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セファクロル

セファクロル 化学構造式
53994-73-3
CAS番号.
53994-73-3
化学名:
セファクロル
别名:
ケフポリン;ルベラール;3-クロロ-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;(6R,7R)-7-[[(R)-アミノフェニルアセチル]アミノ]-3-クロロ-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;セファクロール;クリレール;ザルツクラール;ケフラール;エリカナール;エリカナール-L;シーシーエル;アレンフラール;L-シーシーエル;セファクロル;L-ケフラール;トキクロル;パノラール;セクロール;セクロダン;セファクロル (JP17)
英語化学名:
Cefaclor
英語别名:
S 6472;Kefral;Alfacet;panoral;CEFACLOR;Cefachlor;Cephaclor;Cefaclorum;lilly99638;Cefaclor CRS
CBNumber:
CB9390436
化学式:
C15H14ClN3O4S
分子量:
367.81
MOL File:
53994-73-3.mol

セファクロル 物理性質

沸点 :
713.4±60.0 °C(Predicted)
比重(密度) :
1.3575 (rough estimate)
屈折率 :
1.6100 (estimate)
貯蔵温度 :
Keep in dark place,Inert atmosphere,2-8°C
溶解性:
1 M HCl: 50 mg/mL, clear to very faintly turbid, yellow
酸解離定数(Pka):
pKa 1.5±0.2(H2O) (Uncertain)
外見 :
powder
色:
Crystal
水溶解度 :
10g/L(temperature not stated)
BRN :
8176092
CAS データベース:
53994-73-3(CAS DataBase Reference)
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
Sフレーズ  22-36/37-45
WGK Germany  2
RTECS 番号 XI0363000
HSコード  29349990
毒性 TDLo orl-cld: 131 mg/kg/7D-I:MSK,SKN CMAJAX 126,1032,82
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
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
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
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。
P342+P311 呼吸に関する症状が出た場合:医師に連絡すること。

セファクロル 価格 もっと(3)

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
Sigma-Aldrich Japan C6895 セファクロル
Cefaclor
53994-73-3 100mg ¥9840 2021-03-23 購入
Sigma-Aldrich Japan 72579 セファクロル analytical standard
Cefaclor analytical standard
53994-73-3 50mg ¥10300 2018-12-25 購入
Sigma-Aldrich Japan C6895 セファクロル
Cefaclor
53994-73-3 1g ¥45840 2021-03-23 購入

セファクロル 化学特性,用途語,生産方法

用途

第 1 世代セフェム系抗生物質 です。細菌の細胞壁合成を阻害することによ り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

ケフラール (共和薬品工業); ケフラール (共和薬品工業); ケフラール (共和薬品工業); セファクロル (シオノケミカル); セファクロル (シオノケミカル); セファクロル (日医工); セファクロル (日医工); セファクロル (東和薬品); セファクロル (沢井製薬); セファクロル (沢井製薬); セファクロル (辰巳化学); セファクロル (長生堂製薬); セファクロル (長生堂製薬); トキクロル (コーアイセイ)

説明

Cefaclor differs from cephalexin primarily in the bio-isosteric replacement of methyl by chlorine at C-3 and is quite acid stable, allowing oral administration. It also is quite stable to metabolism. It is less active against Gram-negative bacteria compared with the other second-generation cephalosporins but is more active against Gram-negative bacteria compared with the first-generation drugs.

化学的特性

white crystalline solid

Originator

Ceclor,Lilly,US,1979

使用

Cefaclor belongs to the family of antibiotics known as the cephalosporins (cefalosporins). The cephalosporins are broad-spectrum antibiotics that are used for the treatment of septicaemia, pneumonia, meningitis, biliary-tract infections, peritonitis, and

使用

radioopaque agent

定義

ChEBI: A cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.

Manufacturing Process

Preparation of 7-amino-3-chloro-3-cephem-4-carboxylic acid: To a solution of 750 mg (185 mmol) of p-nitrobenzyl 7amino-3-chloro-3cephem-4-carboxylate hydrochloride in 20 ml of tetrahydrofuran and 40 ml of methanol was added a suspension of 750 mg of prereduced 5% palladium on carbon catalyst in 20 ml of ethanol and the suspension was hydrogenated under 50 psi of hydrogen at room temperature for 45 minutes. The catalyst was filtered and washed with THF and water. The filtrate and catalyst washes were combined and evaporated to dryness, The residue was dissolved in a water-ethyl acetate mixture and the pH adjusted to pH 3. The insoluble product was filtered and triturated with acetone. The product was then dried to yield 115 mg of 7- amino-3-chloro-3-cephem-4-carboxylic acid.
Preparation of 7-(D-α-phenylglycylamido)-3-chloro-3-cephem-4-carboxylic acid: To a suspension of 280 mg (1.2 mmol) of 7-amino-3-chloro-3-cephem- 4-carboxylic acid in 14 ml of acetonitrile was added with stirring at room temperature 0.5 ml of N,O-bis-(trimethylsilyl)acetamide to form the soluble disilylmethyl derivative thereof. The solution was cooled to 0 C and was slowly added to a solution of the mixed anhydride formed by reacting 408 mg (1.5 mmol) of methyl-3-α-carboxybenzylaminocrotonate sodium salt with 161 mg (1.7 mmol) of methyl chloroformate in the presence to 2 drops of N,N-dimethylbenzyl amine in 7 ml of acetonitrile.
The mixture was stirred at ice bath temperature for 2 hours, 1 ml of methanol was added and the mixture was filtered to remove insoluble impurities. Two milliliters of water were added to the filtrate and the pH was adjusted momentarily to pH 1.5, to effect removal of the enamine block, and then to pH 4.5 with triethylamine. After stirring for an additional hour at ice bath temperature the reaction product, 7-(D-α-phenylglycylamido)-3-chloro-3- cephem-4-carboxylic acid (zwitterion) precipitated from the reaction mixture as a crystalline solid. The product was filtered, washed with acetonitrile and dried in vacuo to yield 200 mg.

brand name

Ceclor (Lilly); Raniclor (Ranbaxy).

Therapeutic Function

Antibiotic

抗菌性

It is less resistant than other group 2 cephalosporins to staphylococcal β-lactamase. It is active against N. gonorrhoeae and H. influenzae and against most enterobacteria, but it is susceptible to common enterobacterial β-lactamases. Pr. vulgaris and Providencia, Acinetobacter and Serratia spp. are resistant. B. fragilis and clostridia are resistant but other anaerobes are commonly susceptible.

薬物動態学

Oral absorption: c. 90%
Cmax 250 mg oral: c. 6–7 mg/L after 50 min
Plasma half-life: 0.5–1 h
Volume of distribution: 0.37 L
Plasma protein binding: 25%
Absorption
Food intake increases the time taken to reach peak plasma levels and reduces the peak by 25–50%. The actual amount absorbed is unaffected. In children receiving 15 mg/kg per day (maximum daily dose 1 g) the mean peak serum level was 16.8 mg/L at 0.5–1 h. There is no accumulation of the drug during repeated administration.
Distribution
In patients receiving 500 mg every 8 h for 10 days, concentrations were 0–1.7 (mean 0.5) mg/L in mucoid sputum and 0–2.8 (mean 1.0) mg/L in purulent sputum. In children with chronic serous otitis media receiving 15 mg/kg per day, the mean peak concentration in middle ear secretion was 3.8 mg/L within 30 min of the dose when the mean simultaneous serum concentration was 12.8 mg/L.
Metabolism and excretion No metabolites have been identified, but the drug probably chemically degrades in serum. About half of the dose is recovered from the urine in the first 6 h and 70% in 24 h. Probenecid prolongs the plasma levels but in renal insufficiency the plasma half-life is only moderately increased. In patients with creatinine clearance values of 5–15 mL/min the mean plasma elimination half-life rose to 2.3 h and the 24 h urinary excretion fell to less than 10%. In patients requiring intermittent hemodialysis and receiving 500 mg every 8 h for 10 days, the half-life rose to 2.9 h. Dialysis removed 34% of the dose

臨床応用

Cefaclor (Ceclor) is an orally active semisyntheticcephalosporin that was introduced in the American market in1979. It differs structurally from cephalexin in that the 3-methyl group has been replaced by a chlorine atom. It issynthesized from the corresponding 3-methylenecepham sulfoxideester by ozonolysis, followed by halogenation of theresulting β-ketoester. The 3-methylenecepham sulfoxideesters are prepared by rearrangement of the corresponding 6-acylaminopenicillanic acid derivative. Cefaclor is moderatelystable in acid and achieves enough oral absorption to provideeffective plasma levels (equal to about two-thirds of thoseobtained with cephalexin). The compound is apparentlyunstable in solution, since about 50% of its antimicrobial activityis lost in 2 hours in serum at 37°C. The antibacterialspectrum of activity is similar to that of cephalexin, but it isclaimed to be more potent against some species sensitiveto both agents. Currently, the drug is recommended for thetreatment of non–life-threatening infections caused by H.influenzae, particularly strains resistant to ampicillin.

臨床応用

Uses are similar to those of other group 2 cephalosporins. It is among the few suitable for use in respiratory infections because of its activity against H. influenzae.

副作用

Apart from mild gastrointestinal disturbance, the drug is well tolerated. Transiently increased transaminase levels and symptomatic vaginal candidosis have been noted. Clusters of a serum sickness-like illness have been described in children.

安全性プロファイル

Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: joints, dermatitis, increased body temperature. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Clí, SOx, an

Chemical Synthesis

Cefaclor, (6R,7R)-7-[(R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia- 1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.48), is synthesized from the most accessible antibiotic of this series, cefalotin (32.1.2.1), in which the carboxyl group is protected by esterification by a reaction with 4-nitrobenzylbromide in triethylamine, giving the 4-nitrobenzyl ester of 7-(2-thienylacetamido)-cephalosporanic acid (32.1.2.40). Reacting this with potassium ethyl xantogenate replaces the acetoxy group in the third position of the cephalosporin system, giving the corresponding S-derivative (32.1.2.41). Upon reducing this compound using zinc in formic acid, the product is desulfurized, giving the 4-nitrobenzyl ester of 3-exo-methylen-7-(2-thienylacetamido)-cefem-4-carboxylic acid (32.1.2.42). The exomethylene group is oxidized by ozone and the resulting dicarbonyl derivative tautomerizes to the enol form (32.1.2.43) upon reaction with sulfur anhydride. Then, the hydroxyl group is replaced with a chlorine atom upon reaction with thionyl chloride, giving the 4-nitrobenzyl ester of 3-chloro-7-(2-thienylacetamido)-3-cefem-4-carboxylic acid (32.1.2.44). The resulting product undergoes deacylation upon reaction with a mixture of pyridine with phosphorous pentachloride in isobutanol, forming the hydrochloride of 4-nitrobenzyl ester of 7-amino-3-chloro-3-cefem-4-carboxylic acid (32.1.2.45). This is acylated with an N-protected derivative of phenylglycine, (N-tert-butoxycarbonyl)-D-α-phenylglycine in the presence of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline in tetrahydrofuran, giving the product (32.1.2.46). The tert-butoxycarbonyl protection in this molecule is removed by heating in acetonitrile in the presence of p-toluenesulfonic acid. Finally, upon hydrogen reduction using zinc and hydrochloric acid in dimethylformamide, the 4-nitrobenzyl protecting group is removed from the resulting tosylate (32.1.2.47) giving cefaclor (32.1.2.48).

Veterinary Drugs and Treatments

Cefaclor may potentially be useful when an oral cephalosporin is desired to treat infections that are susceptible to it but resistant to first generation cephalosporins such as cephalexin or cefadroxil. Little information is available with regard to its clinical use in small animals, however.

セファクロル 上流と下流の製品情報

原材料

準備製品


セファクロル 生産企業

Global( 242)Suppliers
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53994-73-3(セファクロル)キーワード:


  • 53994-73-3
  • 8-(2-AMINO-2-PHENYL-ACETYL)AMINO-4-CHLORO-7-OXO-2-THIA-6-AZABICYCLO[4.2.0]OCT-4-ENE-5-CARBOXYLIC ACID
  • 7-(D-2-AMINO-2-PHENYLACETAMIDO)-3-CHLORO-3-CEPHEM-4-CARBOXYLIC ACID
  • CEFACLOR
  • (6R,7R)-7-[[(2S)-2-amino-1-oxo-2-phenylethyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(aminophenylacetyl)amino]-3-chloro-8-oxo-, [6R-[6α,7β(R*)]]-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-aminophenylacetyl]amino]-3-chloro-8-oxo-, (6R,7R)-
  • Alfacet
  • Kefral
  • S 6472
  • (6R,7R)-7-[[(R)-Aminophenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefaclor (Ceclor)
  • (6R,7R)-7-{[(2R)-2-AMINO-2-PHENYLACETYL]AMINO}-3-CHLORO-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID
  • Cefachlor
  • Cefaclorum
  • 7-(D-2-AMINO-2-PHENYLACETAMIDO)-3-CHLORO-3-CEPHEM-4-CARBOXYLIC
  • (6r-(6-alpha,7-beta(r*)))-ino)-3-chloro-8-oxo
  • 3-chloro-7-d-(2-phenylglycinamido)-3-cephem-4-carboxylicacid
  • 7-(D-2-Amino-2-phenylacetamido-3-chloro-3-cephem-4-carboxylicacidmonohydrate
  • Cephaclor
  • lilly99638
  • panoral
  • Cefaclor CRS
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-, (6R,7R)-
  • (6R,7R)-7-((R)-2-Amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefaclor USP/EP/BP
  • ケフポリン
  • ルベラール
  • 3-クロロ-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
  • (6R,7R)-7-[[(R)-アミノフェニルアセチル]アミノ]-3-クロロ-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
  • セファクロール
  • クリレール
  • ザルツクラール
  • ケフラール
  • エリカナール
  • エリカナール-L
  • シーシーエル
  • アレンフラール
  • L-シーシーエル
  • セファクロル
  • L-ケフラール
  • トキクロル
  • パノラール
  • セクロール
  • セクロダン
  • セファクロル (JP17)
  • セファロスポリン類
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