Tetracycline
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| Category | Antibiotics |
| Catalog number | BBF-03503 |
| CAS | 60-54-8 |
| Molecular Weight | 444.43 |
| Molecular Formula | C22H24N2O8 |
| Purity | >98% by HPLC |
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Description
Tetracycline is an antibiotic produced by various Streptomyces such as Str. viridifaciens BL-567201 and Str. aureofacies NRRL 2209. It has antibacterial and mycobacterial activity, and has cross-resistance with oxytetracycline and chlortetracycline. Human serum does not affect its antibacterial activity. It has the effect of inhibiting large viruses and the main gram. It is widely used in clinics to treat chlamydia, rickettsia, mycoplasma and bacterial infections.
Specification
| Related CAS | 6591-49-7 (Deleted CAS) 929020-51-9 (Deleted CAS) 1172112-85-4 (Deleted CAS) |
| Synonyms | Oxytetracycline EP Impurity B; (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; Abramycin; Achromycin; (-)-Tetracycline; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, [4S-(4α,4aα,5aα,6β,12aα)]-; NSC 108579; Dispatetrin; Economycin; Biocycline; Cytome; Limecycline; Medocycline; Veracin; Oxytetracycline Dihydrate EP Impurity B; Oxytetracycline Hydrochloride EP Impurity B |
| Storage | Store at -20°C |
| IUPAC Name | (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide |
| Canonical SMILES | O=C(N)C=1C(=O)C2(O)C(O)=C3C(=O)C=4C(O)=CC=CC4C(O)(C)C3CC2C(C1O)N(C)C |
| InChI | InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1 |
| InChI Key | OFVLGDICTFRJMM-WESIUVDSSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Crystal |
| Application | Antibiotics, Tetracycline; protein synthesis inhibitors |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Boiling Point | 790.6±60.0°C at 760 mmHg |
| Melting Point | 170-173°C(dec.) |
| Density | 1.64±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
| LogP | -1.3 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 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 = 808mg/kg (oral, mice). |
Reference Reading
1. Chromatographic methods for tetracycline analysis in foods
C C Walker, S A Barker J Chromatogr . 1992 Oct 30;624(1-2):195-209. doi: 10.1016/0021-9673(92)85679-n.
The tetracyclines have served for decades as an important class of antibiotics in food animal health and production. As such, they have also been a source of concern for residue monitoring authorities around the world. In response to this concern a number of microbial inhibition, immunoassay and bacterial receptor methods have evolved for the detection of this class of compounds in various foods of animal origin. However, these methods often lack specificity and are subject to false positive and false negative results. For these reasons a number of chromatographic methods for the separation and determination of the tetracyclines isolated from foods have been developed that are capable of identifying and quantifying individual tetracycline drugs. We present here an overview of tetracycline analytical methods, including microbial inhibition, immunoassay and receptor technologies for detection, techniques for isolation from food matrices, and thin-layer chromatographic, high-performance liquid chromatographic, gas chromatographic and mass spectrometric procedures for determination of this class of compounds. A discussion of the variables involved in such methodology and a review of method criteria are offered.
2. Tetracycline compounds with non-antimicrobial organ protective properties: possible mechanisms of action
Francisco J Villarreal, Guillermo Ceballos, Michael O Griffin Pharmacol Res . 2011 Feb;63(2):102-7. doi: 10.1016/j.phrs.2010.10.004.
Tetracyclines were developed as a result of the screening of soil samples for antibiotics. The first(t) of these compounds, chlortetracycline, was introduced in 1947. Tetracyclines were found to be highly effective against various pathogens including rickettsiae, as well as both gram-positive and gram-negative bacteria, thus becoming the first class of broad-spectrum antibiotics. Many other interesting properties, unrelated to their antibiotic activity, have been identified for tetracyclines which have led to widely divergent experimental and clinical uses. For example, tetracyclines are also an effective anti-malarial drug. Minocycline, which can readily cross cell membranes, is known to be a potent anti-apoptotic agent. Another tetracycline, doxycycline is known to exert anti-protease activities. Doxycycline can inhibit matrix metalloproteinases which contribute to tissue destruction activities in diseases such as periodontitis. A large body of literature has provided additional evidence for the "beneficial" actions of tetracyclines, including their ability to act as reactive oxygen species scavengers and anti-inflammatory agents. This review provides a summary of tetracycline's multiple mechanisms of action as a means to understand their beneficial effects.
3. Tetracycline and its analogues: a therapeutic paradigm in periodontal diseases
M Bral, M A Weinberg Crit Rev Oral Biol Med . 1998;9(3):322-32. doi: 10.1177/10454411980090030501.
This article discusses the use of tetracyclines in the clinical management of periodontal infections. A review of the drugs pharmacology, pharmacokinetics, and potential adverse effects shows that they are relatively safe if used in appropriate dosages and under controlled conditions. Current data suggest that the routine use of tetracyclines in conjunction with the treatment of periodontitis is unnecessary. However, their distinctive characteristics can be utilized in different delivery systems as an adjunctive aid to conventional treatment of juvenile and refractory forms of periodontitis.
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: C22H24N2O8
Molecular Weight (Monoisotopic Mass): 444.1533 Da
Molecular Weight (Avergae Mass): 444.4346 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: C22H24N2O8
Molecular Weight (Monoisotopic Mass): 444.1533 Da
Molecular Weight (Avergae Mass): 444.4346 Da
LC-MS/MS Spectrum - LC-ESI-QFT , negative
Experimental Conditions
Instrument Type: LC-ESI-QFT
Ionization Mode: negative
Ionization Mode: negative
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: C22H24N2O8
Molecular Weight (Monoisotopic Mass): 444.1533 Da
Molecular Weight (Avergae Mass): 444.4346 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C22H24N2O8
Molecular Weight (Monoisotopic Mass): 444.1533 Da
Molecular Weight (Avergae Mass): 444.4346 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
