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クロラムフェニコール

クロラムフェニコール 化学構造式
56-75-7
CAS番号.
56-75-7
化学名:
クロラムフェニコール
别名:
クロラムフェニコール;クロロシジンC;ケミセチン;D-クロランフェニコール;(1R,2R)-1-(4-ニトロフェニル)-2-[(ジクロロアセチル)アミノ]プロパン-1,3-ジオール;2,2-ジクロロ-N-[(αR,βR)-β-ヒドロキシ-α-ヒドロキシメチル-4-ニトロフェネチル]アセトアミド;アルフィセチン;シプラマイセト;クロロシジンCテトラン;クロマイ;シントミセチンR;D-トレオ-クロランフェニコール;クロマイコール;クロロカプス;ミクロセチナ;2,2-ジクロロ-N-[(1R,2R)-2-ヒドロキシ-1-(ヒドロキシメチル)-2-(4-ニトロフェニル)エチル]アセトアミド;レボミトセチン;[1R,2R,(±)]-1-(4-ニトロフェニル)-2-(ジクロロアセチルアミノ)-1,3-プロパンジオール;D-スレオクロラムフェニコール;スタノマイセチン
英語化学名:
Chloramphenicol
英語别名:
CAF;i337a;GCN5L;Enicol;Mychel;Opclor;u-6062;I 337A;GCN5L1;Ambofen
CBNumber:
CB3364529
化学式:
C11H12Cl2N2O5
分子量:
323.13
MOL File:
56-75-7.mol

クロラムフェニコール 物理性質

融点 :
148-150 °C(lit.)
比旋光度 :
19.5 º (c=6, EtOH)
比重(密度) :
1.6682 (rough estimate)
屈折率 :
20 ° (C=5, EtOH)
闪点 :
14 °C
貯蔵温度 :
2-8°C
溶解性:
absolute ethanol: soluble5-20mg/mL (as a stock solution)
外見 :
powder
色:
white
水溶解度 :
2.5 g/L (25 º C)
Merck :
14,2077
BRN :
2225532
InChIKey:
WIIZWVCIJKGZOK-RKDXNWHRSA-N
CAS データベース:
56-75-7(CAS DataBase Reference)
NISTの化学物質情報:
Chloramphenicol(56-75-7)
EPAの化学物質情報:
Acetamide, 2,2-dichloro-N-[(1R,2R)-2- hydroxy-1-(hydroxymethyl)- 2-(4-nitrophenyl)ethyl]-(56-75-7)
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  T,F
Rフレーズ  45-11-39/23/24/25-23/24/25
Sフレーズ  53-45-16-36/37
RIDADR  2811
WGK Germany  3
RTECS 番号 AB6825000
3-10
TSCA  Yes
国連危険物分類  3
国連危険物分類  IRRITANT
HSコード  29414000
有毒物質データの 56-75-7(Hazardous Substances Data)
PRTR法 第二種指定化学物質
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
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
H303 飲み込むと有害のおそれ 急性毒性、経口 5 P312
H333 吸入すると有害のおそれ 急性毒性、吸入 5 P304+P312
H340 遺伝性疾患のおそれ 生殖細胞変異原性 1A, 1B 危険
H350 発がんのおそれ 発がん性 1A, 1B 危険
H351 発がんのおそれの疑い 発がん性 2 警告 P201, P202, P281, P308+P313, P405,P501
H361 生殖能または胎児への悪影響のおそれの疑い 生殖毒性 2 警告 P201, P202, P281, P308+P313, P405,P501
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
H372 長期にわたる、または反復暴露により臓器の障 害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P314, P501
H373 長期にわたる、または反復暴露により臓器の障 害のおそれ 特定標的臓器有害性、単回暴露 2 警告 P260, P314, P501
注意書き
P201 使用前に取扱説明書を入手すること。
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
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。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ 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。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P405 施錠して保管すること。
P501 内容物/容器を...に廃棄すること。

クロラムフェニコール 価格 もっと(44)

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) W01CHDASB-00003428 クロラムフェニコール
Chloramphenicol
56-75-7 1g ¥16800 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00003429 クロラムフェニコール
Chloramphenicol
56-75-7 250mg ¥28300 2018-12-26 購入
東京化成工業 C2255 クロラムフェニコール >98.0%(HPLC)(T)
Chloramphenicol >98.0%(HPLC)(T)
56-75-7 250g ¥22600 2018-12-04 購入
東京化成工業 C2255 クロラムフェニコール >98.0%(HPLC)(T)
Chloramphenicol >98.0%(HPLC)(T)
56-75-7 25g ¥4300 2018-12-04 購入
関東化学株式会社(KANTO) 08162-96 クロラムフェニコール標準品 >98.0%(HLC)
Chloramphenicol standard >98.0%(HLC)
56-75-7 200mg ¥5400 2018-12-13 購入

クロラムフェニコール MSDS


Chloromycetin

クロラムフェニコール 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〜結晶性粉末

溶解性

水, エーテルに難溶。エタノール, 酢酸エチルに可溶。メタノール, エタノールに易溶、水, エーテルに難溶。エタノールに溶けやすく、水に溶けにくい。

用途

作用機序の研究用。

用途

クロラムフェニコール (Chloramphenicol) は、バクテリア Streptomyces venezuelae 由来の抗生物質であり、現在は化学合成によって作られている。 類似化合物にフロルフェニコールがあるが、こちらは動物のみでヒトには用いられていない。 クロラムフェニコールはグラム陽性、陰性にかかわらず、多くの微生物に対して有効であるが、再生不良性貧血を含む骨髄の損傷など人体に重大な副作用があるため、先進国においては腸チフスなど重大で生命の危機がある感染症、もしくは多剤耐性のため本剤以外に選択肢がない場合にのみ用いられる。

用途

培地添加剤、食品中の残留クロラムフェニコールの分析、耐性菌の研究。

用途

クロラムフェニコール系抗生 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。抗菌スペ クトルは広く、多くの細菌やリケッチケアな どに抗菌力を示します。

用途

クロラムフェニコール系抗生 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。抗菌スペ クトルは広く、多くの細菌やリケッチケア等 に抗菌力を示します。

効能

抗生物質, 抗リケッチア, タンパク質合成阻害薬

商品名

クロマイ (アルフレッサファーマ); クロラムフェニコール (富士製薬工業); クロラムフェニコール (日東メディック); クロロマイセチン (アルフレッサファーマ); クロロマイセチン (アルフレッサファーマ); クロロマイセチン (アルフレッサファーマ); クロロマイセチン (アルフレッサファーマ); ハイセチン (富士製薬工業)

確認試験

(1) 本品の定量法で得た試料溶液につき,紫外可視吸光度 測定法〈2.24〉により吸収スペクトルを測定し,本品のスペ クトルと本品の参照スペクトル又はクロラムフェニコール標 準品について同様に操作して得られたスペクトルを比較する とき,両者のスペクトルは同一波長のところに同様の強度の 吸収を認める.
(2) 本品につき,赤外吸収スペクトル測定法〈2.25〉の臭 化カリウム錠剤法により試験を行い,本品のスペクトルと本 品の参照スペクトル又はクロラムフェニコール標準品のスペ クトルを比較するとき,両者のスペクトルは同一波数のとこ ろに同様の強度の吸収を認める.

定量法

本品及びクロラムフェニコール標準品約0.1g(力価)に 対応する量を精密に量り,それぞれをメタノール20mLに溶 かし,水を加えて正確に100mLとする.この液20mLずつを 正確に量り,それぞれに水を加えて正確に100mLとする. 更に,この液10mLずつを正確に量り,それぞれに水を加え て正確に100mLとし,試料溶液及び標準溶液とする.試料 溶液及び標準溶液につき,紫外可視吸光度測定法〈2.24〉に より波長278nmにおける吸光度AT及びASを測定する.
クロラムフェニコール(C11H12Cl2N2O5)の量[μg(力価)] =MS × AT/AS × 1000
MS:クロラムフェニコール標準品の秤取量[mg(力価)]

純度試験

(1) 重金属〈1.07〉 本品1.0gをとり,第2法により操作し, 試験を行う.比較液には鉛標準液2.5mLを加える(25ppm以 下).
(2) ヒ素〈1.11〉 本品2.0gをとり,第4法により検液を調 製し,試験を行う(1ppm以下).
(3) 類縁物質 本品0.10gをメタノール10mLに溶かし, 試料溶液とする.この液1mLを正確に量り,メタノールを 加えて正確に100mLとし,標準溶液(1)とする.標準溶液 (1)10mLを正確に量り,メタノールを加えて正確に20mLと し,標準溶液(2)とする.これらの液につき,薄層クロマト グラフィー〈2.03〉により試験を行う.試料溶液,標準溶液 (1)及び標準溶液(2)20μLずつを薄層クロマトグラフィー用シ リカゲル(蛍光剤入り)を用いて調製した薄層板にスポットす る.次にクロロホルム/メタノール/酢酸(100)混液(79: 14:7)を展開溶媒として約15cm展開した後,薄層板を風乾 する.これに紫外線(主波長254nm)を照射するとき,試料溶 液から得た主スポット及び原点のスポット以外のスポットは, 標準溶液(1)から得たスポットより濃くない.また,試料溶 液から得た主スポット及び原点のスポット以外のスポットの合計は,2.0%以下である.

貯法

容器 気密容器.

乾燥減量

0.5%以下(1g,105℃,3時間).

強熱残分

0.1%以下(1g).

化学的特性

White to grey-white crystalline powder

化学的特性

Chloramphenicol is a white to grayish-white or yellowish-white crystalline solid.

使用

antibacterial, antirickettsial, inhibits protein synthesis

使用

Chloramphenicol is unusual nitroaromatic metabolite produced by Streptomyces venezuelae, first published in 1947. Chloramphenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Although restricted to ocular use, antibiotic resistance to other classes has refocused attention on this class. Chloramphenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Chloramphenicol has been extensively studied with over 35,000 literature citations.

使用

Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial

定義

ChEBI: An organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions.

brand name

Chloromycetin (Parke-Davis);Acne-sol;Acnoxin;Actimac;Actinac;Alficetyn susp.;Altabactin;Ambrasynth;Amphemycin-prednisonum;Ampliomicetin;Amseclim;Angimidone;Angiters;Antibiopto;Aquapred;Armacol;Arrlicetin;Aviatrin;Balkamycin;B-cpct;Bemacol;Berlicetin;Biofeniol;Biophtas;Biotocap;Bismophenyl;Bitencyl;C. o fluo-fenicol;C. o hidrocor-clora;Cafenolo;Calmina;Campiol;Caosol;Cavumycetina;Ccombinado balsamico;Ccorticol;Cebenicol;Chemibal;Chemyzin;Chloramfenicol;Chloramol;Chloramphenicol intervetra;Chloramphenicol-pos;Chloramphycin;Chloramplast;Chloramson;Chloranfeni-mck;Chloranfeni-opipno;Chloranfeni-otico;Chloranfeni-ungena;Chloreptic;Chlorical;Chloroantibion;Chlorocortal;Chlorofair;Chloroject s;Chloromex;Chloromik;Chloromimyxin;Chloromycetin kapseals;Chloromycetin palmitate;Chloroptic p. oint.;Chlorostrep;Clorbiotina;Clorbis supp.;Cloromicetin;Cloromycetin;Cloroptic farmicetina;Clorosyntex;Colidene;Colimy-c;Cortican;Cortidermale;Cortimisin;Cortiphenicol;Cortison-quemicet;Cortivert;Cutispray no. 4;Cyphenicol;Cysticat;Davuron sedante;Dectamicina;Delta optil;Devamycetin;Dexa-biofinicol;Dorsec;Duphenicol;Econoclor;Ejificol strept;Ejificol sulfa;Elase chloromycel;Enttocetrin;Erittronicol;Erteilen;Esterofenil;Estevecicina cloranfenico;Extracicilina;Fago-praxin;Fluorobioptal;Furacol l;Furamecetil alpha magna;Furamecetil magna;Furatrimon;Furokatin;Gammaphenicol;Ginetris;Gino-dectacil;Gliscol;Globveticol;Goticas;Nova-phenicol;Novoclorocap;Oftan;Ophthaphenicol;Opthalon;Oralmisetin;Otiprin;Otopred ear drops;Pantofenicol;Parcyclin;Pedimycetin;Pentocetina;Pertaril;Pimabiciron;Pinimentac;Plastoderma;Prednomycetine;Procusulf;Protercicline;Prurivet;Pulmo vinco;Quitrase antibiotico;Ranphenicol;Ranstrepcol;Reclor;Redidropsol;Renegen;Reocetin;Reostop;Rheofin;Rivomycin sulfa;Rolintrex;Roncovita;Ronphenil;Roscomycin;Rovictor;Samaphenicol;Scanicoline;Scieramycetin;Sergo-amigdalar;Serviclofen;Sigmicilina;Sintomitsin;Snophenicol;Soludectancil;Sopamycetin;Spasmo-paraxin;Spersanicol;Strepticine;Streptoglobenicol;Streptophenicol;Subital supp.;Suismycetin;Sulfaglobenicol;Sulfamycetin;Synthomycetina;Synthophtone;Tardomyocel;Tega-cetin;Tetrachlorasone;Tetracol;Tetranfen;Tetraphenicol;Tetra-phenicol oculos;Tiframilk;Tiromycetin;Toramin;Transicetina;Transpulmycin;Tribiotic;Trophen;Troymycetin;Tusolone;Tycloran;Uro-gliscal 500;Uroletten-s;Uroplex 4;Ut forte;Uvomycin;Variolan;V-crayolan;Vetical;Vetophenicol;Viceton;Viklorin;Virogin;Vitaklorin;Vsmpozim;Wintetil;Zoppib spray blu;Gotimycetin;Ichthoseptal;Iruxolum;Isicetina;Isopto fenicol;Kavipe;Kloramfex.

世界保健機関(WHO)

Chloramphenicol, an antibiotic isolated from Streptomyces venezuelae in 1947, first became available for general clinical use in 1948. By 1950 it was evident that its use could cause serious, sometimes fatal, blood dyscrasias. However, it remains one of the most effective antibiotics for treating invasive typhoid fever and salmonellosis, some rickettsioses and serious infections caused by Haemophilus influenzae or anaerobic organisms. This is considered to justify its retention in the WHO Model List of Essential Drugs. (Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO Expert Committee, 722, , 1985)

抗菌性

It is active against a very wide range of organisms. Minimum inhibitory concentrations (MICs) (mg/L) for other organisms are: Staphylococcus epidermidis, 1–8; Corynebacterium diphtheriae, 0.5–2; Bacillus anthracis, 1–4; Clostridium perfringens, 2–8; Mycobacterium tuberculosis, 8–32; Legionella pneumophila, 0.5–1; Bordetella pertussis, 0.25–4; Brucella abortus, 1–4; Campylobacter fetus, 2–4; Pasteurella spp., 0.25–4; Serratia marcescens, 2–8; Burkholderia pseudomallei, 4–8. Most Gramnegative bacilli are susceptible, but Pseudomonas aeruginosa is resistant. Leptospira spp., Treponema pallidum, chlamydiae, mycoplasmas and rickettsiae are all susceptible, but Nocardia spp. are resistant. It is widely active against anaerobes, including Actinomyces israelii (MIC 1–4 mg/L), Peptostreptococcus spp. (MIC 0.1–8 mg/L), and Fusobacterium spp. (MIC 0.5–2 mg/L), but Bacteroides fragilis is only moderately susceptible (MIC about 8 mg/L).
It is strictly bacteristatic against almost all bacterial species, but exerts a bactericidal effect at 2–4 times the MIC against some strains of Gram-positive cocci, Haemophilus influenzae and Neisseria spp. The minimum bactericidal concentrations (MBCs) for penicillin-resistant pneumococci are often significantly higher than those for penicillin- susceptible strains, although this cannot be detected by conventional disk susceptibility testing or MIC determination. Its bacteristatic effect may inhibit the action of penicillins and other β-lactam antibiotics against Klebsiella pneumoniae and other enterobacteria in vitro, but the clinical significance of this is doubtful. The presence of ampicillin does not affect the bactericidal effect of chloramphenicol on H. influenzae.

獲得抵抗性

The prevalence of resistant strains in many Gram-positive and Gram-negative organisms reflects usage of the antibiotic. Over-the-counter sales are believed to have compounded the problem in some countries. For example, it has long been the drug of choice for the treatment of typhoid and paratyphoid fevers, but widespread use led to a high prevalence of resistant Salmonella enterica serotype Typhi. Outbreaks of infection caused by chloramphenicol-resistant S. Typhi have been seen since the early 1970s. Use of co-trimoxazole and fluoroquinolones in typhoid has resulted in a decline in chloramphenicol resistance in some endemic areas. Many hospital outbreaks caused by multiresistant strains of enterobacteria, notably Enterobacter, Klebsiella and Serratia spp., have been described.
Plasmid-borne resistance was first noted in shigellae in Japan and subsequently spread widely in Central America, where it was responsible for a huge outbreak. Strains of S. Typhi resistant to many antibiotics including chloramphenicol are particularly common in the Indian subcontinent. Resistance in shigellae is also relatively common in some parts of the world.
Resistant strains of H. influenzae (some also resistant to ampicillin), Staph. aureus and Streptococcus pyogenes are also encountered. Most N. meningitidis strains remain susceptible,but high-level resistance (MIC >64 mg/L) due to the production of chloramphenicol acetyltransferase has been described; the nucleotide sequence of the resistance gene was indistinguishable from that found on a transposon in Cl. perfringens. Resistant strains of Enterococcus faecalis are relatively common, and resistance to chloramphenicol is found in some multiresistant pneumococci.
Resistance in Staph. aureus is caused by an inducible acetyltransferase; additionally, the cfr (chloramphenicol– florfenicol resistance) gene encodes a 23S rRNA methyltransferase that also confers resistance to linezolid. In Escherichia coli, the capacity to acetylate chloramphenicol (at least three enzymes are involved) is carried by R factors. Replacement of the 3-OH group, which is the target of acetylation, accounts for the activity of fluorinated analogs against strains resistant to chloramphenicol and thiamphenicol. The resistance of B. fragilis and some strains of H. influenzae is also due to elaboration of a plasmid-encoded acetylating enzyme; in others it is due to reduced permeability resulting from loss of an outer membrane protein. Some resistant bacteria reduce the nitro group or hydrolyze the amide linkage. Resistance of Ps. aeruginosa is partly enzymic and partly due to impermeability.

危険性

Has deleterious and dangerous side effects. Must conform to FDA labeling requirements. Use is closely restricted. Probable carcinogen.

接触アレルゲン

This broad spectrum phenicol group antibiotic has been implicated in allergic contact dermatitis. Cross-sensitivity to thiamphenicol is possible, but not systematic.

薬物動態学

Oral absorption: 80–90%
Cmax 500 mg oral: 10–13 mg/L after 1–2 h
Plasma half-life: 1.5–3.5 h
Volume of distribution: 0.25–2 L/kg
Plasma protein binding: c. 25–60%
Absorption
The plasma concentration achieved is proportional to the dose administered. Suspensions for oral administration to children contain chloramphenicol palmitate, a tasteless and bacteriologically inert compound, which is hydrolyzed in the gut to liberate chloramphenicol. Following a dose of 25 mg/kg, peak plasma levels around 6–12 mg/L are obtained, but there is much individual variation.
Pancreatic lipase is deficient in neonates and, because of poor hydrolysis, the palmitate should be avoided. In very young infants, deficient ability to form glucuronides, and low glomerular and tubular excretion greatly prolong the plasma half-life. For parenteral use, chloramphenicol sodium succinate, which is freely soluble and undergoes hydrolysis in the tissues with the liberation of chloramphenicol, can be injected intravenously or in small volumes intramuscularly. The plasma concentrations after administration by these routes are unpredictable, and approximate to only 30–70% of those obtained after the same dose by the oral route. Protein binding is reduced in cirrhotic patients and neonates, with correspondingly elevated concentrations of free drug.
Distribution
Free diffusion occurs into serous effusions. Penetration occurs into all parts of the eye, the therapeutic levels in the aqueous humor being obtained even after local application of 0.5% ophthalmic solution. Concentrations obtained in cerebrospinal fluid (CSF) in the absence of meningitis are 30–50% of those of the blood and greater in brain. It crosses the placenta into the fetal circulation and appears in breast milk.
Metabolism
It is largely inactivated in the liver by conjugation with glucuronic acid or by reduction to inactive arylamines; clearance of the drug in patients with impaired liver function is depressed in relation to the plasma bilirubin level. It has been suggested that genetically determined variance of hepatic glucuronyl transferase might determine the disposition and toxicity of the drug.
Excretion
It is excreted in the glomerular filtrate, and in the newborn elimination may be impaired by the concomitant administration of benzylpenicillin, which is handled early in life by the same route. Inactive derivatives are eliminated partly in the glomerular filtrate and partly by active tubular secretion. Over 24 h, 75–90% of the dose appears in the urine, 5–10% in biologically active forms and the rest as metabolites, chiefly as a glucuronide conjugate. Excretion diminishes linearly with renal function and at a creatinine clearance of <20 ml/min, maximum urinary concentrations are 10–20 mg/L rather than the 150–200 mg/L found in normal subjects. Because of metabolism, blood levels of active drug are only marginally elevated in renal failure, but microbiologically inactive metabolites accumulate. The plasma half-life of the products in the anuric patient is around 100 h, and little is removed by peritoneal or hemodialysis. Dosage modification is normally unnecessary in renal failure as the metabolites are less toxic than the parent compound. About 3% of the administered dose is excreted in the bile, but only 1% appears in the feces, and this mostly in inactive forms.
Interactions
Induction of liver microsomal enzymes, for example by phenobarbital (phenobarbitone) or rifampicin (rifampin), diminishes blood levels of chloramphenicol; conversely, chloramphenicol, which inhibits hepatic microsomal oxidases, potentiates the activity of dicoumarol (dicumarol), phenytoin, tolbutamide and those barbiturates that are eliminated by metabolism. It also depresses the action of cyclophosphamide, which depends for its cytotoxicity on transformation into active metabolites. It is uncertain whether this interaction may lead to a clinically significant level of inhibition of the activity of cyclophosphamide. The half-life of chloramphenicol is considerably prolonged if paracetamol (acetaminophen) is given concurrently, and co-administration of these drugs should be avoided.

臨床応用

Typhoid fever and other severe infections due to salmonellae
Rickettsial infections
Meningitis
Invasive infection caused by H. influenzae
Destructive lung lesions involving anaerobes
Eye infections (topical)
Reference is made to its use in cholera, plague, tularemia and bartonellosis, melioidosis, Whipple’s disease and relapsing fever. In enteric fever in adults, fluoroquinolones are associated with a lower clinical relapse rate. Treatment for other serious infections should be restricted to organisms that are resistant or much less susceptible to other antibiotics. A study in low resource countries found ampicillin plus gentamicin superior to injectable chloramphenicol for the treatment of very severe communityacquired pneumonia in children.
It has been used with varying success to treat infections caused by glycopeptide-resistant enterococci. Meningitis caused by penicillin-resistant pneumococci responds poorly, apparently due to failure to achieve bactericidal concentrations in CSF. It should never be given systemically for minor infections. Topical use in the treatment of eye infections is controversial given the unsubstantiated risk of bone marrow aplasia. A placebo-controlled study in children with infective conjunctivitis in the community found no clinical benefit in the use of chloramphenicol eye drops.
The daily dose should not normally exceed 2 g, and the duration of the course should be limited (e.g. 10 days). Although patients may show toxic manifestations after receiving very little drug, the danger is almost certainly increased by excessive or repeated dosage or by the treatment of patients with impaired hepatic or renal function, including those at the extremes of life. The wide pharmacokinetic variability of the antibiotic in neonates makes monitoring of serum concentrations advisable. Determination of full blood counts should be carried out twice weekly.

副作用

Glossitis, associated with overgrowth of Candida albicans, is fairly common if the course of treatment exceeds 1 week. Stomatitis, nausea, vomiting and diarrhea may occur, but are uncommon. Hypersensitivity reactions are very uncommon. Jarisch–Herxheimer-like reactions have been described in patients treated for brucellosis, enteric fever and syphilis.
Bone marrow effects
Chloramphenicol exerts a dose-related but reversible depressant effect on the marrow of all those treated, resulting in vacuolization of erythroid and myeloid cells, reticulocytopenia and ferrokinetic changes indicative of decreased erythropoiesis. Evidence of bone-marrow depression is regularly seen if the plasma concentration exceeds 25 mg/L, and leukopenia and thrombocytopenia may be severe. There is no evidence that this common marrow depression is the precursor of potentially fatal aplasia, which differs in that it is fortunately rare, late in onset, usually irreversible and may follow the smallest dose. Aplasia can follow systemic, oral and even ophthalmic administration and may be potentiated by cimetidine. Liver disease, uremia and pre-existing bone marrow dysfunction may increase the risk. It is unusual for manifestations to appear during treatment, and the interval between cessation of treatment and onset of dyscrasia can be months. A few patients survive with protracted aplasia, and myeloblastic leukemia then often supervenes.
It is thought that the toxic agent is not chloramphenicol itself but an as yet unidentified metabolite. Chloramphenicol is partially metabolized to produce oxidized, reduced and conjugated products. The toxic metabolite may be a shortlived product of reduction of the nitro group, which damages DNA by helix destabilization and strand breakage.
Predisposition to aplasia may be explained by genetically determined differences in metabolism of the agent. Risk of fatal aplastic anemia has been estimated to increase 13-fold on average treatment with 4 g of chloramphenicol. Corresponding increases are 10-fold in patients treated with mepacrine (quinacrine) and 4-fold in patients treated with oxyphenbutazone.
Children
Infants given large doses may develop exceedingly high plasma levels of the drug because of their immature conjugation and excretion mechanisms. A life-threatening disorder called the ‘gray baby’ syndrome, characterized by vomiting, refusal to suck and abdominal distention followed by circulatory collapse, may appear when the plasma concentration exceeds 20 mg/L. If concentrations reach 200 mg/L, the disorder can develop in older children or even adults.
Optic neuritis has been described in children with cystic fibrosis receiving prolonged treatment for pulmonary infection. Most improve when the drug is discontinued, but central visual acuity can be permanently impaired. There is some experimental evidence that ear drops containing 5% chloramphenicol sodium succinate can damage hearing. One study identified an increased risk of acute leukemia following childhood administration of chloramphenicol, particularly for durations exceeding 10 days.

安全性プロファイル

Confirmed human carcinogen producing leukemia, aplastic anemia, and other bone marrow changes. Experimental tumorigenic data. Poison by intravenous and subcutaneous routes. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by an unknown route: changes in plasma or blood volume, unspecified liver effects, and hemorrhaging. Experimental teratogenic and reproductive effects. Human mutation data reported. An antibiotic. When heated to decomposition it emits very toxic fumes of NOx and Cl-. See also other chloramphenicol entries.

職業ばく露

An antibiotic derived from streptomyces venezuelae. A potential danger to those involved in the manufacture, formulation, and application of this antibiotic and antifungal agent

Veterinary Drugs and Treatments

Chloramphenicol is used for a variety of infections in small animals and horses, particularly those caused by anaerobic bacteria. The FDA has prohibited the use of chloramphenicol in animals used for food production because of the human public health implications.

Carcinogenicity

Chloramphenicol is reasonably anticipated to be a human carcinogen, based on limited evidence of carcinogenicity from studies in humans.

代謝経路

Six metabolites of chloramphenicol are identified, among which the sulfate conjugate is characterized in goat urine.

輸送方法

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1- Poisonous materials, Technical Name Required.

純化方法

Purify chloramphenicol by recrystallisation from H2O (solubility is 2.5mg/mL at 25o) or ethylene dichloride as needles or long plates, and by sublimation at high vacuum. It has A 1cm 298 at max 278nm, and it is slightly soluble in H2O (0.25%) and propylene glycol (1.50%) at 25o but is freely soluble in MeOH, EtOH, BuOH, EtOAc and Me2CO. [Relstock et al. J Am Chem Soc 71 2458 1949, Confroulis et al. J Am Chem Soc 71 2463 1949, Long & Troutman J Am Chem Soc 71 2469, 2473 1949, Ehrhart et al. Chem Ber 90 2088 1957, Beilstein 13 IV 2742.]

不和合性

Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines), releasing substantial heat, water, and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur).

廃棄物の処理

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

法令条例

Food and Drug Administration (FDA)
Chloramphenicol is a prescription drug subject to specific labeling requirements.
Extra-label use of chloramphenicol in food-producing animals is prohibited.
Chloramphenicol in ophthalmic and topical dosage form and in tablet form must not be used in animals producing meat, eggs, or milk.

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