Chloramphenicol CAS 56-75-7
Introduction：Basic information about Chloramphenicol CAS 56-75-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Chloramphenicol Basic informationDescription Chemical Properties Uses Antimicrobial Spectrum Mechanism of action Pharmacokinetics Indications resistance Drug interactions Adverse reactions and precautions Methods of production
| Product Name: | Chloramphenicol |
| Synonyms: | ,[theta-(theta,theta)]-;[R-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]ethanamide;2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-acetamid;2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-,[R-(R*,R*)]-Acetamide;2,2-dichloro-n-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-acetamid;Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl);Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,R*)]-;Acetamide, 2,2-dichloro-N-[beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)- |
| CAS: | 56-75-7 |
| MF: | C11H12Cl2N2O5 |
| MW: | 323.13 |
| EINECS: | 200-287-4 |
| Product Categories: | Pyridines;Active Pharmaceutical Ingredients;Antibiotics for Research and Experimental Use;Biochemistry;Others (Antibiotics for Research and Experimental Use);Antibiotic Explorer;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;API;Pharmaceutical intermediates;CHLOROMYCETIN;antibiotic;Chiral Reagents;Pharmaceutical intermediate;56-75-7;Elisa Kit-plant ELISA Kit |
| Mol File: | 56-75-7.mol |
Chloramphenicol Chemical Properties
| Melting point | 148-150 °C(lit.) |
| alpha | 19.5 º (c=6, EtOH) |
| Boiling point | 644.9±55.0 °C(Predicted) |
| density | 1.6682 (rough estimate) |
| refractive index | 20 ° (C=5, EtOH) |
| Fp | 14 °C |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | absolute ethanol: soluble5-20mg/mL (as a stock solution) |
| pka | 11.03±0.46(Predicted) |
| form | powder |
| color | white |
| Water Solubility | 2.5 g/L (25 º C) |
| Merck | 14,2077 |
| BRN | 2225532 |
| BCS Class | 3 |
| Major Application | pharmaceutical (small molecule) |
| InChI | 1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1 |
| InChIKey | WIIZWVCIJKGZOK-RKDXNWHRSA-N |
| SMILES | OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O |
| LogP | 1.140 |
| CAS DataBase Reference | 56-75-7(CAS DataBase Reference) |
| IARC | 2A (Vol. Sup 7, 50) 1990 |
| NIST Chemistry Reference | Chloramphenicol(56-75-7) |
| EPA Substance Registry System | Chloramphenicol (56-75-7) |
Safety Information
| Hazard Codes | T,F |
| Risk Statements | 45-11-39/23/24/25-23/24/25 |
| Safety Statements | 53-45-16-36/37 |
| RIDADR | 2811 |
| WGK Germany | 3 |
| RTECS | AB6825000 |
| F | 3-10 |
| TSCA | TSCA listed |
| HazardClass | 3 |
| HazardClass | IRRITANT |
| HS Code | 29414000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Carc. 2 Eye Dam. 1 Repr. 2 |
| Hazardous Substances Data | 56-75-7(Hazardous Substances Data) |
| Toxicity | LD50 oral in rat: 2500mg/kg |
| Description | Chloramphenicol, also known as chlornitromycin, is a broad-spectrum, bacteriostatic antibiotic derived from Streptomyces venezuelae. It is first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. The synthetic product is racemic, also called synthomycin. Syntomycin is a mixture of chloramphenicol L-isomer and d-isomer. Because of dextroisomer antibacterial effect, the effect of synthomycin is only half of the natural products. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It is effective against several gram-positive and gram-negative bacteria and commonly used in researching protein synthesis and to select for chloramphenicol-resistant transformed cells or the bacterial CAT gene. Chloramphenicol is a semisynthetic, broad-spectrum antibiotic derived from Streptomyces venequelae with primarily bacteriostatic activity. Chloramphenicol diffuses through the bacterial cell wall and reversibly binds to the bacterial 50S ribosomal subunit. The binding interferes with peptidyl transferase activity, thereby prevents transfer of amino acids to the growing peptide chains and blocks peptide bond formation. As a result bacterial protein synthesis is blocked and impede bacterial cell proliferation. |
| Chemical Properties | It is white or yellowish green needle like crystals. The melting point is 150.5-151.5℃ (149.7-150.7℃). Under the high vacuum it can be sublimated, slightly soluble in water (2.5mg/ml at 25℃), slightly soluble in propylene glycol (150.8mg/ml), soluble in methanol, ethanol, butanol, ethyl acetate, acetone, insoluble in ether, benzene, petroleum ether, vegetable oil. Taste is very bitter. |
| Uses |
Chloramphenicol is available only with your doctor's prescription. |
| Antimicrobial Spectrum | Chloramphenicol is bacteriostatic and a broad-spectrum antibiotic active against both gram-positive and gram-negative bacteria including rickettsia (cause of rocky-mountain spotted fever) and chlamydia. It is also found effective against Haemophilus influenzae causing meningitis.
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| Mechanism of action | Inhibition of protein synthesis, Chloramphenicol irreversibly binds to a receptor site on the 50S subunit of the bacterial ribosome, inhibiting peptidyl transferase. This inhibition consequently results to the prevention of amino acid transfer to growing peptide chains, ultimately leading to inhibition of protein formation. |
| Pharmacokinetics | After oral administration, it is rapidly and completely absorbed, can be widely distributed in body tissues and body fluids. In the cerebrospinal fluid concentration distribution were higher than other antibiotics, oral bioavailability was 75%~90%. After oral half hour of in the blood can reach the effective concentration, It can reach the peak in 2 to 3 hours. Take oral 0.5g, 1g and 2g, blood drug concentration was 4mg/L, 8~10mg/L and 16~21mg/L in 2 hours, 1~2g, 4 times a day, can make the blood to maintain long-term effective concentration of 10mg/L~5. After intravenous injection, the average is similarity with oral blood drug concentration of the same dose. After intramuscular absorption is slow and irregular, blood concentration is only oral amounts of 50%, but the maintenance time is long. The plasma protein binding rate is 50%~60%., the half-life of 2 to 3 hours, the half-life of newborns was significantly higher than that of adults, under the age of 2 is about 24 hours, 2 to 4 years is about 12 hours. This product is absorbed and widely distributed in the body each Reduce the concentrations of blood concentration in the blood to body fluids and tissues of liver and kidney was the highest, followed by the lung, spleen, heart, intestine and brain. Bile content is low, about 20%~50%, but also can enter the pleural effusion and ascites, milk, fetal circulation and ocular tissue. Through the blood brain barrier to reach the cerebrospinal fluid (CSF), in normal cerebrospinal fluid (CSF) in concentrations is up to 20%~50%, inflammation is up to 50%~100%. It is mainly in the liver metabolism, binding with glucuronic acid to inactivation, about 75%~90% of the metabolites in 24 hours urine, of which 5%~15% for the prototype drug. 1 g orally, urine concentration is 70~150mg/L. serious liver disease patients, the half-life may be extended due to hepatic metabolism and poisoning caused by accumulation. |
| Indications | This product is fat soluble, synthetic peptide can inhibit the formation and prevent protein. Is a bacteriostatic agent, high concentration or effect highly sensitive to the bacteria to this product showed bactericidal action. This product is applicable to the general application of typhoid and paratyphoid salmonella, and other Bacteroides fragilis. 1. Chloramphenicol is the preferred treatment of typhoid and paratyphoid fever, and can be used for typhoid Salmonella infections. 2. Used for pneumococcal in patients allergic to penicillin, ampicillin B Hib meningitis or tolerance, meningococcal meningitis, sensitive to the change of gram negative bacilli meningitis. 3. Used for aerobic and anaerobic bacteria mixed infection of otogenic brain abscess. 4. Used for serious anaerobic infections, such as Bacteroides fragilis infection. 5. Used as aminoglycoside drugs in the treatment of infection caused by sensitive bacteria and other microorganisms, such as influenza bacillus, Salmonella and other gram negative bacilli to sepsis, pulmonary infection. 6. Used for the local treatment of flu from Escherichia coli, bacillus, Klebsiella pneumoniae, Staphylococcus aureus, Streptococcus and eye, ear superficial infection. 7. It is effective for Rickettsia, mycoplasma, and infection. 8. Coli and Serratia of Pseudomonas aeruginosa is infections. 9. Chloramphenicol eye drops for the treatment of infections caused by sensitive bacteria caused by the eye, such as trachoma, conjunctivitis, keratitis, blepharitis etc.. 10. This medicine local ear drops can be used for treating sensitive bacteria infections caused by otitis externa, acute and chronic otitis media, the drug ear plugs can also be for inflammation of the ear canal and radical mastoidectomy postoperative oozing pus. |
| resistance | Drug resistance of gram negative bacilli on chloramphenicol acetyltransferase, mostly due to drug inactivation, the enzyme is mediated by the R factor. Drug resistance of gram positive bacteria, may also be due to similar mechanisms, but not fully clear. Some strains of Pseudomonas aeruginosa and Proteus, Klebsiella, are another way to generate drug resistance, which prompted the permeability change, and chloramphenicol cannot enter the cell. Bacterial resistance to chloramphenicol resistant strains both in vitro and in vivo, increased gradually in recent years. Escherichia coli, Salmonella and other gram negative bacilli can be due to drug resistance factor factor (R) transfer and acquire resistance. It has been proven that with R factor of Escherichia coli can produce acetyl transferase, chloramphenicol acetylation of failure; chloramphenicol resistant Staphylococcus aureus can also produce some inducible enzyme, under the participation of acetyl CoA, the acetylation of chloramphenicol. |
| Drug interactions | Chloramphenicol inhibits hepatic microsomal enzyme of phenytoin and tolbutamide (Jia Tangning) and chlorpropamide and dicoumarol (and possibly other drug metabolism, and the prolonged in vivo half-life, increased concentrations of serum. Poisoning aggravate that death is also reported. On the other side, phenobarbital, phenytoin, rifampin (are, 1985) can decrease the serum concentration of chloramphenicol, which was estimated to be due to the inductive effect of drugs on the liver enzymes. Therefore, at the same time, the application effect of chloramphenicol pharmacokinetics of drugs, should be paid attention to the monitoring of serum concentration of chloramphenicol. Chloramphenicol can delay the iron, folic acid and vitamin B12 on anemia treatment response. It can interfere with the host to tetanus toxoid anamnestic response. Therefore, at the same time, the application situation chloramphenicol and active immune agents should be avoided. Antagonistic effects of chloramphenicol on penicillin bactericidal effect, which is verified in vitro and animal experiments, but its clinical significance is not clear. This kind of combination, only in the proof of such treatment is benefit, began to be used. |
| Adverse reactions and precautions | 1. Inhibition of bone marrow hematopoietic function: for the most serious toxicity of chloramphenicol, such as red blood cells, granulocyte and platelet reduce. There are two types: one is the reversible inhibition, manifested as neutropenia and thrombocytopenia, and anemia, related to dose and duration can be gradually recovered after drug withdrawal; Second is irreversible aplastic anemia, with dosage and duration without direct relationship, low incidence, once often occur difficult to reverse, high mortality rate and a few survivors can development for granulocytic leukemia, women, children, and liver and kidney function not entire occurrence rate is high. This is the main reason to limit the clinical application. 2. In the liver, metabolism rate of this product is very high, on the function of the liver, it has impaired the appropriate quantity (adult day not more than 1 g) or not as much as possible. 3. Chloramphenicol is only 5%~10% prototype drug discharge from the kidney, it is not appropriate for the treatment of urinary tract infection. 4. Premature infants and neonatal as much as possible. 5. I see the spirit of neurological symptoms, should be promptly discontinued. 6. During late pregnancy and lactation are not suitable for this application, because this product in vivo is conjugated with glucuronic acid and detoxification, conjugates excreted by the kidneys. And this product can be through the placenta to the fetus, fetal and neonatal, due to not perfect of enzyme system in the liver, glucuronic acid combined with the ability is poor and excretory function of the kidney is weak. Therefore, it is very easy to cause drug accumulation, the newborn gray baby syndromes. Gray cyanosis, dyspnea, vomiting, abdominal distension and circulatory failure with unique performance, high fatality rate. In addition, this product can damage the hematopoietic system, can make the pregnant women aplastic anemia, neonatal thrombocytopenia and other consequences. |
| Methods of production | Methods for producing countries in the world to chloramphenicol had a lot of research, summed up: (1) p-nitroacetophenone method; (2) styrene method; (3) Cinnamyl alcohol method; (4) The nitro cinnamic alcohol method; (5) P-nitrobenzaldehyde method. China use p-nitroacetophenone method, the method is by ethylbenzene via nitration, oxidation, bromide, salt, hydrolysis, acetylation, addition, reduction, decomposition, split second chloride acetylation and chloramphenicol. |
| Description | Chloramphenicol was originally produced by fermentation of Streptomyces venezuelae, but its comparativelysimple chemical structure soon resulted in several efficient total chemical syntheses. With two asymmetriccenters, it is one of four diastereomers, only one of which (1R,2R) is significantly active. Because totalsynthesis produces a mixture of all four, the unwanted isomers must be removed before use.Chloramphenicol is a neutral substance that is only moderately soluble in water, because both nitrogenatoms are nonbasic under physiologic conditions (one is an amide and the other a nitro moiety). It was thefirst broad-spectrum oral antibiotic used in the United States and was once very popular. Severepotential blood dyscrasia has greatly decreased its use in North America. Although its cheapness andefficiency makes it still very popular in much of the rest of the world where it can often be purchasedover-the-counter without a prescription |
| Chemical Properties | White to grey-white crystalline powder |
| Chemical Properties | Chloramphenicol is a white to grayish-whiteor yellowish-white crystalline solid. |
| Originator | Leukomycin,Bayer,W. Germany |
| Uses | antibacterial, antirickettsial, inhibits protein synthesis |
| Uses | 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. |
| Uses | 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 |
| Definition | ChEBI: Chloramphenicol is an organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions. It has a role as an antimicrobial agent, an antibacterial drug, a protein synthesis inhibitor, an Escherichia coli metabolite, a Mycoplasma genitalium metabolite and a geroprotector. It is an organochlorine compound, a diol, a C-nitro compound and a carboxamide. |
| Indications | Resistance to chloramphenicol is usually explained by the presence of a plasmid thatdetermines the production of chloramphenicol acetyltransferase. This enzyme acetylatesthe drug, giving it unable to bind with 50 S subunits of bacterial ribosomes. Chloramphenicol is a potentially toxic drug and has a few indications for use. It is the drugof choice for treating typhoid fever, and it is used for treating brain abscesses. Untilrecently, it was the drug of choice for therapy of bacterial meningitis in children (in combination with ampicillin). However, third-generation cephalosporins are currently preferred for such purposes. Chloramphenicol is an effective alternative for a number ofinfections in situations, where drugs of choice cannot be used for one reason or another.However, it should never be used for infections that can readily be treated with otherantimicrobial drugs. Synonyms of this drug are levomycetin, amindan, aquamycetin,chloromycetin, ophthoclor, opulets, leukomycin, and many others. |
| Manufacturing Process | Chloramphenicol may be prepared by fermentation or by chemical synthesis.The fermentation route to chloramphenicol is described in US Patents2,483,871 and 2,483,892. To quote from US Patent 2,483,892: The cultivationof Streptomyces venezuelae may be carried out in a number of different ways.For example, the microorganism may be cultivated under aerobic conditionson the surface of the medium, or it may be cultivated beneath the surface ofthe medium, i.e., in the submerged condition, if oxygen is simultaneouslysupplied. Briefly stated, the production of chloramphenicol by the surface culturemethod involves inoculating a shallow layer, usually less than about 2 cm, of asterile, aqueous nutrient medium with Streptomyces venezuelae andincubating the mixture under aerobic conditions at a temperature betweenabout 20° and 40°C, preferably at room temperature (about 25°C), for aperiod of about 10 to 15 days. The mycelium is then removed from the liquidand the culture liquid is then treated by methods described for isolating therefrom the desired chloramphenicol.The synthetic route to chloramphenicol is described in US Patent 2,483,884 asfollows: 1.1 g of sodium is dissolved in 20 cc of methanol and the resultingsolution added to a solution of 5 g of benzaldehyde and 4.5 g of betanitroethanol in 20 cc of methanol. After standing at room temperature for ashort time the gel which forms on the mixing of the reactants changes to awhite insoluble powder. The precipitate is collected, washed with methanol andether and then dried. The product thus produced is the sodium salt of 1-phenyl-2-nitropropane-1,3-diol. Eighteen grams of the sodium salt of 1-phenyl-2-nitropropane-1,3-diolisdissolved in 200 cc of glacial acetic acid. 0.75 g of palladium oxidehydrogenation catalyst is added and the mixture shaken at room temperatureunder three atmospheres pressure of hydrogen overnight. The reaction vesselis opened, 2.5 g of 10% palladium on carbon hydrogenation catalyst addedand the mixture shaken under three atmospheres pressure of hydrogen for 3hours. The catalyst is removed from the reaction mixture by filtration and thefiltrate concentrated under reduced pressure. Fifty cubic centimeters of npropanol is added to the residue and the insoluble inorganic salt removed byfiltration. The filtrate is treated with excess hydrochloric acid and evaporated to obtain apale yellow oil. Five grams of the oil thus obtained is treated with 15 cc ofsaturated potassium carbonate solution and the mixture extracted with 50 ccof ether, then with 30 cc of ethyl acetate and finally with two 30 cc portions ofethanol. Evaporation of the solvent from the extract gives the followingquantities of the desired 1-phenyl-2-aminopropane-1,3-diol: 0.5 g, 1.0 g and3.1 g. 1.7 g of 1-phenyl-2-aminopropane-1,3-diol is treated with 1.6 g of methyldichloroacetate and the mixture heated at 100°C for 1.25 hours. The residueis washed with two 20 cc portions of petroleum ether and the insolubleproduct collected. Recrystallization from ethyl acetate yields the desired (dl)-reg.-1-phenyl-2-dichloroacetamidopropane-1,3-diol in pure form; MP 154° to156°C.Five hundred milligrams of (dl)-reg.-1-phenyl-2-dichloroacetamidopropane-1,3-diolis added to a solution consisting of 1 cc of pyridine and 1 cc of aceticanhydride and the resulting reaction mixture heated at 100°C for 1/2 hour.The reaction mixture is evaporated to dryness under reduced pressure and theresidue taken up in and crystallized from methanol. Recrystallization frommethanol produces the pure diacetate of (dl)-reg.-1-phenyl-2-dichloroacetamidopropane-1,3-diol (MP 94°C).Two hundred milligrams of the diacetate of (dl)-reg.-1-phenyl-2-dichloroacetamidopropane1,3-diol is added to a mixture consisting of 0.25 ccof concentrated nitric acid and 0.25 cc of concentrated sulfuric acid at 0°C.The reaction mixture is stirred until solution is complete, poured onto 25 g ofice and the mixture extracted with ethyl acetate. The ethyl acetate extractsare evaporated under reduced pressure and the diacetate of (dl)-reg.-1-pnitrophenyl-2-dichloroacetamidopropane-1,3-diol so produced purified byrecristallization from ethanol; MP 134°C. Five hundred milligrams of the diacetate of (dl)-reg.-1-p-nitrophenyl-2-dichloroacetamidopropane-1,3-diol is dissolved in a mixture consisting of 25cc of acetone and an equal volume of 0.2 N sodium hydroxide solution at 0°Cand the mixture allowed to stand for one hour. The reaction mixture isneutralized with hydrochloric acid and evaporated under reduced pressure todryness. The residue is extracted with several portions of hot ethylenedichloride, the extracts concentrated and then cooled to obtain the crystalline(dl)-reg.-1- p-nitrophenyl-2-dichloroacetamidopropane-1,3-diol; MP 171°C. |
| 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. |
| Therapeutic Function | Antimicrobial |
| World Health Organization (WHO) | Chloramphenicol, an antibiotic isolated from Streptomycesvenezuelae in 1947, first became available for general clinical use in 1948. By 1950it was evident that its use could cause serious, sometimes fatal, blood dyscrasias.However, it remains one of the most effective antibiotics for treating invasivetyphoid fever and salmonellosis, some rickettsioses and serious infections causedby Haemophilus influenzae or anaerobic organisms. This is considered to justify itsretention in the WHO Model List of Essential Drugs.(Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO ExpertCommittee, 722, , 1985) |
| Antimicrobial activity | It is active against a very wide range of organisms. Minimum inhibitory concentrations (MICs) (mg/L) for otherorganisms are: Staphylococcus epidermidis, 1–8; Corynebacteriumdiphtheriae, 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; Serratiamarcescens, 2–8; Burkholderia pseudomallei, 4–8. Most Gramnegativebacilli are susceptible, but Pseudomonas aeruginosais resistant. Leptospira spp., Treponema pallidum, chlamydiae,mycoplasmas and rickettsiae are all susceptible, but Nocardiaspp. are resistant. It is widely active against anaerobes, includingActinomyces israelii (MIC 1–4 mg/L), Peptostreptococcusspp. (MIC 0.1–8 mg/L), and Fusobacterium spp. (MIC 0.5–2mg/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 MICagainst some strains of Gram-positive cocci, Haemophilusinfluenzae and Neisseria spp. The minimum bactericidalconcentrations (MBCs) for penicillin-resistant pneumococciare often significantly higher than those for penicillin-susceptible strains, although this cannot be detectedby conventional disk susceptibility testing or MIC determination.Its bacteristatic effect may inhibit the action ofpenicillins and other β-lactam antibiotics against Klebsiellapneumoniae and other enterobacteria in vitro, but the clinical significance of this is doubtful. The presence of ampicillindoes not affect the bactericidal effect of chloramphenicolon H. influenzae. |
| Acquired resistance | The prevalence of resistant strains in many Gram-positiveand Gram-negative organisms reflects usage of the antibiotic.Over-the-counter sales are believed to have compounded theproblem in some countries. For example, it has long been thedrug of choice for the treatment of typhoid and paratyphoidfevers, but widespread use led to a high prevalence of resistantSalmonella enterica serotype Typhi. Outbreaks of infectioncaused by chloramphenicol-resistant S. Typhi have beenseen since the early 1970s. Use of co-trimoxazole and fluoroquinolonesin typhoid has resulted in a decline in chloramphenicolresistance in some endemic areas. Many hospitaloutbreaks caused by multiresistant strains of enterobacteria,notably Enterobacter, Klebsiella and Serratia spp., have beendescribed. Plasmid-borne resistance was first noted in shigellae inJapan and subsequently spread widely in Central America,where it was responsible for a huge outbreak. Strains ofS. Typhi resistant to many antibiotics including chloramphenicolare particularly common in the Indian subcontinent.Resistance in shigellae is also relatively common insome parts of the world. Resistant strains of H. influenzae (some also resistant toampicillin), Staph. aureus and Streptococcus pyogenes are alsoencountered. Most N. meningitidis strains remain susceptible,but high-level resistance (MIC >64 mg/L) due to the productionof chloramphenicol acetyltransferase has beendescribed; the nucleotide sequence of the resistance gene wasindistinguishable from that found on a transposon in Cl. perfringens.Resistant strains of En   |