cilopen
benzylpenicillin
CAS: 61-33-6
Molecular Formula: C16H18N2O4S
cilopen - Names and Identifiers
| Name | benzylpenicillin |
| Synonyms | cilopen cilloral Pfizerpen Penicillin G benzylpenicillin PENICILLIN G K-SALT PENICILLIN G POTASSIUM (phenylmethyl)-penicilli (phenylmethyl)penicillin (5r,6r)-benzylpenicillin (phenylmethyl)-penicillinicaci 6-(2-phenylacetamido)penicillanic acid (5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| CAS | 61-33-6 |
| EINECS | 200-506-3 |
| InChI | InChI=1/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12?,14-/m1/s1 |
cilopen - Physico-chemical Properties
| Molecular Formula | C16H18N2O4S |
| Molar Mass | 334.39 |
| Density | 1.2729 (rough estimate) |
| Melting Point | 82-83 °C |
| Boling Point | 663.3±55.0 °C(Predicted) |
| Specific Rotation(α) | D +282° (ethanol) |
| Flash Point | 355°C |
| Water Solubility | 2.675g/L(25 ºC) |
| Solubility | H2O: 100mg/mL |
| Vapor Presure | 1.69E-18mmHg at 25°C |
| Appearance | powder |
| Color | Crystals |
| pKa | 2.45±0.50(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.6930 (estimate) |
cilopen - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 42/43 - May cause sensitization by inhalation and skin contact. |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 2 |
| RTECS | XH9700000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 32041900 |
| Toxicity | LD50 orl-rat: 8 g/kg ANTCAO 12,249,62 |
cilopen - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Chemical properties | penicillin is an organic acid that is stable and insoluble in water. It can be combined with metal ions or organic base to form salt, and sodium salt and potassium salt are commonly used in clinic. penicillin potassium or sodium salt is white crystalline powder, odorless or slightly specific odor, with hygroscopicity. The dried product is stable in nature, can be stored at room temperature for several years without failure, and is heat-resistant. In case of acid, alkali, heavy metal ions and oxidants such as rapid failure. Very soluble in water, ethanol-soluble, insoluble in fatty oil or liquid paraffin. The aqueous solution is extremely unstable, and the potency decreases rapidly at room temperature. 10% aqueous solution pH is 5.5~7.5. |
| History of discovery | British bacteriologist A. The penicillin and its bacteriostasis were discovered by the Flemming in the laboratory, from 1938. W.F. Flory and E.B. Chann was isolated from penicillin, and found that it has a good therapeutic effect on many serious systemic bacterial infections, is a high efficiency and low toxicity antibiotics. The emergence of penicillin, initiated the history of antibiotic drug therapy in medicine, and played a very important role in the treatment of human and animal inflammation. In the early stage of penicillin production, the surface culture is carried out in the culture bottle, and the concentration can only reach 8 to 12 units per ml. In this way, hundreds of bottles are produced in an amount sufficient for use by only one patient. It was not until 1943 that penicillin was successfully produced by submerged culture with aeration and agitation in a fermenter. at present, the volume of the fermentation tank for the production of penicillin has been expanded to more than one hundred tons, and the concentration of the fermentation broth has reached about 60000 units per milliliter. However, with the extensive use of penicillin, the phenomenon of bacterial resistance to penicillin is becoming more and more serious, especially the spread of Staphylococcus aureus resistant strains has become a serious clinical problem. Secondly, penicillin also exists antibacterial spectrum is not wide enough, easy to cause allergic reactions and other problems, so its application is limited. In 1959, J.C. Hiheng and K.R. Henry-Langen isolated penicillin mother nucleus 6APA from penicillin fermentation broth and successfully synthesized the first semi-synthetic penicillin, phenoxyethylpenicillin. From then on, the research on the structural modification of penicillin was studied, and many new semi-synthetic penicillins with different characteristics were produced by the combination of microbial synthesis and chemical synthesis, which made the penicillins more widely used. |
| natural penicillin | the production of penicillin G can be divided into two steps: strain fermentation and extraction and purification. (1) strain fermentation: The Penicillium chrysogenum was inoculated on a solid medium and cultured at 25 ° C. For 7-10 days to obtain a spore culture of Penicillium. The spore suspension is inoculated into the sterilized medium in the seed tank with sterile water, and the sterile air is introduced and stirred, and the culture is carried out at 27 ° C for 24 to 28 hours, then, the seed culture solution was inoculated into the culture medium containing phenylacetic acid precursor sterilized in the fermenter, and the culture was conducted at 27 ° C. For 7 days with passage of sterile air and stirring. Phenylacetic acid precursor and appropriate medium should be added in the fermentation process. (2) extraction and purification: the penicillin fermentation broth was cooled and filtered. Under the condition of pH 2~2.5, the filtrate is extracted by Multistage countercurrent extraction with butyl acetate in the extractor to obtain butyl ester extract, which is transferred to a buffer solution of pH 7.0~7.2, and then transferred to butyl ester, the butyl ester extract was decolorized by activated carbon, and then the salt forming agent was added to obtain penicillin G potassium salt by azeotropic distillation. The sodium salt of penicillin G is prepared by passing the potassium salt of penicillin G through an ion exchange resin (sodium form). |
| pharmacological action and clinical application | penicillin is a narrow spectrum bactericidal antibiotic with strong antibacterial effect. Penicillin for a variety of gram-positive bacteria (including Streptococcus, Pneumonia cocci, sensitive Staphylococcus and bacilli), Some Gram-negative cocci (including meningococcus, Neisseria gonorrhoeae), spirochete and Actinomyces have strong antibacterial activity and are sensitive to gram-positive bacilli including diphtheria bacillus, Bacillus anthracis and gram-positive anaerobic bacilli, such as tetanus Bacillus and perfringens; but the role of gram-negative bacilli is very weak, the Mycobacterium tuberculosis, Rickettsia, Virus and so on. penicillin is a bactericide in the reproductive period of bacteria, which mainly produces antibacterial effect by interfering with the synthesis of bacterial cell wall. It can inhibit the synthesis of mucopeptide, the basic component of bacterial cell wall, cause cell wall defect, and make water penetrate into bacterial cytoplasm, leading to swelling and deformation of bacteria, and finally cracking and death. Because the content of cell wall mucin of gram-positive bacteria is higher than that of gram-negative bacteria, it has a strong effect on the former. Human and animal cells have no cell wall, so penicillin is almost non-toxic to them. clinically, it is mainly used for various infections caused by gram-positive bacteria, such as septicemia, Pneumonia, nephritis, mastitis, endometritis, wound infection, swine erysipelas, swine lymph node swelling, rabbit and poultry Staphylococcus disease, streptococcus disease, anthrax, malignant edema, emphysema, horse gland disease, etc. Penicillin can also be used to treat Actinomyces and leptospirosis. Penicillin can also be applied locally, such as intraductal, intra-uterine and intra-articular injection, to treat mastitis, endometritis and arthritis. In addition, our people with streptomycin in combination, injection of postpartum fish, prevention and treatment of secondary infection. Penicillin is also used to treat enterococcal pericarditis, Clostridium-induced tetanus and gas gangrene, epidemic encephalomyelitis, listeriosis, etc. In the operation or postoperative, in order to prevent the occurrence of inflammation, penicillin is also used as the drug of choice. This product is not resistant to acid and enzyme, and is not suitable for oral administration. Poor stability in aqueous solution, rapid degradation, prevention and treatment of poultry disease is generally not free to use mixed drink medicine, but can be used "thirst" mixed drink medicine, for local intestinal infections, such as necrotic enteritis, ulcerative enteritis, coccidiosis, as well as secondary bacterial infections of the Virus disease. |
| pharmacokinetics | This product is not resistant to acid and enzyme, and has poor oral absorption, only 10% ~ 25% is absorbed; the absorption of intramuscular injection is fast and complete, and the peak of blood drug concentration is reached 15~30 minutes after intramuscular injection. A single dose of 1 million U intramuscular injection, 30 minutes to reach the peak blood concentration, 20,000 U/L. It is widely distributed in most tissues and body fluids in the body, with higher content in kidney, small intestine, lung, striated muscle and spleen. Easy to penetrate into the chest, abdominal cavity, pericardium and joint cavity, but in the abscess and necrosis area of the drug concentration is low. The drug concentration in the cerebrospinal fluid is low, but the penetration of the meningitis is more, and the effective antibacterial concentration can be achieved. Can penetrate into the placenta and into the fetal circulation, a small amount of into the milk. The concentration secreted into the bile is about 1 to 5 times the concentration in the blood. This product has a large degree of dissociation, low fat solubility, most of the original form of excretion by the kidney, a few in the liver quickly inactivated. Plasma half-life of 30 minutes, newborns and the elderly due to renal insufficiency, half-life will be extended, the half-life of patients with renal failure can be increased to 10 hours. The plasma protein binding rate is about 60%. With Probenecid can increase the blood concentration of this product, but due to blocking the secretion of acidic metabolites, can lead to or aggravate the patient's acid-base balance disorder, it is generally not routine use. |
| note | penicillin is stable under dry conditions, it will decompose quickly when wet, and it is extremely unstable in aqueous solution, it should be dissolved before use and used up as soon as possible. If it is not used up at a time, it can be temporarily stored in a 4 ℃ refrigerator and used up within the same day to ensure the efficacy and reduce allergic and other adverse reactions. penicillin is relatively stable in near-neutral (pH = 6-7) solution, which can be accelerated in acidic or alkaline solution. It is best to use water for injection or saline solution, dissolved in glucose also have a certain degree of decomposition. Penicillin in alkaline solution decomposition is very fast, it is strictly prohibited to alkaline solution (such as sodium bicarbonate) and its compatibility. Penicillin in the case of chlorpromazine hydrochloride, heavy metal salt decomposition or precipitation failure. it should be noted that the compatibility and interaction with other drugs, such as penicillins and tetracyclines, chloramphenicol, macrolides, sulfa drugs showed antagonistic effect, should not be combined. This product is less toxic, the more serious reaction is anaphylactic shock, dogs, cats, other animals also occur occasionally, should pay attention to observation. Immediately after the occurrence of allergic reactions should be intramuscular or intravenous epinephrine (a dose, horses, cattle 2~5mg, sheep, pigs 0.2~1mg, dogs 0.1~0.5mg, cats 0.1~0.5mg) for first aid, if necessary, can add glucocorticoids and antiallergic drugs to enhance or stabilize the efficacy. Cross-allergic reactions: a sick animal who is allergic to one type of penicillin may be allergic to other penicillins as well as to cephalosporins. Penicillin skin sensitivity test can be done before injection. The concentration of skin test solution is 500U per milliliter of penicillin, and 0.1 is injected intradermally. |
| category | toxic substances |
| toxicity grade | low toxicity |
| Acute toxicity | oral-rat LD50: 8000 mg/kg; Oral-mouse LD50: > 5000 mg/kg |
| flammability hazard characteristics | toxic nitrogen and sulfur oxide fumes produced by combustion; Side effects of drug injection: structural and functional changes in the inner ear; Dyspnea, convulsion |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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