CAS Number58-14-0
SynonymsDaraclor; Pyremethamine; Primethamine; 5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine; TCMDC-125860; WR 2978; Pyrimethamin; Malocid; pirimetamin; bw50-63; 5-(4-chlorophényl)-6-éthylpyrimidine-2,4-diamine; Malacid; Daraprim; Malocide; 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine; 5-(4-Chlorphenyl)-6-ethylpyrimidin-2,4-diamin; MFCD00057350; T6N CNJ BZ DZ ER DG& F2; RP 4753; chloridine; darachlor; pirimecidan; Pyrimethamine; Pirimetamina; EINECS 200-364-2; TCMDC-123831; 4753r.p.
Molecular FormulaC12H13ClN4
Molecular Weight248.71
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point368.4±52.0 °C at 760 mmHg
Melting Point233-234°C
Appearancepowder
EINECS200-364-2
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 58-14-0 |
| Catalog No. | 2A-9016766 |
| Chinese Name | 乙胺嘧啶 |
| Synonyms | Daraclor; Pyremethamine; Primethamine; 5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine; TCMDC-125860; WR 2978; Pyrimethamin; Malocid; pirimetamin; bw50-63; 5-(4-chlorophényl)-6-éthylpyrimidine-2,4-diamine; Malacid; Daraprim; Malocide; 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine; 5-(4-Chlorphenyl)-6-ethylpyrimidin-2,4-diamin; MFCD00057350; T6N CNJ BZ DZ ER DG& F2; RP 4753; chloridine; darachlor; pirimecidan; Pyrimethamine; Pirimetamina; EINECS 200-364-2; TCMDC-123831; 4753r.p. |
| Molecular Formula | C12H13ClN4 |
| Molecular Weight | 248.71 |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 368.4±52.0 °C at 760 mmHg |
| Melting Point | 233-234°C |
| Appearance | powder |
| Water Solubility | <0.01 g/100 mL at 21 ºC |
| Storage Condition | 0-6°C |
| Packaging | III |
| Application | Pyrimethamine (RP4753) can interfere with the synthesis of tetrahydrofolate by inhibiting dihydrofolate reductase (DHFR), and can act on protozoan infections. |
| EINECS | 200-364-2 |
| HTC | 2933990090 |
| MDL Number | MFCD00057350 |
| SMILES | Clc1ccc(cc1)c2c(nc(nc2CC)N)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) |
| InChI Key | WKSAUQYGYAYLPV-UHFFFAOYSA-N |
| NACRES Code | NA.21 |
| UNSPSC | 12352116 |
| Hazard Symbols | 6.1(b) |
| Risk Codes | R22 |
| MSDS | msds/16766_1_58_14_0.pdf |
| Bioactivity | Pyrimethamine(RP4753) is a medication used for protozoal infections; interferes with tetrahydrofolic acid synthesis from folic acid by inhibiting the enzyme dihydrofolate reductase (DHFR).IC50 Value: 15.4 nM (Plasmodium falciparum) [1]Target: DHFR; antifolatein vitro: Three susceptibility levels (susceptible, intermediate, and resistant) were observed in the response of culture-adapted clones and strains to pyrimethamine (50% inhibitory concentration [IC50]) < 100, 100-2,000, and > 2,000 nM) and cycloguanil (IC50 < 50, 50-500, and > 500 nM). Based on these susceptibility levels, 73 and 68 of 96 fresh clinical isolates were susceptible to pyrimethamine (mean IC50 15.4 nM) and cycloguanil (mean IC50 11.1 nM), respectively [1]. We tested pyrimethamine(previously reported to suppress SOD1 expression), several compounds currently in trials in human and murine ALS, and a set of 1040 FDA-approved compounds. In a PC12 cell-based assay, no compounds reduced SOD1 promoter activity without concomitant cytotoxicity. Additionally,pyrimethamine failed to repress levels of SOD1 protein in HeLa cells or homogenates of liver, spinal cord and brain of wild-type mice [3].in vivo: (131)I-Pyrimethamine (specific activity: 7.08 MBq/ mol) was injected intravenously into the tail vein of the control and infected rats. Static whole body images of the rats were acquired under the gamma camera at 5 min, 45 min, 2 h, 6 h, and 24 h following the intravenous administration of the radioactivity (3.7 MBq/rat) [2]. The 10-day treatment with 10mg/kg/day of fluconazole combined with 40/1mg/kg/day sulfadiazine and pyrimethamine resulted in 93% survival of CF1 mice acutely infected with the highly virulent T. gondii RH strain, versus 36% of mice treated with just sulfadiazine and pyrimethamine [4].Toxicity: Sulfadoxine/pyrimethamine is well tolerated as treatment and when used as intermittent preventive treatment in pregnant African women. Sulfadoxine/pyrimethamine is no longer used as prophylaxis because it may cause toxic epidermal necrolysis and Stevens Johnson syndrome [5]. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate Signaling Pathways >> Anti-infection >> Parasite Research Areas >> Infection References [1]. Basco LK, et al. In vitro activity of pyrimethamine, cycloguanil, and other antimalarial drugs against African isolates and clones of Plasmodium falciparum. Am J Trop Med Hyg. 1994 Feb; 50(2):193-9. [2]. Inceboz T, et al. Preparation of (131)I-Pyrimethamine and evaluation for scintigraphy of experimentally Toxoplasma gondii-infectedrats. J Drug Target. 2013 Feb;21(2):175-9. [3]. Wright PD, et al. Screening for inhibitors of the SOD1 gene promoter: pyrimethamine does not reduce SOD1 levels in cell and animal models. Neurosci Lett. 2010 Oct 4;482(3):188-92. [4]. Martins-Duarte ES, et al. Toxoplasma gondii: the effect of fluconazole combined with sulfadiazine and pyrimethamine against acute toxoplasmosis in murine model. Exp Parasitol. 2013 Mar;133(3):294-9. [5]. Taylor WR, et al. Antimalarial drug toxicity: a review. Drug Saf. 2004;27(1):25-61. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 368.4±52.0 °C at 760 mmHg Melting Point 233-234°C Molecular Formula C12H13ClN4 Molecular Weight 248.711 Flash Point 176.6±30.7 °C Exact Mass 248.082870 PSA 77.82000 LogP 1.03 Vapour Pressure 0.0±0.8 mmHg at 25°C Index of Refraction 1.667 InChIKey WKSAUQYGYAYLPV-UHFFFAOYSA-N SMILES CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1 Storage condition 0-6°C Stability Stable, but light sensitive. Combustible. Incompatible with strong oxidizing agents. Water Solubility <0.01 g/100 mL at 21 ºC |
| Use of | Properties Articles72 Name pyrimethamine Synonym More Synonyms pyrimethamine Biological Activity Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate Signaling Pathways >> Anti-infection >> Parasite Research Areas >> Infection References [1]. Basco LK, et al. In vitro activity of pyrimethamine, cycloguanil, and other antimalarial drugs against African isolates and clones of Plasmodium falciparum. Am J Trop Med Hyg. 1994 Feb; 50(2):193-9. [2]. Inceboz T, et al. Preparation of (131)I-Pyrimethamine and evaluation for scintigraphy of experimentally Toxoplasma gondii-infectedrats. J Drug Target. 2013 Feb;21(2):175-9. [4]. Martins-Duarte ES, et al. Toxoplasma gondii: the effect of fluconazole combined with sulfadiazine and pyrimethamine against acute toxoplasmosis in murine model. Exp Parasitol. 2013 Mar;133(3):294-9. [5]. Taylor WR, et al. Antimalarial drug toxicity: a review. Drug Saf. 2004;27(1):25-61. Chemical & Physical Properties Exact Mass 248.082870 PSA 77.82000 Index of Refraction 1.667 InChIKey WKSAUQYGYAYLPV-UHFFFAOYSA-N Stability Stable, but light sensitive. Combustible. Incompatible with strong oxidizing agents. |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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