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738-70-5 molecular structure
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5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

ChemBase ID: 323
Molecular Formular: C14H18N4O3
Molecular Mass: 290.31772
Monoisotopic Mass: 290.13789046
SMILES and 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

Cite this record

CBID:323 http://www.chembase.cn/molecule-323.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
IUPAC Traditional name
trimethoprim
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Brand Name
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
Synonyms
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
2,4-二氨基-5-(3,4,5-三甲氧基苄基)嘧啶
甲氧苄啶
CAS Number
738-70-5
EC Number
212-006-2
MDL Number
MFCD00036761
Beilstein Number
625127
PubChem SID
160963786
46507125
24870616
24889615
24278201
PubChem CID
5578
CHEBI ID
45924
ATC CODE
QJ51EA01
J01EA01
CHEMBL
22
Chemspider ID
5376
DrugBank ID
DB00440
KEGG ID
D00145
Unique Ingredient Identifier
AN164J8Y0X
Wikipedia Title
Trimethoprim
Medline Plus
a684025

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.334406  H Acceptors
H Donor LogD (pH = 5.5) 0.020083463 
LogD (pH = 7.4) 1.0960962  Log P 1.2839073 
Molar Refractivity 81.5094 cm3 Polarizability 29.759577 Å3
Polar Surface Area 105.51 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.26  LOG S -2.67 
Solubility (Water) 6.15e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
12.1 mg/mL expand Show data source
Chloroform expand Show data source
chloroform/ethanol (1:1): soluble50 mg/mL, clear, colorless expand Show data source
DMF expand Show data source
DMSO expand Show data source
DMSO: soluble expand Show data source
Methanol (hot) expand Show data source
Apperance
Off-White Solid expand Show data source
white powder expand Show data source
Melting Point
192-195°C expand Show data source
199-203 °C expand Show data source
199-203°C expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source
Storage Condition
2-8°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
UV8225000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
R:25 expand Show data source
Safety Statements
S:28-29-36/37/39-45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Others expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
90–100% expand Show data source
Excretion
renal 50–60% expand Show data source
Half Life
8–10 hours expand Show data source
Metabolism
hepatic expand Show data source
Legal Status
POM (UK) expand Show data source
S4 (Australia) expand Show data source
Pregnancy Category
B3 (Australia) expand Show data source
C (US) expand Show data source
Gene Information
human ... DHFRP1(573971), KCNH1(3756)rat ... Dhfr(24312) expand Show data source
Mechanism of Action
Bacterial biosynthesis of nucleic acids and proteins is blocked by interference with normal bacterial metabolism of folinate expand Show data source
Binding to bacterial enzyme is stronger than to the corresponding mammalian enzyme expand Show data source
Blocks production of tetrahydrofolate from dihydrofolate expand Show data source
Folate antagonist expand Show data source
Reversible dihydrofolate-reductase-inhibitor expand Show data source
Purity
≥98% (TLC) expand Show data source
≥99.0% (HPLC) expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source
Application(s)
Active against common urinary-tract pathogens except for Pseudomonas aeruginosa expand Show data source
Active against Haemophilus-influenzae. expand Show data source
Antibacterial agent expand Show data source
Antiseptic expand Show data source
Inhibits dihydrofolate reductase from bacterial sources and from malaria parasites expand Show data source
Quality
crystallized expand Show data source
Pharmacopeia Traceability
traceable to BP 344 expand Show data source
traceable to PhEur T220000 expand Show data source
traceable to USP 1692505 expand Show data source
Empirical Formula (Hill Notation)
C14H18N4O3 expand Show data source

DETAILS

DETAILS

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
Commission Regulation (EU) No 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin
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.
Legal Information
VETRANAL is a trademark of 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.

REFERENCES

REFERENCES

From Suppliers 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
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