Cilastatin sodium - 81129-83-1
Cilastatin sodium
Catalog Number: BT-254212
CAS Number: 81129-83-1
Molecular Formula: C16H25N2NaO5S
Molecular Weight: 380.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Cilastatin sodium is a potent inhibitor of renal dehydropeptidase I (DHP-I) that is used in combination with imipenem to treat severe bacterial infections. It was first introduced in the 1980s and has since been widely used in clinical practice. This paper aims to provide a comprehensive review of cilastatin sodium, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges.
Properties
CAS Number
81129-83-1
Product Name
Cilastatin sodium
IUPAC Name
sodium;(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoate
Molecular Formula
C16H25N2NaO5S
Molecular Weight
380.4 g/mol
InChI
InChI=1S/C16H26N2O5S.Na/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21;/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23);/q;+1/p-1/b12-6-;/t10-,11+;/m1./s1
InChI Key
QXPBTTUOVWMPJN-QBNHLFMHSA-M
SMILES
CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)[O-])C.[Na+]
Synonyms
Cilastatin
Cilastatin Monosodium Salt
Cilastatin Sodium
MK 0791
MK 791
MK-791
MK0791
MK791
Monosodium Salt, Cilastatin
Salt, Cilastatin Monosodium
Sodium, Cilastatin
Canonical SMILES
CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)[O-])C.[Na+]
Isomeric SMILES
CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)[O-])C.[Na+]
Method of Synthesis or Extraction
Cilastatin sodium is synthesized by the condensation of 7-aminocephalosporanic acid (7-ACA) with N-formimidoyl thienamycin (NFM) in the presence of a coupling agent such as dicyclohexylcarbodiimide (DCC). The reaction yields cilastatin, which is then converted to cilastatin sodium by neutralization with sodium hydroxide. Other methods of synthesis include the use of N,N'-carbonyldiimidazole (CDI) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC).
The efficiency and yield of each method vary, with the DCC method being the most commonly used and yielding the highest amount of cilastatin. However, the use of DCC has environmental and safety considerations, as it is a toxic and hazardous chemical. The CDI and EDC methods are more environmentally friendly and safer to use but have lower yields.
Chemical Structure and Biological Activity
Cilastatin sodium is a white crystalline powder with a molecular weight of 380.4 g/mol. Its chemical structure consists of a beta-lactam ring, a thiazolidine ring, and a pyridinium cation. Cilastatin sodium acts as a competitive inhibitor of Cilastatin sodium, which is responsible for the breakdown of imipenem in the kidneys. By inhibiting Cilastatin sodium, cilastatin sodium increases the half-life of imipenem and enhances its antibacterial activity.
Biological Effects
Cilastatin sodium has been shown to have various biological effects on cell function and signal transduction. It has been reported to inhibit the growth of cancer cells and induce apoptosis in vitro. However, its potential therapeutic and toxic effects in vivo are still under investigation.
Applications
In medical research, cilastatin sodium plays a crucial role in drug development, particularly in the development of new antibiotics. Clinical trials have shown that the combination of cilastatin sodium and imipenem is effective in treating severe bacterial infections, including those caused by multidrug-resistant bacteria. However, the use of cilastatin sodium is not without potential side effects, such as allergic reactions and renal impairment.
In environmental research, cilastatin sodium has been found to have effects on ecosystems, particularly on the microbial community in soil and water. It is also used in pollution management to degrade antibiotics in wastewater and soil. However, its sustainability and environmental impact are still being studied.
In industrial research, cilastatin sodium is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are essential in the use of cilastatin sodium in industrial settings.
Future Perspectives and Challenges
The current limitations in the use and study of cilastatin sodium include its potential toxicity and the emergence of antibiotic resistance. Possible solutions and improvements include the development of new antibiotics and the use of alternative methods of synthesis or extraction. Future trends and prospects in the application of cilastatin sodium in scientific research include the development of new therapeutic applications and the investigation of its potential in cancer treatment.
Conclusion:
Cilastatin sodium is a potent inhibitor of Cilastatin sodium that is used in combination with imipenem to treat severe bacterial infections. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges have been discussed in this paper. Further research is needed to fully understand the potential therapeutic and toxic effects of cilastatin sodium and to develop new antibiotics to combat antibiotic resistance.
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