Doxycycline

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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
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) (IPA: [ ˌdɒksɪˈsaɪklin ]) is a member of the tetracycline antibiotics group and is commonly used to treat a variety of infections. Brand names include Monodox®, Periostat®, Vibramycin®, Vibra-Tabs®, Doryx®, Vibrox®, Adoxa®, Doxyhexal® and Atridox® (topical doxycycline hyclate for Periodontitis).

1 Indicated uses
2 Cautions and side effects
3 Experimental applications
4 References and notes
5 External link

[edit] 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, acne and rosacea. In addition it is used in the treatment and prophylaxis of Bacillus anthracis (anthrax) and malaria. Its mechanism of action against malaria is to specifically impair in the progeny the apicoplast genes resulting in their abnormal cell division.^[1]

It is also effective against Yersinia pestis (the infectious agent of bubonic plague) and is prescribed for the treatment of Lyme disease 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. Doxycycyline was shown in 2003 to kill the symbiotic Wolbachia bacteria upon which the nematodes are dependent.^[2] Field trials in 2005 showed that Doxycycline almost completely eliminates blood-borne filaria when given for an 8 week course.^[3]^[4]

Generic 100 mg doxycycline capsules

[edit] 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 contraceptive pill due to CYP450 induction, and physicians recommend the use of barrier contraception for people taking the drug to prevent unwanted pregnancy.

It should be taken with a full glass of water to prevent irritation of the esophagus or stomach. Also, there is a slim risk of liver damage during prolonged use of the drug. However, other medicines that treat conditions such as acne have a higher risk.

[edit] 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.^[5]

Doxycycline has also been used to regulate transgene expression in mice using the Tet-on gene control system.

[edit] References and notes

^ 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.
^ 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.
^ 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.
^ Outland, Katrina. "New Treatment for Elephantitis: Antibiotics", The Journal of Young Investigators, 2005 Volume 13.
^ Moses MA, Harper J, Folkman J (2006). "Doxycycline treatment for lymphangioleiomyomatosis with urinary monitoring for MMPs". N Engl J Med 354 (24): 2621–22.