La Mesalamina meglio conosciuta come mesalazina o 5-aminosalicilico (5-ASA), è un farmaco antinfiammatorio utilizzato principalmente per il trattamento delle malattie infiammatorie croniche intestinali, come la colite ulcerosa e la malattia di Crohn. È un composto con proprietà anti-infiammatorie che agisce direttamente sul tratto gastrointestinale, riducendo l'infiammazione e alleviando i sintomi associati a queste patologie.

Composizione Chimica e Struttura

La mesalazina è un derivato dell'acido salicilico, la cui struttura chimica è composta da un anello benzenico legato a un gruppo amminico (-NH₂) e un gruppo carbossilico (-COOH). 

• Formula chimica: C₇H₇NO₃

• Struttura: La mesalazina è costituita da un anello benzenico con un gruppo amminico (-NH2) in posizione 5 e un gruppo carbossilico (-COOH) in posizione 1, che la distingue dagli altri salicilati.

Proprietà Fisiche

• Aspetto: La mesalazina è una polvere cristallina bianca o leggermente giallastra.

• Solubilità: È solubile in acqua, ma la sua solubilità può variare a seconda della formulazione farmaceutica.

• Odore: Ha un odore quasi neutro, che non interferisce con l'uso in formulazioni farmaceutiche.

Benefici e Funzioni

• Antinfiammatorio: La mesalazina è utilizzata per ridurre l'infiammazione nel tratto intestinale, specialmente nel trattamento della colite ulcerosa e della malattia di Crohn. Agisce localmente nell'intestino, riducendo l'infiammazione senza effetti sistemici significativi.

• Trattamento delle malattie infiammatorie intestinali: La mesalazina è il trattamento di scelta per mantenere la remissione e ridurre le esacerbazioni della colite ulcerosa. È spesso somministrata per via orale o rettale, a seconda della posizione dell'infiammazione.

• Prevenzione delle recidive: Viene utilizzata anche per prevenire le recidive nei pazienti con malattie infiammatorie croniche intestinali.

Applicazioni

Farmaceutica

• Trattamento della colite ulcerosa e della malattia di Crohn: La mesalazina è comunemente prescritta come farmaco per il trattamento e il controllo della colite ulcerosa e della malattia di Crohn, poiché aiuta a ridurre l'infiammazione e a prevenire i sintomi ricorrenti.

• Preparazioni orali e rettali: Viene somministrata in diverse forme farmaceutiche, come compresse, capsule a rilascio modificato, sospensioni liquide e supposte rettali, per trattare le infiammazioni localizzate nel colon.

• Combinazione con altre terapie: La mesalazina viene talvolta usata in combinazione con altre terapie per migliorare l'efficacia del trattamento nelle malattie intestinali infiammatorie.

Cosmetici

• Trattamenti per la pelle: Sebbene non sia una funzione principale, alcune formulazioni cosmetiche per la pelle sensibile o con infiammazioni cutanee potrebbero contenere composti simili o derivati della mesalazina, anche se l'uso più comune è nei trattamenti gastrointestinali.

Considerazioni Ambientali e di Sicurezza

• Sicurezza: La mesalazina è generalmente ben tollerata, ma può causare effetti collaterali, come mal di testa, nausea, diarrea o disturbi gastrointestinali. In rari casi, può causare reazioni allergiche o danni ai reni.

• Precauzioni d'uso: Il farmaco deve essere usato con cautela in persone con problemi renali o epatici. È importante che venga prescritto e monitorato da un medico per garantire l'efficacia e ridurre il rischio di effetti collaterali.

• Biodegradabilità: Essendo un farmaco, la mesalazina non è destinata al contatto con l'ambiente, ma viene eliminata tramite il metabolismo e l'escrezione corporea.

Molecular Formula  C₇H₇NO₃

Molecular Weight  153.14 g/mol

CAS     89-57-6

UNII    4Q81I59GXC

EC Number  201-919-1

Synonyms:

Mesalamine

Mesalazine

5-Aminosalicylic acid

Bibliografia__________________________________________________________________________

Picchio M, Elisei W, Tursi A. Mesalazine to treat symptomatic uncomplicated diverticular disease and to prevent acute diverticulitis occurrence. A systematic review with meta-analysis of randomized, placebo-controlled trials. J Gastrointestin Liver Dis. 2018 Sep;27(3):291-297. doi: 10.15403/jgld.2014.1121.273.pic. 

Abstract. Background and aims: Symptomatic Uncomplicated Diverticular disease (SUDD) affects about 25% of patients harboring colonic diverticula. We assessed the effectiveness of mesalazine in improving symptoms (namely abdominal pain, primary outcome) and in preventing diverticulitis occurrence (secondary outcome) in patients with SUDD. Methods: Pertinent studies were selected from the Medline and the Cochrane Central Register of Controlled Trials. Only randomized clinical trials (RCTs) (irrespective of language, blinding, or publication status), which compared mesalazine, irrespective of the dosage assumption, with placebo in SUDD were evaluated. Results: Four RCTs enrolled 379 patients, 197 treated with mesalazine and 182 with placebo. Two studies provided data on symptom relief according to definition: it was achieved in 97/121 (80%) patients in the mesalazine group and in 81/129 (62.7%) patients in the placebo group (OR 0.43; 95% CI 0.24-0.75; p=0.003 in favour of the mesalazine group). Two studies provided information regarding occurrence of diverticulitis during follow-up. It occurred in 23/119 (19.3%) patients in the mesalazine group and in 34/102 (33.3%) patients in the placebo group (OR 0.35; 95% CI 0.17-0.70; p=0.003 in favour of the mesalazine group). Conclusions: Treatment with mesalazine seems to be effective in achieving symptom relief and in the primary prevention of diverticulitis in patients with SUDD.

Gautam P, Akhter MH, Anand A, Rab SO, Jaremko M, Emwas AH. Mesalamine loaded ethyl cellulose nanoparticles: optimization andin vivoevaluation of antioxidant potential in ulcerative colitis. Biomed Mater. 2024 Nov 22;20(1). doi: 10.1088/1748-605X/ad920e. 

Abstract. This study aimed to optimize mesalamine (MES)-nanoparticles (NPs) using Box Behnken Design and investigate itsin vivoantioxidant potential in colon drug targeting. The formulation was prepared using oil/water (O/W) emulsion solvent evaporation technique for time dependent colonic delivery. The optimal formulation with the following parameters composition was selected: polymer concentration (% w/w) (A) = 0.63, surfactant concentration (% w/w) (B) = 0.71, sonication duration (min) (C) = 6. The outcomes showed that ethyl cellulose (EC) NP containing MES has particles size of 142 ± 2.8 nm, zeta potential (ZP) of -24.8 ± 2.3 mV, % EE of 87.9 ± 1.6%, and PDI of 0.226 ± 0.15. Scanning electron microscopy revealed NPs has a uniform and spherical shape. Thein-vitrorelease data disclosed that the EC NPs containing MES showed bursts release of 52% ± 1.6% in simulated stomach media within 2 h, followed by a steady release of 93% ± 2.9% in simulated intestinal fluid that lasted for 48 h. The MES release from NP best match with the Korsmeyer-Peppas model (R2= 0.962) and it followed Fickian diffusion case I release mechanism. The formulation stability over six-months at 25 °C ± 2 °C with 65% ± 5% relative humidity, and 40 °C ± 2 °C with 75% ± 5% relative humidity showed no significant changes in colour, EE, particle sizes and ZP. As perin vivoresults, MES-NP effectively increased glutathione, SOD level and reduces the LPO level as compared to other treatment groups. The findings hold promise that the developed formulation can suitably give in ulcerative colitis.

Słoka J, Madej M, Strzalka-Mrozik B. Molecular Mechanisms of the Antitumor Effects of Mesalazine and Its Preventive Potential in Colorectal Cancer. Molecules. 2023 Jun 29;28(13):5081. doi: 10.3390/molecules28135081. 

Abstract. Chemoprevention is one of the ways to fight colorectal cancer, which is a huge challenge in oncology. Numerous pieces of evidence indicate that chronic inflammation in the course of Crohn's disease or ulcerative colitis (UC) is a significant cancer risk factor. Epidemiologic studies suggest that long-term use of non-steroidal anti-inflammatory drugs (NSAIDs), including mesalazine, has beneficial effects on colitis-associated colorectal cancer. Mesalazine is a first-line therapy for UC and is also widely used for maintaining remission in UC. Data showed that mesalazine has antiproliferative properties associated with cyclooxygenase (COX) inhibition but can also act through COX-independent pathways. This review summarizes knowledge about mesalazine's molecular mechanisms of action and chemopreventive effect by which it could interfere with colorectal cancer cell proliferation and survival.

Mesalamine Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Mesalamine. 2024 Sep 15. 

Abstract. Mesalamine is poorly excreted into breastmilk. However, rather high levels of the mesalamine metabolite N-acetyl-5-ASA appear in breastmilk and its effects on breastfed infants are unknown. A few cases of diarrhea have been reported in infants exposed to mesalamine, although the rate is not high. Most experts consider mesalamine derivatives to be safe during breastfeeding.[1-6] If mesalamine is required by the mother, it is not a reason to discontinue breastfeeding, but carefully observe breastfed infants for diarrhea during maternal use of mesalamine.

Park B, Han G, Jin DY, Gil KC, Shin D, Lee J, Park JY, Jang H, Park D, Lee S, Kim K, Yang Y, Kim Y, Kim JS, Kim SH, Shim MK. Mucoadhesive Mesalamine Prodrug Nanoassemblies to Target Intestinal Macrophages for the Treatment of Inflammatory Bowel Disease. ACS Nano. 2024 Jun 25;18(25):16297-16311. doi: 10.1021/acsnano.4c05544. 

Abstract. While mesalamine, a 5-aminosalicylic acid (5-ASA), is pivotal in the management of inflammatory bowel disease (IBD) through both step-up and top-down approaches in clinical settings, its widespread utilization is limited by low bioavailability at the desired site of action due to rapid and extensive absorption in the upper gastrointestinal (GI) tract. Addressing mesalamine's pharmacokinetic challenges, here, we introduce nanoassemblies composed exclusively of a mesalamine prodrug that pairs 5-ASA with a mucoadhesive and cathepsin B-cleavable peptide. In an IBD model, orally administered nanoassemblies demonstrate enhanced accumulation and sustained retention in the GI tract due to their mucoadhesive properties and the epithelial enhanced permeability and retention (eEPR) effect. This retention enables the efficient uptake by intestinal pro-inflammatory macrophages expressing high cathepsin B, triggering a burst release of the 5-ASA. This cascade fosters the polarization toward an M2 macrophage phenotype, diminishes inflammatory responses, and simultaneously facilitates the delivery of active agents to adjacent epithelial cells. Therefore, the nanoassemblies show outstanding therapeutic efficacy in inhibiting local inflammation and contribute to suppressing systemic inflammation by restoring damaged intestinal barriers. Collectively, this study highlights the promising role of the prodrug nanoassemblies in enhancing targeted drug delivery, potentially broadening the use of mesalamine in managing IBD.

King-Nakaoka EA, Yu LX. Mesalamine as Treatment of Neovaginal Ileitis: Case Report and Review of Literature. J Pediatr Adolesc Gynecol. 2025 Apr;38(2):210-212. doi: 10.1016/j.jpag.2024.12.002. Epub 2024 Dec 13. PMID: 39674397.

Kim H, Kim YZ, Kim SY, Choe YH, Kim MJ. Comparison of Effects on 6-Thioguanine Nucleotides According to Mesalazine Formulation in Pediatric Patients with Ulcerative Colitis. Clin Ther. 2025 Mar;47(3):196-203. doi: 10.1016/j.clinthera.2024.12.007. Epub 2025 Jan 2. PMID: 39753503.

Szigeti R, Kellermayer R. Immunotherapy withdrawal by step-down to mesalamine in pediatric patients with ulcerative colitis. JPGN Rep. 2024 Feb 5;5(2):97-100. doi: 10.1002/jpr3.12048. PMID: 38756120; PMCID: PMC11093912.