2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
Pyrimethamine
CAS: 58-14-0
Molecular Formula: C12H13ClN4
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Names and Identifiers
| Name | Pyrimethamine |
| Synonyms | bw50-63 BW 50-63 Pyrimethamine PyriMethaMine,darapriM Pyrimethamine (200 mg) 5-(p-chlorophenyl)-6-ethyl-4-pyrimidinediamine 2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine 2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diyldiamine [2-amino-5-(4-chlorophenyl)-6-ethyl-pyrimidin-4-yl]amine Pyrimethamine,5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine |
| CAS | 58-14-0 |
| EINECS | 200-364-2 |
| InChI | InChI=1/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) |
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Physico-chemical Properties
| Molecular Formula | C12H13ClN4 |
| Molar Mass | 248.71 |
| Density | 1.2171 (rough estimate) |
| Melting Point | 233-234°C |
| Boling Point | 393.35°C (rough estimate) |
| Flash Point | 251°C |
| Water Solubility | <0.01 g/100 mL at 21 ºC |
| Solubility | <0.01 g/100 mL at 21°C |
| Vapor Presure | 8.34E-10mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| Maximum wavelength(λmax) | ['276nm(lit.)'] |
| Merck | 14,7985 |
| BRN | 219864 |
| pKa | pKa 7(t=20.0) (Uncertain) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Stable, but light sensitive. Combustible. Incompatible with strong oxidizing agents. |
| Sensitive | Light `sensitive`. inflammable |
| Refractive Index | 1.6110 (estimate) |
| MDL | MFCD00057350 |
| Physical and Chemical Properties | Melting point 233-234°C water-soluble <0.01g/100 mL at 21°C |
| Use | Antimalarial drugs for the etiological prevention and anti-relapse treatment of malaria |
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36 - Irritating to the eyes |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | UV8140000 |
| HS Code | 29335990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 oral in rat: 440mg/kg |
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Standard
Authoritative Data Verified Data
This product is 2, 4-diamino-5-(p-phenyl)-6-ethylpyrimidine. The content of C12H13C1N4 shall not be less than 99.0%.
Last Update：2024-01-02 23:10:35
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Trait
Authoritative Data Verified Data
- This product is white crystalline powder; Odorless.
- This product is slightly soluble in ethanol or chloroform, and is almost insoluble in water.
absorption coefficient
take this product, precision weighing, plus O. 1 mol/L hydrochloric acid solution dissolved, and quantitative dilution of 1ml containing about 13mg of solution, according to UV-visible spectrophotometry (General 0401), at the wavelength of 272nm absorbance, the absorption coefficient (PPM) was 309 to 329.
Last Update：2022-01-01 11:29:04
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Introduction
Odorless, tasteless. Slightly soluble in general organic solvents such as ethanol, chloroform, etc. Almost insoluble in cold water. Soluble in dilute inorganic acid.
Last Update：2022-10-16 17:26:36
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Differential diagnosis
Authoritative Data Verified Data
- the solution under the term of absorption coefficient has the maximum absorption at the wavelength of 272nm as determined by ultraviolet-visible spectrophotometry (General rule 0401), there is minimal absorption at a wavelength of 261nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 3).
- take this product about 0. lg, add anhydrous sodium carbonate 0. 5G, after mixing, burning, and cooling, the residue is immersed in water, filtered, and the filtrate is added dropwise with nitric acid until the red color of litmus test paper is observed, and the chloride is identified (1) response (General rule 0301).
Last Update：2022-01-01 11:29:05
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Exam
Authoritative Data Verified Data
pH
take this product 0. 30g, add 15ml water, after boiling, cool, filtered, add 2 drops of Methyl red indicator liquid in the filtrate, not red; Add hydrochloric acid titration solution (0. 05mol/L)0. 10ml, should be red.
Related substances
take this product, add chloroform-methanol (9 : 1) to make a solution containing 20mg per 1ml, as a test solution; Take the appropriate amount of precision, A solution containing 50mg per 1ml was prepared by dilution with the same solvent as a control solution. According to the thin layer chromatography (General 0502) test, absorb 1(^ 1) of each of the above two solutions, respectively point on the same silica gel GF254 thin layer plate, with toluene-glacial acetic acid-N-propanol-chloroform (25 : 10 : 10 : 2) as the developing solvent, it was spread out, dried, and placed under UV light (254nm). Test solution such as impurity spots, compared with the control solution of the main spot, not deeper (0.25).
ignition residue
not over 0841 (general rule).
Last Update：2022-01-01 11:29:06
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Content determination
Authoritative Data Verified Data
take this product about 0. 15g, precision weighing, add glacial acetic acid 20ml, heat and dissolve, let cool, add 2 drops of quinaldine red indicator solution, and use perchloric acid titration solution (0. 1 mol/L) titration to a solution almost colorless, and the results of the titration were corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/l) corresponds to 24.87 mg of C12H13C1N4.
Last Update：2022-01-01 11:29:06
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Category
Authoritative Data Verified Data
antimalarial drugs.
Last Update：2022-01-01 11:29:07
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:29:07
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Pyrimethamine Tablets
Authoritative Data Verified Data
This product contains pyrimethamine (C12 HI3C1N4) should be 90.0% ~ 110.
trait
This product is white tablet.
identification
- take an appropriate amount of fine powder of this product (about 5mg of pyrimethamine), add 2ml of dilute sulfuric acid, heat to dissolve pyrimethamine, cool, filter, add 2 drops of potassium iodide test solution to the filtrate, that is, a milky white precipitate was generated.
- take the solution under the content determination item, according to UV-visible spectrophotometry (General 0401), there is a maximum absorption at the wavelength of 272nm, there is minimal absorption at a wavelength of 261nm.
- take an appropriate amount of fine powder of this product (about 0.1g of pyrimethamine), and show the same reaction according to item (3) of identification under the item of pyrimethamine.
examination
- Content uniformity take 1 tablet of this product, put it in a 100ml measuring flask, add 0. lm o l/L hydrochloric acid solution appropriate amount, ultrasonic to dissolve pyrimethamine, let cool, with 0. Dilute lm o l/L hydrochloric acid solution to the scale, shake well, filter, Take 5ml of the continuous filtrate accurately, put it in a 25ml measuring flask, use 0. lm o l/L hydrochloric acid solution is diluted to the scale, shaken, according to the method under the content determination item, from the "ultraviolet-visible spectrophotometry", according to the law, the provisions shall be met (General rule 0941).
- dissolution of this product, according to the dissolution and release determination method (General 0931 second method), with 0.500ml of 1 mol/L hydrochloric acid solution is the dissolution medium, and the rotation speed is 75 rpm, and it is operated according to law. After 45 minutes, the appropriate amount of the solution is filtered, and the filtrate is taken according to the method under the content determination item, from the "UV-visible spectrophotometry", the dissolution amount of each tablet was calculated according to the law. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 20 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 25mg equivalent to pyrimethamine), put it in a 100ml measuring flask, add 0.lmol/L hydrochloric acid solution 70ml, slightly warm and constantly shake to dissolve pyrimethamine, let cool, use 0. Dilute 1 mol/L hydrochloric acid solution to the scale, shake well, filter, Take 5ml of filtrate accurately, put it in another 100ml measuring flask, use 0.1 mol/L hydrochloric acid solution diluted to the scale, shake, according to UV-visible spectrophotometry (General 0401), at the wavelength of 272rxm absorbance, the absorption coefficient (eλ2) of C12H13C1N4 was calculated as 319.
category
Same as pyrimethamine.
specification
6. 25mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:29:08
2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine - Reference Information
| Update Date: | 2022/11/12 10:05:38 |
| (IARC) carcinogen classification | 3 (Vol. 13, Sup 7) 1987 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| antigenic insect veterinary drug | pyrimethamine, also known as asimatadine, it is a broad-spectrum veterinary drug widely used in antigenic insects. In addition, pyrimethamine is also used in the breeding of aquatic products, which can enhance the disease resistance of aquatic fish. But the side effects of pyrimethamine is large, the use of excessive can damage the reproductive system of livestock and poultry, and is not easy to recover. Pyrimethamine has inhibitory effect on the primary infrared phase of some falciparum malaria and vivax malaria, and is a better preventive drug. Although there is no obvious effect on Plasmodium gametophytes, but the drug containing blood into the body of the mosquito, can affect the development of gametophytes in the body of the mosquito, it can block the spread. The principle of action is to inhibit dihydrofolate reductase, affect the use of tetrahydrofolate, reduce nucleic acid synthesis, inhibit malaria parasite reproduction. At the same time, pyrimethamine and chloroquine can protect the pathological changes of placenta after malaria infection by reducing the level of oxidative stress and apoptosis, and can also effectively reduce the proportion of infected red blood cells in the blood, so as to achieve a very good malaria treatment effect. And in aquatic products with enrichment, beyond a certain range, people can cause hemolytic anemia after eating, and even have direct toxicity to the central nervous system. This product is mainly used for the prevention of malaria, but also for the treatment of toxoplasmosis. It can inhibit the primary infrared phase of some falciparum malaria and vivax malaria, and is a better preventive drug. Due to the slow excretion, the effect is more lasting, a medication, the preventive effect can be maintained for more than 1 weeks. This product has no obvious effect on the gametophyte of Plasmodium, but when the mosquito inhales the blood containing the drug, Can affect the development of gametophytes in mosquitoes, it can block the spread. Because of its effect on the infrared phase of Plasmodium, it is often used in combination with primaquine to resist recurrence. This product is white crystalline powder; Odorless, tasteless. Insoluble in water, slightly soluble in ethanol, chloroform, acetone, soluble in dilute acid. The melting point was 232-235 °c. Figure 1 structural formula of pyrimethamine |
| function and use | This product can inhibit dihydrofolate reductase, so that dihydrofolate cannot be converted into tetrahydrofolate, this results in a reduction in the synthesis of nucleic acids, which inhibits the propagation of Plasmodium. Mainly for the prevention of malaria, can also be combined with primaquine, to prevent the recurrence of malaria. |
| pharmacokinetics | after oral administration, the gastrointestinal absorption was complete, but slowly, and the blood concentration reached the peak at 4 hours. The plasma protein binding rate was more than 80%. Mainly distributed in the liver, lung, kidney and other tissues, but also distributed in the milk. The half-life is about 90 hours, and only 10% ~ 20% of the original drug is excreted from the urine within 5~7 days after taking the drug, and the effective concentration in the blood can be maintained for two weeks. Therefore, a drug, its preventive effect can be maintained for more than 1 week. |
| adverse reactions | 1. Such as a large number of use can appear fatigue, Nausea, Vomit, Abdominal Pain, Fever, cyanosis, jaundice, splenomegaly and other symptoms of acute poisoning, should be promptly discontinued, and gastric lavage, fluid infusion and symptomatic treatment. Because of the sweet taste of this product, it is better for children to take poisoning by mistake, and special attention should be paid to the storage. 2. Long-term use can interfere with the use of folic acid in the body, resulting in megaloblastic anemia, should be regularly checked blood, after the emergence of calcium folinate treatment. |
| note | 1. Lactation women, renal dysfunction with caution, early pregnant women disabled, children under the age of 1 should not be used. 2. The taste is not bitter and slightly fragrant, should prevent children from poisoning caused by accidental ingestion, convulsions (children under 6 years of age can be poisoned to death by 50~100mg). Barbiturates may counteract their central excitatory effects. 4. An overdose or continuous long-term use of this product may result in inhibition of bone marrow and digestive tract function, leading to megaloblastic anemia and leukopenia. Timely withdrawal of the drug can restore itself, and calcium formyl folinate can improve bone marrow function. Adults A service 150 ~ 200mg, that is, the risk of poisoning, often 1~5 hours in Nausea, Vomit, Head Pain, dizziness and other symptoms, severe Coma convulsions. Children under 6 years of age have died of poisoning due to daily service of 50~100mg, so attention should be paid. First aid methods: gastric lavage, vomiting, a lot of drinking 10% sugar water or radish juice. Glucose infusion and diuretics were given. Thiopental was injected for spasm and convulsion. 6. Renal function damage, disturbance of consciousness, 6-GPD deficiency and giant cell anemia patients with caution. |
| drug interaction | in combination with a dihydrofolate synthase inhibitor such as sulfadoxine or dapsone, can double block the malaria parasite folic acid metabolism and enhance its efficacy, delay or prevent the emergence of drug-resistant strains. Can not be used with other dihydrofolate reductase inhibitors, because can enhance the toxicity. (2016-01-24) |
| usage and dosage | preventive medication: should be taken 1~2 weeks before entering affected area, generally should be taken to leave affected area after 6 to 8 weeks, 1 times a week, 25 mg each time. Children each 0.9 mg/kg, 1 times a week, the highest dose is limited to adults. Chloroquine resistant strains caused by falciparum malaria: Daily 50 mg, divided into 2 times. Children 0.3 mg/kg, 3 times a day. The course of treatment was 3 days. Toxoplasmosis: Daily 50~100 mg, daily service, 1~3 days after The Daily Service 25 mg, a course of 4~6 weeks. Children daily 1 mg/kg, divided into 2 times, after taking 1~3 days to daily 0.5 mg/kg, divided into 2 times, the course of treatment for 4~6 weeks. |
| Use | antimalarial drugs for the prevention of malaria etiology and anti-relapse treatment antimalarial drugs, for the etiological prevention and anti-relapse treatment of malaria |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:55:45
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