Penicillin
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| Category | Antibiotics |
| Catalog number | BBF-00759 |
| CAS | 525-94-0 |
| Molecular Weight | 359.40 |
| Molecular Formula | C14H21N3O6S |
| Purity | 95% |
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Description
It is produced by the strain of Cephalosporium aceemonium, C. salmosynnematum, Emericellopsis salmosynnemata. It has weak anti-gram-positive bacteria (activity against Staphylococcus aureus is only 1% of penicillin G) and anti-gram-negative bacteria activity, and can be broken down by penicillinase and cross-resistant to penicillin G.
Specification
| Synonyms | Penicillin N; Synnematin B; Cephalosporin N; Adicillin; Salmotin; SYNNEMATINB; Adicillinum; Synnematin N; (2S,5R,6R)-6-(5-Amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure; Cephalosphorin R; 6-N-((5-Amino-5-carboxy)pentanoyl)aminopenicillansaeure; (4-Amino-4-carboxybutyl)penicillin; NSC 113137; (D-4-Amino-4-carboxybutyl) penicillinic acid |
| IUPAC Name | (2S,5R,6R)-6-[[(5R)-5-amino-5-carboxypentanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| Canonical SMILES | CC1(C(N2C(S1)C(C2=O)NC(=O)CCCC(C(=O)O)N)C(=O)O)C |
| InChI | InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8-,9+,11-/m1/s1 |
| InChI Key | MIFYHUACUWQUKT-GPUHXXMPSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 739.2 °C at 760 mmHg |
| Density | 1.50 g/cm3 |
| Solubility | Soluble in Water; Hardly soluble in Ethanol, Ether |
Reference Reading
1.Investigations on recyclisation and hydrolysis in avibactam mediated serine β-lactamase inhibition.
Choi H1, Paton RS2, Park H3, Schofield CJ2. Org Biomol Chem. 2016 Apr 13. [Epub ahead of print]
β-Lactams inhibit penicillin-binding proteins (PBPs) and serine β-lactamases by acylation of a nucleophilic active site serine. Avibactam is approved for clinical use in combination with ceftazidime, and is a breakthrough non β-lactam β-lactamase inhibitor also reacting via serine acylation. Molecular dynamics (MD) and quantum chemical calculations on avibactam-mediated inhibition of a clinically relevant cephalosporinase reveal that recyclisation of the avibactam derived carbamoyl complex is favoured over hydrolysis. In contrast, we show that analogous recyclisation in β-lactam mediated inhibition is disfavoured. Avibactam recyclisation is promoted by a proton shuttle, a 'structural' water protonating the nucleophilic serine, and stabilization of the negative charge developed on aminocarbonyl oxygen. The results imply the potential of calculations for distinguishing between bifurcating pathways during inhibition and in generating hypotheses for predicting resistance.
2.Current Perspectives on Prevention of Mother-to-Child Transmission of Syphilis.
Lago EG1. Cureus. 2016 Mar 9;8(3):e525. doi: 10.7759/cureus.525.
This article aims to provide an update on the prevention of mother-to-child transmission of syphilis by drawing upon some important basic concepts and reviewing the most recent literature on the diagnosis and treatment of syphilis in pregnancy. New technologies, such as automated and point-of-care immunologic tests, are shifting some paradigms, which will certainly be further investigated in the forthcoming years. This is the time to carefully evaluate traditional as well as new strategies to prevent congenital syphilis. Adverse outcomes of mother-to-child transmission of syphilis can be prevented with antenatal screening and penicillin therapy, which proved to have an excellent cost-benefit ratio even in populations with a low prevalence of syphilis. However, syphilis epidemiology is influenced by socioeconomic and cultural factors, and major challenges are faced by poor and developing countries in which the severity of the problem is extremely alarming.
3.Cofactor bypass variants reveal a conformational control mechanism governing cell wall polymerase activity.
Markovski M1, Bohrhunter JL1, Lupoli TJ2, Uehara T1, Walker S3, Kahne DE4, Bernhardt TG5. Proc Natl Acad Sci U S A. 2016 Apr 11. pii: 201524538. [Epub ahead of print]
To fortify their cytoplasmic membrane and protect it from osmotic rupture, most bacteria surround themselves with a peptidoglycan (PG) exoskeleton synthesized by the penicillin-binding proteins (PBPs). As their name implies, these proteins are the targets of penicillin and related antibiotics. We and others have shown that the PG synthases PBP1b and PBP1a ofEscherichia colirequire the outer membrane lipoproteins LpoA and LpoB, respectively, for their in vivo function. Although it has been demonstrated that LpoB activates the PG polymerization activity of PBP1b in vitro, the mechanism of activation and its physiological relevance have remained unclear. We therefore selected for variants of PBP1b (PBP1b*) that bypass the LpoB requirement for in vivo function, reasoning that they would shed light on LpoB function and its activation mechanism. Several of these PBP1b variants were isolated and displayed elevated polymerization activity in vitro, indicating that the activation of glycan polymer growth is indeed one of the relevant functions of LpoB in vivo.
4.Nanotube Formation: A Rapid Form of "Alarm Signaling"?
Weng Z1, Zhang B1, Tsilioni I2, Theoharides TC3. Clin Ther. 2016 Apr 13. pii: S0149-2918(16)30127-8. doi: 10.1016/j.clinthera.2016.02.030. [Epub ahead of print]
PURPOSE: Tunneling nanotubes (TNTs) are extremely thin (50-200 nm), actin-containing cell surface protrusions up to a few microns in length that can develop rapidly and connect various cell types. Mast cells (MCs) are unique immunomodulatory cells that are found perivascularly in all tissues. MCs communicate with many other cell types through the release of inflammatory, neurosensitizing, and vasoactive molecules, through which they are involved in the pathogenesis of many inflammatory diseases. We, therefore, investigated the possibility that MCs may form TNTs and communicate among themselves and with glioblastoma cells.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
