피리메타민

피리메타민 · Pyremethamine · Daraprim · Fansidar · Chloridine · Pirimetamina · PYRIMETHAMIN · wr2978

식별자 및 물리적 특성

CAS No.	58-14-0
분자식	C12H13ClN4
평균 분자량	248.71 g/mol
단동위원소 질량	248.0828741 g/mol
SMILES	CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1
InChIKey	WKSAUQYGYAYLPV-UHFFFAOYSA-N
PubChem CID	4993
ChEMBL	CHEMBL36
ChEBI	CHEBI:8673
EC No.	200-364-2
DTXSID	DTXSID9021217
현지명	피리메타민

화학 및 물리적 성질

XLogP	2.7
극성 표면적	77.8
수소 결합 공여자 수	2
수소 결합 수용자 수	4
회전 가능 결합 수	2
무거운 원자 수	17
형식 전하	0
복잡도	243
의약품	Pharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties	15N nuclear magnetic resonance spectrum
LogP(분배 계수)	log Kow = 2.692.7
Color/Form	CrystalsWhite scored tablets contains 25 mg pyrimethamine /Daraprim/
용해도	less than 0.1 mg/mL at 70 °F (NTP, 1992)In water, 10 mg/L (temperature not specified)Practically insoluble in waterslightly soluble in ethanol (about 9 g/L), in dilute HCl (about 5 g/L)soluble in boiling ethanol (about 25 g/L)Very sparingly soluble in propylene glycol and dimethylacetamide at 70 °C1.79e-01 g/L>37.3 [ug/mL] (The mean of the results at pH 7.4)Prepare the solution immediately before use. Dissolve 0.25 g in a mixture of 1 volume of methanol R and 3 volumes of methylene chloride R and dilute to 10 mL with the same mixture of solvents. The solution is clear (2.2.1) and not more intensely coloured than reference solution BY6 (2.2.2, Method II).
Human Drugs	Breast FeedingLactationMilk, HumanAnti-infective AgentsAntiparasitic AgentsAntimalarialsAntiprotozoal AgentsFDA approved drugs -> Active ingredientAntipneumocystosis and antitoxoplasmosis medicines
Animal Drugs	Active Ingredients (Pyrimethamine) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Decomposition	When heated to decomposition it emits very toxic fumes of /HCl and oxides of nitrogen/.
녹는점	451 to 453 °F (capillary) (NTP, 1992)233-234 °C (capillary)240-242 °C (copper block)233.5 °C233-234°C
Physical Description	Pyrimethamine is an odorless white crystalline powder. Tasteless. An antimalarial drug.Solid
Dissociation Constants	7.34 (at 20 °C)pKa = 7.34 at 20 °C (conjugate acid)
Collision Cross Section	158.8 Å² [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID9021217]155.8 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]153.6 Å² [M+Na]+ [CCS Type: TW
끓는 점	393.35°C (rough estimate)
밀도	1.2171 (rough estimate)
굴절률	1.6110 (estimate)
저장 조건	Keep in dark place,Inert atmosphere,Room temperature
물리적 상태	Solid
pKa(산도 계수)	pKa 7(t=20.0) (Uncertain)
색상	흰색에서 황백색까지
용해도	21 ºC에서 <0.01g/100mL
Merck	14,7985
BRN	219864
헨리 상수	9.1×104 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	2 (CLogP), 4 (LogP),3
안정성	안정적이지만 빛에 민감합니다. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
주요 응용	임상 시험
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	CCC1=NC(N)=NC(N)=C1C2=CC=C(Cl)C=C2
NIST	Pyrimethamine(58-14-0)
EPA	Pyrimethamine (58-14-0)

화학적 성질

White Solid

안전 및 규제

GHS 분류	WarningH302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 133 reports by companies from 7 notifications to the ECHA C&L Inventory.
규제 정보	Hazard Traits - Developmental Toxicity
기타 안전 정보	IMAP assessments - 2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl-: Environment tier I assessment
운송 라벨(DOT)	Poison
화재 위험	Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
건강 유해성	SYMPTOMS: Symptoms of exposure to this compound include megaloblastic anemia, leukopenia, thrombocytopenia, pancytopenia, atrophic glossitis, vomiting, convulsions, respiratory failure and death. Chronic exposure may cause depression of hemopoiesis due to interference in the metabolism of folic acid. Skin rashes may also occur.
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including pyrimethamine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.Oral dosage form new animal drug. Sulfadiazine/pyrimethamine suspension. ... For the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona. Limitations: Do not use in horses intended for human consumption. Federal law restricts this drug to use by or on the order of a licensed veterinarian.The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Pyrimethamine is included on this list.
반응성 그룹	Amines, Phosphines, and Pyridines
Reactivity Profile	PYRIMETHAMINE is sensitive to exposure to light (NTP, 1992). Neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

용도

For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine. Pyrimethamine is a dihydrofolate reductase inhibitor, like the biguanides, and is structurally related to trimethoprim. It is seldom used alone. Pyrimethamine in fixed combinations with dapsone or sulfadoxine is used for treatment and prophylaxis of chloroquine-resistant falciparum malaria. The synergistic activities of pyrimethamine and sulfonamides are similar to those of trimethoprim/sulfonamide combinations. Resistant strains of Plasmodium falciparum have appeared world wide. Prophylaxis against falciparum malaria with pyrimethamine alone is therefore not recommended. Most strains of Plasmodium vivax have remained sensitive. Pyrimethamine is also used in combination with a sulfonamide for the treatment of Toxoplasmosis. It is slowly absorbed from the gastrointestinal tract with peak plasma levels 4–6 hours after dosing. Pyrimethamine is bound to plasma proteins and is extensively metabolized before excretion. Its elimination half-life is 3–5 days.

일반 설명

Odorless white crystalline powder. Tasteless. An antimalarial drug.