Mesalazine

Last updated

Mesalazine
Mesalazine structure.svg
Clinical data
Trade names Asacol, Lialda, Pentasa, Delzicol, others [1]
Other namesmesalamine, 5-aminosalicylic acid, 5-ASA, Mesalamine (USAN US)
AHFS/Drugs.com Monograph
MedlinePlus a688021
License data
Pregnancy
category
Routes of
administration
By mouth, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability orally: 20–30% absorbed
rectally: 10–35%
Metabolism Rapidly & extensively metabolized intestinal mucosal wall and the liver
Elimination half-life 5 hours after initial dose.
At steady state 7 hours
Identifiers
  • 5-Amino-2-hydroxybenzoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.745 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C7H7NO3
Molar mass 153.137 g·mol−1
3D model (JSmol)
Melting point 283 °C (541 °F)
  • O=C(O)c1cc(ccc1O)N
  • InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11) Yes check.svgY
  • Key:KBOPZPXVLCULAV-UHFFFAOYSA-N Yes check.svgY
   (verify)

Mesalazine, also known as mesalamine or 5-aminosalicylic acid (5-ASA), is a medication used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease. [1] It is generally used for mildly to moderately severe disease. [1] It is taken by mouth or rectally. [1] The formulations which are taken by mouth appear to be similarly-effective. [12]

Contents

Common side-effects include headache, nausea, abdominal pain, and fever. [1] Serious side-effects may include pericarditis, liver problems, and kidney problems. [1] [12] Use in pregnancy and breastfeeding appears safe. [12] In people with a sulfa allergy certain formulations may result in problems. [1] Mesalazine is an aminosalicylate and anti-inflammatory. [1] [12] It works by direct contact with the intestines. [1]

Mesalazine was approved for medical use in the United States in 1987. [1] [8] It is on the World Health Organization's List of Essential Medicines. [13] It is available as a generic medication. [1] [14] [15] [16] In 2021, it was the 239th most commonly prescribed medication in the United States, with more than 1 million prescriptions. [17] [18]

Medical uses

It is used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease (effective only in colonic diseases). [1]

In 2022 Germany introduced guidance to use mesalamine to treat acute uncomplicated diverticulitis. [19]

Side-effects

Most often reported side-effects are gastrointestinal (GI) (but may also include headache), including: nausea, diarrhea, and abdominal pain. [7]

Very rarely, use of mesalazine has been associated with an exacerbation of the symptoms of colitis, Stevens Johnson syndrome, and erythema multiforme. [7]

Pregnancy

There is no data on use in pregnant women, but the drug does cross the placenta and is excreted in breast milk. The drug should not be used in children under two years of age, [7] people with kidney disease, [7] or people who are allergic to aspirin. [7]

Chemistry

Mesalazine is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine. [20] It is also the active component of the prodrug balsalazide along with the inert carrier molecule 4-aminobenzoyl-beta-alanine. [21] It is in the category of disease-modifying antirheumatic drugs (DMARDs) family of medications. [22] It is unclear exactly how it works. [22] Mesalazine is claimed to be a PPAR-γ agonist. [23]

Mechanism of action

Exact mechanism of mesalazine is unknown, but is speculated that mesalazine decreases synthesis of prostaglandin and leukotriene, modulating the inflammatory response derived from the cyclooxygenase and lipooxygenase pathways. [24] It appears to act locally on colonic mucosa. [25]

Society and culture

Brand names

Mesalazine is sold under various names including Apriso, Asacol, Asacol HD, Canasa, Delzicol, Fivasa, Lialda, Salofalk, Pentasa, Rowasa, Octasa, and Sfrowasa. In Europe, it is sold under the name Salofalk (rectal suppository). [26] [27]

Related Research Articles

<span class="mw-page-title-main">Ulcerative colitis</span> Inflammatory bowel disease that causes ulcers in the colon

Ulcerative colitis (UC) is one of the two types of inflammatory bowel disease (IBD), with the other type being Crohn's disease. It is a long-term condition that results in inflammation and ulcers of the colon and rectum. The primary symptoms of active disease are abdominal pain and diarrhea mixed with blood (hematochezia). Weight loss, fever, and anemia may also occur. Often, symptoms come on slowly and can range from mild to severe. Symptoms typically occur intermittently with periods of no symptoms between flares. Complications may include abnormal dilation of the colon (megacolon), inflammation of the eye, joints, or liver, and colon cancer.

<span class="mw-page-title-main">Infliximab</span> Biopharmaceutical drug for autoimmune disorders

Infliximab, a chimeric monoclonal antibody, sold under the brand name Remicade among others, is a medication used to treat a number of autoimmune diseases. This includes Crohn's disease, ulcerative colitis, rheumatoid arthritis, ankylosing spondylitis, psoriasis, psoriatic arthritis, and Behçet's disease. It is given by slow injection into a vein, typically at six- to eight-week intervals.

<span class="mw-page-title-main">Hematochezia</span> Bowel movement consisting of fresh blood

Haematochezia is the passage of fresh blood through the anus, usually in or with stools. The term is from Greek αἷμα ("blood") and χέζειν. Hematochezia is commonly associated with lower gastrointestinal bleeding, but may also occur from a brisk upper gastrointestinal bleed. The difference between hematochezia and rectorrhagia is that, in the latter, rectal bleeding is not associated with defecation; instead, it is associated with expulsion of fresh bright red blood without stools. The phrase bright red blood per rectum is associated with hematochezia and rectorrhagia.

<span class="mw-page-title-main">Sulfasalazine</span> Chemical compound

Sulfasalazine, sold under the brand name Azulfidine among others, is a medication used to treat rheumatoid arthritis, ulcerative colitis, and Crohn's disease. It is considered by some to be a first-line treatment in rheumatoid arthritis. It is taken by mouth or can be administered rectally.

<span class="mw-page-title-main">Diverticular disease</span> Medical condition

Diverticular disease is when problems occur due to diverticulosis, a benign condition defined by the formation of pouches (diverticula) from the weak spots in the wall of the large intestine. This disease spectrum includes diverticulitis, symptomatic uncomplicated diverticular disease (SUDD), and segmental colitis associated with diverticulosis (SCAD). The most common symptoms across the disease spectrum are abdominal pain and bowel habit changes such as diarrhea or constipation. Otherwise, diverticulitis presents with systemic symptoms such as fever and elevated white blood cell count whereas SUDD and SCAD don’t. Treatment ranges from conservative bowel rest to medications such as antibiotics, antispasmodics, acetaminophen, mesalamine, rifaximin, and corticosteroids depending on the specific conditions.

Adalimumab, sold under the brand name Humira and others, is a disease-modifying antirheumatic drug and monoclonal antibody used to treat rheumatoid arthritis, juvenile idiopathic arthritis, psoriatic arthritis, ankylosing spondylitis, Crohn's disease, ulcerative colitis, plaque psoriasis, hidradenitis suppurativa, and uveitis. It is administered by subcutaneous injection. It works by inactivating tumor necrosis factor-alpha (TNFα).

<span class="mw-page-title-main">4-Aminosalicylic acid</span> Anti-tuberculosis and anti-inflammatory drug

4-Aminosalicylic acid, also known as para-aminosalicylic acid (PAS) and sold under the brand name Paser among others, is an antibiotic primarily used to treat tuberculosis. Specifically it is used to treat active drug resistant tuberculosis together with other antituberculosis medications. 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.

<span class="mw-page-title-main">Blood in stool</span> Medical condition

Blood in stool or rectal bleeding looks different depending on how early it enters the digestive tract—and thus how much digestive action it has been exposed to—and how much there is. The term can refer either to melena, with a black appearance, typically originating from upper gastrointestinal bleeding; or to hematochezia, with a red color, typically originating from lower gastrointestinal bleeding. Evaluation of the blood found in stool depends on its characteristics, in terms of color, quantity and other features, which can point to its source, however, more serious conditions can present with a mixed picture, or with the form of bleeding that is found in another section of the tract. The term "blood in stool" is usually only used to describe visible blood, and not fecal occult blood, which is found only after physical examination and chemical laboratory testing.

An aminosalicylate is a class of medications that is often used to treat ulcerative colitis and Crohn's disease. The class includes among others:

<span class="mw-page-title-main">Balsalazide</span> Anti-inflammatory drug

Balsalazide is an anti-inflammatory drug used in the treatment of inflammatory bowel disease. It is sold under the brand names Giazo, Colazal in the US and Colazide in the UK. It is also sold in generic form in the US by several generic manufacturers.

<span class="mw-page-title-main">Olsalazine</span> Pharmaceutical drug

Olsalazine is an anti-inflammatory medication used in the treatment of ulcerative colitis. It is sold under the brand name Dipentum.

Management of Crohn's disease involves first treating the acute symptoms of the disease, then maintaining remission. Since Crohn's disease is an immune system condition, it cannot be cured by medication or surgery. Treatment initially involves the use of medications to eliminate infections and reduce inflammation. Surgery may be required for complications such as obstructions, fistulae, abscesses, or if the disease does not respond to drugs within a reasonable time. However, surgery cannot cure Crohn's disease. It involves removing the diseased part of the intestine and rejoining the healthy ends, but the disease tends to recur after surgery.

Management of ulcerative colitis involves first treating the acute symptoms of the disease, then maintaining remission. Ulcerative colitis is a form of colitis, a disease of the intestine, specifically the large intestine or colon, that includes characteristic ulcers, or open sores, in the colon. The main symptom of active disease is usually diarrhea mixed with blood, of gradual onset which often leads to anaemia. Ulcerative colitis is, however, a systemic disease that affects many parts of the body outside the intestine.

<span class="mw-page-title-main">Biological therapy for inflammatory bowel disease</span>

Biological therapy, the use of medications called biopharmaceuticals or biologics that are tailored to specifically target an immune or genetic mediator of disease, plays a major role in the treatment of inflammatory bowel disease. Even for diseases of unknown cause, molecules that are involved in the disease process have been identified, and can be targeted for biological therapy. Many of these molecules, which are mainly cytokines, are directly involved in the immune system. Biological therapy has found a niche in the management of cancer, autoimmune diseases, and diseases of unknown cause that result in symptoms due to immune related mechanisms.

Ustekinumab, sold under the brand name Stelara among others, is a monoclonal antibody medication developed by Janssen Pharmaceuticals, for the treatment of Crohn's disease, ulcerative colitis, plaque psoriasis and psoriatic arthritis, targeting both IL-12 and IL-23.

<span class="mw-page-title-main">Tofacitinib</span> Medication

Tofacitinib, sold under the brand Xeljanz among others, is a medication used to treat rheumatoid arthritis, psoriatic arthritis, ankylosing spondylitis, polyarticular course juvenile idiopathic arthritis, and ulcerative colitis. It is a janus kinase (JAK) inhibitor, discovered and developed by the National Institutes of Health and Pfizer.

<span class="mw-page-title-main">Budesonide</span> Type of corticosteroid medication

Budesonide, sold under the brand name Pulmicort, among others, is a steroid medication. It is available as an inhaler, nebulization solution, pill, nasal spray, and rectal forms. The inhaled form is used in the long-term management of asthma and chronic obstructive pulmonary disease (COPD). The nasal spray is used for allergic rhinitis and nasal polyps. Modified-release pills or capsules and rectal forms may be used for inflammatory bowel disease including Crohn's disease, ulcerative colitis, and microscopic colitis.

Mirikizumab, sold under the brand name Omvoh, is a monoclonal antibody used for the treatment of ulcerative colitis. It is designed to attach to interleukin-23 (IL-23) and block its activity.

<span class="mw-page-title-main">Segmental colitis associated with diverticulosis</span> Medical condition

Segmental colitis associated with diverticulosis (SCAD) is a condition characterized by localized inflammation in the colon, which spares the rectum and is associated with multiple sac-like protrusions or pouches in the wall of the colon (diverticulosis). Unlike diverticulitis, SCAD involves inflammation of the colon between diverticula, while sparing the diverticular orifices. SCAD may lead to abdominal pain, especially in the left lower quadrant, intermittent rectal bleeding and chronic diarrhea.

<span class="mw-page-title-main">Etrasimod</span> Medication

Etrasimod, sold under the brand name Velsipity, is a medication that is used for the treatment of ulcerative colitis. It is a selective sphingosine-1-phosphate (S1P) receptor modulator that modifies the activity of the immune system. It is taken by mouth.

References

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