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CAS NO.68-41-7
| D-Cycloserine Basic information |
| Product Name: | D-Cycloserine |
| Synonyms: | CYCLOSERINE;D-CYCLOSERINE;D-CYCLOSERINE, STREPTOMYCES ORCHIDACEUS;D-4-AMINO-3-ISOXAZOLIDINONE;(R)-(+)-CYCLOSERINE;(R)-4-AMINO-ISOXAZOLIDIN-3-ONE;(R)-4-AMINO-3-ISOXAZOLIDINONE;R(+)-4-AMINO-3-ISOXAZOLIDINONE |
| CAS: | 68-41-7 |
| MF: | C3H6N2O2 |
| MW: | 102.09 |
| EINECS: | 200-688-4 |
| Product Categories: | VARIOUSAMINE;Miscellaneous Biochemicals;chiral;Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Amino Acids;Glutamate receptor;Glutamate;Antibiotics;API;SEROMYCIN;amino;Inhibitors;Amino acid |
| Mol File: | 68-41-7.mol |
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| D-Cycloserine Chemical Properties |
| mp | 147 °C (dec.)(lit.) |
| alpha | 111 º (C=5, 2N NaOH) |
| storage temp. | −20°C |
| form | powder |
| Water Solubility | SOLUBLE |
| Sensitive | Air Sensitive |
| Merck | 14,2751 |
| BRN | 80798 |
| CAS DataBase Reference | 68-41-7(CAS DataBase Reference) |
| NIST Chemistry Reference | Cycloserine(68-41-7) |
| Safety Information |
| Hazard Codes | Xn |
| Risk Statements | 5-20 |
| Safety Statements | 38-36/37-24/25 |
| WGK Germany | 2 |
| RTECS | NY2975000 |
| F | 10-23 |
| Hazardous Substances Data | 68-41-7(Hazardous Substances Data) |
| MSDS Information |
| Provider | Language |
|---|---|
| D-Cycloserine | English |
| ACROS | English |
| SigmaAldrich | English |
| ALFA | English |
| D-Cycloserine Usage And Synthesis |
| A second-line anti-TB drug |
D-cycloserine is a broad-spectrum polypeptide antibiotic produced by Streptomyces lavendulae and Streptomyces orchidaceus or synthesized by chemical methods. As white crystals with strong hygroscopic nature, it is soluble in water, slightly soluble in lower alcohols, acetone and dioxane, and hardly soluble in chloroform and petroleum ether. It is relatively stable in alkaline solution and decomposes rapidly in acidic or neutral solutions. As a broad-spectrum antibiotic, cycloserine is inhibitive against most Gram-positive and Gram-negative bacteria, rickettsia and some protozoa, with the exception of Mycobacterium tuberculosis., It is also effective on some of the Mycobacterium tuberculosis strains with tolerance to streptomycin, vinactane para-aminosalicylic acid, isoniazid and pyrazinamide. Cycloserine slightly synergizes with isoniazid in the inhibition of Mycobacterium tuberculosis H37RV, but it neither synergizes nor antagonizes against streptomycin. The product is a bacteriostatic agent, and thus won’t exert bactericidal effect even when increasing the dose or prolonging the action time with bacteria. The Mechanism of D-cycloserine’s antibacterial action is to inhibit the biosynthesis of peptidoglycan of the cell wall. As it is a structural analog of D-alanine, D-cycloserine can competitively inhibit the activities of alanine racemase and D-alanyl-D-alanine synthetase, which are two important enzymes in peptidoglycan synthesis. D-cycloserine shows weak inhibitive activity against Mycobacterium tuberculosis which is only 1/10 to 1/20 that of streptomycin. The advantage of the product is that it is effective on drug-resistant Mycobacterium tuberculosis strains and less likely to induce drug resistance. The product can be used with other anti-tuberculosis drugs in the treatment of tuberculosis caused by drug-resistant Mycobacterium tuberculosis. Cycloserine is a second-line anti-tuberculosis drug. It can inhibit the growth of Mycobacterium tuberculosis, but the effect is relatively weaker than that of the first-line drugs. Its efficacy in tuberculosis treatment is relatively low. Use the drug alone may produce drug resistance, but the resistance occurs slowly compared with that of other anti-tuberculosis drugs. No cross-resistance has been found between cycloserine and other anti-tuberculosis drugs. The mechanism of its antibacterial action is to inhibit the synthesis of peptidoglycan of bacterial cell wall, causing defective in cell wall architecture. The main structural component of the bacterial cell wall is peptidoglycan, which is composed of N-acetylglucosamine (GNAc) and N-acetylmuramic acid (MNAc). N-acetylmuramic acid is linked with pentapeptide and connects N-acetylglucosamine in a reduplicated and alternative manner. The formation of cytoplasmic peptidoglycan precursor may be hampered by cycloserine, as the latter can hinder the racemase and the synthetase of D-alanine, and thus blocks the formation of N-acetylmuramic acid. The above information is edited by the Chemicalbook of Liu Huimin. |
| Chemical properties | Colorless needle or leafy crystals, or amorphous powder; melting point 155-156℃ (decomposition). Soluble in water; slightly soluble in methanol, ethanol, butanol, propylene glycol, isopropyl alcohol and acetone; and hardly soluble or insoluble in toluene, chloroform, ether, pyridine, benzene and carbon disulfide. |
| Application |
1. Used as an antibiotic medicine in the treatment of drug-resistant Mycobacterium tuberculosis infection. 2. Biochemical research |
| Production process | D-Cycloserine can be obtained through fermentation technique or through direct synthesis. The bacteria used in the fermentation is Actinomyces laven-dulae. The fermentation medium consists of dextrin, dextrose, starch, soybean powder, yeast powder, ammonium sulfate, ammonium nitrate, calcium carbonate, sodium chloride, magnesium sulfate and soybean oil. In the synthesis process, D-cycloserine is obtained from β-aminooxy alanine ethyl ester hydrochloride by reaction with potassium hydroxide in a cyclization reaction. |
| Chemical Properties | White to pale yellow cryst. powder |
| Usage | antibacterial (tuberculostatic) |
| Usage | D-Cycloserine inhibits cell wall biosynthesis (D-Ala peptide bond formation). D-Cycloserine also prevents conversion of D-Ala to L-Ala. D-Cycloserine is an bacteriostatic. D-Cycloserine is an antibiot ic against Gram-negative bacteria. |
| D-Cycloserine Preparation Products And Raw materials |
| Raw materials | Calcium carbonate-->Ammonium nitrate-->SOYBEAN OIL-->Dextrin-->streptomyces avermifilis-->D-Alanine |
Henan Sunlake Enterprise Corporation , facing global High-tech pharmaceutical raw materials, high value-added new type intermediates fine chemicals custom synthesis, scale-up production and rare chemicals trade. We have experienced research staff, strong technical force, well-equipped machine, and considerate marketing team service, with a strict customer intellectual property security system, we are already become good partner of customers from difficult and complex chemical and biological chemical field. Our high quality & low price and effective services shortened new product development cycle,reduced the development and production cost for numerous partners.
The company has completed numerous domestic and overseas famous pharmaceutical, chemical, biological and other large and medium-sized company R&D outsourcing services, synthesis process development and optimization services, chemical intermediates customized service, special chemical processing and production services, etc., We hope to become continuous mutually beneficial partnership with you, to create a better business opportunities together.
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1. Samples synthetic, Our strong r&d team has accumulated abundant experience in synthesis design and exploring synthesis of new technology. Not only good at heterocyclic chemistry, chiral chemicals (asymmetric synthesis and enzyme reaction), metal organic synthesis, high throughput chemistry, also specializes in bioorganic chemistry including nucleosides, nucleotides, sugar chemical, peptide chemistry, etc, to complete the synthesis from mg to kg samples in lab scale. Our efficient management and good communication skills and ability to solve the problem rapidly in order to ensure quality, timely delivery, based on the standard client confidential system and competitive price products,we has been recognized and praised by many customers in chemical industry.
2. Scale-up production, based on our rich laboratory experience and advanced equipment in production base, also depend on accumulation of advantages in many aspects as industrialized technology development, the production cost control, to provide from kg class to wt class custom synthesis scale-up production services to the global fine chemical industry, can be carried out oxidation, hydrogenation pressure (70 kg), halide, and acylation, esterification, condensation, cyclization, formatting, ammoniation, diazotization and azide reaction, our experienced production management, strict and perfect management system can quickly provide customers with competitive and fine mass production services.
3.Technology transfer, the company has accumulated a large number of production processes of drugs, intermediates and raw material. Based on the principle of mutual benefit, and some technology transfer to industry manufacturers, also provides them marketing support.
4. Purchasing agency service, Our excellence professional sales team, timely and thoughtful service, in addition to the necessary good language communication ability of professional sales staff, also equipped with professional chemical technical sales consultant, who can answer the customer's academic professional question, we are in line with the aim of offering customer wholehearted service, with our advanced testing equipment checks and abundant R&D and production of domestic partner contacts, to provide rare chemicals with standard purity, reasonable price and cost-effective purchasing agency service to foreign customers, and the help you shorten the sourcing time, reduce the purchasing cost.
