fradiomycin

フラジオマイシン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/04 00:55:49」(JST)

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Neomycin

Systematic (IUPAC) name
(2RS,3S,4S,5R)-5-amino-2-(aminomethyl)-6-((2R,3S,4R,5S)-5-((1R,2R,5R,6R)-3,5-diamino-2-((2R,3S,4R,5S)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yloxy)-6-hydroxycyclohexyloxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yloxy)tetrahydro-2H-pyran-3,4-diol
Clinical data
Trade names	Neo-rx
AHFS/Drugs.com	monograph
MedlinePlus	a682274
Pregnancy category	US: D (Evidence of risk)
Legal status	OTC
Routes of administration	Topical, Oral
Pharmacokinetic data
Bioavailability	0% Oral, Unknown Topical,
Protein binding	N/A
Metabolism	N/A
Biological half-life	2 to 3 hours
Identifiers
CAS Registry Number	1404-04-2 Y
ATC code	A01AB08 A07AA01, B05CA09, D06AX04, J01GB05, R02AB01, S01AA03, S02AA07, S03AA01
PubChem	CID: 8378
IUPHAR/BPS	709
DrugBank	DB00994 Y
ChemSpider	8075 Y
UNII	I16QD7X297 Y
KEGG	D08260 Y
ChEBI	CHEBI:7508 Y
ChEMBL	CHEMBL449118 N
Synonyms	Framycetin
Chemical data
Formula	C23H46N6O13
Molecular mass	614.644 g/mol
SMILES O([C@H]3[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@H]1O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]1N)[C@H]2O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4N)CN
InChI InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7+,8?,9+,10+,11-,12+,13+,14-,15+,16-,17+,18-,19+,20-,21+,22-,23-/m0/s1 N Key:PGBHMTALBVVCIT-DPNHOFNISA-N N
N (what is this?)  (verify)

Neomycin is an aminoglycoside antibiotic found in many topical medications such as creams, ointments, and eyedrops. The discovery of neomycin dates back to 1949. It was discovered in the lab of Selman Waksman, who was later awarded the Nobel Prize in Physiology or Medicine in 1951. Neomycin belongs to aminoglycoside class of antibiotics that contain two or more aminosugars connected by glycosidic bonds. Due to the inherent oto- and nephrotoxicity of these substances, systemic use has declined, as safer alternatives have become available.

Uses

Neomycin is typically used as a topical preparation, such as Neosporin. It can also be given orally, where it is usually combined with other antibiotics. Neomycin is not absorbed from the gastrointestinal tract and has been used as a preventive measure for hepatic encephalopathy and hypercholesterolemia. By killing bacteria in the intestinal tract, it keeps ammonia levels low and prevents hepatic encephalopathy, especially prior to GI surgery. It has also been used to treat small intestinal bacterial overgrowth. It is not given via injection, as neomycin is extremely nephrotoxic (causes kidney damage), even when compared to other aminoglycosides. The exception is when neomycin is included, in very small quantities, as a preservative in some vaccines – typically 0.025 mg per dose.

Molecular biology

Neomycin resistance is conferred by either one of two aminoglycoside phosphotransferase genes. A neo gene is commonly included in DNA plasmids used by molecular biologists to establish stable mammalian cell lines expressing cloned proteins in culture; many commercially available protein expression plasmids contain neo as a selectable marker. Non-transfected cells will eventually die off when the culture is treated with neomycin or similar antibiotic. Neomycin or kanamycin can be used for prokaryotes, but geneticin (G418) is, in general, needed for eukaryotes.

Spectrum

Similar to other aminoglycosides, neomycin has excellent activity against Gram-negative bacteria, and has partial activity against Gram-positive bacteria. It is relatively toxic to humans, and many people have allergic reactions to it. See: Hypersensitivity. Physicians sometimes recommend using antibiotic ointments without neomycin, such as Polysporin. The following represents MIC susceptibility data for a few medically significant Gram-negative bacteria.

• Enterobacter cloacae: >16 μg/ml
• Escherichia coli: 1 μg/ml
• Proteus vulgaris: 0.25 μg/ml

Composition

Standard grade neomycin is composed of a number of related compounds including neomycin A (neamine), neomycin B (framycetin), neomycin C, and a few minor compounds found in much lower quantities. Neomycin B is the most active component in neomycin followed by neomycin C and neomycin A. Neomycin A is not a unique structure, but rather a compositional degradation product of the C and B isomers. The quantities of these components in neomycin vary from lot-to-lot depending on the manufacturer and manufacturing process.

Safety

Patch test

In 2005–06, neomycin was the fifth-most-prevalent allergen in patch test results (10.0%).

History

Neomycin was discovered in 1949 by the microbiologist Selman Waksman and his student Hubert Lechevalier at Rutgers University. It is produced naturally by the bacterium Streptomyces fradiae. Synthesis requires specific nutrient conditions in either stationary or submerged aerobic conditions. The compound is then isolated and purified from the bacterium.

DNA binding

Aminoglycosides such as neomycin are known for their ability to bind to duplex RNA with high affinity. The association constant for neomycin with A-site RNA has been found to be in the 10⁹ M⁻¹ range. However, more than 50 years after its discovery, its DNA-binding properties were still unknown. Neomycin has been shown to induce thermal stabilization of triplex DNA, while having little or almost no effect on the B-DNA duplex stabilization. Neomycin was also shown to bind to structures that adopt A-form structure, triplex DNA being one of them. Neomycin also includes DNA:RNA hybrid triplex formation.

References

English Journal

• Prevalence, patterns of use, and socio-demographic factors of self medication with antibiotics in Yogyakarta City Indonesia: cross sectional population based survey.

• Widayati A, Suryawati S, de Crespigny C, Hiller JE.AbstractABSTRACT: Self medication with antibiotics has become an important factor driving antibiotic resistance. This study investigated the period prevalence, patterns of use, and socio-demographic factors associated with self medication with antibiotics in Yogyakarta City Indonesia. This cross-sectional population-based survey used a pre-tested questionnaire which was self-administered to randomly selected respondents (over 18 years old) in Yogyakarta City Indonesia in 2010 (N=625). Descriptive statistics, chi-square and logistic regression were applied. A total of 559 questionnaires were analyzed (response rate = 90%). The period prevalence of self medication with antibiotics during the month prior to the study was 7.3 %. Amoxicillin was the most popular (77%) antibiotic for self medication besides ampicillin, fradiomycin-gramicidin, tetracycline, and ciprofloxacin to treat the following symptoms: the common-cold including cough and sore throat, headache, and other minor symptoms; with the length of use was mostly less than five days. Doctors or pharmacists were the most common source of information about antibiotics for self medication (52%). Antibiotics were usually purchased without prescription in pharmacies (64%) and the cost of the purchases was commonly less than US $1 (30%). Previous experience was reported to be the main reason for using non-prescribed antibiotics (54%). There were no socio-demographic variables significantly associated with the actual practice of using non-prescribed antibiotics. However, gender, health insurance, and marital status were significantly associated with the intent to self medicate with antibiotics (P < 0.05). Being male (Odds Ratio = 1.7 (1.2 - 2.6)) and having no health insurance (Odds Ratio = 1.5 (1.0 -2.3)) is associated with the intent to self medicate with antibiotics. Usage of non-prescribed antibiotics as well as intent of doing so is common across socio-demographic categories. Given the findings, factors influencing people's intentions to self medicate with antibiotics are required to be investigated to better understand such behavior. Impact of health insurance coverage on self medication with antibiotics should also be further investigated.
• BMC research notes.BMC Res Notes.2011 Nov 11;4(1):491. [Epub ahead of print]
• ABSTRACT: Self medication with antibiotics has become an important factor driving antibiotic resistance. This study investigated the period prevalence, patterns of use, and socio-demographic factors associated with self medication with antibiotics in Yogyakarta City Indonesia. This cross-sectional p
• PMID 22078122

• Antimicrobial Activity and Frequency of Spontaneous Gentamicin-resistant Mutants in Bacteria Related Skin Infections.

• Iwaki M, Noguchi N, Nakaminami H, Sasatsu M, Ito M.SourceDepartment of Microbiology, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences.
• Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.Yakugaku Zasshi.2011;131(11):1653-9.
• Gentamicin is used in an ointment form for the treatment of skin infections. To investigate the effect of gentamicin used as an ointment, the antimicrobial susceptibilities against Staphylococcus aureus, coagulase-negative staphylococci, Streptococcus pyogenes, and Pseudomonas aeruginosa isolated fr
• PMID 22041705

Japanese Journal

• 症例 リン酸ベタメタゾン・硫酸フラジオマイシン配合剤による接触皮膚炎の1例

• 山村 里恵,敷地 孝法
• 皮膚科の臨床 53(8), 1137-1142, 2011-08
• NAID 40018942662

• 皮膚感染症関連菌に対するゲンタマイシンの抗菌力と突然変異耐性菌出現頻度

• 岩木 真生,野口 雅久,中南 秀将 [他],笹津 備規,伊藤 正俊
• YAKUGAKU ZASSHI 131(11), 1653-1659, 2011
• … To investigate the effect of gentamicin used as an ointment, the antimicrobial susceptibilities against Staphylococcus aureus, coagulase-negative staphylococci, Streptococcus pyogenes, and Pseudomonas aeruginosa isolated from community and medical settings were studied and compared with other antibacterial agents such as fradiomycin, chloramphenicol, and bacitracin used as active ingredient for each ointment. …
• NAID 130001491121

• 症例 扁平苔癬に続発した硫酸フラジオマイシンによる接触皮膚炎--当初外陰部Paget病を疑った1例

• 矢田 康子,安田 正人,永井 弥生 [他]
• 皮膚科の臨床 52(9), 1259-1262, 2010-09
• NAID 40017288956

Related Links

• フラジオマイシン【fradiomycin】の意味 - 国語辞書 - goo辞書

フラジオマイシン【fradiomycin】とは。意味や解説。アミノグリコシド系抗生物質。眼疾患や腸管感染症などに用いられる。副作用が強い。 - goo辞書は国語、英和、和英、中国語、百科事典等からまとめて探せる辞書検索サービスです。

• 医薬品インタビューフォーム - 製品情報｜田辺三菱製薬 医療 ...

Ⅱ．名称に関する項目 1．販売名 （1）和名： フルコート F （2）洋名： FLUCORT F （3）名称の由来： ハイドロコーチゾンにF（フッ素）が導入された化合物であることより。フラジオマイシン硫酸塩（Fradiomycin Sulfate）を添加したフル ...

Related Pictures

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★リンクテーブル★

リンク元	「ネオマイシン」「FRM」

「ネオマイシン」

　　[★]

英

neomycin NM

同

硫酸フラジオマイシン fradiomycin sulfate フラジオマイシン fradiomycin fradiomycinum FRM、フラマイセチン framycetin

商

フラジオ、(軟膏)ソフラチュール、(軟膏)(フラジオマイシン・フルオシノロン)フルコート、デルモラン、(軟膏)(フラジオマイシン・クロラムフェニコール)クロマイ、ハイセチン、(軟膏)(フラジオマイシン・メチルプレドニゾロン)ネオメドロール、(軟膏)(フラジオマイシン・バシトラシン)バラマイシン、(軟膏)(フラジオマイシン・ヒドロコルチゾン)プロクトセディル、(軟膏)(フラジオマイシン・ヒドロコルチゾン・ジフェンヒドラミン)レスタミンコーチゾン、(軟膏)(フラジオマイシン・ベタメタゾン)ベトネベート、(含嗽)デンターグル、(点眼・点鼻)(ベタメタゾン・フラジオマイシン)ベルベゾロン、リンデロン、(噴霧液)(プレドニゾロン・フラジオマイシン)エアゾリン、(噴霧液)(コリスチン・フラジオマイシン)コリマイフォーム、(その他)フランセチン、ヘモレックス

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ja

ネオマイシン : 約 76,000 件
フラジオマイシン : 約 20,000 件

en

neomycin : 約 1,170,000 件
fradiomycin : 約 18,200 件

• 抗菌薬

• 蛋白合成阻害

• アミノグリコシド系抗菌薬

「FRM」

　　[★] フラジオマイシン fradiomycin