Dicloxacillin sodium monohydrate
Catalog Number: BT-264457
CAS Number: 13412-64-1
Molecular Formula: C19H18Cl2N3NaO6S
Molecular Weight: 511.3 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Dicloxacillin sodium monohydrate is a narrow-spectrum antibiotic that belongs to the penicillin family. It is commonly used to treat bacterial infections caused by gram-positive bacteria, including Staphylococcus aureus. Dicloxacillin sodium monohydrate is a white crystalline powder that is soluble in water and has a molecular weight of 510.51 g/mol.
Properties
CAS Number
13412-64-1
Product Name
Dicloxacillin sodium monohydrate
IUPAC Name
sodium;(2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrate
Molecular Formula
C19H18Cl2N3NaO6S
Molecular Weight
511.3 g/mol
InChI
InChI=1S/C19H17Cl2N3O5S.Na.H2O/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
InChI Key
SIGZQNJITOWQEF-VICXVTCVSA-M
SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].O.[Na+]
Solubility
Soluble in DMSO
Synonyms
Cilpen
Dichloroxacillin
Diclocil
Dicloxaciclin
Dicloxacillin
Dicloxacillin Sodium
Dicloxacillin, Monosodium Salt, Anhydrous
Dicloxacillin, Monosodium Salt, Mono-Hydrate
Dicloxacycline
Dicloxsig
Distaph
Ditterolina
Dycill
Dynapen
InfectoStaph
Pathocil
Posipen
Sodium, Dicloxacillin
Dichloroxacillin
Diclocil
Dicloxaciclin
Dicloxacillin
Dicloxacillin Sodium
Dicloxacillin, Monosodium Salt, Anhydrous
Dicloxacillin, Monosodium Salt, Mono-Hydrate
Dicloxacycline
Dicloxsig
Distaph
Ditterolina
Dycill
Dynapen
InfectoStaph
Pathocil
Posipen
Sodium, Dicloxacillin
Canonical SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].O.[Na+]
Isomeric SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].O.[Na+]
Method of Synthesis or Extraction
Dicloxacillin sodium monohydrate can be synthesized by the reaction of 6-amino-penicillanic acid with 2,6-dichlorobenzoyl chloride in the presence of a base. The reaction yields dicloxacillin, which is then converted to its sodium salt by reacting with sodium hydroxide. The efficiency and yield of this method are high, and the reaction can be carried out on a large scale. However, the process requires the use of toxic and hazardous chemicals, which can pose a risk to the environment and human health. Therefore, safety measures must be taken during the synthesis process.
Chemical Structure and Biological Activity
Dicloxacillin sodium monohydrate has a chemical structure similar to other penicillin antibiotics. It contains a beta-lactam ring that is responsible for its antibacterial activity. The mechanism of action of dicloxacillin sodium monohydrate involves the inhibition of bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs). This leads to the disruption of the bacterial cell wall, causing the bacteria to lyse and die. Dicloxacillin sodium monohydrate is active against gram-positive bacteria, including Staphylococcus aureus, Streptococcus pyogenes, and Streptococcus pneumoniae. It has no activity against gram-negative bacteria.
Biological Effects
Dicloxacillin sodium monohydrate has several biological effects on cell function and signal transduction. It can cause the release of inflammatory cytokines, such as interleukin-1 and tumor necrosis factor-alpha, from immune cells. It can also activate the complement system, which is a part of the immune system that helps to clear bacterial infections. However, dicloxacillin sodium monohydrate can also have potential therapeutic and toxic effects. It can cause allergic reactions, such as skin rash, hives, and anaphylaxis. It can also cause gastrointestinal side effects, such as nausea, vomiting, and diarrhea.
Applications
Dicloxacillin sodium monohydrate has several applications in medical research. It is commonly used in drug development to test the efficacy of new antibiotics against gram-positive bacteria. It has also been used in clinical trials to treat bacterial infections, such as skin and soft tissue infections, bone and joint infections, and respiratory tract infections. The benefits of dicloxacillin sodium monohydrate include its narrow-spectrum activity, which reduces the risk of developing antibiotic resistance. However, it can also have potential side effects, such as allergic reactions and gastrointestinal side effects.
In environmental research, dicloxacillin sodium monohydrate can have effects on ecosystems. It can enter the environment through wastewater and can have an impact on aquatic organisms. It can also contribute to the development of antibiotic resistance in bacteria in the environment. Therefore, it is important to monitor the levels of dicloxacillin sodium monohydrate in the environment and to develop strategies to reduce its impact.
In industrial research, dicloxacillin sodium monohydrate is used in manufacturing processes to improve product quality and efficiency. It can also have health and safety considerations, as it is a hazardous chemical that can pose a risk to workers. Therefore, safety measures must be taken during the manufacturing process to prevent exposure to dicloxacillin sodium monohydrate.
In environmental research, dicloxacillin sodium monohydrate can have effects on ecosystems. It can enter the environment through wastewater and can have an impact on aquatic organisms. It can also contribute to the development of antibiotic resistance in bacteria in the environment. Therefore, it is important to monitor the levels of dicloxacillin sodium monohydrate in the environment and to develop strategies to reduce its impact.
In industrial research, dicloxacillin sodium monohydrate is used in manufacturing processes to improve product quality and efficiency. It can also have health and safety considerations, as it is a hazardous chemical that can pose a risk to workers. Therefore, safety measures must be taken during the manufacturing process to prevent exposure to dicloxacillin sodium monohydrate.
Future Perspectives and Challenges
The use of dicloxacillin sodium monohydrate is limited by the development of antibiotic resistance in bacteria. Therefore, there is a need to develop new antibiotics that can overcome this problem. One possible solution is to develop antibiotics that target multiple bacterial pathways, which can reduce the risk of developing resistance. Another challenge is to develop antibiotics that are effective against gram-negative bacteria, which are more difficult to treat than gram-positive bacteria.
In conclusion, dicloxacillin sodium monohydrate is a narrow-spectrum antibiotic that has several applications in medical, environmental, and industrial research. It has a high efficiency and yield in the synthesis process, but safety measures must be taken to prevent exposure to hazardous chemicals. Dicloxacillin sodium monohydrate has a chemical structure similar to other penicillin antibiotics and has a mechanism of action that involves the inhibition of bacterial cell wall synthesis. It has several biological effects on cell function and signal transduction and can have potential therapeutic and toxic effects. The future perspectives and challenges of dicloxacillin sodium monohydrate include the development of new antibiotics that can overcome antibiotic resistance and are effective against gram-negative bacteria.
In conclusion, dicloxacillin sodium monohydrate is a narrow-spectrum antibiotic that has several applications in medical, environmental, and industrial research. It has a high efficiency and yield in the synthesis process, but safety measures must be taken to prevent exposure to hazardous chemicals. Dicloxacillin sodium monohydrate has a chemical structure similar to other penicillin antibiotics and has a mechanism of action that involves the inhibition of bacterial cell wall synthesis. It has several biological effects on cell function and signal transduction and can have potential therapeutic and toxic effects. The future perspectives and challenges of dicloxacillin sodium monohydrate include the development of new antibiotics that can overcome antibiotic resistance and are effective against gram-negative bacteria.
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