Home > Compound List > Compound details
58-14-0 molecular structure
click picture or here to close

5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

ChemBase ID: 90
Molecular Formular: C12H13ClN4
Molecular Mass: 248.71142
Monoisotopic Mass: 248.08287412
SMILES and 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

Cite this record

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

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
IUPAC Traditional name
pyrimethamine
Brand Name
Darachlor
Daraclor
Darapram
Daraprim
Daraprime
Disulone
Erbaprelina
Fansidar
Khloridin
Malacid
Malocid
Malocide
Maloprim
Pirimecidan
Tindurin
Tinduring
Synonyms
Pyrimethamine Hcl
Pyrimethamin
Pyremethamine
Ethylpyrimidine
Diaminopyritamin
CD
Chloridin
Chloridine
Primethamine
Pirimetamina
Pirimetamin
Chloridyn
Pyrimethamine
Daraprim
Malocide
Pirimecidan
Pyrimethamine
5-[4-Chlorophenyl]-6-ethyl-2,4-pyrimidinediamine
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
Khloridin
Pirimetmin
NSC 3061
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine
5-(4-Chlorophenyl)-6-ethylpyriMidine-2,4-diaMine
RP 4753
6-乙基-5-(4-氯苯基)-2,4-嘧啶二胺
乙胺嘧啶
CAS Number
58-14-0
EC Number
200-364-2
MDL Number
MFCD00057350
Beilstein Number
219864
PubChem SID
46505987
24898876
24870381
160963553
PubChem CID
4993
CHEBI ID
8673
ATC CODE
P01BD01
CHEMBL
36
Chemspider ID
4819
DrugBank ID
DB00205
KEGG ID
D00488
Unique Ingredient Identifier
Z3614QOX8W
Wikipedia Title
Pyrimethamine
Medline Plus
a601050

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.222044  H Acceptors
H Donor LogD (pH = 5.5) 0.9725773 
LogD (pH = 7.4) 2.2334282  Log P 2.7483032 
Molar Refractivity 71.542 cm3 Polarizability 27.221851 Å3
Polar Surface Area 77.82 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.62  LOG S -3.14 
Solubility (Water) 1.79e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
121 mg/L expand Show data source
DMSO expand Show data source
Ethanol (hot) expand Show data source
Apperance
White Solid expand Show data source
Melting Point
233-234°C expand Show data source
Hydrophobicity(logP)
2.7 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
UV8140000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
S:36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
well-absorbed expand Show data source
Excretion
Renal expand Show data source
Half Life
96 hours expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
87% expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
B3 (Australia) expand Show data source
C (US) expand Show data source
Gene Information
human ... CYP2C9(1559), DHFRP1(573971)rat ... Dhfr(24312) expand Show data source
Purity
97% 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
Empirical Formula (Hill Notation)
C12H13ClN4 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC Wikipedia Wikipedia MP Biomedicals MP Biomedicals
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]
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
Sigma Aldrich - 46706 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - P997240 external link
Dihydrofolate reductase inhibitor; generally used in combination with other antimicrobial agents. Antiprotozoal (Toxoplasma); antimalarial.
MP Biomedicals - 02194180 external link
Antiprotozoal compound
For Research Use Only

REFERENCES

REFERENCES

From Suppliers 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)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle