6,7-dihydro-3H-purine-6-thione

• ChemBase编号: 905
• 分子式: C5H4N4S
• 平均质量: 152.17706
• 单一同位素质量: 152.01566715
• SMILES: S=c1nc[nH]c2nc[nH]c12
• Canonical SMILES: S=c1nc[nH]c2c1[nH]cn2
• InChI: InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
• InChIKey: GLVAUDGFNGKCSF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6,7-dihydro-3H-purine-6-thione
• IUPAC传统名: 6-mercaptopurine
• 商标名: Ismipur; Leukerin; Leupurin; Mercaleukim; Mercaleukin; Mern; Puri-Nethol; Purimethol; Purinethol
• 别名: Purinethol; 6-MP; Mercaptopurine Monohydrate; Mercapurin; 6 MP; MP; 6-Mercaptopurine; Mercaptopurine

登记号

• CAS号: 50-44-2
• PubChem SID: 46506988; 160964368
• PubChem CID: 667490

理论计算性质

JChem

• Acid pKa: 9.498602
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.123077706
• LogD (pH = 7.4): -0.12507708
• Log P: -0.121789195
• 摩尔折射率: 43.6027 cm^3
• 极化性: 15.407385 Å^3
• 极化表面积: 53.07 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.13
• LOG S: -2.32
• 溶解度: 7.35e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; 6.85 mg/mL
• 疏水性(logP): -0.4

安全信息

• 保存条件: -20°C

药理学性质

• 作用靶点: DNA/RNA synthesis

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB01033

• Drug Groups: approved
• Description: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. [PubChem]
• Indication: For remission induction and maintenance therapy of acute lymphatic leukemia.
• Pharmacology: Mercaptopurine is one of a large series of purine analogues which interfere with nucleic acid biosynthesis and has been found active against human leukemias. It is an analogue of the purine bases adenine and hypoxanthine. It is not known exactly which of any one or more of the biochemical effects of mercaptopurine and its metabolites are directly or predominantly responsible for cell death.
• Toxicity: Signs and symptoms of overdosage may be immediate such as anorexia, nausea, vomiting, and diarrhea; or delayed such as myelosuppression, liver dysfunction, and gastroenteritis. The oral LD₅₀ of mercaptopurine was determined to be 480 mg/kg in the mouse and 425 mg/kg in the rat.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Degradation primarily by xanthine oxidase. The catabolism of mercaptopurine and its metabolites is complex. In humans, after oral administration of ^35S-6-mercaptopurine, urine contains intact mercaptopurine, thiouric acid (formed by direct oxidation by xanthine oxidase, probably via 6-mercapto-8-hydroxypurine), and a number of 6-methylated thiopurines. The methylthiopurines yield appreciable amounts of inorganic sulfate.
• Absorption: Clinical studies have shown that the absorption of an oral dose of mercaptopurine in humans is incomplete and variable, averaging approximately 50% of the administered dose. The factors influencing absorption are unknown.
• Half Life: Triphasic: 45 minutes, 2.5 hours, and 10 hours.
• Protein Binding: Plasma protein binding averages 19% over the concentration range 10 to 50 µg/mL (a concentration only achieved by intravenous administration of mercaptopurine at doses exceeding 5 to 10 mg/kg).
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1305

Research Area: Infection
Biological Activity:
Mercaptopurine is used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, psoriatic arthritis, and inflammatory bowel disease. It has demonstrated some in vitro effectiveness against Mycobacterium paratuberculosis 6-MP ribonucleotide inhibits purine nucleotide synthesis and metabolism. This alters the synthesis and function of RNA and DNA. Mercaptopurine interferes with nucleotide interconversion and glycoprotein synthesis. [1]

参考文献

• http://en.wikipedia.org/wiki/Mercaptopurine