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Merck
CN

P7771

Pyrimethamine

Synonym(s):

5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine

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About This Item

Empirical Formula (Hill Notation):
C12H13ClN4
CAS Number:
58-14-0
Molecular Weight:
248.71
EC Number:
200-364-2
UNSPSC Code:
12352100
PubChem Substance ID:
24898876
Beilstein/REAXYS Number:
219864
MDL number:
MFCD00057350

Key Documents

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InChI key

WKSAUQYGYAYLPV-UHFFFAOYSA-N

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)

SMILES string

CCC1=NC(N)=NC(N)=C1C2=CC=C(Cl)C=C2

Gene Information

human ... CYP2C9(1559), DHFRP1(573971)
rat ... Dhfr(24312)

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
122H0821
088F0320
017H1127
010K0270

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Ramesh Gujjar et al.
Journal of medicinal chemistry, 54(11), 3935-3949 (2011-04-27)
Malaria is one of the leading causes of severe infectious disease worldwide; yet, our ability to maintain effective therapy to combat the illness is continually challenged by the emergence of drug resistance. We previously reported identification of a new class
Alyson M Auliff et al.
Antimicrobial agents and chemotherapy, 54(9), 3927-3932 (2010-06-23)
Plasmodium vivax resistance to antifolates is prevalent throughout Australasia and is caused by point mutations within the parasite dihydrofolate reductase (DHFR)-thymidylate synthase. Several unique mutations have been reported in P. vivax DHFR, and their roles in resistance to classic and
Alexis Nzila et al.
Antimicrobial agents and chemotherapy, 54(6), 2603-2610 (2010-03-31)
Drug resistance against dihydrofolate reductase (DHFR) inhibitors-such as pyrimethamine (PM)-has now spread to almost all regions where malaria is endemic, rendering antifolate-based malaria treatments highly ineffective. We have previously shown that the di-amino quinazoline QN254 [5-chloro-N'6'-(2,5-dimethoxy-benzyl)-quinazoline-2,4,6-triamine] is active against the
Tao Wu et al.
Journal of medicinal chemistry, 54(14), 5116-5130 (2011-06-08)
Starting from a hit series from a GNF compound library collection and based on a cell-based proliferation assay of Plasmodium falciparum, a novel imidazolopiperazine scaffold was optimized. SAR for this series of compounds is discussed, focusing on optimization of cellular
Albert J Ndakala et al.
Journal of medicinal chemistry, 54(13), 4581-4589 (2011-06-08)
A novel class of antimalarial pyrido[1,2-a]benzimidazoles were synthesized and evaluated for antiplasmodial activity and cytotoxicity following hits identified from screening commercially available compound collections. The most active of these, TDR86919 (4c), showed improved in vitro activity vs the drug-resistant K1
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