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セファレキシン

セファレキシン 化学構造式
15686-71-2
CAS番号.
15686-71-2
化学名:
セファレキシン
别名:
タイセレキシン;セポレックス;L-ラスポリジン;セポレキシン;セファザール;セファレキシン(無水物);ケフレックス;イワレキシン;ガラシン;シーエックス;セファレキシン;スシラリン;トキオレキシン;メピラシン;デランテール;センセファリン;マドレキシン;セファロマックス;L-キサール;(6R)-7α-[(R)-2-アミノ-2-フェニルアセチルアミノ]-3-メチル-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
英語化学名:
Cephalexin
英語别名:
cex;s6437;syncl;oracef;oroxin;keforal;larixin;CEPOREX;Cefadal;Cefadin
CBNumber:
CB1210543
化学式:
C16H17N3O4S
分子量:
347.39
MOL File:
15686-71-2.mol

セファレキシン 物理性質

融点 :
196-198°C
比旋光度 :
[α]D20 +144~+158° (c=0.5, H2O) (Calculated on dehydrous basis)
沸点 :
727.4±60.0 °C(Predicted)
比重(密度) :
1.3040 (rough estimate)
屈折率 :
1.6320 (estimate)
貯蔵温度 :
2-8°C
溶解性:
NH4OH 1 M: 50 mg/mL, clear, yellow
酸解離定数(Pka):
5.2, 7.3(at 25℃)
外見 :
neat
PH:
pH (5g/l, 25℃) 3.5~5.5
水溶解度 :
12.5g/L(25 ºC)
Merck :
13,1986
InChIKey:
AVGYWQBCYZHHPN-CYJZLJNKSA-N
CAS データベース:
15686-71-2(CAS DataBase Reference)
EPAの化学物質情報:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)- (15686-71-2)
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
Rフレーズ  42/43
Sフレーズ  22-36/37-45
WGK Germany  3
RTECS 番号 XI0350000
HSコード  29419000
有毒物質データの 15686-71-2(Hazardous Substances Data)
毒性 TDLo orl-hmn: 14 mg/kg/D:GIT AACHAX -,361,68
絵表示(GHS)
注意喚起語 Danger
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
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H317 アレルギー性皮膚反応を起こすおそれ 感作性、皮膚 1 警告 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 重篤な眼の損傷 眼に対する重篤な損傷性/眼刺激 性 1 危険 P280, P305+P351+P338, P310
H334 吸入するとアレルギー、喘息または、呼吸困難 を起こすおそれ 感作性、呼吸器 1 危険 P261, P285, P304+P341, P342+P311,P501
H401 水生生物に毒性 水生環境有害性、急性毒性 2 P273, P501
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P284 呼吸用保護具を着用すること。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P342+P311 呼吸に関する症状が出た場合:医師に連絡すること。

セファレキシン 価格 もっと(5)

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) W01W0103-1105 セファレキシン
Cefalexin
15686-71-2 5g ¥3800 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01W0103-1105 セファレキシン
Cefalexin
15686-71-2 25g ¥10000 2018-12-26 購入
Sigma-Aldrich Japan 33989 セファレキシン VETRANAL?, analytical standard
Cefalexin VETRANAL?, analytical standard
15686-71-2 100mg-r ¥20600 2018-12-25 購入
Sigma-Aldrich Japan PHR1848 Pharmaceutical Secondary Standard; Certified Reference Material
Cephalexin Pharmaceutical Secondary Standard; Certified Reference Material
15686-71-2 1g ¥21700 2018-12-25 購入
富士フイルム和光純薬株式会社(wako) W01W0103-2237 セファレキシン標準品
Cefalexin Standard
15686-71-2 100mg ¥20000 2018-12-26 購入

セファレキシン 化学特性,用途語,生産方法

外観

白色~わずかにうすい黄色, 結晶性粉末~粉末

溶解性

水に溶ける。

用途

薬理研究用。

用途

第 1 世代セフェム系抗生物質 です。ペニシリン結合タンパク質に結合し、 細胞壁の合成阻害作用を示します。抗菌スペ クトルは狭いが、ブドウ球菌などに抗菌作用 を示します。

用途

第 1 世代のセファロスポリン 系抗生物質です。ペニシリン結合タンパクに 結合し、細胞壁の合成阻害作用を示します。 抗菌スペクトルは狭いが、ブドウ球菌等に抗 菌作用を示します。

効能

抗生物質, 細胞壁合成阻害薬

商品名

ケフレックス (共和薬品工業); ケフレックス (共和薬品工業); ケフレックス (共和薬品工業); ケフレックス (共和薬品工業); セファレキシン (日医工); セファレキシン (日医工); セファレキシン (東和薬品); セファレキシン (東和薬品); セファレキシン (東和薬品); セファレキシン (長生堂製薬); ラリキシン (富士フイルム富山化学); ラリキシン (富士フイルム富山化学)

説明

Use of the ampicillin-type side chain conveys oral activity to cephalexin. Whereas it no longer has an activating side chain at C-3 and, as a consequence, is somewhat less potent, it does not undergo metabolic deactivation and, thus, maintains potency. It is rapidly and completely absorbed from the GI tract and has become quite popular. Somewhat puzzling is the fact that the use of the ampicillin side chain in the cephalosporins does not result in a comparable shift in antimicrobial spectrum. Cephalexin, like the other first-generation cephalosporins is active against many Gram-positive aerobic cocci but is limited against Gram-negative bacteria. It is a widely used drug, particularly against Gram-negative bacteria causing urinary tract infections, Gram-positive infections (Staphyl ococcus aureus, Streptococcus pneumoni ae and Streptococcus pyogenes) of soft tissues, pharyngitis, and minor wounds.

化学的特性

White cryst. powder

Originator

Ceporex,Glaxo,UK,1970

使用

Antibacterial.

定義

ChEBI: A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and G am-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.

Manufacturing Process

To a 1 liter flask containing dimethylformamide at 0°C, was added 24.8 g sodium N-(2-methoxycarbonyl-1-methylvinyl)-D-α-phenylglycine (prepared from sodium D-α-phenylglycine and methyl acetoacetate). The mixture was cooled to -40°C and methyl chloroformate (7.5 ml) and dimethylbenzylamine (0.26 ml) added. After stirring for 25 minutes, p-nitrobenzyl 7- aminodesacetoxycephalosporanate (32.8 g) in the form of its hydrochloride salt was added, followed by triethylamine (12.1 ml) and dimethylformamide (140 ml) over a period of 20 minutes. The reaction mixture was stirred for 2 hours at -25°C to -35°C, then warmed to 0°C and water (32 ml) added. To the resultant solution, hydrochloric acid (54 ml) was added followed by zinc (21.8 g) in portions over a period of 5 minutes, the temperature being maintained at 5°C to 10°C. Further hydrochloric acid (35 ml) was added and the solution stirred at 15°C to 20°C for 7 hours.
The pH was adjusted to 3.3 with triethylamine and semicarbazidehydrochloride (9.5 g) added. The mixture was brought back to pH 3 with further triethylamine, then stirred for 30 minutes at pH 3. The resultant mixture was adjusted slowly over 4 hours to pH 6.8 by addition of triethylamine, seeding being carried out when pH 4.5 was reached. The precipitated cephalexin was filtered off, washed with dimethylformamide (200 ml) and the cephalexin recovered, yield 75%.

brand name

Keflex (Panixine (Ranbaxy).

Therapeutic Function

Antibiotic

抗菌性

It is resistant to staphylococcal β-lactamase. Gram-positive rods and fastidious Gram-negative bacilli, such as Bordetella spp. and H. influenzae, are relatively resistant. It is active against a range of enterobacteria, but it is degraded by many enterobacterial β-lactamases. Citrobacter, Edwardsiella, Enterobacter, Hafnia, Providencia and Serratia spp. are all resistant. Gram-negative anaerobes other than B. fragilis are susceptible. Because of its mode of action it is only slowly bactericidal to Gram-negative bacilli.

薬物動態学

Oral absorption: >90%
Cmax 500 mg oral: c. 10–20 mg/L after 1 h
Plasma half-life: 0.5–1 h
Volume of distribution: 15 L
Plasma protein binding: 10–15%
Absorption and distribution
It is almost completely absorbed when given by mouth, the peak concentration being delayed by food. Intramuscular preparations are not available: injection is painful and produces delayed peak plasma concentrations considerably lower than those obtained by oral administration.
In synovial fluid, levels of 6–38 mg/L have been described after a 4 g oral dose, but penetration into the CSF is poor. Useful levels are achieved in bone (9–44 mg/kg after 1 g orally) and in purulent sputum. Concentrations of 10–20 mg/L have been found in breast milk. Concentrations in cord blood following a maternal oral dose of 0.25 g were minimal.
Metabolism and excretion
It is not metabolized. Almost all the dose is recoverable from the urine within the first 6 h, producing urinary concentrations exceeding 1 g/L. The involvement of tubular secretion is indicated by the increased plasma peak concentration and reduced urinary excretion produced by probenecid. Renal clearance is around 200 mL/min and is depressed in renal failure, although a therapeutic concentration is still obtained in the urine. It is removed by peritoneal and hemodialysis. Some is excreted in the bile, in which therapeutic concentrations may be achieved.

臨床応用

Cephalexin, 7α-(D-amino-α-phenylacetamido)-3-methylcephemcarboxylicacid (Keflex, Keforal), was designed purposelyas an orally active, semisynthetic cephalosporin. Theoral inactivation of cephalosporins has been attributed to twocauses: instability of the β-lactam ring to acid hydrolysis(cephalothin and cephaloridine) and solvolysis or microbialtransformation of the 3-methylacetoxy group (cephalothin,cephaloglycin). The α-amino group of cephalexin renders itacid stable, and reduction of the 3-acetoxymethyl to a methylgroup circumvents reaction at that site.
Cephalexin occurs as a white crystalline monohydrate. Itis freely soluble in water, resistant to acid, and absorbed wellorally. Food does not interfere with its absorption. Becauseof minimal protein binding and nearly exclusive renal excretion,cephalexin is recommended particularly for the treatmentof urinary tract infections. It is also sometimes used forupper respiratory tract infections. Its spectrum of activity isvery similar to those of cephalothin and cephaloridine.Cephalexin is somewhat less potent than these two agentsafter parenteral administration and, therefore, is inferior tothem for the treatment of serious systemic infections.

臨床応用

As for group 2 cephalosporins . It should not be used in infections in which H. influenzae is, or is likely to be, implicated. It should not be used as an alternative to penicillin in syphilis.

副作用

Nausea, vomiting and abdominal discomfort are relatively common. Pseudomembranous colitis has been described and overgrowth of Candida with vaginitis may be troublesome. Otherwise, mild hypersensitivity reactions and biochemical changes common to cephalosporins occur. Very rare neurological disturbances have been described, particularly in patients in whom very high plasma levels have been achieved. There are rare reports of Stevens–Johnson syndrome and toxic epidermal necrolysis.

安全性プロファイル

Poison by intraperitoneal route.Moderately toxic by ingestion and other routes. An experimental teratogen. Other experimental reproductiveeffects. Human systemic effects by ingestion: nausea,vomiting, and diarrhea. When heated to decomposition itemits

Veterinary Drugs and Treatments

There are no approved cephalexin products for veterinary use in the USA. However, it has been used clinically in dogs, cats, horses, rabbits, ferrets, and birds, particularly for susceptible Staphylococcal infections.

セファレキシン 上流と下流の製品情報

原材料

準備製品


セファレキシン 生産企業

Global( 272)Suppliers
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15686-71-2(セファレキシン)キーワード:


  • 15686-71-2
  • (6r-(6alpha,7beta(r*)))-ino)-3-methyl-8-oxo
  • 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((aminophenylacetyl)am
  • 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-(2-amino-2-phenylaceta
  • 7-(d-2-amino-2-phenylacetamido)-3-methyl-delta(sup3)-cephem-4-carboxylica
  • 7-(d-2-amino-2-phenylacetamido)-3-methyl-delta3-cephem-4-carboxylicacid
  • 7-(d-alpha-aminophenylacetamido)desacetoxycephalosporanicacid
  • 7-beta-(d-alpha-amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxyli
  • cefa-iskia
  • cefaloto
  • ceporexin
  • cex
  • d-mido)-3-methyl-8-oxo
  • keforal
  • larixin
  • lexibiotico
  • lilly66873
  • madlexin
  • neolexina
  • oracef
  • oroxin
  • ortisporina
  • s6437
  • sartosona
  • sencephalin
  • syncl
  • (6R,7R)-7-((R)-2-AMINO-2-PHENYL-ACETYLAMINO)-3-METHYL-8-OXO-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID
  • 7-(D-ALPHA-AMINO-PHENYLACETAMIDO)-3-METHYL-3-CEPHEME-4-CARBOXYLIC ACID
  • CEPOREX
  • CEPOREXINE
  • CEPHALEXIN
  • タイセレキシン
  • セポレックス
  • L-ラスポリジン
  • セポレキシン
  • セファザール
  • セファレキシン(無水物)
  • ケフレックス
  • イワレキシン
  • ガラシン
  • シーエックス
  • セファレキシン
  • スシラリン
  • トキオレキシン
  • メピラシン
  • デランテール
  • センセファリン
  • マドレキシン
  • セファロマックス
  • L-キサール
  • (6R)-7α-[(R)-2-アミノ-2-フェニルアセチルアミノ]-3-メチル-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
  • サリテックス
  • 3-メチル-7β-[[(R)-アミノフェニルアセチル]アミノ]セファム-3-エン-4-カルボン酸
  • オラセフ
  • オーレキシン
  • オラコシン
  • オロキシン
  • ケホラール
  • セファレキシン-R
  • キサール
  • (6R,7R)-7-[[(R)-アミノフェニルアセチル]アミノ]-3-メチル-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
  • L-ケフレックス
  • L-パシビドール
  • セポール
  • シンクル
  • パリトレックス
  • ママレキシン
  • ラリキシン
  • シポミン
  • セファレックスSR
  • セフロング
  • リラネザ-ル
  • セゴラミン
  • 7(Dαアミノαフェニルアセトアミド)3メチル3セフェン4カルボン酸
  • セファレキシン標準品
  • セファレキシン (JP17)
  • セファロスポリン類
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