a4014c
pleuromulin
CAS: 125-65-5
Molecular Formula: C22H34O5
a4014c - Names and Identifiers
| Name | pleuromulin |
| Synonyms | bc757 a4014c PLEUROMULIN pleuromulin drosopholinb PLEUROMUTILIN Pleuromutilin antibioticbc757 l-3a,9-propano-3ah-cyclopentacycloocten-1(4h)-one glycolicacid,8-esterwithoctahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-viny 6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate (3aS,4R,5S,6S,8R,9S,9aR,10S)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate |
| CAS | 125-65-5 |
| EINECS | 204-747-5 |
| InChI | InChI=1/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14-,16+,18-,19-,20+,21+,22-/m0/s1 |
| InChIKey | YSBXUHAJXRCCET-BKUNHTPHSA-N |
a4014c - Physico-chemical Properties
| Molecular Formula | C22H34O5 |
| Molar Mass | 378.5 |
| Density | 1.15±0.1 g/cm3(Predicted) |
| Melting Point | 170-1710C |
| Boling Point | 482.8±45.0 °C(Predicted) |
| Specific Rotation(α) | D24 +20° (c = 3 in abs ethanol) |
| Flash Point | 158.7°C |
| Solubility | DMSO: >10mg/mL (warmed) |
| Vapor Presure | 2.38E-11mmHg at 25°C |
| Appearance | Crystalline solid |
| Color | white to beige |
| pKa | 12.91±0.10(Predicted) |
| Storage Condition | -20°C Freezer |
| Refractive Index | 1.537 |
| Use | This product is for scientific research only and shall not be used for other purposes. |
a4014c - Risk and Safety
| WGK Germany | 3 |
| RTECS | MC5408000 |
| Toxicity | LD50 in mice: >60 mg/kg (Kavanagh, 1952) |
a4014c - Reference Information
| Diterpene antibiotics | Pleurotus truncate (Pleuromutilin) is a broad-spectrum diterpene produced by Pleurotus (Pleurotus mutilus) The class of antibiotics is the precursor of semi-synthetic derivatives of Pleurotus truncate drugs. Pleurotus truncated antibiotics are a new family of antibiotics with good antibacterial activity and resistance, which can effectively inhibit most gram-positive bacteria, mycoplasma and some gram-negative bacteria. The discovery of Pleurotus truncate drugs was in the 1970s, and it was only in 1978 that Novartis of Switzerland first listed the first drug-tiamectin, which is mainly used to treat pig dysentery, pneumonia and other related diseases. Up to now, Pleurotus truncate drugs have developed four tiamectin, Vonimerin, azamorin and Ritapalin. Telemarin and Warnimerin are relatively toxic, and are currently only used as animal-specific drugs, and Telemarin is the most effective and most used. Azamolin and Ritapaline were later developed drugs for human use. Azamolin was shelved due to water solubility and bioavailability issues. Currently, only Ritapaline is used in human medicine. Pleurotus truncated antibiotics are composed of tricyclic diterpenes. The most basic structure is an eight-membered ring. The carbonyl group on the five-membered ring and the hydroxyl group on the C- 11 in the molecular structure are the functional groups necessary for the basic activity of this kind of antibiotics. Most foreign studies have chemically modified their C- 14 to obtain antibacterial activity and new drugs with higher bioavailability. |
| Antibacterial mechanism | Pleurotus truncatum is a broad-spectrum diterpene antibiotic produced by Pleurotus euphratica. It can inhibit the protein synthesis of bacteria, so as to inhibit the growth of bacteria. Its mode of action is different from other types of antibiotics. in terms of the mechanism of action. Pleurotus truncated antibiotics mainly act on the ribosome level of bacterial cells. It inhibits the activity of peptide acyltransferase and hinders the synthesis of bacterial proteins, thereby achieving a broad-spectrum antibacterial effect. Pleurotus truncated drugs are composed of three rings to form the main skeleton, and the basic structure of the group is an eight-membered ring; the carbonyl group on the five-membered ring and the hydroxyl group on the C- 11 are necessary groups for activity. Most foreign studies are The C- 14 is chemically modified to greatly improve its antibacterial activity and bioavailability. because the C- 14 of pleurotin drugs contain free hydroxyl groups, it has no activity. By structural modification of the C- 14 site, derivatives with enhanced antibacterial activity against bacteria and mycoplasma can be obtained. Moreover, the antibacterial activity of the compound that C- 14 the side chain to connect the neutral group or the acidic group is extremely low, and the activity of connecting the two basic side chains is also low; and the thioether-based side chain that connects a basic center, The activity of its derivatives is a decisive improvement. For example, the drug tyamectin fumarate contains thioether-based side chains. However, if the sulfur atom in the thioether group is replaced by an oxygen atom, it can cause a sharp decline in the activity of pleurotin drugs. If other basic substituents, such as guanidine or primary amine, are connected to the side chain at the C- 14 position, the activity level of the derivative containing thioether group cannot be reached, and it is easy to be hydrolyzed and inactivated in vivo. therefore, acylation modification of the C- 14 site of Pleurotus truncated compounds can significantly reduce the minimum inhibitory concentration and improve the antibacterial activity. |
| Research and development history | Pleurotin and its derivatives can inhibit bacterial protein synthesis at the ribosomal level, and have a unique effect on many gram-positive bacteria and mycoplasma infections. in 1951, Kavanagh et al. reported for the first time the separation and characterization of the crystalline antibacterial substance of Pleurotus truncatatum. In 1974, the Sandoz Institute discovered a derivative that is 10-100 times more active than Pleurotus truncatenin-tamarin. This compound replaces the C- 14 hydroxyl group of Pleurotus truncatenin with (diethylamine ethyl) sulfhydryl. In addition to the antibacterial activity of Pleurotus truncatenin, it shows strong antibacterial activity against Shigella, Klebsiella and Escherichia coli, it is one of the commonly used veterinary antibiotics in the veterinary drug market. It mainly treats the gastrointestinal and respiratory diseases of livestock and poultry in the form of feed additives and veterinary medicine drinking water. in 1976, knauseder f et al. made a preliminary study on the fermentation conditions, chemical structure and biosynthetic path of pleurotin-producing bacteria. The subsequent launch of Vonimilin (Valnemulin) is also used as an animal-specific antibacterial drug to treat respiratory diseases in pigs and chickens and epidemic enteritis in rabbits. Warnimerin (valnemulin) is a new generation of pleurotin (pleuromutilin) semi-synthetic antibiotics. It belongs to diterpenes and belongs to the same class of drugs as tyamicin. It is a special antibiotic for animals and is mainly used to prevent pigs, Mycoplasma disease and gram-positive bacteria infection in cattle, sheep and poultry. It is mainly concentrated in the lungs and is an ideal drug for the treatment of lung diseases caused by various mycoplasma. in 2007, that is, nearly 50 years after the discovery of pleurotin drug, the first human-used pleurotin antibiotic retaline (Retapamulin) was approved for clinical use and was only used as a topical drug to treat pustulosis caused by staphylococcus aureus and streptococcus pyogenes in adults and children over 9 months old. in 2019, after nearly 60 years of development, the latest pleurotin drug Lefamulin(BC-3781) completed phase 3 clinical trials in 2018 and submitted a new drug application to FDA in February 2019. it is expected to become the first human pleurotin antibiotic that can be used for systemic drugs to treat community acquired bacterial pneumonia (intravenous or oral administration). |
| biological activity | Pleuromutilin (Drosophilin B) can inhibit bacterial protein synthesis by binding the ribosomal subunit 50S of bacteria. |
Last Update：2024-04-09 21:54:55
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