Identification
- Summary
Olsalazine is an anti-inflammatory agent used in the treatment of inflammatory bowel disease and ulcerative colitis.
- Brand Names
- Dipentum
- Generic Name
- Olsalazine
- DrugBank Accession Number
- DB01250
- Background
Olsalazine is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease and Ulcerative Colitis. Olsalazine is a derivative of salicylic acid. Inactive by itself (it is a prodrug), it is converted by the bacteria in the colon to mesalamine. Mesalamine works as an anti-inflammatory agent in treating inflammatory diseases of the intestines.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Olsalazine (DB01250)
- Weight
- Average: 302.239
Monoisotopic: 302.053886062 - Chemical Formula
- C14H10N2O6
- Synonyms
- Olsalazine
Pharmacology
- Indication
For the treatment of Inflammatory Bowel Disease and Ulcerative Colitis.
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- Contraindications & Blackbox Warnings
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Olsalazine is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease and Ulcerative Colitis. Olsalazine reduces the bowel inflammation, diarrhea (stool frequency), rectal bleeding, and abdominal pain. Olsalazine is thought to work like balsalazide, delivering mesalazine or 5-aminosalicylic acid past the small intestine to the large intestine to act on the site of disease.
- Mechanism of action
Orally administered olsalazine is converted to mesalamine which is thought to be the therapeutically active agent in the treatment of ulcerative colitis. The mechanism of action of mesalamine (and sulfasalazine) is unknown, but appears to be topical rather than systemic. Mucosal production of arachidonic acid (AA) metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes (LTs) and hydroxyelcosatetraenoic acids (HETEs) is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalamine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin (PG) production in the colon.
Target Actions Organism AThiopurine S-methyltransferase inhibitorHumans AInterferon gamma Not Available Humans - Absorption
After oral administration, olsalazine, has limited systemic bioavailability. 98-99% of the dose is converted to mesalamine (5-ASA) in the colon, which is absorbed slowly resulting in very high local concentrations in the colon.
- Volume of distribution
Not Available
- Protein binding
Olsalazine and olsalazine-S are more than 99% bound to plasma proteins. Mesalamine (5-ASA) is 74% bound to plasma proteins.
- Metabolism
Most (98 to 99%) of an oral dose is rapidly converted into two molecules of 5-aminosalicylic acid (5-ASA) by colonic bacteria and the low prevailing redox potential found in this environment. The conversion of olsalazine to mesalamine in the colon is similar to that of sulfasalazine, which is converted into sulfapyridine and mesalamine. Approximately 0.1% of an oral dose of olsalazine is metabolized in the liver to olsalazine-O-sulfate (olsalazine-S)
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- Route of elimination
Approximately 0.1% of an oral dose of olsalazine is metabolized in the liver to olsalazine-O-sulfate (olsalazine-S).The remaining 5-ASA is partially acetylated and is excreted in the feces.
- Half-life
Olsalazine has an elimination half-life of 0.9 hours, however, olsalazine-S has a half-life of 7 days.
- Clearance
Not Available
- Adverse Effects
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Maximum single oral doses of 5g/kg in mice and rats and 2 g/kg in dogs were not lethal.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Olsalazine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Olsalazine is combined with Abciximab. Acarbose Olsalazine may increase the hypoglycemic activities of Acarbose. Acebutolol Olsalazine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The therapeutic efficacy of Olsalazine can be decreased when used in combination with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Olsalazine is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Olsalazine is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Olsalazine. Acetazolamide The risk or severity of adverse effects can be increased when Olsalazine is combined with Acetazolamide. Acetohexamide Olsalazine may increase the hypoglycemic activities of Acetohexamide. 
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- Take with food.
Products
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Ingredient UNII CAS InChI Key Olsalazine sodium Y7JEW0XG7I 6054-98-4 QQWFSVYVHLECFP-XBPUGJBTSA-L - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dipentum Capsule 250 mg Oral Atnahs Pharma Uk Limited 1995-12-31 Not applicable Canada 
Dipentum Capsule, gelatin coated 250 mg/1 Oral Alaven Pharmaceutical 1990-07-31 2017-05-11 US 
Dipentum Capsule 250 mg/1 Oral Unither Manufacturing, LLC 1990-07-31 2010-07-31 US Dipentum Capsule, gelatin coated 250 mg/1 Oral Carilion Materials Management 2015-05-15 Not applicable US Dipentum Capsule, gelatin coated 250 mg/1 Oral Meda Pharmaceuticals Inc. 2015-05-15 Not applicable US Dipentum Capsule, gelatin coated 250 mg/1 Oral Carilion Materials Management 1990-07-31 Not applicable US
Categories
- ATC Codes
- A07EC03 — Olsalazine
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Alimentary Tract and Metabolism
- Aminosalicylate
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Benzene Derivatives
- Benzoates
- Gastrointestinal Agents
- Hydroxy Acids
- Hydroxybenzoates
- Intestinal Antiinflammatory Agents
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Phenols
- Salicylates
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azobenzenes
- Sub Class
- Not Available
- Direct Parent
- Azobenzenes
- Alternative Parents
- Salicylic acids / Benzoic acids / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / Dicarboxylic acids and derivatives / Vinylogous acids / Azo compounds / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Organopnictogen compounds show 3 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Azo compound / Azobenzene / Benzenoid / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Carboxylic acid / Carboxylic acid derivative show 16 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- ULS5I8J03O
- CAS number
- 15722-48-2
- InChI Key
- QQBDLJCYGRGAKP-FOCLMDBBSA-N
- InChI
- InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+
- IUPAC Name
- 5-[(1E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
- SMILES
- OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O
References
- General References
- FDA Approved Drug Products: Dipentum (olsalazine sodium) capsule for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0015380
- KEGG Drug
- D00727
- KEGG Compound
- C07323
- PubChem Compound
- 6003770
- PubChem Substance
- 46506356
- ChemSpider
- 10642377
- 32385
- ChEMBL
- CHEMBL425
- ZINC
- ZINC000003812865
- PharmGKB
- PA450700
- PDBe Ligand
- JBC
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Olsalazine
- PDB Entries
- 7era
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Ankylosing Spondylitis (AS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Alaven Pharmaceutical
- Pfizer Inc.
- Pharmacia Inc.
- UCB Pharma
- Dosage Forms
Form Route Strength Capsule Oral Capsule Oral 250 mg Capsule Oral 250 mg/1 Capsule, gelatin coated Oral 250 mg/1 Tablet - Prices
Unit description Cost Unit Dipentum 250 mg capsule 1.8USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) Sodium salt decomposes at 240 °C Not Available logP 2.3 Not Available Caco2 permeability -6.96 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0781 mg/mL ALOGPS logP 2.77 ALOGPS logP 4.39 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 2.93 ChemAxon pKa (Strongest Basic) -0.019 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 139.78 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 78.85 m3·mol-1 ChemAxon Polarizability 28.61 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8502 Blood Brain Barrier + 0.6279 Caco-2 permeable - 0.6449 P-glycoprotein substrate Non-substrate 0.7433 P-glycoprotein inhibitor I Non-inhibitor 0.8628 P-glycoprotein inhibitor II Non-inhibitor 0.9525 Renal organic cation transporter Non-inhibitor 0.8844 CYP450 2C9 substrate Non-substrate 0.7774 CYP450 2D6 substrate Non-substrate 0.8748 CYP450 3A4 substrate Non-substrate 0.6636 CYP450 1A2 substrate Non-inhibitor 0.8006 CYP450 2C9 inhibitor Non-inhibitor 0.7804 CYP450 2D6 inhibitor Non-inhibitor 0.9047 CYP450 2C19 inhibitor Non-inhibitor 0.8638 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8912 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.5546 Biodegradation Not ready biodegradable 0.8701 Rat acute toxicity 1.4882 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9506 hERG inhibition (predictor II) Non-inhibitor 0.9453
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Thiopurine s-methyltransferase activity
- Specific Function
- Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
- Gene Name
- TPMT
- Uniprot ID
- P51580
- Uniprot Name
- Thiopurine S-methyltransferase
- Molecular Weight
- 28180.09 Da
References
- Lewis LD, Benin A, Szumlanski CL, Otterness DM, Lennard L, Weinshilboum RM, Nierenberg DW: Olsalazine and 6-mercaptopurine-related bone marrow suppression: a possible drug-drug interaction. Clin Pharmacol Ther. 1997 Oct;62(4):464-75. [Article]
- Lennard L: TPMT in the treatment of Crohn's disease with azathioprine. Gut. 2002 Aug;51(2):143-6. [Article]
- Lennard L: Clinical implications of thiopurine methyltransferase--optimization of drug dosage and potential drug interactions. Ther Drug Monit. 1998 Oct;20(5):527-31. [Article]
- Shipkova M, Niedmann PD, Armstrong VW, Oellerich M, Wieland E: Determination of thiopurine methyltransferase activity in isolated human erythrocytes does not reflect putative in vivo enzyme inhibition by sulfasalazine. Clin Chem. 2004 Feb;50(2):438-41. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Interferon-gamma receptor binding
- Specific Function
- Produced by lymphocytes activated by specific antigens or mitogens. IFN-gamma, in addition to having antiviral activity, has important immunoregulatory functions. It is a potent activator of macrop...
- Gene Name
- IFNG
- Uniprot ID
- P01579
- Uniprot Name
- Interferon gamma
- Molecular Weight
- 19348.165 Da
References
- Egan LJ, Sandborn WJ: Inhibition of nuclear factor kappaB by sulfasalazine: a new target for inflammatory bowel disease therapy? Gastroenterology. 1998 Nov;115(5):1295-6. [Article]
- Ito R, Shin-Ya M, Kishida T, Urano A, Takada R, Sakagami J, Imanishi J, Kita M, Ueda Y, Iwakura Y, Kataoka K, Okanoue T, Mazda O: Interferon-gamma is causatively involved in experimental inflammatory bowel disease in mice. Clin Exp Immunol. 2006 Nov;146(2):330-8. [Article]
Drug created at March 30, 2007 12:25 / Updated at June 27, 2022 14:55