Azlocillin
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| Category | Bioactive by-products |
| Catalog number | BBF-00621 |
| CAS | 37091-66-0 |
| Molecular Weight | 461.49 |
| Molecular Formula | C20H23N5O6S |
| Purity | 95% |
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Description
Azlocillin is produced by the strain of 6-APA and Ampicillin. It has a wide antibacterial spectrum, and has good effects on gram-positive cocci (except penicillin-resistant Staphylococcus aureus), negative bacilli including Pseudomonas aerumindole-negative proteus, etc. The experimental efficacy is better than Carbencillin and Ticarcillin, and it is widely applied in clinical practice.
Specification
| Related CAS | 37091-65-9 (sodium) |
| Synonyms | AZLOCILLIN ACID; 3,3-Dimethyl-6-oxo-7-[2-(2-oxoimidazolidin-1-yl)carbonylamino-2-phenyl-acetyl]amino-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic acid; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-7-oxo-6-[[[[(2-oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]-, [2S-[2a,5a,6b(S*)]]- |
| IUPAC Name | (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| Canonical SMILES | CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C |
| InChI | InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1 |
| InChI Key | JTWOMNBEOCYFNV-NFFDBFGFSA-N |
Properties
| Appearance | Dull Yellow Crystalline |
| Antibiotic Activity Spectrum | gram-positive bacterial; gram-negative bacteria |
| Density | 1.55 g/cm3 |
| Solubility | Soluble in water, methanol, ethanol(slightly). |
Reference Reading
1.Molecular taxonomy, phylogeny and evolution in the family Stichopodidae (Aspidochirotida: Holothuroidea) based on COI and 16S mitochondrial DNA.
Byrne M1, Rowe F, Uthicke S. Mol Phylogenet Evol. 2010 Sep;56(3):1068-81. doi: 10.1016/j.ympev.2010.04.013. Epub 2010 Apr 23.
The Stichopodidae comprise a diverse assemblage of holothuroids most of which occur in the Indo-Pacific. Phylogenetic analyses of mitochondrial gene (COI, 16S rRNA) sequence for 111 individuals (7 genera, 17 species) clarified taxonomic uncertainties, species relationships, biogeography and evolution of the family. A monophyly of the genus Stichopus was supported with the exception of Stichopus ellipes. Molecular analyses confirmed genus level taxonomy based on morphology. Most specimens harvested as S. horrens fell in the S. monotuberculatus clade, a morphologically variable assemblage with others from the S. naso clade. Taxonomic clarification of species fished as S. horrens will assist conservation measures. Evolutionary rates based on comparison of sequence from trans-ithmian Isostichopus species estimated that Stichopus and Isostichopus diverged ca. 5.5-10.7Ma (Miocene). More recent splits were estimated to be younger than 1Ma.
2.Aeromonas spp.: An Emerging Nosocomial Pathogen.
Batra P1, Mathur P1, Misra MC2. J Lab Physicians. 2016 Jan-Jun;8(1):1-4. doi: 10.4103/0974-2727.176234.
Aeromonads are hallophillic, nonacid fast, nonspore forming, Gram-negative rods which are widely distributed in the soil, foodstuffs, and aquatic environment. Since times immemorial, they are important zoonotic pathogens of poikilotherms but are now emerging as important human pathogens. These emerging enteric pathogens flourish in the water distribution system by forming biofilms. They possess large number of virulence factors including inherent resistance to various antibiotics and ability to form biofilms using quorum sensing. These properties make them easy pathogens for human infections. Aeromonads are important enteric pathogens, but, with the growing level of immunosuppression in the population, they have been associated with various extraintestinal infections, such as skin and soft-tissue infections, traumatic wound infections, and lower respiratory tract/urinary tract infections. The average annual incidence of bacteremia in Southern Taiwan due to Aeromonas spp.
3.Crystal structures of penicillin-binding protein 3 in complexes with azlocillin and cefoperazone in both acylated and deacylated forms.
Ren J1, Nettleship JE1,2, Males A1,2, Stuart DI1,3, Owens RJ1,2. FEBS Lett. 2016 Jan;590(2):288-97. doi: 10.1002/1873-3468.12054. Epub 2016 Jan 23.
Penicillin-binding protein 3 (PBP3) from Pseudomonas aeruginosa is the molecular target of β-lactam-based antibiotics. Structures of PBP3 in complexes with azlocillin and cefoperazone, which are in clinical use for the treatment of pseudomonad infections, have been determined to 2.0 Å resolution. Together with data from other complexes, these structures identify a common set of residues involved in the binding of β-lactams to PBP3. Comparison of wild-type and an active site mutant (S294A) showed that increased thermal stability of PBP3 following azlocillin binding was entirely due to covalent binding to S294, whereas cefoperazone binding produces some increase in stability without the covalent link. Consistent with this, a third crystal structure was determined in which the hydrolysis product of cefoperazone was noncovalently bound in the active site of PBP3. This is the first structure of a complex between a penicillin-binding protein and cephalosporic acid and may be important in the design of new noncovalent PBP3 inhibitors.
4.Interactions of some commonly used drugs with human α-thrombin.
Nair DG1, Narayanan SP, Chittalakkottu S. J Biomol Struct Dyn. 2015;33(5):1008-15. doi: 10.1080/07391102.2014.923329. Epub 2014 Jun 19.
Adverse side effects of drugs are often caused by the interaction of drug molecules to targets other than the intended ones. In this study, we investigated the off-target interactions of some commercially available drugs with human α-thrombin. The drugs used in the study were selected from Super Drug Database based on the structural similarity to a known thrombin inhibitor argatroban. Interactions of these drugs with thrombin were initially checked by in silico docking studies and then confirmed by thrombin inhibition assay using a fluorescence microplate-based method. Results show that the three commonly used drugs piperacillin (anti-bacterial), azlocillin (anti-bacterial), and metolazone (anti-hypertensive and diuretic) have thrombin inhibitory activity almost similar to that of argatroban. The Ki values of piperacillin, azlocillin, and metolazone with thrombin are .55, .95, and .62 nM, respectively. The IC50 values of piperacillin, azlocillin, and metolazone with thrombin are 1.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
