WordNet

a yellow crystalline antibiotic (trademark Terramycin) obtained from a soil actinomycete; used to treat various bacterial and rickettsial infections (同)hydroxytetracycline, oxytetracycline_hydrochloride, Terramycin

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/16 16:52:08」(JST)

wiki en

Oxytetracycline was the second of the broad-spectrum tetracycline group of antibiotics to be discovered.

Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection and the remaining bacteria are killed by the immune system or eventually die.

Oxytetracycline is a broad-spectrum antibiotic, active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections.

Oxytetracycline is still used to treat infections caused by Chlamydia (e.g. the chest infection psittacosis, the eye infection trachoma, and the genital infection urethritis) and infections caused by Mycoplasma organisms (e.g. pneumonia).

Oxytetracycline is also used to treat acne, due to its activity against the bacteria on the skin that cause acne (Propionibacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against the bacteria usually responsible, Haemophilus influenzae. Oxytetracycline may also be used to treat other rarer infections, such as those caused by a group of micro-organisms called rickettsiae (e.g. Q fever). To make sure the bacteria causing an infection are susceptible to it, a tissue sample is usually taken, for example a swab from the infected area, or a urine or blood sample.

Oxytetracycline was patented in 1949 and came into commercial use in 1950.^[1]

Medical uses

Oxytetracycline, like other tetracyclines, is used to treat many infections, both common and rare (see Tetracycline antibiotics group). Its better absorption profile makes it preferable to tetracycline for moderately severe acne at a dosage of 250–500 mg four times a day for usually six to eight weeks at a time, but alternatives should be sought if no improvement occurs by three months.^[2] Avoid milk, iron, zinc or indigestion remedies while taking oxytetracycline. Take before food or on an empty stomach. Always follow your doctors' instructions and instruction leaflet.

It is sometimes used to treat spirochaetal infections, clostridial wound infection and anthrax in patients sensitive to penicillin. Oxytetracycline is used to treat infections of the respiratory and urinary tracts, skin, ear, eye and gonorrhoea, although its use for such purposes has declined in recent years due to large increases in bacterial resistance to this class of drugs. The drug is particularly useful when penicillins and/or macrolides cannot be used due to allergy. It may be used to treat Legionnaire's disease as a substitute for a macrolide or quinolone.

Oxytetracycline is especially valuable in treating nonspecific urethritis, Lyme disease, brucellosis, cholera, typhus, tularaemia. and infections caused by Chlamydia, Mycoplasma and Rickettsia. Doxycycline is now preferred to oxytetracycline for many of these indications because it has improved pharmacologic features.

The standard dose is 250–500 mg six-hourly by mouth. In particularly severe infections, this dose may be increased accordingly. Occasionally, oxytetracycline is given by intramuscular injection or topically in the form of creams, ophthalmic ointments or eye drops.

Side effects

Side effects are mainly gastrointestinal and photosensitive allergic reactions common to the tetracycline antibiotics group. It can also damage calcium-rich organs, such as teeth and bones, although this is very rare. It sometimes causes nasal cavities to erode; quite commonly, the BNF suggests, because of this, tetracyclines should not be used to treat pregnant or lactating women and children under 12 except in certain conditions where it has been approved by a specialist because there are no obvious substitutes. Candidiasis (thrush) is not uncommon following treatment with broad-spectrum antibiotics.

History

It was first found near Pfizer laboratories in a soil sample yielding the soil actinomycete, Streptomyces rimosus by Finlay et al. In 1950, a celebrated American chemist, Robert B Woodward, worked out the chemical structure of oxytetracycline, enabling Pfizer to mass-produce the drug under the trade name, Terramycin. This discovery by Woodward was a major advancement in tetracycline research and paved the way for the discovery of an oxytetracycline derivative, doxycycline, which is one of the most popularly used antibiotics today.

Veterinary indications

Oxytetracycline is used to control the outbreak of American foulbrood and European foulbrood in honeybees.

Oxytetracycline can also be used to correct breathing disorders in livestock. It is administered in a powder or through an intramuscular injection. American livestock producers apply oxytetracycline to livestock feed to prevent diseases and infections in cattle and poultry. The antibiotic is partially absorbed in the gastrointestinal tract of the animal and the remaining is deposited in manure. Researchers at the Agricultural Research Service studied the breakdown of oxytetracycline in manure depending on various environmental conditions. They found the breakdown slowed with increased saturation of the manure and concluded this was a result of decreased oxygen levels. [1] This research helps producers understand the effects of oxytetracycline in animal feed on the environment, bacteria, and antimicrobial resistance.

References

^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 9783527607495.
^ British National Formulary 45 March 2003

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. テトラサイクリン tetracyclines
2. 眼性酒さ ocular rosacea
3. リケッチア痘瘡 rickettsialpox
4. 外陰部の扁平苔癬 vulvar lichen planus
5. 酒さのマネージメント management of rosacea

English Journal

Adsorption and removal of tetracycline antibiotics from aqueous solution by graphene oxide.

Gao Y, Li Y, Zhang L, Huang H, Hu J, Shah SM, Su X.SourceDepartment of Analytical Chemistry, College of Chemistry, Jilin University, Changchun 130012, China.
Journal of colloid and interface science.J Colloid Interface Sci.2012 Feb 15;368(1):540-6. Epub 2011 Nov 15.
Significant concerns have been raised over pollution of antibiotics including tetracyclines in aquatic environments in recent years. Graphene oxide (GO) is a potential effective absorbent for tetracycline antibiotics and can be used to remove them from aqueous solution. Tetracycline strongly deposit
PMID 22138269

Preparation of activated carbon derived from cotton linter fibers by fused NaOH activation and its application for oxytetracycline (OTC) adsorption.

Sun Y, Yue Q, Gao B, Li Q, Huang L, Yao F, Xu X.SourceShandong Provincial Key Laboratory of Water Pollution Control and Resource Reuse, School of Environmental Science and Engineering, Shandong University, Jinan 250100, China.
Journal of colloid and interface science.J Colloid Interface Sci.2012 Feb 15;368(1):521-7. Epub 2011 Nov 6.
The objective of this research is to produce high surface area-activated carbon derived from cotton linter fibers by fused NaOH activation and to examine the feasibility of removing oxytetracycline (OTC) from aqueous solution. The cotton linter fibers activated carbon (CLAC) was characterized by N(2
PMID 22137171

Zoonotic bacteria, antimicrobial use and antimicrobial resistance in ornamental fish: a systematic review of the existing research and survey of aquaculture-allied professionals.

Weir M, Rajić A, Dutil L, Cernicchiaro N, Uhland FC, Mercier B, Tuševljak N.SourceDepartment of Population Medicine, Ontario Veterinary College, University of Guelph, Guelph, Ontario, Canada.
Epidemiology and infection.Epidemiol Infect.2012 Feb;140(2):192-206. Epub 2011 Sep 12.
Using systematic review methodology, global research reporting the frequency of zoonotic bacterial pathogens, antimicrobial use (AMU) and antimicrobial resistance (AMR) in ornamental fish, and human illness due to exposure to ornamental fish, was examined. A survey was performed to elicit opinions o
PMID 21906415

Japanese Journal

Treatment of tetracycline antibiotics by laccase in the presence of 1-hydroxybenzotriazole

Suda Tomoyo,Hata Takayuki,Kawai Shingo,Okamura Hideo,Nishida Tomoaki
Bioresource technology 103(1), 498-501, 2011-10-20
… In this study, tetracycline (TC), chlortetracycline (CTC), doxycycline (DC) and oxytetracycline (OTC) were treated with laccase from the white rot fungus Trametes versicolor in the presence of the redox mediator 1-hydroxybenzotriazole (HBT). …
NAID 120003535063

Application of α-glucosidase activity and drug susceptibility tests to epidemiological studies on the fish pathogen Nocardia seriolae

ISMAIL Tamer Fawzy,TAKESHITA Akira,UMEDA Naoko,ITAMI Toshiaki,YOSHIDA Terutoyo
Fisheries science : FS 77(1), 113-118, 2011-01-01
NAID 10027411228

ホルトノキ萎黄病罹病木におけるオキシテトラサイクリン製剤樹幹注入後のオキシテトラサイクリン濃度およびファイトプラズマ検出

河辺祐嗣,津田城栄,松浦邦昭 [他]
樹木医学研究 15(3), 97-101, 2011
NAID 40018970532

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」「オキシテトラサイクリン」「OTC」
拡張検索	「oxytetracycline hydrochloride」

「テトラサイクリン系抗菌薬」

Oxytetracycline
Clinical data
Pregnancy; category	AU: D; US: D (Evidence of risk); ;
Routes of; administration	Oral, Ophthalmic
ATC code	D06AA03 (WHO) G01AA07 (WHO) J01AA06 (WHO) S01AA04 (WHO) QG51AA01 (WHO) QJ51AA06 (WHO)
Legal status
Legal status	Prescription only;
Pharmacokinetic data
Biological half-life	6-8 hours
Excretion	Renal
Identifiers
	IUPAC name (4S,4aR,5S,5aR,6S,12aS) -4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy -6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene -2-carboxamide;
CAS Number	79-57-2
PubChem (CID)	54675779
DrugBank	DB00595
ChemSpider	10482174
UNII	SLF0D9077S
KEGG	D00205
ChEBI	CHEBI:27701
ChEMBL	CHEMBL1517
PDB ligand ID	OAQ (PDBe, RCSB PDB)
E number	E703 (Citation needed) (antibiotics)
ECHA InfoCard	100.001.103
Chemical and physical data
Formula	C22H24N2O9
Molar mass	460.434 g/mol
3D model (Jmol)	Interactive image
	SMILES CN(C)[C@@H]3C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@@](C)(O)[C@H]2[C@H](O)[C@@H]34 ;
	InChI InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1 ; Key:IWVCMVBTMGNXQD-PXOLEDIWSA-N ;
(verify)

　　[★]

英: tetracyclines antibiotics
関: 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