Doxycycline

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Doxycycline
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200px
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
Pregnancy
category
  • US: D (Evidence of risk)
Routes of
administration		 oral, buccal, iv, im
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: Prescription Only (U.S.)
Pharmacokinetic data
Bioavailability 100%
Metabolism hepatic,minimally
Biological half-life 18-22 hours
Excretion urine, feces
Identifiers
CAS Number 564-25-0
ATC code J01AA02 (WHO) A01AB22
PubChem CID 11256
DrugBank APRD00597
ChemSpider 10482106
Chemical data
Formula C22H24N2O8
Molar mass 444.435 g/mol[[Script error: No such module "String".]]
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File:Doxycycline 100mg capsules.jpg
Generic 100 mg doxycycline capsules

Doxycycline (INN) (pronounced /ˌdɒksɪˈsaɪkliːn/) is a member of the tetracycline antibiotics group and is commonly used to treat a variety of infections. Doxycycline is a semi-synthetic tetracycline invented and clinically developed in the early 1960s by Pfizer Inc. and marketed under the brand name Vibramycin. Vibramycin received U.S. Food and Drug Administration (FDA) approval in 1967, becoming Pfizer's first once-a-day broad-spectrum antibiotic. Other brand names include Monodox, Microdox, Periostat, Vibra-Tabs, Oracea, Doryx, Vibrox, Adoxa, Doxyhexal, Doxylin, and Atridox (topical doxycycline hyclate for periodontitis).

Indicated uses

Main article: Tetracycline antibiotics
Further information: Oxytetracycline

As well as 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,[1][2] acne, rosacea,[3][4] and Rickettsial infections.

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. Its mechanism of action against malaria is to specifically impair the progeny of the apicoplast genes resulting in their abnormal cell division.[5]

It can be used in a treatment plan in combination with other agents, such as quinine.[6]

Antibacterial

It is used in the treatment and prophylaxis of Bacillus anthracis (anthrax).


It is also effective against Yersinia pestis (the infectious agent of bubonic plague) and is prescribed for the treatment of Lyme disease,[7][8][9], ehrlichiosis[10][11] 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, doxycycline is not indicated for use in children under the age of 8 years. Doxycycline, like other antibiotics, will not work for colds, flu, or other viral infections.

File:Doxycycline.jpg
Doxycycline package.

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

Antihelmintic

Elephantiasis is the end-stage condition of lymphatic filariases caused by one of two genera of filarial nematodes (roundworms): Wuchereria or Brugia (primarily Wuchereria bancrofti). Elephantiasis is characterized by permanently swollen limbs or genitals and permanent damage to the lymph system (often accompanied by severe secondary fungal and bacterial infections). This results from blockage of lymph flow caused by immune response against dead or dying adult worms in the lymphatics. This condition affects over 120 million people worldwide, with 1 billion at risk[12]. Previous anti-nematode treatments have been limited by poor levels of effectiveness, drug side effects and high costs. Doxycycline was shown in 2003 to kill the symbiotic Wolbachia bacteria in the filarial worms' reproductive tracts, rendering them sterile, thus reducing transmission of the disease.[13] Field trials in 2005 showed that Doxycycline almost completely eliminates the release of microfilariae when given for an 8 week course.[14][15] However, doxycycline only reduces transmission and the relatively light pathology associated with microfilaraemia; there is currently no cure for lymphatic filariasis.

Cautions and side effects

Cautions and side effects are similar to 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 sensitive and thin skin.

Unlike some other members of the tetracycline group, it may be used in those with renal impairment.

Previously, it was believed that doxycycline impairs 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 antibiotic (including doxycycline), although many physicians still recommend the use of barrier contraception for people taking the drug to prevent unwanted pregnancy.[16][17][18]

It should be taken with a full glass of water and patients should be upright for at least 30 minutes after administration to prevent irritation of the esophagus and stomach. Also, there is a slim risk of liver damage during prolonged use of the drug.[19] It is also recommended that it be taken with a small meal of a non-dairy nature if upset stomach, nausea or fatigue occur.

Doxycycline is not approved for use in children under the age of 8 years for two reasons: 1) it can cause permanent yellowing or graying of the teeth, and 2), according to CDC patient information on doxycycline, it can inhibit bone growth in premature infants during the time the medication is taken; this last effect disappears when the doxycycline treatment is over. 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. Expired doxycycline can cause a dangerous syndrome resulting in damage to the kidneys.

DA pregnancy category D. This medication can cause harm to an unborn baby, including permanent discoloration of the teeth later in life. Doxycycline can make birth control pills less effective. Doxycycline passes into breast milk and may affect bone and tooth development in a nursing infant.

Experimental applications

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.[20] Doxycycline has been used successfully in the treatment of one patient with lymphangioleiomyomatosis, an otherwise progressive and fatal disease.[21] Doxycyline has also been shown to attenuate cardiac hypertrophy (in mice), a deadly consequence of prolonged hypertension.[22]

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:

References

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External links

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af:Doxisiklien

ar:دوكسيسايكلين zh-min-nan:Doxycycline cs:Doxycyklin de:Doxycyclin dv:ޑޮކްސީސައިކްލިން es:Doxiciclina fa:داکسی سایکلین fr:Doxycycline it:Doxiciclina ht:Doksisiklin nl:Doxycycline ja:ドキシサイクリン pl:Doksycyklina pt:Doxiciclina ru:Доксициклин sr:Доксициклин fi:Doksisykliini sv:Doxycyklin th:ดอกซีไซคลีน tr:Doksisiklin

zh:多西环素
  1. ↑ 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. 
  2. ↑ 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. 
  3. ↑ 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. 
  4. ↑ 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. 
  5. ↑ 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 Freely accessible. PMID 16940111. 
  6. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  7. ↑ 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. doi:10.1001/archinte.117.2.273. PMID 1637021. 
  8. ↑ 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. 
  9. ↑ 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. 
  10. ↑ Weinstein RS (1996). "Human ehrlichiosis". Am Fam Physician. 54 (6): 1971–6. PMID 8900357. 
  11. ↑ 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. 
  12. ↑ Watkins, B.M. Drugs for the control of parasitic diseases: current status and development. TRENDS in Parasitology (2003)19:11
  13. ↑ 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. 
  14. ↑ 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. 
  15. ↑ Outland, Katrina (2005 Volume 13). "New Treatment for Elephantitis: Antibiotics". The Journal of Young Investigators.  Check date values in: |date= (help)
  16. ↑ 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. 
  17. ↑ Dréno B, Bettoli V, Ochsendorf F, Layton A, Mobacken H, Degreef H (2004). "European recommendations on the use of oral antibiotics for acne". Eur J Dermatol. 14 (6): 391–9. PMID 15564203. 
  18. ↑ 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. 
  19. ↑ Center for Drug Evaluation and Research (November–December 2004). "European recommendations on the use of oral antibiotics for acne". Food and Drug Administration. Retrieved 2008-01-31. 
  20. ↑ 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. 
  21. ↑ 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. 
  22. ↑ 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. doi:10.1124/jpet.107.133975. PMID 18089841. 
  23. ↑ Saraiva IH, Jones RN, Erwin M, Sader HS (1997). "[Evaluation of antimicrobial sensitivity of 87 clinical isolates of vancomycin-resistant enterococci]". Rev Assoc Med Bras (in Portuguese). 43 (3): 217–22. doi:10.1590/S0104-42301997000300009. PMID 9497549. 
  24. ↑ 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. 
  25. ↑ Sreekanth VR, Handa R, Wali JP, Aggarwal P, Dwivedi SN (2000). "Doxycycline in the treatment of rheumatoid arthritis--a pilot study". J Assoc Physicians India. 48 (8): 804–7. PMID 11273473. 
  26. ↑ Nordström D, Lindy O, Lauhio A, Sorsa T, Santavirta S, Konttinen YT (1998). "Anti-collagenolytic mechanism of action of doxycycline treatment in rheumatoid arthritis". Rheumatol. Int. 17 (5): 175–80. doi:10.1007/s002960050030. PMID 9542777. 
  27. ↑ 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. 
  28. ↑ 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. 
  29. ↑ 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. 
  30. ↑ El Sayed F, Dhaybi R, Ammoury A (2006). "Subcutaneous nodular sarcoidosis and systemic involvement successfully treated with doxycycline". J Med Liban. 54 (1): 42–4. PMID 17044634. 
  31. ↑ "Antibiotics 'could help slow MS'". BBC News. 2007-12-11. Retrieved 2008-01-31. 
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