CAS 58-15-1|Aminopyrine|Dipyrine|4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one|4-DIMETHYLAMINOANTIPYRINE|Aminophenazone|4-Dimethylaminoantipyrine|4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,...

基本信息

化学结构

分子式

C₁₃H₁₇N₃O

分子量

231.29358

精确质量

231.13716218

电荷

InChI

InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

InChIKey

RMMXTBMQSGEXHJ-UHFFFAOYSA-N

Canonic Smiles

CN(c1c(C)n(n(c1=O)c1ccccc1)C)C

Isomeric Smiles

O=c1n(n(c(c1N(C)C)C)C)c1ccccc1

计算属性

JChem

LogD (pH = 7.4)

1.15

LogD (pH = 5.5)

1.14

Log P

1.15

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

3.66

极化表面积

26.79

极化性

25.86

摩尔折射率

70.11

LOG S

-1.37

数据来源

名称和标识

别名

AminopyrineDipyrine4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one4-DIMETHYLAMINOANTIPYRINEAminophenazone4-DimethylaminoantipyrineAmidopyrine4-DimethylaminoantipyrineAMINOPYRINE4-(Dimethylamino)antipyrine4-Dimethylamino-2,3-dimethyl-1-phenylpyrazol-5-one4-二甲氨基-2,3-二甲氧-1-苯基吡唑-5-酮3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazoleDimethylaminophenazone4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one4-Dimethylamino-1-phenyl-2,3-dimethylpyrazolone4-DimethylaminoantipyrineDimethylaminophenazon1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazoloneAminofenazoneDimethylaminophenyldimethylpyrazolone4-(Dimethylamino)antipyrine4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-oneAminophenazonDimethylaminoantipyrine1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazoloneDimethylaminoazophene4-DimethylaminophenazoneAminopyrine2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one(Dimethylamino)phenazoneDipyrineaminophenazone1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone

IUPAC标准名

4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

IUPAC传统名

aminophenazone

国际非专利药品(INN)

aminofenazonaaminophenazoneaminophenazonum

名称和标识

数据登录号

EC号

200-365-8

CAS号

58-15-1

PubChem CID

6009

PubChem SID

465049751609646922489417885359595

MDL号

MFCD00003142

默克索引号

14474

LINCS数据库

LSM-20000

UniProt数据库

P33264P33263Q08078Q27712P33265O23976P98138

MassBank数据库

EA070210EA070213EA070203EA070214EA070202EA070209EA070204EA070201EA070208EA070207EA070206EA070212EA070211EA070205

BKMS React数据库

BRENDA数据库

Beilstein号

MetaboLights数据库

BindingDB数据库

ACToR数据库

BRENDA Ligand数据库

SABIO-RK数据库

DrugBank ID

PubMed文献链接

236038972442868323727364

SureChEMBL数据库

SCHEMBL26293

Gmelin ID

103164

Drug Central Database

KEGG DRUG Database

HMDB数据库

维基百科标题

CHEBI ID

KEGG ID

Reaxys Registry

CHEMBL

CompTox数据库

数据登录号

化合物性质

理化性质

溶解度

54.4 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

疏水性(logP)

1.00 [HANSCH,C ET AL. (1995)]

熔点

107-109

105-109°C

产品相关信息

下载链接

98+%

Free Base

药理学性质

Others

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

DB01424

Drug Groups

approved; withdrawn

Description

A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]

Indication

Formerly widely used as an antipyretic and analgesic in rheumatism, neuritis, and common colds. Currently used to measure total body water.

Pharmacology

Aminophenazone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [Wikipedia]

Toxicity

Can cause life-threatening agranulocytosis.

Affected Organisms

Humans and other mammals

References

• Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. [Pubmed]

External Links

• [Wikipedia]

MP Biomedicals

02157785

Free Base
Crystalline

05214044

MP Biomedicals Rare Chemical collection

Sigma Aldrich

D8015

Biochem/physiol Actions
Antipyrine was found to be nonmutagenic when screened against Salmonella typhimurium tester strains TA100, TA98, TA97, TA102 and TA104.3
Application
Oxidation by Fe(VI) has potential to remove N-nitrosodimethylamine precursors, including 4-dimethylaminoantipyrine, from drinking water.1 4-Dimethylaminoantipyrine is itself an effective scavenger of reactive nitrogen compounds nitric oxide and peroxynitrite, important in the inflammatory response.2

ChEBI

CHEBI:160246

A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.

描述信息

参考文献

PubChem文献

数据源提供

• Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性