化合物信息

ID:905

基本信息

化学结构

分子式

C₅H₄N₄S

分子量

152.17706

精确质量

152.01566715

电荷

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

Canonic Smiles

S=c1nc[nH]c2c1[nH]cn2

Isomeric Smiles

S=c1nc[nH]c2nc[nH]c12

计算属性

JChem

Acid pKa

9.498602

质子受体

质子供体

LogD (pH = 5.5)

-0.123077706

LogD (pH = 7.4)

-0.12507708

Log P

-0.121789195

摩尔折射率

43.6027

极化性

15.407385

极化表面积

53.07

可自由旋转的化学键

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

数据来源

学术数据

产品目录

数据来源

名称和标识

商标名

MercaleukinPuri-NetholLeukerinLeupurinMercaleukimPurinetholIsmipurPurimetholMern

别名

Mercaptopurine Monohydrate6 MPMercapurinMPMercaptopurine6-MercaptopurinePurinethol6-MP

IUPAC标准名

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

IUPAC传统名

6-mercaptopurine

名称和标识

数据登录号

PubChem CID

667490

PubChem SID

16096436846506988

CAS号

50-44-2

数据登录号

化合物性质

理化性质

溶解度

6.85 mg/mL

DMSO

疏水性(logP)

-0.4

产品相关信息

成盐信息

Free Base

药理学性质

作用靶点

DNA/RNA synthesis

安全信息

保存条件

-20°C

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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]

描述信息

参考文献

PubChem文献

数据源提供

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

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

• ALOGPS 2.1

数据来源

• 学术数据

• 产品目录

名称和标识

• 商标名

• 别名

• IUPAC标准名

• IUPAC传统名

数据登录号

• PubChem CID

• PubChem SID

• CAS号

化合物性质

• 理化性质

• 产品相关信息

• 药理学性质

• 安全信息

分子相关蛋白质

分子图谱

描述信息

• DrugBank

• Selleck Chemicals

描述信息

参考文献

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

商标名

MercaleukinPuri-NetholLeukerinLeupurinMercaleukimPurinetholIsmipurPurimetholMern

别名

Mercaptopurine Monohydrate6 MPMercapurinMPMercaptopurine6-MercaptopurinePurinethol6-MP

IUPAC标准名

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

IUPAC传统名

6-mercaptopurine

PubChem SID

16096436846506988

理化性质

溶解度

6.85 mg/mL

DMSO

疏水性(logP)

-0.4

产品相关信息

成盐信息

Free Base

药理学性质

作用靶点

DNA/RNA synthesis

安全信息

保存条件

-20°C

数据源提供

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

DrugBank

DB01033

Drug Groups

approved

Description

Indication

For remission induction and maintenance therapy of acute lymphatic leukemia.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

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