D-Cycloserine

Product Details

Name D-Cycloserine
Alias Seromycin; 4-amino-3-isoxazolidinone
CAS  No. 68-41-7
Formula C3H6N2O2
Weight 102.092 g/mol
Usage Pharmaceuticals
Appearance White or light yellow crystalline powder

Product Description

D-cycloserine is a broad-spectrum antibiotic of the polypeptide produced by Streptomyces lavendulae and S. orchidaces or chemically synthesized. It is white crystal, strong hygroscopicity, soluble in water, soluble in lower alcohol, acetone, and dioxane, insoluble in chloroform and petroleum ether; stable in alkaline solution, in acidic and neutral solution Decompose quickly. Cycloserine has a broad antibacterial spectrum. In addition to Mycobacterium tuberculosis, it also inhibits most Gram-positive and negative bacteria, Rickettsia and certain protozoa. For streptomycin, zirconia, and amino-sodium M. tuberculosis resistant to acid, isoniazid, pyrazinamide, etc. also has a role. Cycloserine and isoniazid have a mild synergistic effect on Mycobacterium tuberculosis H37RV, and neither synergistic nor antagonism with streptomycin. This product is a bacteriostatic agent, increasing the dose or prolonging the time of action with bacteria, and does not cause bactericidal action.


Cycloserine is a second-line anti-tuberculosis drug that inhibits the growth of Mycobacterium tuberculosis, but its effect is weaker than that of first-line drugs, and its efficacy against tuberculosis is also low. It can produce drug resistance alone, but drug resistance is slower than other anti-tuberculosis drugs. There is no cross-resistance with other anti-tuberculosis drugs. Its antibacterial mechanism is to inhibit the synthesis of bacterial cell wall mucin peptides, thereby causing cell wall defects. The main structural component of the bacterial cell wall is the mucoid peptide, which is formed by the repeated alternating association of N-acetylglucosamine (GNAc) and N-acetylmuramic acid (MNAc) linked to the pentapeptide. The formation of cytosolic internal mucopeptide precursors can be blocked by cycloserine, which blocks the formation of N-acetylmuramic acid pentapeptide by inhibiting the racemase and synthetase of D-alanine.

It is not easy to produce drug resistance, but the anti-tuberculosis effect is weaker than streptomycin, and it is mainly used for the infection of drug-resistant Mycobacterium tuberculosis. Have gastrointestinal discomfort and fever reaction, mainly toxic to the nervous system.

Function

The mechanism of the antibacterial action of D-cycloserine is to inhibit the biosynthesis of cell wall peptidoglycan, which is a structural analog of D-alanine, which can competitively inhibit the synthesis of peptidoglycan with D-alanine. Two important enzymes - alanine racemase and D-alanyl-D-alanine synthetase. Its ability to resist Mycobacterium tuberculosis is weak, only 1/10 to 1/20 of streptomycin. The advantage is that it is effective against the resistant strain of the bacteria, and it is not easy to develop resistance to it. This product can be combined with other anti-tuberculosis drugs to treat tuberculosis caused by drug-resistant M. tuberculosis.

  • Inhibition of cell wall synthesis (D-alanine peptide bond formation). Conversion of D-alanine to L-alanine is also prevented.

 

Application

Tuberculosis

For the treatment of tuberculosis, cycloserine is classified as a second-line drug, ie its use is only considered if one or more first-line drugs cannot be used. Hence, cycloserine is restricted for use only against multiple drug-resistant and extensively drug-resistant strains of M. tuberculosis. Another reason for limited use of this drug is the neurological side effects it causes, since it is able to penetrate into the central nervous system (CNS) and cause headaches, drowsiness, depression, dizziness, vertigo, confusion, paresthesias, dysarthria, hyperirritability, psychosis, convulsions, and shaking (tremors). The overdose of cycloserine may result in paresis, seizures, and coma, while alcohol consumption may increase the risk of seizures. Coadministration of pyridoxine can reduce the incidence of some of these CNS side effects (eg convulsions) caused by cycloserine.

Psychiatry

A 2015 Cochrane review found no evidence of benefit in anxiety disorders as of 2015. [8] Another review found preliminary evidence of benefit.  Evidence for use in addiction is tentative but also unclear.

Other Uses

  • Biochemical research
  • Enzyme inhibitor

 


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