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Dicloxacillin

Catalog Number: BT-264456

CAS Number: 3116-76-5

Molecular Formula: C19H17Cl2N3O5S

Molecular Weight: 470.3 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Dicloxacillin 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 is a semi-synthetic derivative of penicillin, and its chemical structure is similar to other penicillin antibiotics.

Properties

CAS Number

3116-76-5

Product Name

Dicloxacillin

IUPAC Name

(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-carboxylic acid

Molecular Formula

C19H17Cl2N3O5S

Molecular Weight

470.3 g/mol

InChI

InChI=1S/C19H17Cl2N3O5S/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)/t13-,14+,17-/m1/s1

InChI Key

YFAGHNZHGGCZAX-JKIFEVAISA-N

SMILES

CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O

Solubility

3.63 mg/L
In water, 3.63 mg/L at 25 °C (est)
2.96e-02 g/L

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

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

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

Method of Synthesis or Extraction

Dicloxacillin is synthesized by the acylation of 6-amino-penicillanic acid with 2,6-dimethoxybenzoyl chloride. The reaction takes place in the presence of a base, such as triethylamine, and a solvent, such as dichloromethane. The yield of dicloxacillin synthesis is around 70-80%, and the reaction is considered efficient. However, the synthesis process requires the use of toxic and hazardous chemicals, which can pose environmental and safety concerns.

Chemical Structure and Biological Activity

Dicloxacillin has a beta-lactam ring, which is responsible for its antibacterial activity. The beta-lactam ring inhibits the bacterial cell wall synthesis by binding to the penicillin-binding proteins (PBPs) present in the bacterial cell membrane. Dicloxacillin is active against gram-positive bacteria, including Staphylococcus aureus, Streptococcus pyogenes, and Streptococcus pneumoniae. It is not effective against gram-negative bacteria due to their outer membrane barrier.

Biological Effects

Dicloxacillin affects cell function and signal transduction by inhibiting the bacterial cell wall synthesis. It can cause potential therapeutic and toxic effects, depending on the dose and duration of treatment. The therapeutic effects of dicloxacillin include the treatment of bacterial infections, such as skin and soft tissue infections, respiratory tract infections, and bone and joint infections. The toxic effects of dicloxacillin include allergic reactions, gastrointestinal disturbances, and liver toxicity.

Applications

Dicloxacillin has various applications in medical research, environmental research, and industrial research. In medical research, dicloxacillin plays a significant role in drug development, clinical trials, and findings. It is used to treat bacterial infections and has shown promising results in the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infections. In environmental research, dicloxacillin's effects on ecosystems and its role in pollution management are studied. In industrial research, dicloxacillin is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are essential in the industrial use of dicloxacillin.

Future Perspectives and Challenges

The current limitations in the use and study of dicloxacillin include the emergence of antibiotic-resistant bacteria, the potential for adverse effects, and the need for alternative antibiotics. Possible solutions and improvements include the development of new antibiotics, the use of combination therapy, and the implementation of antibiotic stewardship programs. Future trends and prospects in the application of dicloxacillin in scientific research include the development of new formulations, the use of nanotechnology, and the exploration of its potential in cancer treatment.
Conclusion:
Dicloxacillin is a narrow-spectrum antibiotic that has various applications in medical research, environmental research, and industrial research. Its chemical structure and biological activity make it effective against gram-positive bacteria, and its therapeutic effects have been proven in the treatment of bacterial infections. However, the potential for adverse effects and the emergence of antibiotic-resistant bacteria pose challenges in its use and study. Future research should focus on the development of new antibiotics and alternative therapies to combat bacterial infections.

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