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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/03 02:04:31」(JST)

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Doxycycline is an antibiotic that is used in the treatment of a number of types of infections caused by bacteria and protozoa. It is useful for bacterial pneumonia, acne, chlamydia infections, early Lyme disease, cholera and syphilis. It is also useful for the treatment of malaria when used with quinine and for the prevention of malaria. Doxycycline can be used either by mouth or intravenously.^[1]

Common side effects include diarrhea, nausea, vomiting, a red rash, and an increased risk of a sunburn. If used during pregnancy or in young children may result in permanent problems with the teeth including changes in their color. Its use during breastfeeding is probably safe.^[1] Doxycycline is a broad-spectrum antibiotic of the tetracycline class.^[1] Like other agents of this class it kills bacteria and protozoa by inhibiting protein production.^[1]^[2]

Doxycycline came into use in 1967.^[3] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.^[4] Doxycycline is available as a generic medicine and is generally inexpensive.^[1]^[5] The wholesale cost in much of the world is between 0.01 and 0.04 USD per pill.^[6] In the United States 10 days of treatment is about 14 USD, however some in 2014 were selling it for more than 3.00 to 10.00 USD per pill.^[1]^[7]

Medical use

Generic 100 mg doxycycline capsules

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,^[8]^[9] acne, rosacea,^[10]^[11] and rickettsial infections.^[12]

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, which is to specifically impair the progeny of the apicoplast genes, resulting in their abnormal cell division.^[13]

It can be used in a treatment plan in combination with other agents, such as quinine.^[14]

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.^[15]

It is used in the treatment and prophylaxis of anthrax (caused by Bacillus anthracis) and Leptospirosis.^[16] It is also effective against Yersinia pestis (the infectious agent of bubonic plague), and is prescribed for the treatment of Lyme disease,^[17]^[18]^[19]^[20] ehrlichiosis^[21]^[22] 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, it is not indicated for use in children under the age of eight years.

Doxycycline is indicated for treatment of:^[23]^[24]

Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever,^[25] rickettsialpox, and tick fevers caused by Rickettsia
Respiratory tract infections caused by Mycoplasma pneumoniae^[26]
Lymphogranuloma venereum, trachoma, inclusion conjunctivitis, and uncomplicated urethral, endocervical, or rectal infections in adults caused by Chlamydia trachomatis
Psittacosis (ornithosis) caused by Chlamydia psittaci
Nongonococcal urethritis caused by Ureaplasma urealyticum
Relapsing fever due to Borrelia recurrentis
Chancroid caused by Haemophilus ducreyi
Plague due to Yersinia pestis
Tularemia due to Francisella tularensis
Cholera caused by Vibrio cholerae
Campylobacter fetus infections
Brucellosis caused by Brucella species (in conjunction with streptomycin)
Bartonellosis caused by Bartonella bacilliformis
Granuloma inguinale caused by Calymmatobacterium granulomatis

When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat these infections caused by Gram-negative bacteria:^[23]^[24]

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. When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat these infections caused by Gram-positive bacteria:^[23]^[24]

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

Doxycycline package

When penicillin is contraindicated, doxycycline can be used to treat:^[23]^[24]

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.^[23]^[24]

The first-line for treatment brucellosis is combination of doxycycline and streptomycin and the second-line is combination of Doxyxycline and rifampin (rifampicin).^[27]

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.^[28] Field trials in 2005 showed an eight-week course of doxycycline almost completely eliminates the release of microfilariae.^[29]

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 μg/ml – 2 μg/ml
Streptococcus pneumoniae: 0.06 μg/ml – 32 μg/ml^[30]

Adverse effects

Cautions and side effects are similar to those of other members of the tetracycline antibiotic group.

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.^[31]

Unlike some other members of the tetracycline group, it may be used in those with renal impairment.^[32] Doxycycline is contraindicated in the pediatric treatment of acute bacterial rhinosinusitis.

Interactions

The combination of doxycycline with dairy, antacids, calcium supplements, iron products, and laxatives containing magnesium is not inherently dangerous, but any of these foods and supplements may decrease doxycycline's effectiveness.^[33]

Previously, doxycycline was believed to impair 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 antibiotics (including doxycycline), although many physicians still recommend the use of barrier contraception for people taking the drug to prevent unwanted pregnancy.^[34]^[35]^[36]

Pregnancy and lactation

Doxycycline is categorized by the FDA as a class D drug in pregnancy. As with all tetracycline antibiotics, it is contraindicated in pregnancy through infancy and childhood up to eight years of age, due to the potential for disrupting bone and tooth development.^[37] Therefore, doxycycline should not be administered to children under the age of eight except in the treatment of anthrax, or where other medications are contraindicated or ineffective.^[23]

Doxycycline crosses into breastmilk. The adverse effects on teeth and long bones of children directly administered tetracycline antibiotics is documented, but these effects have not been recorded in infants exposed through breastmilk. Although the dose an infant would receive through breastfeeding would likely be minimal, a theoretical risk exists.^[38]

Pharmacokinetics

Doxycycline–metal ion complexes are unstable at acid pH, therefore more doxycycline enters the duodenum for absorption than the earlier tetracycline compounds. In addition, food has less effect on absorption than on absorption of earlier drugs with doxycycline serum concentrations being reduced by about 20% by test meals compared with 50% for tetracycline.^[39]

Physical and chemical properties

Expired tetracyclines or tetracyclines allowed to stand at a pH less than 2 are reported to be nephrotoxic due to the formation of a degradation product, anhydro-4-epitetracycline^[40]^[41] causing Fanconi syndrome.^[42] In the case of doxycycline, the absence of a hydroxyl group in C-6 prevents the formation of the nephrotoxic compound.^[41] Nevertheless, tetracyclines and doxycycline itself have to be taken with precaution in patients with kidney injury, as they can worsen azotemia due to catabolic effects.^[42]

History

After penicillin revolutionized the treatment of bacterial infections in WWII, many chemical companies moved into the field of discovering antibiotics by bioprospecting. American Cyanamid was one of these, and in the late 1940s chemists there discovered chlortetracycline, the first member of the tetracycline class of antibiotics.^[43] Shortly thereafter, scientists at Pfizer discovered terramycin and it was brought to market. Both compounds, like penicillin, were natural products and it was commonly believed that nature had perfected them, and further chemical changes could only degrade their effectiveness. Scientists at Pfizer led by Lloyd Conover modified these compounds, which led to the invention of tetracycline itself, the first semi-synthetic antibiotic. Charlie Stephens at Pfizer worked on further analogs and created one with greatly improved stability and pharmacological efficacy: doxycycline. It was clinically developed in the early 1960s and approved by the FDA in 1967.^[43]

As its patent grew near to expiring in the early 1970s, the patent became the subject of lawsuit between Pfizer and International Rectifier^[44] that wasn't resolved until 1983; at the time it was the largest litigated patent case in US history.^[45] Instead of a cash payment for infringement, Pfizer took the veterinary and feed-additive businesses of International Rectifier's subsidiary, Rachelle Laboratories.^[45]

In January 2013, the FDA reported shortages of some, but not all, forms of doxycyline "caused by increased demand and manufacturing issues".^[46] Companies involved included an unnamed major generics manufacturer that ceased production in February 2013, Teva (which ceased production in May 2013), Mylan, Actavis, and Hikma Pharmaceuticals.^[47]^[48] The shortage came at a particularly bad time, since there were also shortages of an alternative antibiotic, tetracycline, at the same time.^[49] The market price for doxycycline dramatically increased in the United States in 2013 and early 2014 (from $20 to over $1800 for a bottle of 500 tablets),^[50]^[51]^[52] before decreasing again.^[53]^[54]

Society and culture

Doxycycline is available worldwide under many brand names.^[55] Doxycycline is available as a generic medicine and is inexpensive.^[1]^[5] The wholesale cost is between 0.01 and 0.04 USD per pill.^[6]

Research

Tet-ON inducible shRNA system

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.^[56] Doxycycline has been demonstrated to reduce the in vitro growth of human breast and prostate cancer cells, possibly through G₁ phase cell cycle arrest.^[57]^[58] Doxycycline and other tetracyclines are also highly osteotropic, and in animal models of breast cancer bone metastases, doxycycline treatments have reduced the growth of breast cancer tumours in the bone.^[59] Doxycycline has been used successfully in the treatment of one patient with lymphangioleiomyomatosis, an otherwise progressive and fatal disease.^[60] It has also been shown to attenuate cardiac hypertrophy (in mice), a deadly consequence of prolonged hypertension.^[61] In chronic obstructive pulmonary disease, doxycycline has been shown to improve lung functions in patients with stable symptoms.^[62] 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 treating:

Vancomycin-resistant enterococcus^[63]
Infected animal bite wounds (Pasteurella multocida, Pasteurella pneumotropica)^[64]
Rheumatoid arthritis instead of minocycline (both of which have demonstrated modest efficacy for this disease)^[65]
Chronic inflammatory lung diseases (panbronchiolitis, asthma, cystic fibrosis, bronchitis).^[66]^[67] Both doxycycline and minocycline have shown effectiveness in asthma due to immune suppressing effects.^[68]
Sarcoidosis^[69]^[70]
Pancreatic cancer
Prevention of aortic aneurysm in people with Marfan syndrome and vascular Ehlers-Danlos syndrome^[71]
Multiple sclerosis^[72]^[73]
Meibomian gland dysfunction
Treatment of filariasis and onchocerciasis due to filariae and onchocercae. In general, harbouring endosymbiotic Wolbachia bacteria, doxycycline kills the bacteria, and (by removal of the endosymbiotes) the nematodes.
Idiopathic pulmonary fibrosis^[74]

References

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External links

Patient Information Leaflet
Drugs.com Article on Doxycycline
U.S. National Library of Medicine: Drug Information Portal – Doxycycline
Research webpage of Mark Taylor who has pioneered the use of doxycycline as an antihelmintic
The Anti-Wolbachia Consortium uses drugs like doxycycline to treat parasitic diseases

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1. フルオロキノロン類、ドキシサイクリン、およびトリメトプリムスルファメトキサゾールに対する肺炎レンサ球菌の耐性 resistance of streptococcus pneumoniae to the fluoroquinolones doxycycline and trimethoprim sulfamethoxazole
2. クラミジア・トラコマチス感染の治療 treatment of chlamydia trachomatis infection
3. 旅行者におけるマラリア感染の予防 prevention of malaria infection in travelers
4. テトラサイクリン tetracyclines
5. ライム病の治療 treatment of lyme disease

English Journal

Matrix metalloproteinases and their tissue inhibitor after reperfused ST-elevation myocardial infarction treated with doxycycline. Insights from the TIPTOP trial.

Cerisano G1, Buonamici P2, Gori AM3, Valenti R2, Sciagrà R4, Giusti B5, Sereni A5, Raspanti S4, Colonna P6, Gensini GF7, Abbate R5, Schulz R8, Antoniucci D2.
International journal of cardiology.Int J Cardiol.2015 Oct 15;197:147-53. doi: 10.1016/j.ijcard.2015.06.024. Epub 2015 Jun 18.
BACKGROUND: The TIPTOP (Early Short-term Doxycycline Therapy In Patients with Acute Myocardial Infarction and Left Ventricular Dysfunction to Prevent The Ominous Progression to Adverse Remodelling) trial demonstrated that a timely, short-term therapy with doxycycline is able to reduce LV dilation, a
PMID 26134371

Identification of integrons and phylogenetic groups of drug-resistant Escherichia coli from broiler carcasses in China.

Wu H1, Xia S2, Bu F3, Qi J4, Liu Y5, Xu H6.
International journal of food microbiology.Int J Food Microbiol.2015 Oct 15;211:51-6. doi: 10.1016/j.ijfoodmicro.2015.07.004. Epub 2015 Jul 9.
The dissemination of drug-resistant Escherichia coli in poultry products is becoming a public concern, as it endangers food security and human health. It is very common for E. coli to exhibit drug resistance in the poultry industry in China due to the excessive use of antibiotics. However, few studi
PMID 26173199

Transoral Sclerotherapy for Deep Space Cervical Lymphatic Malformations in Children With Acute Airway Compromise.

Cheng J1, Yoo MJ2.
The Annals of otology, rhinology, and laryngology.Ann Otol Rhinol Laryngol.2015 Oct;124(10):824-8. doi: 10.1177/0003489415585868. Epub 2015 May 5.
INTRODUCTION: Cervical lymphatic malformations in children rarely present with acute airway compromise. During an acute exacerbation or hemorrhage, lymphatic malformations involving the deep neck spaces may precipitate critical airway obstruction. These are rare clinical entities and tracheotomy is
PMID 25944596

Japanese Journal

感染根管歯におけるナノバブルと超音波を用いた根管内無菌化と歯髄再生

藤田将典,庵原耕一郎,堀場直樹,立花克郎,中村洋,中島美砂子
日本歯科保存学雑誌 57(2), 170-179, 2014
目的 : 当研究室では, イヌ抜髄後の根管内に歯髄幹細胞を自家移植して歯髄を再生させることに成功している. しかしながら, この歯髄再生治療を感染根管治療に応用する際には根管内の無菌化が必要である. 一方, ナノバブルと超音波を併用することで薬剤を象牙細管内に深く浸透させ, 根管内を短期間で無菌化できる可能性が示唆されている. したがって本研究では, イヌ感染根管モデルにおいて, この …
NAID 130004669778

過誤腫性肺脈管筋腫症の１例　開胸肺生検術後の気胸発症例:開胸肺生検術後の気胸発症例

平泰彦,長田博昭,横手薫美夫,栗栖純穂,山手昇,柿本伸一,三宅啓史
日本呼吸器外科学会雑誌呼吸器外科 6(2), 159-165, 1992
症例は42歳の女性で, 数年来の進行性呼吸困難と背部痛とを主訴に来院した。胸部単純レ線像ではび慢性網状影を, CTは全肺野に嚢胞状陰影を認め, 過誤腫性肺脈管筋腫症を疑った.左開胸肺生検により病理学的確診を得た。生検肺組織中のエストロゲンおよびプロゲステロンレセプターは共に高値を示し, プロゲステロン剤投与により症状は改善した.しかし術後1ヵ月にて左気胸を発症し, 胸腔ドレーン挿入下に胸膜癒着を行 …
NAID 130003653499

クラミジア性尿道炎に対するDoxycyclineの臨床効果

伊藤康久,鄭漢彬,波多野紘一,加藤直樹,武田明久,兼松稔,坂義人,西浦常雄,酒井俊助,藤広茂,土井達朗
The Japanese Journal of Antibiotics 39(1), 9-16, 1986
… <I>Chlamydia trachomatis</I>陽性の非淋菌性尿道炎21例にDoxycyline (DOXY, Vibramycin ®) を投与し, 臨床的効果を検討した。 …
NAID 130004394415

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★リンクテーブル★

リンク元	「ドキシサイクリン」
関連記事	「vibramycin」

「ドキシサイクリン」

Doxycycline
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
Pronunciation	/ˌdɒksiˈsaɪklin/
Trade names	Doryx, Doxyhexal, Doxylin among others
AHFS/Drugs.com	monograph
MedlinePlus	a682063
License data	US FDA: Doxycycline;
Pregnancy; category	AU: D; US: D (Evidence of risk); ;
Routes of; administration	by mouth, intravenous
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	100%
Protein binding	90%
Metabolism	Hepatic
Biological half-life	15–25 hours
Excretion	Urine (40%)
Identifiers
CAS Number	564-25-0
ATC code	J01AA02 (WHO) A01AB22 (WHO)
PubChem	CID 11256
DrugBank	DB00254
ChemSpider	10482106
UNII	334895S862
KEGG	D00307
ChEBI	CHEBI:60648
ChEMBL	CHEMBL1433
Chemical data
Formula	C22H24N2O8
Molar mass	444.43 g/mol
	SMILES O.CN(C)[C@@H]3C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@H](C)[C@H]2[C@H](O)[C@@H]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 ; Key:XQTWDDCIUJNLTR-CVHRZJFOSA-N ;
(what is this?) (verify)

　　[★]

英: doxycycline DOXY
化: 塩酸ドキシサイクリン doxycycline hydrochloride
商: ビブラマイシン、ヒドラマイシン、Vibramycin, Doxy
関

テトラサイクリン系抗菌薬

特徴

投与量のほとんどが胆汁中を経て糞便中に排泄されるため、腎障害時(腎不全)でも体内動態が変わらず通常量を投与可能である。

「vibramycin」

　　[★]

同: Vibramycin, Doxy
関: Doxycycline

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Vibramycin