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doxycycline (n.)
1.an antibiotic derived from tetracycline that is effective against many infections"Vibramycin is the trade name of doxycycline"
Doxycycline (n.)
1.(MeSH)A synthetic TETRACYCLINE derivative with similar antimicrobial activity. Animal studies suggest that it may cause less tooth staining than other tetracyclines. It is used in some areas for the treatment of chloroquine-resistant falciparum malaria (MALARIA, FALCIPARUM).
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Doxycycline (n.) (MeSH)
alpha-6-Deoxyoxytetracycline (MeSH), BMY-28689 (MeSH), BU-3839T (MeSH), CollaGenex Brand of Doxycycline (MeSH), Doxycycline Calcium (MeSH), Doxycycline Calcium Salt (1:2) (MeSH), Doxycycline-Chinoin (MeSH), Doxycycline Monohydrate (MeSH), Doxycycline Monohydrochloride, 6-epimer (MeSH), Doxycycline Monohydrochloride, Dihydrate (MeSH), Doxycycline Phosphate (1:1) (MeSH), Hydramycin (MeSH), Oracea (MeSH), Vibramycin (MeSH), Vibramycin Novum (MeSH), Vibravenos (MeSH)
doxycycline (n.)
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⇨ Doxycycline Calcium • Doxycycline Calcium Salt (1:2) • Doxycycline Monohydrate • Doxycycline Monohydrochloride, 6-epimer • Doxycycline Monohydrochloride, Dihydrate • Doxycycline Phosphate (1:1) • Doxycycline-Chinoin
Wikipedia
Systematic (IUPAC) name | |
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(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)- 3,5,10,12,12a-pentahydroxy- 6-methyl- 1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene- 2-carboxamide | |
Clinical data | |
Trade names | Vibramycin |
AHFS/Drugs.com | monograph |
MedlinePlus | a682063 |
Licence data | US FDA:link |
Pregnancy cat. | D (US) |
Legal status | POM (UK) ℞-only (US) |
Routes | oral, buccal, iv, im |
Pharmacokinetic data | |
Bioavailability | 100% |
Metabolism | hepatic,minimally |
Half-life | 18-22 hours |
Excretion | urine, feces |
Identifiers | |
CAS number | 564-25-0 |
ATC code | J01AA02 A01AB22 |
PubChem | CID 11256 |
DrugBank | DB00254 |
ChemSpider | 10482106 |
UNII | 334895S862 |
KEGG | D02129 |
ChEBI | CHEBI:60648 |
ChEMBL | CHEMBL1433 |
Chemical data | |
Formula | C22H24N2O8 |
Mol. mass | 462.46 g/mol |
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Doxycycline is a member of the tetracycline antibiotics group, and is commonly used to treat a variety of infections. Doxycycline is a semisynthetic tetracycline invented and clinically developed in the early 1960s by Pfizer Inc.[citation needed] and marketed under the brand name Vibramycin.[citation needed] Vibramycin received U.S. Food and Drug Administration approval in 1967,[citation needed] becoming Pfizer's first once-a-day, broad-spectrum antibiotic.[citation needed] Other brand names include Monodox, Microdox, Periostat, Vibra-Tabs, Oracea, Doryx[1], Vibrox, Adoxa, Doxyhexal, Doxylin, Doxoral, Doxy-1 and Atridox (topical doxycycline hyclate for periodontitis).
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In addition to the general indications for all members of the tetracycline antibiotics group, doxycycline is frequently used to treat chronic prostatitis, sinusitis, syphilis, chlamydia, pelvic inflammatory disease,[2][3] acne, rosacea,[4][5] and rickettsial infections.[6]
It is used in prophylaxis against malaria. It should not be used alone for initial treatment of malaria, even when the parasite is doxycycline-sensitive, because the antimalarial effect of doxycycline is delayed. This delay is related to its mechanism of action, which is to specifically impair the progeny of the apicoplast genes, resulting in their abnormal cell division.[7]
It can be used in a treatment plan in combination with other agents, such as quinine.[8]
Branhamella catarrhalis, Brucella melitensis, Chlamydia pneumoniae and Mycoplasma pneumoniae species are generally susceptible to Doxycycline, while some Haemophilus spp., Mycoplasma hominis and Pseudomonas aeruginosa have developed resistance to Doxycycline to varying degrees.[9]
It is used in the treatment and prophylaxis of anthrax (caused by Bacillus anthracis).
It is also effective against Yersinia pestis (the infectious agent of bubonic plague), and is prescribed for the treatment of Lyme disease,[10][11][12][13] ehrlichiosis[14][15] and Rocky Mountain spotted fever. In fact, because doxycycline is one of the few medications shown to be effective in treating Rocky Mountain spotted fever (with the next-best alternative being chloramphenicol), doxycycline is indicated even for use in children for this illness. Otherwise, it is not indicated for use in children under the age of eight years. Doxycycline, like other antibiotics, will not work for colds, influenza, or other viral infections.
When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat and prevent:
Doxycycline kills the symbiotic Wolbachia bacteria in the reproductive tracts of parasitic filarial nematodes, making the nematodes sterile, and thus reducing transmission of diseases like Onchocerciasis and Elephantiasis.[17] Field trials in 2005 showed that an eight-week course of doxycycline almost completely eliminates the release of microfilariae.[18][19]
Cautions and side effects are similar to those of other members of the tetracycline antibiotic group. However, the risk of photosensitivity skin reactions is of particular importance for those intending long-term use for malaria prophylaxis, because it can cause permanent sensitivity and thin skin[citation needed], which may lead to sun damage.
An erythematous rash in sun-exposed parts of the body has been reported to occur in 7.3–21.2% of persons taking doxycycline for malaria prophylaxis. One study examined the tolerability of various malaria prophylactic regimens and found that doxycycline did not cause a significantly higher percentage of all skin events (photosensitivity not specified) when compared with other antimalarials. The rash resolves upon discontinuation of the drug[20].
Unlike some other members of the tetracycline group, it may be used in those with renal impairment.[21]
Previously, doxycycline was believed to impair the effectiveness of many types of hormonal contraception due to CYP450 induction. Recent research has shown no significant loss of effectiveness in oral contraceptives while using most tetracycline antibiotics (including doxycycline), although many physicians still recommend the use of barrier contraception for people taking the drug to prevent unwanted pregnancy.[22][23][24]
Taking doxycycline with food and diary products may decrease the amount of medication absorbed. The combination of doxycycline with dairy, antacids, calcium supplements, iron products, and laxatives containing magnesium is not inherently dangerous, but any of these foods and supplements may decrease doxycycline's effectiveness.[25]
Doxycycline, like all tetracyclines, is not approved for general use in children, but specific exceptions are made for potentially fatal illnesses where the benefits outweigh the risks and there are few or no other alternatives, such as with Rocky Mountain spotted fever and anthrax.Pregnant women and underweights (<45Kgs ) are not recommended.
Expired tetracyclines or tetracyclines allowed to stand at a pH less than 2 are reported to be nephrotoxic due to the formation of a degradation product, anhydro-4-epitetracycline[26][27] causing Fanconi syndrome.[28] In the case of doxycycline, the absence of a hydroxyl group in C-6 prevents the formation of the nephrotoxic compound.[27] Nevertheless, tetracyclines and doxycycline itself have to be taken with precaution in patients with kidney injury, as they can worsen azotemia due to catabolic effects.[28]
At subantimicrobial doses, doxycycline is an inhibitor of matrix metalloproteases, and has been used in various experimental systems for this purpose, such as for recalcitrant recurrent corneal erosions.[29] Doxycycline has been demonstrated to reduce the in vitro growth of human breast and prostate cancer cells, possibly through G1 phase cell cycle arrest.[30][31] Doxycycline and other tetracyclines are also highly osteotropic, and in animal models of breast cancer bone metastases, doxycycline treatments have reduced the growth of breast cancer tumours in the bone.[32] Doxycycline has been used successfully in the treatment of one patient with lymphangioleiomyomatosis, an otherwise progressive and fatal disease.[33] It has also been shown to attenuate cardiac hypertrophy (in mice), a deadly consequence of prolonged hypertension.[34] In chronic obstructive pulmonary disease, doxycycline has been shown to improve lung functions in patients with stable symptoms.[35] Doxycycline is also used in "Tet-on" and "Tet-off" tetracycline-controlled transcriptional activation to regulate transgene expression in organisms and cell cultures.
Other experimental applications include treating:
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