doxycycline doxycycline doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. it is used to treat bacterial pneumonia, acne, chlamydia infections, lyme disease, cholera, typhus, and syphilis. it is also used to prevent malaria in combination with quinine. doxycycline may be taken by mouth or by injection into a vein. doxycyclineclinical datapronunciation/ˌdɒksɪˈsaɪkliːn/doks-iss-eye-kleen trade namesdoxy, doryx, vibramycin, othersahfs/drugs.commonographmedlineplusa682063license data us dailymed: doxycycline us fda: doxycycline pregnancycategory au: d routes ofadministrationby mouth, intravenousatc codej01aa02 (who) a01ab22 (who)legal statuslegal status au: s4 (prescription only) uk: pom (prescription only) us: ℞-only pharmacokinetic databioavailability~100%protein binding80–90%metabolismnegligibleelimination half-life10–22 hoursexcretionmainly feces, 40% urineidentifiers 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 cas number564-25-0 ypubchem ciddoxycyclinedrugbankdb00254 ychemspider10482106 yunii334895s862keggd07876 nchebichebi:60648 ychemblchembl1433 ncomptox dashboard (epa)dtxsid0037653 echa infocard100.008.429 chemical and physical dataformulac22h24n2o8molar mass444.440 g·mol−13d model (jsmol)interactive image smiles cn(c)3c(\o)=c(\c(n)=o)c(=o)4(o)c(/o)=c2/c(=o)c1c(cccc1o)(c)2(o)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 ykey:xqtwddciujnltr-cvhrzjfosa-n y ny (what is this?) (verify) common side effects include diarrhea, nausea, vomiting, abdominal pain, and an increased risk of sunburn. use during pregnancy is not recommended. like other agents of the tetracycline class, it either slows or kills bacteria by inhibiting protein production. it kills malaria by targeting a plastid organelle, the apicoplast. doxycycline was patented in 1957 and came into commercial use in 1967. it is on the world health organization's list of essential medicines. doxycycline is available as a generic medicine. in 2020, it was the 79th most commonly prescribed medication in the united states, with more than 9 million prescriptions. medical use generic 100 mg doxycycline capsules doxycycline package in addition to the general indications for all members of the tetracycline antibiotics group, doxycycline is frequently used to treat lyme disease, chronic prostatitis, sinusitis, pelvic inflammatory disease, acne, rosacea, and rickettsial infections. in canada, in 2004, doxycycline was considered a first-line treatment for chlamydia and non-gonococcal urethritis and with cefixime for uncomplicated gonorrhea. antibacterial moraxella catarrhalis, brucella melitensis, chlamydia pneumoniae, and mycoplasma pneumoniae are generally susceptible to doxycycline, while some haemophilus spp., mycoplasma hominis, and pseudomonas aeruginosa have developed resistance to varying degrees. it is used in the treatment and prophylaxis of anthrax and leptospirosis. it is also effective against yersinia pestis (the infectious agent of bubonic plague), and is prescribed for the treatment of lyme disease, ehrlichiosis, and rocky mountain spotted fever. doxycycline is indicated for treatment of: rocky mountain spotted fever, typhus fever and the typhus group, q fever, rickettsialpox, and tick fevers caused by rickettsia respiratory tract infections caused by mycoplasma pneumoniae lymphogranuloma venereum, trachoma, inclusion conjunctivitis, and uncomplicated urethral, endocervical, or rectal infections in adults caused by chlamydia trachomatis psittacosis nongonococcal urethritis caused by ureaplasma urealyticum relapsing fever due to borrelia recurrentis chancroid caused by haemophilus ducreyi plague due to yersinia pestis tularemia cholera campylobacter fetus infections brucellosis caused by brucella species (in conjunction with streptomycin) bartonellosis granuloma inguinale (klebsiella species) lyme disease when bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat these infections caused by gram-negative bacteria: escherichia coli infections enterobacter aerogenes (formerly aerobacter aerogenes) infections 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 caused by klebsiella species some gram-positive bacteria have developed resistance to doxycycline. up to 44% of streptococcus pyogenes and up to 74% of s. faecalis specimens have developed resistance to the tetracycline group of antibiotics. up to 57% of p. acnes strains developed resistance to doxycycline. when bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat these infections caused by gram-positive bacteria: upper respiratory infections caused by streptococcus pneumoniae (formerly diplococcus pneumoniae) skin and soft tissue infections caused by staphylococcus aureus, including methicillin-resistant staphylococcus aureus infections anthrax caused by bacillus anthracis infection when penicillin is contraindicated, doxycycline can be used to treat: syphilis caused by treponema pallidum yaws caused by treponema pertenue listeriosis due to listeria monocytogenes vincent's infection caused by fusobacterium fusiforme actinomycosis caused by actinomyces israelii infections caused by clostridium species doxycycline may also be used as adjunctive therapy for severe acne. the first-line treatment for brucellosis is a combination of doxycycline and streptomycin and the second-line is a combination of doxycycline and rifampicin (rifampin). antimalarial doxycycline is active against the erythrocytic stages of plasmodium falciparum but not against the gametocytes of p. falciparum. it is used to prevent malaria. it is not recommended alone for initial treatment of malaria, even when the parasite is doxycycline-sensitive, because the antimalarial effect of doxycycline is delayed. the world health organization (who) guidelines state that the combination of doxycycline with either artesunate or quinine may be used for the treatment of uncomplicated malaria due to p. falciparum or following intravenous treatment of severe malaria. antihelminthic doxycycline kills the symbiotic wolbachia bacteria in the reproductive tracts of parasitic filarial nematodes, making the nematodes sterile, and thus reducing transmission of diseases such as onchocerciasis and elephantiasis. field trials in 2005 showed an eight-week course of doxycycline almost eliminates the release of microfilariae. spectrum of susceptibility doxycycline has been used successfully to treat sexually transmitted, respiratory, and ophthalmic infections. representative pathogenic genera include chlamydia, streptococcus, ureaplasma, mycoplasma, and others. the following represents mic susceptibility data for a few medically significant microorganisms. chlamydia psittaci: 0.03 μg/ml mycoplasma pneumoniae: 0.016–2 μg/ml streptococcus pneumoniae: 0.06–32 μg/ml sclerotherapy doxycycline is also used for sclerotherapy in slow-flow vascular malformations, namely venous and lymphatic malformations, as well as post-operative lymphoceles. others subantimicrobial-dose doxycycline (sdd) is widely used as an adjunctive treatment to scaling and root planing for periodontitis. significant differences were observed for all investigated clinical parameters of periodontitis in favor of the scaling and root planing + sdd group where sdd dosage regimens is 20 mg twice daily for three months in a meta-analysis published in 2011. contraindications pregnancy and lactation doxycycline is categorized by the fda as a class d drug in pregnancy. doxycycline crosses into breastmilk. other tetracycline antibiotics are contraindicated in pregnancy and up to eight years of age, due to the potential for disrupting bone and tooth development. they include a class warning about staining of teeth and decreased development of dental enamel in children exposed to tetracyclines in utero, during breastfeeding or during young childhood. however, the fda has acknowledged that the actual risk of dental staining of primary teeth is undetermined for doxycycline specifically. the best available evidence indicates that doxycycline has little or no effect on hypoplasia of dental enamel or on staining of teeth and the cdc recommends the use of doxycycline for treatment of q fever and also for tick-borne rickettsial diseases in young children and others advocate for its use in malaria. other other contraindications are severe liver disease and concomitant use of isotretinoin or other retinoids, as both tetracyclines and retinoids can cause intracranial hypertension (increased pressure around the brain) in rare cases. adverse effects adverse effects are similar to those of other members of the tetracycline antibiotic group. doxycycline can cause gastrointestinal upset. oral doxycycline can cause pill esophagitis, particularly when it is swallowed without adequate fluid, or by persons with difficulty swallowing or impaired mobility. doxycycline is less likely than other antibiotic drugs to cause clostridium difficile colitis. 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 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. unlike some other members of the tetracycline group, it may be used in those with renal impairment. doxycycline use has been associated with increased risk of inflammatory bowel disease. in one large retrospective study, patients who were prescribed doxycycline for their acne had a 2.25-fold greater risk of developing crohn's disease. interactions the combination of doxycycline with dairy, antacids, calcium supplements, iron products, laxatives containing magnesium, or bile acid sequestrants is not inherently dangerous, but any of these foods and supplements may decrease doxycycline's effectiveness. breakfast was observed to reduce doxycycline absorption significantly. absorption of tetracycline occurs in the stomach and the upper small intestine. absorption of tetracyclines has been reported to be impaired by milk products, aluminum hydroxide gels, sodium bicarbonate, calcium and magnesium salts, laxatives containing magnesium and iron preparations. the mechanisms responsible for decreased absorption appear to be chelation and an increase in gastric ph. ... in view of these results, it is advisable to instruct the patients to take doxycycline on an empty stomach. previously, doxycycline was believed to impair the effectiveness of many types of hormonal contraception due to cyp450 induction. 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. pharmacology