Article: 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
PubChem	11256
DrugBank	APRD00597
Chemical data
Formula	C22H24N2O8
Mol. weight	444.435 g/mol
Pharmacokinetic data
Bioavailability	100%
Metabolism	liver
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 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®, and Atridox® (topical doxycycline hyclate for gum disease).

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, pelvic inflammatory disease, acne and rosacea. In addition it is used in the treatment and prophylaxis of Bacillus anthracis (anthrax) and malaria.

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.

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.^[1] Field trials in 2005 showed that Doxycycline almost completely eliminates blood-borne filaria when given for an 8 week course.^[2][3]

Cautions and Side effects

Are as for other members of the tetracycline antibiotics 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 Doxcycline.

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

Experimental applications

At subantimicrobial doses, doxycycline is an inhibitor of matrix metalloproteinases, and has been used in various experimental systems for this purpose.

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