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Substance Name: Pyrimethamine [USP:INN:BAN:JAN]
RN: 58-14-0
UNII: Z3614QOX8W
InChIKey: WKSAUQYGYAYLPV-UHFFFAOYSA-N

Notes

  • One of the FOLIC ACID ANTAGONISTS that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis.
  • One of the FOLIC ACID ANTAGONISTS that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis.

    NCI: A synthetic derivative of ethyl-pyrimidine with potent antimalarial properties. Pyrimethamine is a competitive inhibitor of dihydrofolate reductase (DHFR). DHFR is a key enzyme in the redox cycle for production of tetrahydrofolate, a cofactor that is required for the synthesis of DNA and proteins. This agent is often used in combination with other antimalarials for the treatment of uncomplicated falciparum malaria. (NCI Thesaurus)

Molecular Formula

  • C12-H13-Cl-N4

Molecular Weight

  • 248.7157
 

Classification Codes

Classification Codes

  • Anti-Infective Agents
  • Antimalarial
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Pyrimethamine
  • Pyrimethamine [USP:INN:BAN:JAN]

MeSH Heading

  • Pyrimethamine

Synonyms

  • 2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
  • 2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
  • 2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine
  • 2,4-Pyrimidinediamine, 5-(p-chlorophenyl)-6-ethyl-
  • 4753 R.P.
  • 5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine
  • 5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
  • 5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine
  • 5-25-12-00255 (Beilstein Handbook Reference)
  • AI3-25005
  • BRN 0219864
  • BW 50-63
  • CCRIS 546
  • Chloridin
  • Chloridine
  • Chloridyn
  • Darachlor
  • Daraprim
  • Diaminopyritamin
  • EINECS 200-364-2
  • Erbaprelina
  • Ethylpyrimidine
  • HSDB 8042
  • Khloridin
  • Malocid
  • Malocide
  • NCI-C01683
  • NSC 3061
  • Pirimecidan
  • Pirimetamin
  • Pirimetamina
  • Pirimetamina [INN-Spanish]
  • Pirimetamina [Spanish]
  • Pyrimethamine
  • Pyrimethaminum
  • Pyrimethaminum [INN-Latin]
  • RP 4753
  • Tindurin
  • UNII-Z3614QOX8W
  • WR 2978

Systematic Names

  • 2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl-
  • 2,4-Pyrimidinediamine, 5-(p-chlorophenyl)-6-ethyl-
  • Pyrimethamine
  • Pyrimidine, 2,4-diamino-5-(p-chlorophenyl)-6-ethyl-

Superlist Name

  • Pyrimethamine

Mixture Name

  • Fansidar

Registry Numbers

CAS Registry Number

  • 58-14-0

FDA UNII

  • Z3614QOX8W

System Generated Number

  • 0000058140

Structure Descriptors

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

Smiles

CCc1c(c(nc(n1)N)N)c2ccc(cc2)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intraperitoneal 75mg/kg (75mg/kg)   United States Patent Document. Vol. #3919229,
hamster LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Teratology, The International Journal of Abnormal Development. Vol. 4, Pg. 205, 1971.
infant TDLo unreported 19mg/kg/31D-I (19mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: NORMOCYTIC ANEMIA

BEHAVIORAL: COMA
Journal of Analytical Toxicology. Vol. 17, Pg. 248, 1993.
mouse LD50 intraperitoneal 74mg/kg (74mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 658, 1974.
mouse LD50 oral 92mg/kg (92mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 6, Pg. 185, 1951.
mouse LDLo subcutaneous 160mg/kg (160mg/kg)   Journal of Medicinal Chemistry. Vol. 16, Pg. 1399, 1973.
rat LD50 intraperitoneal 70mg/kg (70mg/kg)   "International Congress of Chemotherapy, Proceedings of the 3rd Congress, 1963," Kuemmerle, H.P., and Prezios, P., Stuttgart, Fed. Rep. Ger., Georg Thieme Verlag, 1964Vol. -, Pg. 367, 1964.
rat LD50 oral 440mg/kg (440mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Journal of Chemotherapy. Vol. 5, Pg. 400, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 233.5 deg C   EXP
pKa Dissociation Constant 7.34 (none) 20 EXP
log P (octanol-water) 2.69 (none)   EXP
Water Solubility 121 mg/L 25 EST
Vapor Pressure 6.23E-08 mm Hg 25 EST
Henry's Law Constant 1.08E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.01E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.