Acido 4-amminosalicilico

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Acido 4-amminosalicilico
formula di struttura
formula di struttura
Nomi alternativi
acido para-amminosalicilico
acido p-aminosalicilico
PAS
Caratteristiche generali
Formula bruta o molecolareC7H7NO3
Massa molecolare (u)153,13 g/mol
Aspettosolido bianco o giallognolo
Numero CAS65-49-6
Numero EINECS200-613-5
PubChem4649
DrugBankDBDB00233
SMILES
C1=CC(=C(C=C1N)O)C(=O)O
Proprietà chimico-fisiche
Costante di dissociazione acida a KpKa:
Solubilità in acquabassa
Indicazioni di sicurezza
Simboli di rischio chimico
irritante
attenzione
Frasi H319
Consigli P305+351+338 [1]
Modifica dati su Wikidata · Manuale

L'acido p-amminosalicilico è un derivato dell'acido benzoico come i sulfamidici. Ha attività come antimicobatterico. Utilizzato come farmaco di seconda scelta per il trattamento della tubercolosi, solitamente in associazione con altri farmaci.

Meccanismo d'azione

Analogo a quello dei sulfamidici. Funge da antimetabolita del acido para-aminobenzoico (PABA) nei confronti dell'enzima batterico della diidropteroato sintetasi, enzima fondamentale per la sintesi del tetraidrofolato.

Effetti collaterali

Analogamente ai sulfamidici la sua metabolizzazione causa la formazione di metabolita molto poco solubili e che quindi precipitano nelle urine (cristalluria).

Proprietà

Pochissimo solubile in acqua, solubile in alcool etilico 95°, negli idrossidi e nei carbonati alcalini, poco solubile in etere etilico.

Reattività

  • Il cloridrato corrispondente si ottiene da una soluzione di partenza dell'acido 4-amminosalicilico in etere etilico a cui si aggiunge acido cloridrico in soluzione alcolica. Il precipitato è lavato e ricristallizzato in alcool etilico assoluto. (Punto di fusione 226-230 °C).
  • Se ad una soluzione acquosa si aggiungono poche gocce di una soluzione di cloruro ferrico, si ottiene colorazione rosso vino intensa.

Note

  1. ^ Sigma Aldrich; rev. del 25.10.2012

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