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Pyrimethamin

Pyrimethamine Struktur
58-14-0
CAS-Nr.
58-14-0
Bezeichnung:
Pyrimethamin
Englisch Name:
Pyrimethamine
Synonyma:
Daraprim;Fansidar;Chloridine;PYRIMETHAMIN;Pirimetamina;Pyremethamine;wr2978;bw50-63;RP 4753;WR 2978
CBNumber:
CB8461315
Summenformel:
C12H13ClN4
Molgewicht:
248.71
MOL-Datei:
58-14-0.mol

Pyrimethamin Eigenschaften

Schmelzpunkt:
233-234°C
Siedepunkt:
393.35°C (rough estimate)
Dichte
1.2171 (rough estimate)
Brechungsindex
1.6110 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
L?slichkeit
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).
pka
pKa 7(t=20.0) (Uncertain)
Aggregatzustand
Solid
Farbe
White to Off-White
Wasserl?slichkeit
<0.01 g/100 mL at 21 ºC
maximale Wellenl?nge (λmax)
276nm(lit.)
Merck 
14,7985
BRN 
219864
BCS Class
2 (CLogP), 4 (LogP),3
Stabilit?t:
Stable, but light sensitive. Combustible. Incompatible with strong oxidizing agents.
CAS Datenbank
58-14-0(CAS DataBase Reference)
IARC
3 (Vol. 13, Sup 7) 1987
NIST chemische Informationen
Pyrimethamine(58-14-0)
EPA chemische Informationen
Pyrimethamine (58-14-0)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn
R-S?tze: 22-36
S-S?tze: 26
RIDADR  3249
WGK Germany  3
RTECS-Nr. UV8140000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29335990
Giftige Stoffe Daten 58-14-0(Hazardous Substances Data)
Toxizit?t LD50 oral in rat: 440mg/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Pyrimethamin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R22:Gesundheitssch?dlich beim Verschlucken.

Chemische Eigenschaften

White Solid

Verwenden

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.

Definition

ChEBI: An aminopyrimidine that is pyrimidine-2,4-diamine which is substituted at position 5 by a p-chlorophenyl group and at position 6 by an ethyl group. It is a folic acid antagonist used as an antimalarial or with a sulfonamide to treat toxoplasmo is.

Indications

Pyrimethamine (Daraprim) is the best of a number of 2,4- diaminopyrimidines that were synthesized as potential antimalarial and antibacterial compounds. Trimethoprim (Proloprim) is a closely related compound.
Pyrimethamine is well absorbed after oral administration, with peak plasma levels occurring within 3 to 7 hours. An initial loading dose to saturate nonspecific binding sites is not required, as it is with chloroquine. However, the drug binds to tissues, and therefore, its rate of renal excretion is slow. Pyrimethamine has a half-life of about 4 days. Although the drug does undergo some metabolic alterations, the metabolites formed have not been totally identified.

Allgemeine Beschreibung

Odorless white crystalline powder. Tasteless. An antimalarial drug.

Air & Water Reaktionen

Pyrimethamine is a diaminopyrimidine which is structurally related to trimethoprim. It is effective against erythrocytic stage of Plasmodium (P) falciparum and less so against P. vivax, P. ovale and P. malariae. Pyrimethamine also inhibits the sporogony in the mosquito, resulting in a decrease of transmission of the infection within the community[1].
The mechanism of action of pyrimethamine is related to its inhibition of dihydrofolic reductase necessary for the folic acid synthesis in the parasite. Pyrimethamine acts slowly and is not recommended as monotherapy for acute malaria attacks. Resistance to pyrimethamine developed soon when the drug was used on a large scale as monoprophylaxis [1]. In resistant strains, the enzyme dihydrofolic reductase binds to pyrimethamine several hundred times less than in sensitive strains [2]. This high grade resistance is probably a onestep mutation and cannot be overcome by increasing the dose. However, when combined with long-acting sulphonomides (sulphadoxine), the effect of pyrimethamine is potentiated and the risk of developing resistant strains is far less.

Reaktivit?t anzeigen

Pyrimethamine together with sulphadoxine (Fansidar) is used in the treatment of P. falciparum malaria (cf. Sulphadoxine: Indications). Pyrimethamine is also valuable in the treatment of toxoplasmosis.

Brandgefahr

Pyrimethamine in combination with sulphadoxine (Fansidar) can cause severe cutaneous adverse reactions (cf. Sulphadoxine: Side effects). Agranulocytosis occurs quite frequently (1/2000) and fatalities have been reported when pyrimethamine is combined with dapsone [3]. When given alone, life-threatening adverse reactions are very rare and the drug is generally well tolerated. Megaloblastic anaemia may, however, occur during long-term treatment with high doses (i.e. for toxoplasmosis) and can be prevented by folinic acid supplementation [4].

Biologische Aktivit?t

During long-term treatment with high doses, folinic acid supplement is usually given.

Mechanism of action

The combination of pyrimethamine with a long-acting sulfonamide, sulfadoxine, which blocks dihydrofolate synthesis by blocking incorporation of PABA into the dihydrofolate, is called Fansidar, which produces sequential blockage of tetrahydrofolate synthesis similar to that reported for treatment of bacterial infections. Plasmodium enzymes catalyzing folic acid synthesis differ from those enzymes found in other organisms. A single bifunctional protein present in Plasmodium sp. catalyzes the phosphorylation of 6-hydroxymethyl-7,8-hydropterin (a pyrophosphokinase) and the incorporation of PABA into dihydropteroic acid. A second bifunctional enzyme catalyzes the reduction of dihydropteroic acid and thymidylic acid synthesis. As a result, the drug combination (Fansidar) appears to have improved drug-mediated disruption of folic acid in Plasmodium sp.. This combination has been used with quinine for the treatment and prevention of chloroquine-resistant malaria (Plasmodium falciparum, Plasmodium ovale, Plasmodium vivax, and Plasmodium malaria). The combination therapy (Fansidar) has the added advantage of being inexpensive, which is essential for successful therapy in developing countries. When used on its own, pyrimethamine is a blood schizonticide without effects on the tissue stage of the disease.

Clinical Use

Pyrimethamine has been recommended for prophylactic use against all susceptible strains of plasmodia; however, it should not be used as the sole therapeutic agent for treating acute malarial attacks. As mentioned previously, sulfonamides should always be coadministered with pyrimethamine (or trimethoprim), since the combined antimalarial activity of the two drugs is significantly greater than when either drug is used alone. Also, resistance develops more slowly when they are used in combination. Sulfonamides exert little or no effect on the blood stages of P. vivax, and resistance to the dihydrofolate reductase inhibitors is widespread.
In addition to its antimalarial effects, pyrimethamine is indicated (in combination with a sulfonamide) for the treatment of toxoplasmosis.The dosage required is 10 to 20 times higher than that employed in malarial infections.

Nebenwirkungen

Relatively few side effects are associated with the usual antimalarial dosages. However, signs of toxicity are evident at higher dosages, particularly those used in the management of toxoplasmosis. Many of these reactions reflect the interference of pyrimethamine with host folic acid metabolism, especially that occurring in rapidly dividing cells. Toxic symptoms include anorexia, vomiting, anemia, leukopenia, thrombocytopenia, and atrophic glossitis. CNS stimulation, including convulsions, may follow an acute overdose.The side effects associated with the pyrimethamine–sulfadoxine combination include those associated with the sulfonamide and pyrimethamine alone. In addition, there is evidence of a greater incidence of allergic reactions, particularly toxic epidermal necrolysis and Stevens-Johnson syndrome, with the combination. This carries an estimated mortality of 1:11,000 to 1:25,000 when used as a chemoprophylactic.

Sicherheitsprofil

Poison by ingestion, subcutaneous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx. Used as an antimalarial drug for humans and to treat toxoplasmosis in hogs.

Pyrimethamin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Pyrimethamin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 509)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hebei Weibang Biotechnology Co., Ltd
+8615531157085
abby@weibangbio.com China 8816 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12829 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971
deasea125996@gmail.com China 2472 58
Shaanxi TNJONE Pharmaceutical Co., Ltd
+8618092446649
sarah@tnjone.com China 1143 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106
sales@frappschem.com China 880 50
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806
sales@capot.com China 29791 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21639 55
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29886 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28172 58
Xiamen AmoyChem Co., Ltd
+86-86-5926051114 +8618959220845
sales@amoychem.com China 6383 58

58-14-0(Pyrimethamin)Verwandte Suche:


  • 2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
  • [2-amino-5-(4-chlorophenyl)-6-ethyl-pyrimidin-4-yl]amine
  • Pyrimethamine,5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine
  • Pyrimethamine (200 mg)
  • PyriMethaMine,darapriM
  • 5-(p-chlorophenyl)-6-ethyl-4-pyrimidinediamine
  • BW 50-63
  • bw50-63
  • Chloridin
  • Chloridyn
  • Darachlor
  • Daraclor
  • Darapram
  • 5-(4’-chlorophenyl)-2,4-diamino-6-ethylpyrimidine
  • 5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine
  • 5-(4-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine
  • 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diyldiamine
  • 5-(P-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
  • Pyrimidine,2,4-diamino-5-(p-chlorophenyl)-6-ethyl-
  • RP 4753
  • Tindurin
  • Tinduring
  • WR 2978
  • wr2978
  • PYRIMETHAMINE
  • Daraprime
  • Diaminopyritamin
  • Erbaprelina
  • Khloridin
  • Malacid
  • Malocid
  • Malocide
  • Maloprim
  • NCI-C01683
  • nsc3061
  • NSC-3061
  • Pirimecidan
  • Pirimetamin
  • Primethamine
  • pyrimethamine(INN)
  • Pyrimidine, 2,4-diamino-5-(p-chlorophenyl)-6-ethyl-
  • PYRIMETHAMINE BP
  • 5-(4-CHLOROPHENYL)-6-ETHYL-2,4-PYRIMIDINEDIAMINE
  • 5-(4-CHLOROPHENYL)-6-ETHYL-PYRIMIDINE-2,4-DIAMINE
  • 2,4-diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
  • PYRIMETHAMINE HCL
  • Pyrimeigamine
  • Pyrimethamine BP98 USP23
  • PYRIMETHAMINE VETRANAL, 250 MG
  • 5(4-Chloro Phenyl)-6-Ethyl-2,4-pyridine diamine
  • PYRIMETHAMINE,USP
  • PYRIMETHAMINEUM
  • Pyrimethamine (base and/or unspecified salts)
  • Pirimetmin
  • 2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine
  • 2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl-
  • 2,4-Pyrimidinediamine, 5-(p-chlorophenyl)-6-ethyl-
  • 2,4-Pyrimidinediamine,5-(4-chlorophenyl)-6-ethyl-
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