6-메르캅토퓨린

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Danger

• 유해·위험 문구

  H301：삼키면 유독함

  H341：유전적인 결함을 일으킬 것으로 의심됨 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재)

• 예방조치문구

  P201：사용 전 취급 설명서를 확보하시오.

  P202：모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.

  P264：취급 후에는 손을 철저히 씻으시오.

  P264：취급 후에는 손을 철저히 씻으시오.

  P270：이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.

  P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

  P301+P310：삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.

6-메르캅토퓨린 MSDS

• 6-Mercaptopurine monohydrate

6-메르캅토퓨린 화학적 특성, 용도, 생산

• 개요

  6-Mercaptopurine (6-MP) is an inhibitor of purine synthesis and interconversion. It is rapidly converted to 6-mercaptopurine ribonucleoside-5''-monophosphate, which inhibits phosphoribosyl pyrophosphate (PRPP) amidotransferase, the rate-limiting enzyme in purine synthesis. It also inhibits the conversion of IMP to adenylosuccinic acid and xanthylic acid and blocks AMP formation in vitro. 6-MP (30 mg/kg) inhibits growth of sarcoma 180, adenocarcinoma E 0771, and adenocarcinoma 755 tumors and reduces the size of leukemia L1210 subcutaneous growths in mice. It also decreases delayed-type hypersensitivity and thyroid inflammation in a guinea pig model of thyroiditis when administered pre- or post-disease onset. Formulations containing mercaptopurine have been used for maintenance therapy in patients with acute lymphoblastic leukemia.

• 화학적 성질

  white to light yellow crystal powder

• 용도

  An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin lymphoma, polycythemia vera, and psoriatic arthritis

• Indications

  Mercaptopurine (Purinethol) is an analogue of hypoxanthine and was one of the first agents shown to be active against acute leukemias. It is now used as part of maintenance therapy in acute lymphoblastic leukemia. Mercaptopurine must be activated to a nucleotide by the enzyme HGPRTase. This metabolite is capable of inhibiting the synthesis of the normal purines adenine and guanine at the initial aminotransferase step and inhibiting the conversion of inosinic acid to the nucleotides adenylate and guanylate at several steps. Some mercaptopurine is also incorporated into DNA in the form of thioguanine. The relative significance of these mechanisms to the antitumor action of mercaptopurine is not clear.
  Resistance to mercaptopurine may be a result of decreased drug activation by HGPRTase or increased inactivation by alkaline phosphatase.
  The plasma half-life of an intravenous bolus injection of mercaptopurine is 21 minutes in children and 47 minutes in adults. After oral administration, peak plasma levels are attained within 2 hours. The drug is 20% bound to plasma proteins and does not enter the CSF. Xanthine oxidase is the primary enzyme involved in the metabolic inactivation of mercaptopurine.
  Mercaptopurine is used in the maintenance therapy of acute lymphoblastic leukemia. It also displays activity against acute and chronic myelogenous leukemias.
  The major toxicities of mercaptopurine are myelosuppression, nausea, vomiting, and hepatic toxicity.

• 일반 설명

  Odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284°F.

• 공기와 물의 반응

  6-Mercaptopurine monohydrate is sensitive to light and oxidation. Insoluble in water.

• 반응 프로필

  6-Mercaptopurine monohydrate reacts with strong oxidizing agents, strong bases and strong acids.

• 화재위험

  Flash point data for 6-Mercaptopurine monohydrate are not available. 6-Mercaptopurine monohydrate is probably combustible.

• Mechanism of action

  Because the major mechanism of action of mercaptopurine is inhibition of de novo purine nucleotide biosynthesis rather than apoptosis secondary to the incorporation of false nucleotides into DNA, there is a lower risk for mutagenesis and secondary malignancy compared to thioguanine.

• Clinical Use

  Mercaptopurine is used in the treatment of acute lymphatic and myelogenous leukemias.

• 부작용

  Bone marrow suppression is the major use-limiting toxicity, although the drug can be hepatotoxic in high doses. Dosage adjustments should be considered in the face of renal or hepatic impairment.

• 신진 대사

  It is available in an oral dosage form, but absorption can be erratic and is reduced by the presence of food. The drug is extensively metabolized on first pass and excreted by the kidneys.

• Purification Methods

  Crystallise 6-mercaptopurine from pyridine (30mL/g), wash it with pyridine, then triturate with water (25mL/g) and adjust to pH 5 by adding M HCl. Recrystallise it by heating, then cooling, the solution. Filter off the solid, wash it with water and dry it at 110o. It has also been crystallised from water (charcoal) as yellow crystals of the monohydrate which become anhydrous on drying at 140o. It has UV: at 230 and 312nm ( 14,000 and 19,600) in 0.1N NaOH; 222 and 327nm ( 9,2400 max and 21,300), and 216 and 329nm ( 8,740 and 19,300) in MeOH. It forms a 1:1 complex with Zn2+ , Pb2+ , Co2+, and Ni2+ in aqueous dioxan. It is an antineoplastic. [Albert & Brown J Chem Soc 2060 1954, IR: Brown & Mason J Chem Soc 682 1957, UV: Fox et al. J Am Chem Soc 80 1669 1958, UV: Mason J Chem Soc 2071 1954, Beilstein 26 III/IV 2097.]

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