Sancycline hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-04443 |
| CAS | 6625-20-3 |
| Molecular Weight | 450.87 |
| Molecular Formula | C21H23ClN2O7 |
| Purity | >98% by HPLC |
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Description
The hydrochloride salt of a rare semi-synthetic tetracycline. It is prepared by hydrogenolysis of the chloro and benzylic hydroxy moieties of declomycin. It inhibits protein translation by reversibly binding to the 30S ribosomal subunit and blocking the entry of aminoacyl tRNA into the ribosomal A site. It is a semi-synthetic antibiotic with activity against tetracycline-resistant E. coli, S. aureus and E. faecalis.
Specification
| Related CAS | 808-26-4 (free base) |
| Synonyms | 6-Demethyl-6-deoxytetracycline hydrochloride; NSC 51812; (4S,4aS,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1-11-dioxo-2-naphthacenecarboxamide Hydrochloride; Bonomycin; Norcycline; GS 2147; Minocycline EP Impurity B |
| Storage | Store at -20°C |
| IUPAC Name | (4S,4aS,5aR,12aS)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;hydrochloride |
| Canonical SMILES | CN(C)C1C2CC3CC4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O.Cl |
| InChI | InChI=1S/C21H22N2O7.ClH/c1-23(2)15-10-7-9-6-8-4-3-5-11(24)12(8)16(25)13(9)18(27)21(10,30)19(28)14(17(15)26)20(22)29;/h3-5,9-10,15,24,26-27,30H,6-7H2,1-2H3,(H2,22,29);1H/t9-,10-,15-,21-;/m0./s1 |
| InChI Key | NHHHLWBNBLFCSB-QKYUADJBSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Yellow Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 639.9°C at 760 mmHg |
| Melting Point | >200°C (dec.) |
| Density | 1.61 g/cm3 |
| Solubility | Slightly soluble in Chloroform, Methanol, Water |
Reference Reading
1. Spectrophotometric determination of acidity constants of 4-dedimethylamino sancycline (Col-3), a new antitumor drug
S E Tabibi, F A Alvarez-Núñez, S Pinsuwan, S H Yalkowsky J Pharm Sci . 1999 May;88(5):535-7. doi: 10.1021/js980398l.
A spectrophotometric technique was used to determine the acidity constants of 4-dedimethylamino sancycline (Col-3), a new antitumor drug. The apparent pKa values of Col-3 in 0.5% methanol aqueous media at approximately 25 degrees C with a constant ionic strength of 0.2 were calculated manually and graphically to be 5.64 +/- 0.17 (pKa1) and 8.35 +/- 0.07 (pKa2). In addition, the computer program SQUAD was used to confirm Col-3 pKa values. The pKa values obtained by SQUAD were pKa1 5.63 +/- 0.14 and pKa2 8.39 +/- 0.04. These results are in agreement with the tetracycline-like structure of Col-3.
2. Degradation kinetics of 4-dedimethylamino sancycline, a new anti-tumor agent, in aqueous solutions
S H Yalkowsky, F A Alvarez-Núñez, S Pinsuwan, E S Tabibi Int J Pharm . 1999 Apr 20;181(1):31-40. doi: 10.1016/s0378-5173(98)00417-7.
The kinetics of degradation of the new anti-tumor drug, 4-dedimethylamino sancycline (col-3) in aqueous solution at 25oC were investigated by high-pressure liquid chromatography (HPLC) over the pH-range of 2-10. The influences of pH, buffer concentration, light, temperature, and some additives on the degradation rate were studied. The degradation of col-3 was found to follow first order kinetics. A rate expression covering the degradation of the various ionic forms of the drug was derived and shown to account for the shape of the experimental pH-rate profile. Under basic conditions, the degradation of col-3 involves oxidation, which is catalyzed by metal ions and inhibited by EDTA and Sodium bisulfite.
3. Rapid separation of tetracycline derivatives and their main degradation products by capillary zone electrophoresis
J L Lavandera, A L Crego, C García-Ruiz, M L Marina Electrophoresis . 2001 Aug;22(13):2775-81. doi: 10.1002/1522-2683(200108)22:133.0.CO;2-2.
A mixture of five tetracycline (TC) derivatives: minocycline (MC), demeclocycline (DMCTC), doxycycline (DC), and sancycline (SC), as well as each TC derivative from its main degradation product were separated by capillary zone electrophoresis (CZE). The influence of the pH and the concentration and nature of the background electrolyte (BGE) on the separations was investigated. Ethylenediaminetetraacetic acid (EDTA; 1 mM) was used as additive in a 25 mM phosphate buffer (pH 2.3) because this BGE enabled the rapid separation of the TC derivatives and of each TC derivative from its respective degradation product in less than 6 min. After optimization of the separation conditions, the analytical characteristics of the method were investigated. The parameters involved were linearity, precision (repeatability and reproducibility), and limits of detection (LODs). LODs obtained for the five TC derivatives studied were about 3 microg/mL. Finally, the CZE method developed was applied to study the stability of TC derivatives and to analyze the TC derivative content in three different pharmaceutical preparations.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
