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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
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- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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
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-NSmiles
CCc1nc(N)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.