Doxycycline
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| Category | Antibiotics |
| Catalog number | BBF-01768 |
| CAS | 564-25-0 |
| Molecular Weight | 444.44 |
| Molecular Formula | C22H24N2O8 |
| Purity | >98% by HPLC |
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Description
It is produced by the strain of Oxytetracycline or Methacycline. It is regarded as the third generation of tetracycline. It shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis. Its antibacterial spectrum is similar to Tetracycline, its antibacterial activity is 2-8 times of Tetracycline, its plasma elimination half-life is as long as 18-22h, and it has little effect on renal function.
Specification
| Related CAS | 10592-13-9 (hydrochloride) 17086-28-1 (hydrate) 24390-14-5 (hyclate) |
| Synonyms | 6-Deoxy-5-hydroxytetracycline; 6-Deoxyoxytetracycline; Doxytetracycline; Hydramycin; Medeomycin; Vibramycin; Doxycyclinum; Monodox; Oracea; Doxy-Caps; Vibravenos; 5-Hydroxy-alpha-6-deoxytetracycline; 6-alpha-Deoxy-5-oxytetracycline |
| Storage | -20 °C |
| IUPAC Name | (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide |
| Canonical SMILES | CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O |
| InChI | InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1 |
| InChI Key | SGKRLCUYIXIAHR-AKNGSSGZSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Yellow to orange solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 554.44 °C (Predicted) |
| Melting Point | 206-209 °C (dec.) |
| Density | 1.3809 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
| LogP | -0.02 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Doxycycline is in a class of tetracycline antibiotics. 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. (A7823). 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 = 262 mg/kg (I.P. in rat). |
Reference Reading
1. Doxycycline revisited
D Q Miller, N Joshi Arch Intern Med . 1997 Jul 14;157(13):1421-8.
Although several new antibiotics have recently become available, in several clinical instances conventional antibiotics may be equally efficacious at a considerably lower cost. In today's era of cost containment, it is particularly relevant to revisit older, inexpensive antibiotics to reexplore their role in the face of the emergence of resistant microorganisms and competition from newer agents. Doxycycline is one such antibiotic. It is an inexpensive, broad-spectrum antimicrobial agent that remains the drug of first choice for several infections. In addition, it can be used for a variety of other indications. Adverse effects are infrequent and relatively minor. While interactions occur with several medications, none of these interactions has significant adverse consequences.
2. Doxycycline, salinomycin, monensin and ivermectin repositioned as cancer drugs
Anna Markowska, Joanna Kaysiewicz, Janina Markowska, Adam Huczyński Bioorg Med Chem Lett . 2019 Jul 1;29(13):1549-1554. doi: 10.1016/j.bmcl.2019.04.045.
Chemotherapy is one of the standard methods for the treatment of malignant tumors. It aims to cause lethal damage to cellular structures, mainly DNA. Noteworthy, in recent years discoveries of novel anticancer agents from well-known antibiotics have opened up new treatment pathways for several cancer diseases. The aim of this review article is to describe new applications for the following antibiotics: doxycycline (DOX), salinomycin (SAL), monensin (MON) and ivermectin (IVR) as they are known to show anti-tumor activity, but have not yet been introduced into standard oncological therapy. To date, these agents have been used for the treatment of a broad-spectrum of bacterial and parasitic infectious diseases and are widely available, which is why they were selected. The data presented here clearly show that the antibiotics mentioned above should be recognised in the near future as novel agents able to eradicate cancer cells and cancer stem cells (CSCs) across several cancer types.
3. Doxycycline as Potential Anti-cancer Agent
Stephan J Reshkin, Muntaser E Ibrahim, Khalid O Alfarouk, Isra Ali Anticancer Agents Med Chem . 2017;17(12):1617-1623. doi: 10.2174/1871520617666170213111951.
Cancer cells do create hostile microenvironment (deprivation of nutrients, accumulation of acidity, anoxic habitat). Those cells are not only adapted to this sanctuary environment, blunting of immunity but also, grow, migrate to the distal area (metastasis) and communicate with each other in a unique population structure and organization too (clonal expansion). The adaptation requirements push those types of adaptable cells (cancer cells) to be primitive cells. The prevailing pharmacological approach in treating cancer is developing a chemotherapeutic agent that acts on rapidly proliferating cells that are stuck with normally growing epithelium and bone marrow too. The latter approach has been drafted to work on cellular target under the term of "targeted therapy" believing that each target represents Achilles Heels of cancer. In this article, we try to introduce a new concept of cancer pharmacology, by offering new off-label use of Doxycycline, which is characterized by selective toxicity, as potential anticancer agents. This notion is relying on the absence of taxonomic barriers.
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
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 ╳
