Définitions et usages de : Doxycycline - Dictionnaire de anglais sensagent

Doxycycline


Systematic (IUPAC) name
(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^Y
ATC code	J01AA02 A01AB22
PubChem	CID 11256
DrugBank	DB00254
ChemSpider	10482106^Y
UNII	334895S862^Y
KEGG	D02129^N
ChEBI	CHEBI:60648^Y
ChEMBL	CHEMBL1433^N
Chemical data
Formula	C₂₂H₂₄N₂O₈
Mol. mass	462.46 g/mol
SMILES O.CN(C)[C@@H]3C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@H](C)[C@H]2[C@H](O)[C@@H]34
InChI InChI=1S/C22H24N2O8.H2O/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;/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);1H2/t7-,10+,14+,15-,17-,22-;/m0./s1^Y Key:XQTWDDCIUJNLTR-CVHRZJFOSA-N^Y
N (what is this?) (verify)

Generic 100 mg doxycycline capsules

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).

1 Indicated uses
2 Antiprotozoal
3 Spectrum of Bacterial Susceptibility and Resistance
4 Antibacterial
5 Anthelmintic
6 Cautions and side effects
7 Experimental applications
8 References
9 External links

Indicated uses

Main article: Tetracycline antibiotics

Further information: Oxytetracycline

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]

Antiprotozoal

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]

Spectrum of Bacterial Susceptibility and Resistance

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]

Antibacterial

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.

Doxycycline package

When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat and prevent:

Escherichia coli infections
Chlamydia trachomatis infections
Enterobacter aerogenes (formerly Aerobacter aerogenes) infections
Lyme disease (Lyme borreliosis complex) (caused by B. burgdorferi)
Rocky mountain spotted fever
Folliculitis
Acne and other inflammatory skin diseases, such as hidradenitis suppurativa
Shigella species infections
Acinetobacter species (formerly Mima species and Herellea species) infections
Respiratory tract infections caused by Haemophilus influenzae
Respiratory tract and urinary tract infections
Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae)
Methicillin-resistant Staphylococcus aureus (MRSA) infections
As combined therapy when treating a patient for Chlamydia trachomatis, because up to 50% of patients will be infected with the beta lactam-resistant strain of this bacterium.^[16]

Anthelmintic

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

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]

Experimental applications

Tet-ON inducible shRNA system

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:

Vancomycin-resistant enterococcus (VRE)^[36]
Infected animal bite wounds (Pasteurella multocida, Pasteurella pneumotropica)^[37]
Rheumatoid arthritis instead of minocycline (both of which have demonstrated modest efficacy for this disease)^[38]
Chronic inflammatory lung diseases (panbronchiolitis, asthma, cystic fibrosis, bronchitis)^[39]^[40] Both doxycycline and minocycline have shown effectiveness in asthma due to immune suppressing effects.^[41]
Sarcoidosis^[42]^[43]
Pancreatic cancer
Prevention of aortic aneurysm in people with Marfan syndrome and vascular Ehlers-Danlos syndrome^[44]
Multiple sclerosis^[45]
Meibomian gland dysfunction
Treatment of filariasis and onchocerciasis due to filariae and onchocercae (in general, harbouring endosymbiotic Wolbachia bacteria, doxycycline kills the bacteria, and (by removal of the endosymbiotes) the nematodes)
New daily persistent headache
Idiopathic pulmonary fibrosis^[46]

References

^ Voreacos, David; Decker, Susan (30 April 2012). "Mylan, Impax Win Ruling in Doryx Generics Patent Case". Bloomberg. http://www.bloomberg.com/news/2012-04-30/mylan-impax-win-ruling-in-doryx-generics-patent-case.html.
^ Sweet RL, Schachter J, Landers DV, Ohm-Smith M, Robbie MO (1988). "Treatment of hospitalized patients with acute pelvic inflammatory disease: comparison of cefotetan plus doxycycline and ana doxycycline". Am. J. Obstet. Gynecol. 158 (3 Pt 2): 736–41. PMID 3162653.
^ Gjønnaess H, Holten E (1978). "Doxycycline (Vibramycin) in pelvic inflammatory disease". Acta Obstet Gynecol Scand 57 (2): 137–9. DOI:10.3109/00016347809155893. PMID 345730.
^ Määttä M, Kari O, Tervahartiala T et al. (2006). "Tear fluid levels of MMP-8 are elevated in ocular rosacea--treatment effect of oral doxycycline". Graefes Arch. Clin. Exp. Ophthalmol. 244 (8): 957–62. DOI:10.1007/s00417-005-0212-3. PMID 16411105.
^ Quarterman MJ, Johnson DW, Abele DC, Lesher JL, Hull DS, Davis LS (1997). "Ocular rosacea. Signs, symptoms, and tear studies before and after treatment with doxycycline". Arch Dermatol 133 (1): 49–54. DOI:10.1001/archderm.133.1.49. PMID 9006372.
^ Walker DH, Paddock CD, Dumler JS (November 2008). "Emerging and re-emerging tick-transmitted rickettsial and ehrlichial infections". Med. Clin. North Am. 92 (6): 1345–61, x. DOI:10.1016/j.mcna.2008.06.002. PMID 19061755.
^ Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ (2006). "Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum". Antimicrob. Agents Chemother. 50 (9): 3124–31. DOI:10.1128/AAC.00394-06. PMC 1563505. PMID 16940111. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1563505.
^ Lalloo DG, Shingadia D, Pasvol G et al. (February 2007). "UK malaria treatment guidelines". J. Infect. 54 (2): 111–21. DOI:10.1016/j.jinf.2006.12.003. PMID 17215045. http://linkinghub.elsevier.com/retrieve/pii/S0163-4453(06)00416-6.
^ "Doxycycline spectrum of bacterial susceptibility and Resistance". http://www.toku-e.com/Upload/Products/PDS/20120618002946.pdf. Retrieved 4 May 2012.
^ Nadelman RB, Luger SW, Frank E, Wisniewski M, Collins JJ, Wormser GP (1992). "Comparison of cefuroxime axetil and doxycycline in the treatment of early Lyme disease". Ann. Intern. Med. 117 (4): 273–80. PMID 1637021.
^ Luger SW, Paparone P, Wormser GP et al. (March 1995). "Comparison of cefuroxime axetil and doxycycline in treatment of patients with early Lyme disease associated with erythema migrans". Antimicrob. Agents Chemother. 39 (3): 661–7. PMC 162601. PMID 7793869. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=162601.
^ Nadelman RB, Nowakowski J, Fish D et al. (2001). "Prophylaxis with single-dose doxycycline for the prevention of Lyme disease after an Ixodes scapularis tick bite". N. Engl. J. Med. 345 (2): 79–84. DOI:10.1056/NEJM200107123450201. PMID 11450675. http://content.nejm.org/cgi/content/full/345/2/79.
^ Karlsson M, Hammers-Berggren S, Lindquist L, Stiernstedt G, Svenungsson B (1994). "Comparison of intravenous penicillin G and oral doxycycline for treatment of Lyme neuroborreliosis". Neurologe 44 (7): 1203–7. PMID 8035916.
^ Weinstein RS (1996). "Human ehrlichiosis". Am Fam Physician 54 (6): 1971–6. PMID 8900357.
^ Karlsson U, Bjöersdorff A, Massung RF, Christensson B (2001). "Human granulocytic ehrlichiosis--a clinical case in Scandinavia". Scand. J. Infect. Dis. 33 (1): 73–4. DOI:10.1080/003655401750064130. PMID 11234985.
^ Gladwin, Mark (2007). Clinical Microbiology Made Ridiculously Simple 4th ed.. Miami, FL: MedMaster Inc.. pp. 68. ISBN 0-940780-81-X.
^ Hoerauf A, Mand S, Fischer K et al. (2003). "Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production". Med. Microbiol. Immunol. 192 (4): 211–6. DOI:10.1007/s00430-002-0174-6. PMID 12684759.
^ Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A (2005). "Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial". Lancet 365 (9477): 2116–21. DOI:10.1016/S0140-6736(05)66591-9. PMID 15964448.
^ Outland, Katrina (24 June 2005). "New Treatment for Elephantitis: Antibiotics". 13. The Journal of Young Investigators. http://www.jyi.org/news/nb.php?id=361.
^ Center for Global Health, Centers for Disease Control and Prevention (2011). "Doxycycline for Malaria Chemoprophylaxis and Treatment: Report from the CDC Expert Meeting on Malaria Chemoprophylaxis". The American Journal of Tropical Medicine and Hygiene. http://www.ajtmh.org/content/84/4/517.full. Retrieved 2012-05-17. ^{[verification needed]}
^ Center for Drug Evaluation and Research (November–December 2004). "European recommendations on the use of oral antibiotics for acne". Food and Drug Administration. http://www.jle.com/en/revues/medecine/ejd/e-docs/00/04/07/1B/article.md?type=text.html. Retrieved 2008-01-31. ^{[verification needed]}
^ Archer JS, Archer DF (2002). "Oral contraceptive efficacy and antibiotic interaction: a myth debunked". J. Am. Acad. Dermatol. 46 (6): 917–23. DOI:10.1067/mjd.2002.120448. PMID 12063491.
^ Dréno B, Bettoli V, Ochsendorf F, Layton A, Mobacken H, Degreef H (November–December 2004). "European recommendations on the use of oral antibiotics for acne". Eur J Dermatol 14 (6): 391–9. PMID 15564203. http://www.jle.com/e-docs/00/04/07/1B/vers_alt/VersionPDF.pdf.
^ DeRossi SS, Hersh EV (2002). "Antibiotics and oral contraceptives". Dent. Clin. North Am. 46 (4): 653–64. DOI:10.1016/S0011-8532(02)00017-4. PMID 12436822.
^ National Center for Biotechnology Information (September 2010). "AHFS Consumer Medication Information". U.S. National Library of Medicine. http://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0000563/#a682063-how. Retrieved 2012-07-01.
^ "Principles and methods for the assessment of nephrotoxicity associated with exposure to chemicals". Environmental health criteria: 119. World Health Organization (WHO). ISBN 92-4-157119-5. ISSN 0250-863X. 1991.
^ ^a ^b Foye's Principles of Medicinal Chemistry; David A. Williams; William O. Foye, Thomas L. Lemke
^ ^a ^b Goodman & Gilman's The Pharmacological Basis of Therapeutics, 12ed, Laurence L. Brunton, Bruce A. Chabner, Björn C. Knollmann
^ Dursun D, Kim MC, Solomon A, Pflugfelder SC (2001). "Treatment of recalcitrant recurrent corneal erosions with inhibitors of matrix metalloproteinase-9, doxycycline and corticosteroids". Am. J. Ophthalmol. 132 (1): 8–13. DOI:10.1016/S0002-9394(01)00913-8. PMID 11438047.
^ Duivenvoorden, W. C.; Hirte, H. W.; Singh, G. (1997). "Use of tetracycline as an inhibitor of matrix metalloproteinase activity secreted by human bone-metastasizing cancer cells". Invasion & metastasis 17 (6): 312–322. PMID 9949290. edit
^ Fife, R. S.; Sledge Jr, G. W. (1995). "Effects of doxycycline on in vitro growth, migration, and gelatinase activity of breast carcinoma cells". The Journal of laboratory and clinical medicine 125 (3): 407–411. PMID 7897308. edit
^ Duivenvoorden, W. C.; Popović, S. V.; Lhoták, S.; Seidlitz, E.; Hirte, H. W.; Tozer, R. G.; Singh, G. (2002). "Doxycycline decreases tumor burden in a bone metastasis model of human breast cancer". Cancer research 62 (6): 1588–1591. PMID 11912125. edit
^ Moses MA, Harper J, Folkman J (2006). "Doxycycline treatment for lymphangioleiomyomatosis with urinary monitoring for MMPs". N. Engl. J. Med. 354 (24): 2621–2. DOI:10.1056/NEJMc053410. PMID 16775248.
^ Errami M, Galindo CL, Tassa AT, Dimaio JM, Hill JA, Garner HR (2007). "Doxycycline attenuates isoproterenol- and transverse aortic banding- induced cardiac hypertrophy in mice". J Pharmacol Exp Ther 324 (3): 1196–203. DOI:10.1124/jpet.107.133975. PMID 18089841.
^ Dalvi PS, Singh A, Trivedi HR et al. (2011). "Effect of doxycycline in patients of moderate to severe chronic obstructive pulmonary disease with stable symptoms". Ann Thorac Med 6 (4): 221–6. DOI:10.4103/1817-1737.84777. PMC 3183640. PMID 21977068. http://www.thoracicmedicine.org/article.asp?issn=1817-1737;year=2011;volume=6;issue=4;spage=221;epage=226;aulast=Dalvi.
^ Saraiva IH, Jones RN, Erwin M, Sader HS (1997). "[Evaluation of antimicrobial sensitivity of 87 clinical isolates of vancomycin-resistant enterococci]" (in Portuguese). Rev Assoc Med Bras 43 (3): 217–22. DOI:10.1590/S0104-42301997000300009. PMID 9497549.
^ Dibb WL, Digranes A (1981). "Characteristics of 20 human Pasteurella isolates from animal bite wounds". Acta Pathol Microbiol Scand [B] 89 (3): 137–41. PMID 7315339.
^ Greenwald RA (December 2011). "The road forward: the scientific basis for tetracycline treatment of arthritic disorders". Pharmacol. Res. 64 (6): 610–3. DOI:10.1016/j.phrs.2011.06.010. PMID 21723947.
^ Raza M, Ballering JG, Hayden JM, Robbins RA, Hoyt JC (2006). "Doxycycline decreases monocyte chemoattractant protein-1 in human lung epithelial cells". Exp. Lung Res. 32 (1–2): 15–26. DOI:10.1080/01902140600691399. PMID 16809218.
^ Chodosh S, Tuck J, Pizzuto D (1988). "Comparative trials of doxycycline versus amoxicillin, cephalexin and enoxacin in bacterial infections in chronic bronchitis and asthma". Scand J Infect Dis Suppl 53: 22–8. PMID 3047855.
^ Joks R, Durkin HG (December 2011). "Non-antibiotic properties of tetracyclines as anti-allergy and asthma drugs". Pharmacol. Res. 64 (6): 602–9. DOI:10.1016/j.phrs.2011.04.001. PMID 21501686.
^ Bachelez H, Senet P, Cadranel J, Kaoukhov A, Dubertret L (2001). "The use of tetracyclines for the treatment of sarcoidosis". Arch Dermatol 137 (1): 69–73. PMID 11176663. http://archderm.ama-assn.org/cgi/content/full/137/1/69.
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