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エリスロマイシン

エリスロマイシン 化学構造式
114-07-8
CAS番号.
114-07-8
化学名:
エリスロマイシン
别名:
エリスロマイシン;プロピオシン;エリスロシン【抗生物質】;エリシン;E-マイシン;エリトロマイシンA;アイロタイシン;エリトロマイシン;エリスログラン;エリトロシナ;(-)-エリスロマイシン;エリスロマイシンA;ドチシン;エリスロ;マントミシナ;エリスロマイシン標準品(A,B,C混合物);(-)‐エリスロマイシン
英語化学名:
Erythromycin
英語别名:
em;emu;USP;knin;ERYC;Aknin;E.E.S;Emgel;Ergel;erycin
CBNumber:
CB8300078
化学式:
C37H67NO13
分子量:
733.93
MOL File:
114-07-8.mol

エリスロマイシン 物理性質

融点 :
133-135 °C
比旋光度 :
-74.5 º (c=2, ethanol)
沸点 :
719.69°C (rough estimate)
比重(密度) :
1.1436 (rough estimate)
屈折率 :
-74 ° (C=2, EtOH)
貯蔵温度 :
0-6°C
溶解性:
ethanol: soluble
外見 :
powder
酸解離定数(Pka):
8.8(at 25℃)
色:
white to faint yellow
光学活性 (optical activity):
[α]/D -78 to --71°
水溶解度 :
Soluble in water at 2mg/ml
Merck :
14,3681
BRN :
8183758
EPAの化学物質情報:
Erythromycin(114-07-8)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn,Xi
Rフレーズ  42/43-36/37/38
Sフレーズ  45-37-24-36-26-24/25
WGK Germany  2
RTECS 番号 KF4375000
3-4.3-10
国連危険物分類  3
HSコード  29415000
有毒物質データの 114-07-8(Hazardous Substances Data)
化審法 一般化学物質
絵表示(GHS)
注意喚起語
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H333 吸入すると有害のおそれ 急性毒性、吸入 5 P304+P312
H371 臓器の障害のおそれ 特定標的臓器有害性、単回暴露 2 警告 P260, P264, P270, P309+P311, P405,P501
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P303+P361+P353 皮膚(または髪)に付着した場合:直ちに汚染された衣 類をすべて脱ぐこと/取り除くこと。皮膚を流水/シャワー で洗うこと。
P405 施錠して保管すること。

エリスロマイシン 価格 もっと(56)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01FLC094643 エリスロマイシン
Erythromycin
114-07-8 1g ¥6600 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01FLC094643 エリスロマイシン
Erythromycin
114-07-8 5g ¥11900 2018-12-26 購入
東京化成工業 E0751 エリスロマイシン >98.0%(T)
Erythromycin >98.0%(T)
114-07-8 5g ¥6200 2018-12-04 購入
東京化成工業 E0751 エリスロマイシン >98.0%(T)
Erythromycin >98.0%(T)
114-07-8 25g ¥19200 2018-12-04 購入
関東化学株式会社(KANTO) 22733-2A エリスロマイシン 98%
Erythromycin 98%
114-07-8 25g ¥25200 2018-12-13 購入

エリスロマイシン MSDS


Erythromycin

エリスロマイシン 化学特性,用途語,生産方法

外観

白色の粉末

溶解性

エタノールに極めて易溶:アセトン、クロロホルム、アセトニトリル、酢酸エチルに易溶:エーテル、塩化エチレン、酢酸アミルに微溶:水には2mg/ml溶ける。エタノール及びアセトンに溶けやすく、水に極めて溶けにくい。

用途

エリスロマイシン (erythromycin) はマクロライド系抗生物質の1つである。製品名は「エリスロシン®」(マイランEPD合同会社製造販売)。抗菌スペクトルはペニシリンと類似するが若干幅広く、ペニシリンにアレルギーを持つ人に対してしばしば使用される。呼吸器系への感染症に関しては、マイコプラズマ?クラミドフィラなどの非定型微生物に対しても高い効果を持つが、市中肺炎の原因菌の一つであるインフルエンザ菌には抗菌活性を示さない。

用途

マクロライド系抗生物質です。 細菌リボソーム 50s に結合し、タンパク質合 成阻害作用を示します。グラム陽性・陰性菌 に抗菌作用を示します。

用途

薬理研究用、培地添加用。

化学的特性

White to off white crystalline powder

使用

Macrolide antibacterial

使用

Erythromycin A is a 14-membered macrocyclic lactone with broad spectrum antibiotic activity, isolated from Saccharopolyspora erythraea (formerly Streptomyces erythreus) in 1952. Erythromycin is one of only a handful of microbial metabolites to have profoundly shaped the treatment of bacterial disease in the last 50 years. Erythromycin has given rise to new generations of semi-synthetic derivatives with improved stability and potency. Our product has been HPLC-purified to remove contaminants and degradation products.

使用

For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections

使用

Labeled Erythromycin, intended for use as an internal standard for the quantification of Erythromycin by GC- or LC-mass spectrometry.

定義

An antibiotic produced by growth of Streptomyces erythreus Waksman. It is effective against infections caused by Gram-positive bacteria, including some β-hemolytic streptococci, pneumococci, and staphylococci.

brand name

Ilotycin (Dista).

抗菌性

Gram-positive rods, including Clostridium spp. (MIC50 0.1–1 mg/L), C. diphtheriae (MIC50 0.1–1 mg/L), L. monocytogenes (MIC50 0.1–0.3 mg/L) and Bacillus anthracis (MIC50 0.5–1.0 mg/L), are generally susceptible. Most strains of M. scrofulaceum and M. kansasii are susceptible (MIC50 0.5–2 mg/L), but M. intracellulare is often and M. fortuitum regularly resistant. Nocardia isolates are resistant. H. ducreyi, B. pertussis (MIC50 0.03–0.25 mg/L), some Brucella, Flavobacterium, Legionella (MIC50 0.1–0.5 mg/L) and Pasteurella spp. are susceptible. H. pylori (MIC 0.06–0.25 mg/L) and C. jejuni are usually susceptible, but C. coli may be resistant. Most anaerobic bacteria, including Actinomyces and Arachnia spp., are susceptible or moderately so, but B. fragilis and Fusobacterium spp. are resistant. T. pallidum and Borrelia spp. are susceptible, as are Chlamydia spp. (MIC ≤0.25 mg/L), M. pneumoniae and Rickettsia spp. M. hominis and Ureaplasma spp. are resistant.
Enterobacteriaceae are usually resistant. Activity rises with increasing pH up to 8.5. Incubation in 5–6% CO2 raises the MIC for H. influenzae from 0.5–8 to 4–32 mg/L; MICs for Str. pneumoniae and Str. pyogenes also rise steeply. Activity is predominantly bacteristatic.

獲得抵抗性

In Europe, the USA and other countries the incidence of resistance in Str. pneumoniae ranges from 5% to over 60%. In Str. pneumoniae strains resistant or intermediately susceptible to penicillin G, resistance rates above 80% have been reported. Increasing rates of resistance in clinical isolates of Str. pyogenes have also been reported, threatening its use as an alternative to penicillin G in allergic patients.
Lower rates of resistance have been reported in other bacterial species, including methicillin-resistant Staph. aureus, coagulase-negative staphylococci, Str. agalactiae, Lancefield group C and G streptococci, viridans group streptococci, H. pylori, T. pallidum, C. diphtheriae and N. gonorrhoeae.

一般的な説明

Early in 1952, McGuire et al. reported the isolation oferythromycin (E-Mycin, Erythrocin, Ilotycin) fromStreptomyces erythraeus. It achieved rapid early acceptanceas a well-tolerated antibiotic of value for the treatment ofvarious upper respiratory and soft-tissue infections causedby Gram-positive bacteria. It is also effective against manyvenereal diseases, including gonorrhea and syphilis, andprovides a useful alternative for the treatment of many infectionsin patients allergic to penicillins. More recently,erythromycin was shown to be effective therapy for Eatonagent pneumonia (Mycoplasma pneumoniae), venereal diseasescaused by Chlamydia, bacterial enteritis caused byCampylobacter jejuni, and Legionnaires disease.
The commercial product is erythromycin A, whichdiffers from its biosynthetic precursor, erythromycin B,in having a hydroxyl group at the 12-position of theaglycone. The chemical structure of erythromycin A was reportedby Wiley et al.197 in 1957 and its stereochemistry byCelmer198 in 1965. An elegant synthesis of erythronolide A,the aglycone present in erythromycin A, was described byCorey et al.
The amino sugar attached through a glycosidic link to C-5 is desosamine, a structure found in several other macrolideantibiotics. The tertiary amine of desosamine (3,4,6-trideoxy-3-dimethylamino-D-xylo-hexose) confers a basiccharacter to erythromycin and provides the means by whichacid salts may be prepared. The other carbohydrate structurelinked as a glycoside to C-3 is called cladinose (2,3,6-trideoxy-3-methoxy-3-C-methyl-L-ribo-hexose) and isunique to the erythromycin molecule.

応用例(製薬)

A natural antibiotic produced as a complex of six components (A–F) by Saccharopolyspora erythraea. Only erythromycin A has been developed for clinical use. It is available in a large number of forms for oral administration: the base compound (enteric- or film-coated to prevent destruction by gastric acidity); 2′-propionate and 2′-ethylsuccinate esters; a stearate salt; estolate and acistrate salts of 2′-esters. The 2′-esters and their salts have improved pharmacokinetic and pharmaceutical properties and are less bitter than erythromycin. It is also formulated as the lactobionate and gluceptate forparenteral use.

薬物動態学

absorption and metabolism
The acid lability of erythromycin base necessitates administration in a form giving protection from gastric acid. In acid media it is rapidly degraded (10% loss of activity at pH 2 in less than 4 s) by intramolecular dehydrogenation to a hemiketal and hence to anhydroerythromycin A, neither of which exerts antibacterial activity. Delayed and incomplete absorption is obtained from coated tablets and there is important inter- and intra-individual variation, adequate levels not being attained at all in a few subjects. Food delays absorption of erythromycin base. After 500 mg of the 2′-ethylsuccinyl ester, mean peak plasma levels at 1–2 h were 1.5 mg/L. In subjects given 1 g of the 2′-ethylsuccinate every 12 h for seven doses, the mean plasma concentration 1 h after the last dose was around 1.4 mg/L. Intra- and inter-subject variation and delayed and erratic absorption in the presence of food have not yet been eliminated by new formulations. Improved 500 mg preparations of erythromycin stearate are claimed to produce peak plasma levels of 0.9–2.4 mg/L that are little affected by the presence of food. 2′-Esters of erythromycin are partially hydrolyzed to erythromycin: 2′-acetyl erythromycin is hydrolyzed more rapidly than the 2′-propionyl ester, but more slowly than the 2′-ethylsuccinate.
The stoichiometric mixture with stearate does not adequately protect erythromycin from acid degradation. After an oral dose of erythromycin stearate, equivalent concentrations of erythromycin and its main degradation product, anhydroerythromycin, could be detected.
Doses of 10 mg/kg produced mean peak plasma concentrations around 1.8 mg/L in infants weighing 1.5–2 kg and 1.2 mg/L in those weighing 2–2.5 kg. In infants less than 4 months old, doses of 10 mg/kg of the 2′-ethylsuccinate every 6 h produced steady state plasma levels of around 1.3 mg/L. The apparent elimination half-life was 2.5 h. In children given 12.5 mg/kg of erythromycin 2′-ethylsuccinate every 6 h, the concentration in the plasma 2 h after the fourth dose was around 0.5–2.5 mg/L.
Distribution
Very low levels are obtained in cerebrospinal fluid (CSF), even in the presence of meningeal inflammation, and after parenteral administration. Levels of 0.1 mg/L in aqueous humor were found when the serum level was 0.36 mg/L, but there was no penetration into the vitreous. In children with otitis media given 12.5 mg/kg of erythromycin 2′- ethylsuccinate every 6 h, concentrations in middle ear exudate were 0.25–1 mg/L. In patients with chronic serous otitis media given 12.5 mg/kg up to a maximum of the equivalent of 500 mg, none was detected in middle ear fluid, but on continued treatment levels up to 1.2 mg/L have been described.
Penetration also occurs into peritoneal and pleural exudates. Mean concentrations of 2.6 mg/L have been found in sputum in patients receiving 1 g of erythromycin lactobionate intravenously every 12 h and 0.2–2 mg/L in those receiving an oral stearate formulation. Levels in prostatic fluid are about 40% of those in the plasma. Salivary levels of around 4 mg/L were found in subjects receiving doses of 0.5 g every 8 h at 5 h after a dose, when the plasma concentration was around 5.5 mg/L. Intracellular:extracellular ratios of 4–18 have been found in polymorphonuclear neutrophils.
Fetal tissue levels are considerably higher after multiple doses: when the mean peak maternal serum level was 4.94 (0.66–8) mg/L, the mean fetal blood concentration was 0.06 (0–0.12) mg/L. Concentrations were more than 0.3 mg/L in amniotic fluid and most other fetal tissues, but the concentrations were variable and unmeasurable in some. Erythromycin appears to be concentrated by fetal liver.
excretion
Erythromycin is excreted both in urine and in the bile but only a fraction of the dose can be accounted for in this way. Only about 2.5% of an oral dose or 15% of an intravenous dose is recovered unchanged in the urine. It is not removed to any significant extent by peritoneal dialysis or hemodialysis. Reported changes in apparent elimination half-life in renal impairment may be related to the saturable nature of protein binding. Fairly high concentrations (50–250 mg/L) are found in the bile. In cirrhotic patients receiving 500 mg of the base, peak plasma levels were higher and earlier than in healthy volunteers (2.0 and 1.5 mg/L at 4.6 and 6.3 h, respectively). The apparent elimination half-life was 6.6 h. It is possible that the smaller excretion of the 2′-propionyl ester in the bile in comparison to the base accounts in part for its better-maintained serum levels. There is some enterohepatic recycling, but some of the administered dose is lost in the feces, producing concentrations of around 0.5 mg/g.

副作用

Oral administration, especially of large doses, commonly causes epigastric distress, nausea and vomiting, which may be severe. Solutions are very irritant: intravenous infusions almost invariably produce thrombophlebitis. Cholestatic hepatitis occurs rarely. Transient auditory disturbances have been described after intravenous administration of the lactobionate salt, and occasionally in patients with renal and hepatic impairment in whom oral dosage has produced high plasma levels. Sensorineural hearing impairment can occur and, although this is usually a reversible effect which occurs at high dosage, can be permanent. Prolongation of the apparent elimination half-life of carbamazepine, due to inhibition of its conversion to the epoxide, usually results in central nervous system (CNS) disturbances. Nightmares are troublesome in some patients. Allergic effects occur in about 0.5% of patients.
The estolate is particularly prone to give rise to liver abnormalities, consisting of upper abdominal pain, fever, hepatic enlargement, a raised serum bilirubin, pale stools and dark urine and eosinophilia. The condition is rare and usually seen 10–20 days after the initiation of treatment, with complete recovery on stopping the drug. Recurrence of symptoms can be induced by giving the estolate but not the base or stearate. There is evidence that erythromycin estolate is more toxic to isolated liver cells than is the 2′-propionate or the base, and it is suggested that the essential molecular feature responsible for toxicity is the propionyl–ester linkage. The relative frequency of the reaction, its rapidity of onset (within hours) after second courses of the drug, evidence of hypersensitivity and the histological appearance suggest a mixture of hepatic cholestasis, liver cell necrosis and hypersensitivity. Abnormal liver function tests in patients receiving the estolate must be interpreted with caution, since increased levels of transaminases is often the only abnormality and some metabolites of the estolate can interfere with the measurement commonly used. Elevated levels of transaminases return to normal after cessation of treatment. Serum bilirubin is generally unchanged in these patients, but γ-glutamyl transpeptidase may also be affected.

安全性プロファイル

Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

純化方法

It recrystallises from H2O to form hydrated crystals which melt at ca 135-140o, resolidifies and melts again at 190-193o. The melting point after drying at 56o/8mm is that of the anhydrous material and is at 137-140o. Its solubility in H2O is ~2mg/mL. The hydrochloride has m 170o, 173o (from aqueous EtOH, EtOH/Et2O). [Flynn et al. J Am Chem Soc 76 3121 1954, constitution: Wiley et al. J Am Chem Soc 79 6062 1957]. [Beilstein 18/10 V 398.]

エリスロマイシン 上流と下流の製品情報

原材料

準備製品


エリスロマイシン 生産企業

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114-07-8(エリスロマイシン)キーワード:


  • 114-07-8
  • Erythromycin, Streptomyces erythreus - CAS 114-07-8 - Calbiochem
  • knin
  • (-)-ErythroMycin, Eur.Ph.
  • ErythroMycin COS/CGMP
  • StreptoMyces erythreus
  • ERYTHROMYCIN THICYANATE
  • Ilotycin, ErythroMycin
  • BRAND? USP BLAUBRAND? class AS graduated pipette
  • BRAND? volumetric flask, USP, BLAUBRAND
  • BRAND? volumetric flask BLAUBRAND? USP 27 conformity certified
  • BRAND? volumetric flask BLAUBRAND? USP conformity certified
  • BRAND? volumetric flask BLAUBRAND? USP
  • BRAND? USP BLAUBRAND? class A measuring cylinder, tall form
  • BRAND? USP BLAUBRAND? volumetric pipettes, one-mark
  • Bulb pipettes
  • abboticin
  • abomacetin
  • dotycin
  • em
  • emu
  • e-mycin
  • erycin
  • erycinum
  • erythrocin
  • erythrogran
  • erythroguent
  • erythromast36
  • erythromid
  • erythromycin,compdwithmonododecylsulfate,sodiumsalt
  • erythromycinsodiumlaurylsulfate
  • エリスロマイシン
  • プロピオシン
  • エリスロシン【抗生物質】
  • エリシン
  • E-マイシン
  • エリトロマイシンA
  • アイロタイシン
  • エリトロマイシン
  • エリスログラン
  • エリトロシナ
  • (-)-エリスロマイシン
  • エリスロマイシンA
  • ドチシン
  • エリスロ
  • マントミシナ
  • エリスロマイシン標準品(A,B,C混合物)
  • (-)‐エリスロマイシン
  • マクロライド系 (試験研究用抗生物質)
  • 抗生物質
  • 生化学
  • 試験研究用抗菌剤
  • マクロライド系抗生物質
  • 眼科用薬
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