D-(+)-シクロセリン

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H315：皮膚刺激

  H319：強い眼刺激

  H335：呼吸器への刺激のおそれ

• 注意書き

  P261：粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。

  P271：屋外または換気の良い場所でのみ使用すること。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

D-(+)-シクロセリン 価格

MSDS Information

• D-Cycloserine

D-(+)-シクロセリン 化学特性,用途語,生産方法

• 外観

  白色〜わずかにうすい褐色, 結晶〜粉末

• 溶解性

  水溶状：試験適合

• 解説

  シクロセリンは，抗生物質。数種の放線菌が産生。アミノ酸のD-アラニンと拮抗(きっこう)して細菌の細胞壁合成を阻害する作用があり，おもに耐性結核菌感染症の治療に用いる。副作用として各種の精神障害，神経系障害を起こすことがあるが，このような障害の現れたときは投与を中止する。（図）→耐性菌
  株式会社平凡社 百科事典マイペディアについて　情報

• 効能

  抗結核薬, 細胞壁合成阻害薬

• 商品名

  サイクロセリン (Meiji Seikaファルマ)

• 確認試験

  本品を乾燥し，赤外吸収スペクトル測定法〈2.25〉 の臭化カリウム錠剤法により試験を行い，本品のスペクトル と本品の参照スペクトル又は乾燥したサイクロセリン標準品 のスペクトルを比較するとき，両者のスペクトルは同一波数 のところに同様の強度の吸収を認める．

• 定量法

  次の条件に従い，抗生物質の微生物学的力価試験法 〈4.02〉の円筒平板法により試験を行う．
  (ⅰ) 試験菌 Bacillus subtilis ATCC 6633を用いる．
  (ⅱ) 培地 培地(1)の1)のⅰを用いる．ただし，滅菌後の pHは6.0～6.1とする．
  (ⅲ) 標準溶液 サイクロセリン標準品を60℃で3時間減圧 (0.67kPa以下)乾燥し，その約40mg(力価)に対応する量を精 密に量り，水に溶かして正確に100mLとし，標準原液とす る．標準原液は5℃以下に保存し，24時間以内に使用する． 用時，標準原液適量を正確に量り，pH6.0のリン酸塩緩衝液 を加えて1mL中に100μg(力価)及び50μg(力価)を含むように 正確に薄め，高濃度標準溶液及び低濃度標準溶液とする．
  (ⅳ) 試料溶液 本品約40mg(力価)に対応する量を精密に量り，水に溶かして正確に100mLとする．この液適量を正確 に量り， pH6.0 のリン酸塩緩衝液を加えて1mL 中に 100μg(力価)及び50μg(力価)を含むように正確に薄め，高濃 度試料溶液及び低濃度試料溶液とする．

• 純度試験

  (１) 重金属〈1.07〉 本品1.0gをとり，第4法により操作し， 試験を行う．比較液には鉛標準液2.0mLを加える(20ppm以 下)．
  (２) 縮合生成物 本品20mgをとり，水酸化ナトリウム試 液に溶かし，正確に50mLとする．この液につき，紫外可視 吸光度測定法〈2.24〉により試験を行うとき，波長285nmに おける吸光度は，0.8以下である．

• 乾燥減量

  1.5％以下(0.5g，減圧，60℃，3時間)．

• 化学的特性

  White to pale yellow cryst. powder

• 使用

  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.

• 適応症

  Cycloserine is a broad-spectrum antibiotic produced by Streptomyces orchidaceus. It is structural analogue of Dalanine and acts through a competitive inhibition of the D-alanine that is involved in bacterial cell wall synthesis. Cycloserine is inhibitory to M. tuberculosis and active against Escherichia coli, S. aureus, and Enterococcus, Nocardia, and Chlamydia spp. It is used in the treatment of MDR tuberculosis and is useful in renal tuberculosis, since most of the drug is excreted unchanged in the urine.

• 一般的な説明

  Chemical structure: amino acid derivatives

• 作用機序

  D-Cycloserine is considered to be the active form of the drug, having its action associated with the ability to inhibit two key enzymes, D-alanine racemase and D-alanine ligase. D-Alanine is an important component of the peptidoglycan portion of the mycobacterial cell wall. Mycobacterium are capable of utilizing natural occurring L-alanine and converting the L-alanine to D-alanine via the enzyme D-alanine racemase. The resulting D-alanine is coupled with itself to form a D-alanine–D-alanine complex under the influence of D-alanine ligase, and this complex is incorporated into the peptidoglycan of the mycobacterial cell wall . D-Cycloserine is a rigid analogue of D-alanine; therefore, it competitively inhibits the binding of D-alanine to both of these enzymes and its incorporation into the peptidoglycan. Resistance is associated with an over expression of D-alanine racemase.

• 薬理学

  Cycloserine is readily absorbed orally and distributes throughout body fluids including the cerebrospinal fluid. The concentrations of cycloserine in tissues, body fluids, and the cerebrospinal fluid are approximately equal to the plasma level. Cycloserine is partially metabolized, and 60 to 80% is excreted unchanged by the kidney.

• 臨床応用

  D-(+)-4-Amino-3-isoxazolidinone (Seromycin) is an antibioticthat has been isolated from the fermentation beer of threedifferent Streptomyces species: S. orchidaceus, S. garyphalus,and S. lavendulus. It occurs as a white to pale yellow crystallinematerial that is very soluble in water. It is stable in alkaline,but unstable in acidic, solutions. The compoundslowly dimerizes to 2,5-bis(aminoxymethyl)-3,6-diketopiperazinein solution or standing.
  The structure of cycloserine was reported simultaneouslyby Kuehl et al. and Hidy et al.81 to be D-( +)-4-amino-3-isoxazolidinone. It has been synthesized byStammer et al. and by Smart et al.83 Cycloserine is stereochemicallyrelated to D-serine. However, the L-form hassimilar antibiotic activity.
  Although cycloserine exhibits antibiotic activity invitro against a wide spectrum of both Gram-negative andGram-positive organisms, its relatively weak potency andfrequent toxic reactions limit its use to the treatment of tuberculosis.It is recommended for patients who fail to respondto other tuberculostatic drugs or who are known tobe infected with organisms resistant to other agents. It isusually administered orally in combination with otherdrugs, commonly isoniazid.

• 副作用

  Cycloserine is readily absorbed after oral administration and is widely distributed, including the CNS. Unfortunately, D-cycloserine binds to neuronal N-methylasparate receptors and, in addition, affects synthesis and metabolism of γ-aminobutyric acid, leading to complex series of CNS effects. As a second-line agent, cycloserine should only be used when retreatment is necessary or when the organism is resistant to other drugs. Cycloserine should not be used as a single drug; it must be used in combination.

• 純化方法

  Purify cycloserine by recrystallisation from aqueous EtOH or MeOH or aqueous NH3/EtOH or isoPrOH. Also recrystallise it from aqueous ammoniacal solution at pH 10.5 (100mg/mL) by diluting with 5 volumes of isopropanol and then adjusting to pH 6 with acetic acid. An aqueous solution, buffered to pH 10 with Na2CO3, can be stored in a refrigerator for 1week without decomposition. UV: max at 226nm (A1cm 1% 4.02). The tartrate salt has m 165-166o (dec), 166-168o (dec), and [] D 24 -41o (c 0.7, H2O). [Stammer et al. J Am Chem Soc 79 3236 1959, UV: Kuehl J Am Chem Soc 77 2344 1955, Beilstein 27 III/IV 5549.]

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D-(+)-シクロセリン スペクトルデータ(¹HNMR、¹³CNMR、IR1、IR2、MS、Raman)

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