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Doxycycline



Doxycycline
Systematic (IUPAC) name
(2-(amino-hydroxy-methylidene)-4-dimethylamino

-5,10,11,12a-tetrahydroxy-6-methyl- 4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione

Identifiers
CAS number 564-25-0
ATC code J01AA02 A01AB22
PubChem 11256
DrugBank APRD00597
Chemical data
Formula C22H24N2O8 
Mol. mass 444.435 g/mol
Pharmacokinetic data
Bioavailability 100%
Metabolism hepatic
Half life 18-22 hours
Excretion urine, feces
Therapeutic considerations
Pregnancy cat.

D(US)

Legal status

POM(UK) ℞-only(US)

Routes oral, periodontal, iv, im

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 FDA approval in 1967, becoming Pfizer's first once-a-day broad-spectrum antibiotic. Other brand names include Monodox, Periostat, Vibra-Tabs, Doryx, Vibrox, Adoxa®, Doxyhexal and Atridox (topical doxycycline hyclate for Periodontitis).

Contents

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 and rosacea[3][4]. In addition it is used in the treatment and prophylaxis of Bacillus anthracis (anthrax) and in prophylaxis against malaria. It should not be used alone for initial treatment of malaria, even when the parasite is doxycyline-sensitive, because the antimalarial effect of doxycyline is delayed. This delay is related to its mechanism of action. Its mechanism of action against malaria is to specifically impair in the progeny the apicoplast genes resulting in their abnormal cell division.[5]

It is also effective against Yersinia pestis (the infectious agent of bubonic plague) and is prescribed for the treatment of Lyme disease[6][7][8], ehrlichiosis[9][10] and Rocky Mountain spotted fever. Doxycycline, like other antibiotics, will not work for colds, flu, or other viral infections.

Elephantiasis is a disease caused by a nematode (worm) Wuchereria bancrofti. It causes swollen limbs and genitals (Filariasis) and affects over 120 million people in the world. 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 upon which the nematodes are dependent.[11] Field trials in 2005 showed that Doxycycline almost completely eliminates blood-borne filaria when given for an 8 week course.[12][13]

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

  • Escherichia coli
  • Enterobacter aerogenes (formerly Aerobacter aerogenes)
  • Lyme Disease
  • Acne
  • Shigella species
  • Acinetobacter species (formerly Mima species and Herellea species)
  • Respiratory tract infections caused by Haemophilus influenzae
  • Respiratory tract and urinary tract infections caused by Klebsiella species
  • Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae)
  • [[Methicillin-resistant Staphylococcus aureus (MRSA)]] infections

 

Cautions and side effects

Cautions and side effects are similar to other members of the tetracycline antibiotic group. However the 10% risk of photosensitivity skin reactions is of particular importance for those intending long-term use for malaria prophylaxis. Reports of GERD have been cited with the use of Doxycycline.

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

Doxycycline impairs the effectiveness of many types of hormonal contraception due to CYP450 induction, and physicians recommend the use of barrier contraception for people taking the drug to prevent unwanted pregnancy. It may also reduce the effectiveness of oral contraceptives by decreasing the normal flora in the intestines. Normally, estrogens inside oral contraceptives are glucuronidated in the liver and re-circulated to the gut. Flora presence in the gut help to remove glucuronide groups off of estrogen as it re-enters the GI tract via enterohepatic circulation and thus the estrogen takes effect. However, the decrease of number of flora inside the gut reduce the flora's glucuronide groups removal ability. Therefore, Doxycycline's decrease the efficacy of oral contraceptives up to two-fold.

It should be taken with a full glass of water to prevent irritation of the esophagus and stomach. Also, there is a slim risk of liver damage during prolonged use of the drug.[14]

Experimental applications

At subantimicrobial doses, doxycycline is an inhibitor of matrix metalloproteinases, and has been used in various experimental systems for this purpose. Doxycycline has been used successfully in the treatment of one patient with lymphangioleiomyomatosis, an otherwise progressive and fatal disease.[15]

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:

  • Vancomycin-Resistant Enterococcus (VRE)[16]
  • Infected animal bite wounds (Pasteurella multocida, Pasteurella pneumotropica)[17]
  • Rheumatoid arthritis[18][19] and reactive arthritis.
  • Chronic inflammatory lung diseases (panbronchiolitis, asthma, cystic fibrosis, bronchitis)[20][21]
  • Sarcoidosis[22][23]
  • Prevention of aortic aneurysm in people with Marfan Syndrome.
  • Multiple sclerosis [24]

References

  1. ^ Sweet RL, Schachter J, Landers DV, Ohm-Smith M, Robbie MO. Treatment of hospitalized patients with acute pelvic inflammatory disease: comparison of cefotetan plus doxycycline and cefoxitin plus doxycycline. Am J Obstet Gynecol. 1988 Mar;158(3 Pt 2):736-41.
  2. ^ Gjonnaess H, Holten E. Doxycycline (Vibramycin) in pelvic inflammatory disease. Acta Obstet Gynecol Scand. 1978;57(2):137-9.
  3. ^ Maatta M, Kari O, Tervahartiala T, Peltonen S, Kari M, Saari M, Sorsa T. Tear fluid levels of MMP-8 are elevated in ocular rosacea--treatment effect of oral doxycycline. Graefes Arch Clin Exp Ophthalmol. 2006 Aug;244(8):957-62. Epub 2006 Jan 13.
  4. ^ Quarterman MJ, Johnson DW, Abele DC, Lesher JL Jr, Hull DS, Davis LS. Ocular rosacea. Signs, symptoms, and tear studies before and after treatment with doxycycline. Arch Dermatol. 1997 Jan;133(1):49-54.
  5. ^ Dahl E, Shock J, Shenai B, Gut J, DeRisi J, Rosenthal P (Sep 2006). "Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum.". Antimicrob Agents Chemother 50 (9): 3124-31. PMID 16940111.
  6. ^ Nadelman RB, Luger SW, Frank E, Wisniewski M, Collins JJ, Wormser GP. Comparison of cefuroxime axetil and doxycycline in the treatment of early Lyme disease. Ann Intern Med. 1992 Aug 15;117(4):273-80.
  7. ^ Nadelman RB, Nowakowski J, Fish D, Falco RC, Freeman K, McKenna D, Welch P, Marcus R, Aguero-Rosenfeld ME, Dennis DT, Wormser GP. Prophylaxis with single-dose doxycycline for the prevention of Lyme disease after an Ixodes scapularis tick bite. N Engl J Med. 2001 Jul 12;345(2):79-84.
  8. ^ Karlsson M, Hammers-Berggren S, Lindquist L, Stiernstedt G, Svenungsson B. Comparison of intravenous penicillin G and oral doxycycline for treatment of Lyme neuroborreliosis. Neurology. 1994 Jul;44(7):1203-7.
  9. ^ Weinstein RS. Human ehrlichiosis. Am Fam Physician. 1996 Nov 1;54(6):1971-6.
  10. ^ Karlsson U, Bjoersdorff A, Massung RF, Christensson B. Human granulocytic ehrlichiosis--a clinical case in Scandinavia. Scand J Infect Dis. 2001;33(1):73-4.
  11. ^ Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW (2003). "Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production". Med Microbiol Immunol (Berl) 192 (4): 211-6. PMID 12684759.
  12. ^ 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. PMID 15964448.
  13. ^ Outland, Katrina. "New Treatment for Elephantitis: Antibiotics", The Journal of Young Investigators, 2005 Volume 13. 
  14. ^ http://www.fda.gov/cder/drug/infopage/penG_doxy/QA_doxy.htm
  15. ^ Moses MA, Harper J, Folkman J (2006). "Doxycycline treatment for lymphangioleiomyomatosis with urinary monitoring for MMPs". N Engl J Med 354 (24): 2621–22.
  16. ^ Saraiva IH, Jones RN, Erwin M, Sader HS. Evaluation of antimicrobial sensitivity of 87 clinical isolates of vancomycin-resistant enterococci. Rev Assoc Med Bras. 1997 Jul-Sep;43(3):217-22.
  17. ^ Dibb WL, Digranes A. Characteristics of 20 human Pasteurella isolates from animal bite wounds. Acta Pathol Microbiol Scand [B]. 1981 Jun;89(3):137-41.
  18. ^ Sreekanth VR, Handa R, Wali JP, Aggarwal P, Dwivedi SN. Doxycycline in the treatment of rheumatoid arthritis--a pilot study. J Assoc Physicians India. 2000 Aug;48(8):804-7.
  19. ^ Nordstrom D, Lindy O, Lauhio A, Sorsa T, Santavirta S, Konttinen YT. Anti-collagenolytic mechanism of action of doxycycline treatment in rheumatoid arthritis. Rheumatol Int. 1998;17(5):175-80.
  20. ^ Raza M, Ballering JG, Hayden JM, Robbins RA, Hoyt JC. Doxycycline decreases monocyte chemoattractant protein-1 in human lung epithelial cells. Exp Lung Res. 2006 Jan-Feb;32(1-2):15-26.
  21. ^ Chodosh S, Tuck J, Pizzuto D. Comparative trials of doxycycline versus amoxicillin, cephalexin and enoxacin in bacterial infections in chronic bronchitis and asthma. Scand J Infect Dis Suppl. 1988;53:22-8.
  22. ^ Bachelez H, Senet P, Cadranel J, Kaoukhov A, Dubertret L. The use of tetracyclines for the treatment of sarcoidosis. Arch Dermatol. 2001 Jan;137(1):69-73.
  23. ^ El Sayed F, Dhaybi R, Ammoury A. Subcutaneous nodular sarcoidosis and systemic involvement successfully treated with doxycycline. J Med Liban. 2006 Jan-Mar;54(1):42-4.
  24. ^ http://news.bbc.co.uk/2/hi/health/7136088.stm
v • d • e
Stomatological preparations (A01)
Caries prophylactic agentsSodium fluoride - Sodium monofluorophosphate - Olaflur - Stannous fluoride
Anti-infectives and antisepticsHydrogen peroxide - Chlorhexidine - Amphotericin B - Polynoxylin - Domiphen - Oxyquinoline - Neomycin - Miconazole - Natamycin - Hexetidine - Tetracycline - Benzoxonium chloride - Tibezonium iodide - Mepartricin - Metronidazole - Clotrimazole - Sodium perborate - Chlortetracycline - Doxycycline - Minocycline - Eugenol
CorticosteroidsTriamcinolone - Dexamethasone - Hydrocortisone
OtherEpinephrine/Adrenalone - Benzydamine - Acetylsalicylic acid - Amlexanox
v • d • e
Antibacterials for systemic use: tetracycline antibiotics (J01A)
TetracyclinesChlortetracycline • Clomocycline • Demeclocycline • Doxycycline • Lymecycline • Metacycline • Minocycline • Oxytetracycline • Penimepicycline • Rolitetracycline • Tetracycline
GlycylcyclinesTigecycline
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Doxycycline". A list of authors is available in Wikipedia.
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