigated and reported in this paper. The main focus of the study was on the pH dependent transformation of epichlortetracycline, chlortetracycline and isotetracycline at basic pH. Absorption, emission and time resolved spectroscopy were used to determine the behavior of the three TC derivatives at this condition.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C21H21ClN2O8
Molecular Weight (Monoisotopic Mass): 464.0986 Da
Molecular Weight (Avergae Mass): 464.853 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C21H21ClN2O8
Molecular Weight (Monoisotopic Mass): 464.0986 Da
Molecular Weight (Avergae Mass): 464.853 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C21H21ClN2O8
Molecular Weight (Monoisotopic Mass): 464.0986 Da
Molecular Weight (Avergae Mass): 464.853 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C21H21ClN2O8
Molecular Weight (Monoisotopic Mass): 464.0986 Da
Molecular Weight (Avergae Mass): 464.853 Da
1H NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 1H
Frequency: 100
Nucleus: 1H
Frequency: 100
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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 ╳
