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58-14-0 分子结构
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5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

ChemBase编号:90
分子式:C12H13ClN4
平均质量:248.71142
单一同位素质量:248.08287412
SMILES和InChIs

SMILES:
Clc1ccc(c2c(nc(nc2N)N)CC)cc1
Canonical SMILES:
CCc1nc(N)nc(c1c1ccc(cc1)Cl)N
InChI:
InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
InChIKey:
WKSAUQYGYAYLPV-UHFFFAOYSA-N

引用这个纪录

CBID:90 http://www.chembase.cn/molecule-90.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
IUPAC传统名
pyrimethamine
商标名
Darachlor
Daraclor
Darapram
Daraprim
Daraprime
Disulone
Erbaprelina
Fansidar
Khloridin
Malacid
Malocid
Malocide
Maloprim
Pirimecidan
Tindurin
Tinduring
别名
6-乙基-5-(4-氯苯基)-2,4-嘧啶二胺
乙胺嘧啶
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Khloridin
Pirimetmin
NSC 3061
RP 4753
Pyrimethamine
Daraprim
Malocide
Pirimecidan
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine
5-[4-Chlorophenyl]-6-ethyl-2,4-pyrimidinediamine
Pirimetamin
Chloridyn
Pyrimethamine
Pyrimethamine Hcl
Pyrimethamin
Pyremethamine
Ethylpyrimidine
Diaminopyritamin
CD
Chloridin
Chloridine
Primethamine
Pirimetamina
5-(4-Chlorophenyl)-6-ethylpyriMidine-2,4-diaMine
CAS号
58-14-0
EC号
200-364-2
MDL号
MFCD00057350
Beilstein号
219864
PubChem SID
24870381
160963553
46505987
24898876
PubChem CID
4993
CHEBI ID
8673
ATC码
P01BD01
CHEMBL
36
Chemspider ID
4819
DrugBank ID
DB00205
KEGG ID
D00488
美国药典/FDA物质标识码
Z3614QOX8W
维基百科标题
Pyrimethamine
Medline Plus
a601050

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 17.222044  质子受体
质子供体 LogD (pH = 5.5) 0.9725773 
LogD (pH = 7.4) 2.2334282  Log P 2.7483032 
摩尔折射率 71.542 cm3 极化性 27.221851 Å3
极化表面积 77.82 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.62  LOG S -3.14 
溶解度 1.79e-01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
121 mg/L expand 查看数据来源
DMSO expand 查看数据来源
Ethanol (hot) expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
233-234°C expand 查看数据来源
疏水性(logP)
2.7 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
UV8140000 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
22 expand 查看数据来源
R:22 expand 查看数据来源
安全公开号
S:36/37/39 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
well-absorbed expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
96 hours expand 查看数据来源
代谢
Hepatic expand 查看数据来源
蛋白结合率
87% expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
B3 (Australia) expand 查看数据来源
C (US) expand 查看数据来源
相关基因信息
human ... CYP2C9(1559), DHFRP1(573971)rat ... Dhfr(24312) expand 查看数据来源
纯度
97% expand 查看数据来源
级别
VETRANAL™, analytical standard expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
Empirical Formula (Hill Notation)
C12H13ClN4 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02194180 external link
Antiprotozoal compound
For Research Use Only
DrugBank -  DB00205 external link
Item Information
Drug Groups approved
Description One of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. [PubChem]
Indication For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine
Pharmacology Pyrimethamine is an antiparasitic compound commonly used as an adjunct in the treatment of uncomplicated, chloroquine resistant, P. falciparum malaria. Pyrimethamine is a folic acid antagonist and the rationale for its therapeutic action is based on the differential requirement between host and parasite for nucleic acid precursors involved in growth. This activity is highly selective against plasmodia and Toxoplasma gondii. Pyrimethamine possesses blood schizonticidal and some tissue schizonticidal activity against malaria parasites of humans. However, the 4-amino-quinoline compounds are more effective against the erythrocytic schizonts. It does not destroy gametocytes, but arrests sporogony in the mosquito. The action of pyrimethamine against Toxoplasma gondii is greatly enhanced when used in conjunction with sulfonamides.
Affected Organisms
Plasmodium
Biotransformation Hepatic
Absorption Well absorbed with peak levels occurring between 2 to 6 hours following administration
Half Life 96 hours
Protein Binding 87%
References
Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. [Pubmed]
Sirichaiwat C, Intaraudom C, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y: Target guided synthesis of 5-benzyl-2,4-diamonopyrimidines: their antimalarial activities and binding affinities to wild type and mutant dihydrofolate reductases from Plasmodium falciparum. J Med Chem. 2004 Jan 15;47(2):345-54. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S2006 external link
Research Area: Infection
Biological Activity:
Pyrimethamine is a dihydrofolate reductase(DHFR) inhibitor with an IC50 of 15.4 nM. It is a medication used for protozoal infections. It is commonly used as an antimalarial drug (for both treatment and prevention of malaria), and is also used (combined with sulfadiazine) in the treatment of Toxoplasma gondii infections in immune-compromised patients, such as HIV-positive individuals. It interferes with folic acid synthesis by inhibiting the enzyme dihydrofolate reductase (DHFR). Folic acid is needed for DNA and RNA synthesis in many species, including protozoa. [1]
Sigma Aldrich -  46706 external link
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Toronto Research Chemicals -  P997240 external link
Dihydrofolate reductase inhibitor; generally used in combination with other antimicrobial agents. Antiprotozoal (Toxoplasma); antimalarial.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. Pubmed
  • Sirichaiwat C, Intaraudom C, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y: Target guided synthesis of 5-benzyl-2,4-diamonopyrimidines: their antimalarial activities and binding affinities to wild type and mutant dihydrofolate reductases from Plasmodium falciparum. J Med Chem. 2004 Jan 15;47(2):345-54. Pubmed
  • http://en.wikipedia.org/wiki/Pyrimethamine
  • Loutfy, M.A., et al.: Anal. Profiles Drug Subs., 12, 463 (1983)
  • Leport, C., et al.: Am. J. Med., 84, 94 (1983)
  • McIntosh, H.M., et al.: Ann. Trop. Med., Parasitol., 93, 265 (1983)
  • Plowe, C.V., et al.: Br. Med. J., 328, 545 (1983)
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专利

专利

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