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738-70-5 分子结构
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5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

ChemBase编号:323
分子式:C14H18N4O3
平均质量:290.31772
单一同位素质量:290.13789046
SMILES和InChIs

SMILES:
O(c1cc(Cc2c(nc(nc2)N)N)cc(OC)c1OC)C
Canonical SMILES:
COc1cc(Cc2cnc(nc2N)N)cc(c1OC)OC
InChI:
InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
InChIKey:
IEDVJHCEMCRBQM-UHFFFAOYSA-N

引用这个纪录

CBID:323 http://www.chembase.cn/molecule-323.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-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
IUPAC传统名
trimethoprim
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
商标名
Abacin
Abaprim
Alprim
Apo-Sulfatrim
Bactin
Bactramin
Bactrim
Bactrim DS
Bactrim Pediatric
Baktar
Chemotrim
Co-Trimoxazole
Comox
Cotrim
Cotrim D.S.
Drylin
Eusaprim
Fectrim
Gantaprim
Gantrim
Idotrim
Imexim
Instalac
Ipral
Kepinol
Laratrim
Lidaprim
Methoprim
Microtrim
Monoprim
Monotrim
Monotrimin
Nopil
Oraprim
Priloprim
Primosept
Primsol
Proloprim
Septra
Septra DS
Septra Grape
Septrin
Sigaprim
Sulfamethoprim
Sulfamethoprim-DS
Sulfamethoxazole & Trimethoprim
Sulfatrim
Sulfatrim Pediatric
Sulfatrim-DS
Sulfatrim-SS
Sulfotrim
Sulmeprim
Sulmeprim Pediatric
Sulprim
Sumetrolim
Supracombin
Suprim
Syraprim
Teleprim
Thiocuran
Tiempe
Tmp-Ratiopharm
Trigonyl
Trimanyl
Trimesulf
Trimeth/Sulfa
Trimethioprim
Trimethopriom
Trimetoprim
Trimexazole
Trimogal
Trimopan
Trimpex
Trimpex 200
Triprim
Unitrim
Uretrim
Uro-Septra
Uroplus
Uroplus DS
Uroplus SS
Wellcoprim
别名
2,4-二氨基-5-(3,4,5-三甲氧基苄基)嘧啶
甲氧苄啶
Trimethoprim
5-(3,4,5-Trimethoxybenzyl)-2,4-pyrimidinediamine
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
Trimethoprim
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
Trimpex
2,4-Diamino-5-[3,4,5-trimethoxy-benzyl]pyrimidine
5-[(3,4,5-Trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
2,4-Diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine
Instalac
Monotrim
Proloprim
Syraprim
Tiempe
Trimanyl
Uretrim
Wellcoprim
CAS号
738-70-5
EC号
212-006-2
MDL号
MFCD00036761
Beilstein号
625127
PubChem SID
160963786
24889615
24278201
46507125
24870616
PubChem CID
5578
CHEBI ID
45924
ATC码
QJ51EA01
J01EA01
CHEMBL
22
Chemspider ID
5376
DrugBank ID
DB00440
KEGG ID
D00145
美国药典/FDA物质标识码
AN164J8Y0X
维基百科标题
Trimethoprim
Medline Plus
a684025

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 17.334406  质子受体
质子供体 LogD (pH = 5.5) 0.020083463 
LogD (pH = 7.4) 1.0960962  Log P 1.2839073 
摩尔折射率 81.5094 cm3 极化性 29.759577 Å3
极化表面积 105.51 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.26  LOG S -2.67 
溶解度 6.15e-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
12.1 mg/mL expand 查看数据来源
Chloroform expand 查看数据来源
chloroform/ethanol (1:1): soluble50 mg/mL, clear, colorless expand 查看数据来源
DMF expand 查看数据来源
DMSO expand 查看数据来源
DMSO: soluble expand 查看数据来源
Methanol (hot) expand 查看数据来源
外观
Off-White Solid expand 查看数据来源
white powder expand 查看数据来源
熔点
192-195°C expand 查看数据来源
199-203 °C expand 查看数据来源
199-203°C expand 查看数据来源
疏水性(logP)
0.6 expand 查看数据来源
保存条件
2-8°C expand 查看数据来源
Refrigerator expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
UV8225000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
联合国危险货物编号
2811 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
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
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
III expand 查看数据来源
澳大利亚Hazchem
2X expand 查看数据来源
危险公开号
R:25 expand 查看数据来源
安全公开号
S:28-29-36/37/39-45 expand 查看数据来源
欧盟危险货物分类
T2 expand 查看数据来源
欧盟危险识别号(EUHIN)
6.1B expand 查看数据来源
美国ERG指导号
154 expand 查看数据来源
TSCA收录
false expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
作用靶点
Others expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
90–100% expand 查看数据来源
排泄
renal 50–60% expand 查看数据来源
半衰期
8–10 hours expand 查看数据来源
代谢
hepatic expand 查看数据来源
法定药品分级
POM (UK) expand 查看数据来源
S4 (Australia) 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 ... DHFRP1(573971), KCNH1(3756)rat ... Dhfr(24312) expand 查看数据来源
生物活性机理
Bacterial biosynthesis of nucleic acids and proteins is blocked by interference with normal bacterial metabolism of folinate expand 查看数据来源
Binding to bacterial enzyme is stronger than to the corresponding mammalian enzyme expand 查看数据来源
Blocks production of tetrahydrofolate from dihydrofolate expand 查看数据来源
Folate antagonist expand 查看数据来源
Reversible dihydrofolate-reductase-inhibitor expand 查看数据来源
纯度
≥98% (TLC) expand 查看数据来源
≥99.0% (HPLC) 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
适用性
suitable for 1694 per US EPA expand 查看数据来源
应用领域
Active against common urinary-tract pathogens except for Pseudomonas aeruginosa expand 查看数据来源
Active against Haemophilus-influenzae. expand 查看数据来源
Antibacterial agent expand 查看数据来源
Antiseptic expand 查看数据来源
Inhibits dihydrofolate reductase from bacterial sources and from malaria parasites expand 查看数据来源
品质说明
crystallized expand 查看数据来源
Pharmacopeia Traceability
traceable to BP 344 expand 查看数据来源
traceable to PhEur T220000 expand 查看数据来源
traceable to USP 1692505 expand 查看数据来源
Empirical Formula (Hill Notation)
C14H18N4O3 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02195527 external link
Crystalline
A specific inhibitor of formylation.
DrugBank -  DB00440 external link
Item Information
Drug Groups approved
Description A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to pyrimethamine. The interference with folic acid metabolism may cause a depression of hematopoiesis. It is potentiated by sulfonamides and the trimethoprim-sulfamethoxazole combination is the form most often used. It is sometimes used alone as an antimalarial. Trimethoprim resistance has been reported. [PubChem]
Indication For the treatment of urinary tract infections, uncomplicated pyelonephritis (with sulfamethoxazole) and mild acute prostatitis. May be used as pericoital (with sulfamethoxazole) or continuous prophylaxis in females with recurrent cystitis. May be used as an alternative to treat asymptomatic bacteriuria during pregnancy (only before the last 6 weeks of pregnancy). Other uses include: alternative agent in respiratory tract infections (otitis, sinusitus, bronchitis and pneumonia), treatment of Pneumocystis jirovecii pneumonia (acute or prophylaxis), Nocardia infections, and traveller's diarrhea.
Pharmacology Trimethoprim is a pyrimidine analogue that disrupts folate synthesis, an essential part of the thymidine synthesis pathway. Inhibition of the enzyme starves the bacteria of nucleotides necessary for DNA replication.The drug, therefore, exhibits bactericidal activity.
Toxicity LD50=4850 (orally in mice)
Affected Organisms
Gram negative and gram positive bacteria
Biotransformation Hepatic metabolism to oxide and hydroxylated metabolites.
Absorption Readily and almost completely absorbed in the GI tract with peak serum concentrations attained 1-4 hours after oral administration. Widely distributed to tissues and fluids including kidney, lung, seminal fluid, aqueous humour, middle ear fluid, sputum, vaginal secretions, bile, bone and CSF.
Half Life 8-11 hours in adults with normal renal function
Protein Binding 42-46% bound to plasma proteins
Elimination Ten to twenty percent of trimethoprim is metabolized, primarily in the liver; the remainder is excreted unchanged in the urine.
After oral administration, 50% to 60% of trimethoprim is excreted in the urine within 24 hours, approximately 80% of this being unmetabolized trimethoprim. Trimethoprim also passes the placental barrier and is excreted in human milk.
References
Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. [Pubmed]
Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. [Pubmed]
Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. [Pubmed]
Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. [Pubmed]
Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  T7883 external link
Application
Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
Trimethoprim is primarily used as an antibacterial agent. It has dihydrofolate reductase inhibitor activity with selectivity for the prokaryote enzyme. It is used to treat urinary tract infections, mild acute prostatitis, recurrent cystitis, asymptomatic bacteriuria during pregnancy and respiratory tract infections1.
Other Notes
Specific inhibitor of formulation. Widely used in studies on dihydrofolate reductase2,3.
Biochem/physiol Actions
The combination of trimethoprim and sulfamethoxazole interferes with the cellular metabolism of folic acid in the bacterial cell by blocking the biosynthesis of nucleotides. Trimethoprim binds to dihydrofolate reductase and inhibits the reduction of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF). THF is an essential precursor in the thymidine synthesis pathway and interference with this pathway inhibits bacterial DNA synthesis1.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich -  92131 external link
Application
Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
Trimethoprim is primarily used as an antibacterial agent. It is used in susceptibility studies of Mycobacterium tuberculosis 1 and mechanism of resistance studies in Haemophilus influenzae 2.
Biochem/physiol Actions
Inhibits the synthesis of tetrahydrofolate by procaryote specific dihydrofolate reductase (DHFR).
Trimethoprim is a dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
Other Notes
Specific inhibitor of formulation. Widely used in studies on dihydrofolate reductase3,4.
Sigma Aldrich -  46984 external link
Application
Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
欧洲委员会 (EU) 2009 年 12 月 22 日第 37/2010 号关于动物源食品药理活性物质及其最大残留限值分类的规定。
Other Notes
Specific inhibitor of formulation. Widely used in studies on dihydrofolate reductase1,2.
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Sigma Aldrich -  02718 external link
Application
Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
Other Notes
Specific inhibitor of formulation. Widely used in studies on dihydrofolate reductase1,2.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mol. Pharmacol., 1: 126, (1965).
  • Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. Pubmed
  • Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. Pubmed
  • Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. Pubmed
  • Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. Pubmed
  • Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. Pubmed
  • Manius, G.J., et al.: Anal. Profiles Drug Subs., 7, 445 (1978)
  • Roth, B., et al.: J. Med. Chem., 23, 379 (1978)
  • Brogden, R.N., et al.: Drugs, 23, 405 (1978)
  • Brossi, A. et al., J. Med. Chem., 1971, 14, 462, (synth)
  • Burchall, J.J., Antibiotics (N.Y.), 1975, 3, 304, (rev)
  • Koetzle, T.F. et al., J.A.C.S., 1976, 98, 2074, (cryst struct)
  • Manius, G.J., Anal. Profiles Drug Subst., 1978, 7, 445, (rev, synth, props, anal)
  • Sigel, C.W., Handb. Exp. Pharmacol., 1983, 64, 163, (rev, metab)
  • Roth, B. et al., J. Med. Chem., 1980, 23, 379; 535, (synth)
  • Brogden, R.N. et al., Drugs, 1982, 23, 405, (rev, pharmacol)
  • Bryan, R.F. et al., Acta Cryst. C, 1987, 43, 2412, (cryst struct)
  • Huovinen, P., Antimicrob. Agents Chemother., 1987, 31, 1451, (rev, props)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 219
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4092
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TKX000; TKZ000
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