D-Cyloserine
D-cycloserine
CAS: 68-41-7
Molecular Formula: C3H6N2O2
D-Cyloserine - Names and Identifiers
D-Cyloserine - Physico-chemical Properties
| Molecular Formula | C3H6N2O2 |
| Molar Mass | 102.09 |
| Density | 1.3516 (rough estimate) |
| Melting Point | 147°C (dec.)(lit.) |
| Boling Point | 191.38°C (rough estimate) |
| Specific Rotation(α) | 111 º (C=5, 2N NaOH) |
| Water Solubility | SOLUBLE |
| Solubility | water: soluble50mg/mL, clear, colorless to light yellow |
| Appearance | powder |
| Color | white to off-white |
| Merck | 14,2751 |
| BRN | 80798 |
| pKa | pKa 4.5 (Uncertain) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month. |
| Sensitive | Air Sensitive |
| Refractive Index | 1.5110 (estimate) |
| MDL | MFCD00005353 |
| Physical and Chemical Properties | Colorless needle-like or leaf-like crystal or amorphous powder. Melting point 155-156 °c (decomposition). Soluble in water, slightly soluble in methanol, ethanol, butanol, propylene glycol, isopropanol and acetone, insoluble or insoluble in toluene, chloroform, ether, pyridine, benzene and carbon disulfide. |
D-Cyloserine - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R5 - Heating may cause an explosion R20 - Harmful by inhalation |
| Safety Description | S38 - In case of insufficient ventilation, wear suitable respiratory equipment. S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | NY2975000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29419090 |
D-Cyloserine - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| second-line anti-tuberculosis drugs | D-cycloserine is a type of drug produced by Streptomyces lilacinus and Streptomyces orchid (S.orchidaceus) a broad-spectrum antibiotic of the class of polypeptides produced or synthesized by chemistry. White crystals, strong hygroscopicity, soluble in water, soluble in lower alcohol, acetone and dioxane, insoluble in chloroform and petroleum ether; More stable in alkaline solution, it decomposes rapidly in acidic and neutral solutions. In addition to Mycobacterium tuberculosis, most Gram-positive and negative bacteria, Rickettsia and some protozoa also have inhibitory effect on streptomycin, viamycin, P-aminosalicylic acid, isoniazid, pyrazinamide and other resistant Mycobacterium tuberculosis also have a role. Cycloserine and isoniazid on Mycobacterium tuberculosis H37RV has a mild synergistic effect, and streptomycin neither synergy nor show antagonistic effect. This product is a bacteriostatic agent, increasing the dose or prolonging the time of action with bacteria, and there is no bactericidal effect. The mechanism of the antibacterial effect of D-cycloserine is to inhibit the biosynthesis of cell wall peptidoglycan, because it is a structural analog of D-alanine, two important enzymes in peptidoglycan synthesis, alanine racemase and D-alanyl-D-alanine synthetase, can be inhibited competitively with D-alanine. The ability of anti Mycobacterium tuberculosis (Mycobacterium tuberculosis) is weak, only 1/10~1/20 of streptomycin. The advantage is that the drug resistant strains of the bacteria are effective, and it is not easy to produce resistance to it. This product can be combined with other anti-tuberculosis drugs for the treatment of tuberculosis caused by drug-resistant Mycobacterium tuberculosis. Cycloserine is a second-line anti-tuberculosis drug, which can inhibit the growth of Mycobacterium tuberculosis, but the effect is weaker than the first-line drugs, and the effect on tuberculosis is low, but the drug resistance occurred more slowly than other anti-tuberculosis drugs, and there was no cross-resistance between other anti-tuberculosis drugs. Its antibacterial mechanism is to inhibit the synthesis of bacterial cell wall mucopeptides, so that the cell wall defect. The main structural component of the bacterial cell wall is the cell wall mucopeptide, which is composed of N-acetyl glucosamine (GNAc) and N-acetyl teichoic acid (MNAc) linked to the pentapeptide. The formation of cytosolic mucopeptide precursors can be hindered by cycloserine, which by inhibiting the racemase and synthetase of D-alanine can hinder the formation of N-acetyl teichoate pentapeptide. |
| Use | antibiotics. For infections with drug-resistant Mycobacterium tuberculosis. biochemical studies enzyme inhibitors inhibit cell wall synthesis (D-alanine peptide bond formation). Conversion of D-alanine to L-alanine was also prevented. Bacteriostatic. |
| production method | cycloserine can be prepared by fermentation or direct synthesis. The fermentation producing strain was Actinomyces laven-dulae, and the fermentation medium was dextrin, glucose, starch, soybean meal, yeast powder, ammonium sulfate, ammonium nitrate, calcium carbonate, sodium chloride, magnesium sulfate and soybean oil. The synthesis method is the reaction of β-aminooxyalanine ethyl ester dihydrochloride and potassium hydroxide, I .e. cyclization to obtain cycloserine. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:54:55
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