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4-Aminosalicylsure

4-Aminosalicylic acid Struktur
65-49-6
CAS-Nr.
65-49-6
Bezeichnung:
4-Aminosalicylsure
Englisch Name:
4-Aminosalicylic acid
Synonyma:
4-AMINO-2-HYDROXYBENZOIC ACID;PAS;AMINOSALICYLIC ACID;Pasa;4-Asa;P-AMINOSALICYLIC ACID;Apas;Paser;Aminox;Parasal
CBNumber:
CB9679687
Summenformel:
C7H7NO3
Molgewicht:
153.14
MOL-Datei:
65-49-6.mol

4-Aminosalicylsure Eigenschaften

Schmelzpunkt:
135-145 °C (lit.)
Siedepunkt:
276.03°C (rough estimate)
Dichte
1.3585 (rough estimate)
Brechungsindex
1.5500 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
L?slichkeit
1.69g/l
Aggregatzustand
Powder
pka
3.25(at 25℃)
Farbe
Colorless
PH
3.5 (1g/l, H2O, 20℃)
Wasserl?slichkeit
2 g/L (20 ºC)
Merck 
14,477
BRN 
473071
BCS Class
4/2
Stabilit?t:
Hygroscopic
CAS Datenbank
65-49-6(CAS DataBase Reference)
NIST chemische Informationen
Aminosalicylic acid(65-49-6)
EPA chemische Informationen
4-Aminosalicylic acid (65-49-6)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn,Xi,T
R-S?tze: 22-36-36/37/38-45-35-61
S-S?tze: 26-37/39-45-53-36-36/37/39
RIDADR  UN 1789 8/PG 3
WGK Germany  2
RTECS-Nr. VO1225000
TSCA  Yes
HS Code  29225000
Giftige Stoffe Daten 65-49-6(Hazardous Substances Data)
Toxizit?t LD50 orally in mice: 4 g/kg (Bavin)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P405 Unter Verschluss aufbewahren.

4-Aminosalicylsure Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R22:Gesundheitssch?dlich beim Verschlucken.
R36:Reizt die Augen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R45:Kann Krebs erzeugen.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

beige powder

Verwenden

antimycobacterial antitubercular;NF-kB inhibitor.
4-Aminosalicylic acid (p-aminosalicylic acid, PAS), an antituberculosis drug, is a model active pharmaceutical ingredient to study salt and cocrystal formation in a multiple hydrogen-bonding functionality molecule with carboxylic acid, amine, and phenol groups.
It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease.It is typically taken by mouth.

Definition

ChEBI: An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.

Application

4-Aminosalicylic acid (4-ASA) can be used in the synthesis of:
Azo derivatives of 4-ASA with anti-inflammatory effects.
Ammonium 4-aminosalicylate salt polymorphs which are used as pharmaceutical ingredients.
Salicylic acid-triazole analogs which are used as quorum sensing inhibitors against Pseudomonas aeruginosa.

Indications

p-Aminosalicylic acid is a bacteriostatic that inhibits most tuberculous mycobacteria. In terms of tuberculostatic activity it is inferior to isoniazid and streptomycin. It is nephroand hepatotoxic, and is rarely used. A synonym of this drug is apacizin.

Allgemeine Beschreibung

4-Aminosalicylic acid occurs as a white to yellowish white crystalline solid that darkens on exposure to light or air. It is slightly soluble in water but more soluble in alcohol. Alkali metal salts and the nitric acid salt are soluble in water, but the salts of hydrochloric acid and sulfuric acid are not. The acid undergoes decarboxylation when heated. An aqueous solution has a pH of approximately 3.2. PAS is administered orally in the form of the sodium salt, usually in tablet or capsule form. Symptoms of gastrointestinal irritation are common with both the acid and the sodium salt. Various enteric-coated dosage forms have been used in an attempt to overcome this disadvantage. Other forms that are claimed to improve gastrointestinal tolerance include the calcium salt, the phenyl ester, and a combination with an anion exchange resin (Rezi-PAS). An antacid such as aluminum hydroxide is frequently prescribed. The oral absorption of PAS is rapid and nearly complete, and it is widely distributed into most of the body fluids and tissues, with the exception of the CSF, in which levels are significantly lower.It is excreted primarily in the urine as both unchanged drug and metabolites.

Biologische Aktivit?t

4-Aminosalicylic acid is an antimetabolite of p-aminobenzoic acid (PABA) that has antibacterial activity.It is active against streptomycin-sensitive and -resistant strains of M. tuberculosis (MICs = 0.78 and 0.39 μg/ml, respectively), an effect that can be reversed by PABA. 4-Aminosalicylic acid is an alternative substrate for mycobacterial dihydropteroate synthase (FolP1) and misincorporation into the folate pathway leads to accumulation of several folate-dependent metabolites including serine, homocysteine, dUMP, and AICAR, markers of folate pathway inhibition, in a concentration-dependent manner. It reverses manganese-induced increases in rat hippocampal levels of NOD-like receptor protein 3 (NLRP3), cleaved caspase-1, and phosphorylated p65, markers of NLRP3 inflammasome-dependent pyroptosis, when administered at a dose of 300 mg/kg. 4-Aminosalycilic acid is also a building block that has been used in the synthesis of luminescent lanthanide complexes. Formulations containing 4-aminosalicylic acid have been used in the treatment of tuberculosis.

Mechanism of action

p-aminosalicylic acid is thought to act as an antimetabolite interfering with the incorporation of p-aminobenzoic acid into folic acid. When coadministered with INH, PAS is found to reduce the acetylation of INH, itself being the substrate for acetylation, thus increasing the plasma levels of INH. This action may be especially valuable in patients who are rapid acetylators.

Sicherheitsprofil

Moderately toxic ingestion andother routes. An eye irritant. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

Stoffwechsel

p-aminosalicylic acid is extensively metabolized by acetylation of the amino group and by conjugation with glucuronic acid and glycine at the carboxyl group. It is used primarily in cases of resistance, retreatment, and intolerance of other agents and is available from the CDC.

l?uterung methode

Crystallise the acid from EtOH. [Beilstein 14 IV 1967.]

4-Aminosalicylsure Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


4-Aminosalicylsure Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 581)Lieferanten
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65-49-6(4-Aminosalicylsure)Verwandte Suche:


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  • 4-amino-2-hydroxy-benzoicaci
  • 4-Aminosalicyclic acid
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  • SCHIFF REAGENT SOLUTION, MODIFIED
  • PERIODIC ACID-SCHIFF
  • 4-AMINOSALICYLIC ACID
  • NSC 211698
  • 4-AMINO-2-HYDROXYBENZOIC ACID FOR SYNTHE
  • A 1909
  • Aminopar
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  • Apacil
  • Benzoic acid, 4-amino-2-hydroxy-
  • Benzoicacid,4-amino-2-hydroxy-
  • Deapasil
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  • NIH 2939
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  • nsc2083
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  • Paramycin
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