- 同
- Vibramycin, Doxy
WordNet
- an antibiotic derived from tetracycline that is effective against many infections; "Vibramycin is the trade name of doxycycline" (同)Vibramycin
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/25 21:53:41」(JST)
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| 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 | |
| Trade names | Doryx, Doxyhexal, Doxylin among others |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682063 |
| Licence data | US FDA:link |
|
Pregnancy
category |
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Legal status
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Routes of
administration |
oral, buccal, intravenous therapy, intramuscular injection |
| Pharmacokinetic data | |
| Bioavailability | 100% |
| Protein binding | 90% |
| Metabolism | Hepatic |
| Half-life | 15–25 hours |
| Excretion | Urine (40%) |
| Identifiers | |
|
CAS Registry Number
|
564-25-0 Y |
|
ATC code
|
J01AA02 A01AB22 |
| PubChem | CID 11256 |
| DrugBank | DB00254 Y |
| ChemSpider | 10482106 Y |
| UNII | 334895S862 Y |
| KEGG | D00307 N |
| ChEBI | CHEBI:60648 Y |
| ChEMBL | CHEMBL1433 N |
| Chemical data | |
| Formula | C22H24N2O8 |
|
Molecular mass
|
444.43 g/mol |
|
SMILES
|
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|
InChI
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| N (what is this?) (verify) | |
Generic 100 mg doxycycline capsules
Doxycycline (IPA: /ˌdɒksiˈsaɪklin/) is an antibiotic useful for the treatment of a number of infections. It is in the tetracycline antibiotic class.
Under the brand name Vibramycin, Pfizer's doxycycline product received U.S. Food and Drug Administration approval in 1967.[1] Other brand names include Monodox, Microdox, Periostat, Vibra-Tabs, Oracea, Doryx,[2] Vibrox, Adoxa, Doxyhexal, Doxylin, Doxoral, Doxy-1 and Atridox (topical doxycycline hyclate for periodontitis) It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.[3]
Contents
- 1 Medical uses
- 1.1 Antiprotozoal
- 1.2 Antibacterial
- 1.3 Antihelminthic
- 1.4 Spectrum of susceptibility
- 2 Adverse effects
- 2.1 Interactions
- 2.2 Pregnancy and lactation
- 3 Pharmacokinetics
- 4 Physical and chemical properties
- 5 Research
- 6 History
- 7 Brand names
- 8 References
- 9 External links
Medical uses
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,[4][5] acne, rosacea,[6][7] and rickettsial infections.[8]
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.[9]
It can be used in a treatment plan in combination with other agents, such as quinine.[10]
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.[11]
It is used in the treatment and prophylaxis of anthrax (caused by Bacillus anthracis) and Leptospirosis.[12] It is also effective against Yersinia pestis (the infectious agent of bubonic plague), and is prescribed for the treatment of Lyme disease,[13][14][15][16] ehrlichiosis[17][18] 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:[19][20]
- Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever,[21] rickettsialpox, and tick fevers caused by Rickettsia
- Respiratory tract infections caused by Mycoplasma pneumoniae[22]
- 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:[19][20]
- 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:[19][20]
- 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:[19][20]
- 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.[19][20]
- Doxycycline combination
The first-line for treatment brucellosis is combination of Doxycycline and streptomycin and the second-line is combination of Doxyxycline and rifampin (rifampicin).[23]
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.[24] Field trials in 2005 showed an eight-week course of doxycycline almost completely eliminates the release of microfilariae.[25][26]
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[27]
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.[28]
Unlike some other members of the tetracycline group, it may be used in those with renal impairment.[29] 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.[30][verification needed]
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.[31][32][33]
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.[34] 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.[19]
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.[35]
Pharmacokinetics
Doxycycline–metal ion complexes are unstable at acid pH, therefore more doxycycline enters the duodenum for absorption compared with 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.[36]
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[37][38] causing Fanconi syndrome.[39] In the case of doxycycline, the absence of a hydroxyl group in C-6 prevents the formation of the nephrotoxic compound.[38] 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.[39]
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.[40] Doxycycline has been demonstrated to reduce the in vitro growth of human breast and prostate cancer cells, possibly through G1 phase cell cycle arrest.[41][42] 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.[43] Doxycycline has been used successfully in the treatment of one patient with lymphangioleiomyomatosis, an otherwise progressive and fatal disease.[44] It has also been shown to attenuate cardiac hypertrophy (in mice), a deadly consequence of prolonged hypertension.[45] In chronic obstructive pulmonary disease, doxycycline has been shown to improve lung functions in patients with stable symptoms.[46] 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[47]
- Infected animal bite wounds (Pasteurella multocida, Pasteurella pneumotropica)[48]
- Rheumatoid arthritis instead of minocycline (both of which have demonstrated modest efficacy for this disease)[49]
- Chronic inflammatory lung diseases (panbronchiolitis, asthma, cystic fibrosis, bronchitis)[50][51] Both doxycycline and minocycline have shown effectiveness in asthma due to immune suppressing effects.[52]
- Sarcoidosis[53][54]
- Pancreatic cancer
- Prevention of aortic aneurysm in people with Marfan syndrome and vascular Ehlers-Danlos syndrome[55]
- Multiple sclerosis[56][57]
- 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[58]
- Abdominal Aortic aneurysm or apoplexy[59]
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.[60] 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.[60]
As its patent grew near to expiring in the early 1970s, the patent became the subject of lawsuit between Pfizer and International Rectifier[61] that wasn't resolved until 1983; at the time it was the largest litigated patent case in US history.[62] Instead of a cash payment for infringement, Pfizer took the veterinary and feed-additive businesses of International Rectifier's subsidiary, Rachelle Laboratories.[62]
In January 2013, the FDA reported shortages of some, but not all, forms of doxycyline "caused by increased demand and manufacturing issues".[63] 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.[64][65] The shortage came at a particularly bad time, since there were also shortages of an alternative antibiotic, tetracycline, at the same time.[66] The market price for doxycycline dramatically increased in the United States in 2013 and early 2014 before falling again as more supply came on line.[67][68][69]
Brand names
Doxycycline is available worldwide under many brand names.[70]
References
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- ^ a b The Associated Press, 6 July 1983 Pfizer to Get Rachelle Units The New York Times.
- ^ CDC Health Alert Network 12 June 2013 Nationwide Shortage of Doxycycline: Resources for Providers and Recommendations for Patient Care
- ^ American Society of Health-System Pharmacists. 12 December 2014 Doxycycline Capsules and Tablets
- ^ American Society of Health-System Pharmacists. 12 November 2014 Doxycycline Hyclate Injection
- ^ Consumer Reports News: 4 February 2013 FDA reports shortage of doxycycline antibiotic. What are your options?
- ^ Sudden increase in cost of common drug concerns many, WSMV-TV, 12 March 2013 (updated 26 March 2013).
- ^ Rosenthal, Elisabeth, Officials Question the Rising Costs of Generic Drugs, The New York Times, 7 October 2014.
- ^ Eric Palmer for FiercePharmaManufacturing. 13 March 2014 Hikma hits the jackpot with doxycycline shortage
- ^ drugs.com Drugs.com international availability for doxycycline Page accessed April 29, 2015
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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UpToDate Contents
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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. Traction alopecia
- 3. クラミジア・トラコマチス感染の治療 treatment of chlamydia trachomatis infection
- 4. 旅行者におけるマラリア感染の予防 prevention of malaria infection in travelers
- 5. テトラサイクリン tetracyclines
English Journal
- Adapalene 0.1%/benzoyl peroxide 2.5% gel: a review of its use in the treatment of acne vulgaris in patients aged ?12 years.
- Keating GM.SourceAdis, a Wolters Kluwer Business, Auckland, New Zealand.
- American journal of clinical dermatology.Am J Clin Dermatol.2011 Dec 1;12(6):407-20. doi: 10.2165/11208170-000000000-00000.
- Adapalene 0.1%/benzoyl peroxide 2.5% gel (Epiduo?, Tactuo?) is the only fixed-dose combination product available that combines a topical retinoid with benzoyl peroxide; it targets three of the four main pathophysiologic factors in acne. This article reviews the therapeutic efficacy and tolerabil
- PMID 21967116
- Doxycycline reduces nitric oxide production in guinea pig inner ears.
- Helling K, Wodarzcyk K, Brieger J, Schmidtmann I, Li H, Mann WJ, Heinrich UR.SourceDepartment of Otorhinolaryngology, Head and Neck Surgery, University Medical Center of the Johannes Gutenberg-University Mainz, Langenbeckstrase 1, Mainz, Germany. kai.helling@unimedizin-mainz.de
- Auris, nasus, larynx.Auris Nasus Larynx.2011 Dec;38(6):671-7. Epub 2011 May 26.
- OBJECTIVE: Gentamicin application is an important therapeutic option to control vertigo spells in Meniere's disease. However, even in the case of low-dose intratympanic application, gentamicin might contribute to a pathological NO-increase leading to cochlear damage and hearing impairment. The stu
- PMID 21616617
Japanese Journal
- An EWS-FLI1-Induced Osteosarcoma Model Unveiled a Crucial Role of Impaired Osteogenic Differentiation on Osteosarcoma Development.
- Stem cell reports 6(4), 592-606, 2016-04-12
- NAID 120005756300
- Pelvic Organ Support in Animals with Partial Loss of Fibulin-5 in the Vaginal Wall
- PLoS ONE 11(4), e0152793, 2016-04
- NAID 120005774732
- 片側顔面神経麻痺で発症し抗菌薬を投与したが髄膜炎を再発したライム病の1例
- 臨床神経学 advpub(0), 2016
- NAID 130005161338
Related Links
- ドキシサイクリン塩酸塩（doxycycline hydrochloride, DOXY）は、テトラサイクリン系に 属する抗生物質である。グラム陽性菌・グラム陰性菌やリケッチアに対して優れた抗菌 力を示す。その作用は、細菌体内におけるタンパク質合成阻害によるものである。
- Doxycycline is an antibiotic used to treat bacterial infections, such as urinary tract infections, acne and chlamydia. Includes doxycycline side effects, interactions and indications.
Related Pictures
★リンクテーブル★
| リンク元 | 「テトラサイクリン系抗菌薬」「ドキシサイクリン」 |
| 拡張検索 | 「doxycycline calcium」「doxycycline hydrochloride hydrate」「doxycycline hydrochloride」 |
「テトラサイクリン系抗菌薬」
- first aid step1 2006 p.170
特徴
- 静菌的作用
- 抗菌薬の1st choiceになりやすい
構造
- 六員環が4つ連結した構造 → 日光過敏との関連
作用機序
- 30Sリボソームに結合し、リボソームへのアミノアシルtRNAの結合を阻害→蛋白合成阻害
薬理作用
抗菌スペクトル
- グラム陽性菌、グラム陰性菌、リケッチア、マイコプラズマ、アメーバ
動態
- 酸に強く経口投与可能
- 上部消化管から吸収される
- 脳脊髄液には移行しづらい。
- 胆汁、尿にそのまま排泄される
適応
注意
禁忌
- 妊婦
副作用
- 歯牙の着色：妊婦、授乳中の女性、8歳以下の子供には避ける
- 日光過敏
- 催奇性：骨の発育阻害
- 菌交代症
テトラサイクリン系抗菌薬
「ドキシサイクリン」
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。