Balsalazide
Identification
- Summary
Balsalazide is an aminosalicylate used to treat ulcerative colitis.
- Brand Names
- Colazal
- Generic Name
- Balsalazide
- DrugBank Accession Number
- DB01014
- Background
Balsalazide is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease. It is sold under the name "Colazal" in the US and "Colazide" in the UK.
The chemical name is (E)-5-[[-4-(2-carboxyethyl) aminocarbonyl] phenyl]azo] -2-hydroxybenzoic acid. It is usually administered as the disodium salt.
Balsalazide works by deliverying mesalazine to the large intestine to act directly on ulcerative colitis. Mesalazine is also known as 5-aminosalicylic acid, or 5-ASA.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 357.3175
Monoisotopic: 357.096085227 - Chemical Formula
- C17H15N3O6
- Synonyms
- (E)-5-((4-(((2-carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoic acid
- (E)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylic acid
- 3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acid
- 5-[4-(2-carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoic acid
- Balsalazida
- Balsalazide
- Balsalazidum
Pharmacology
- Indication
For the treatment of mildly to moderately active ulcerative colitis.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Mild ulcerative colitis •••••••••••• ••••••• •••• •••••• Treatment of Moderate ulcerative colitis •••••••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Balsalazide is a prodrug that has little or no pharmacologic activity until it is enzymatically cleaved in the colon to produce mesalamine (5-aminosalicylic acid), an anti inflammatory drug indicated for the treatment of mildly to moderately active ulcerative colitis. Balsalazide disodium is delivered intact to the colon where it is cleaved by bacterial azoreduction to release equimolar quantities of mesalamine, which is the therapeutically active portion of the molecule, and the intert 4-aminobenzoyl-(beta)-alanine. As a result, the spectrum of pharmacologic activity of balsalazide is similar to that of mesalamine.
- Mechanism of action
The mechanism of action of 5-aminosalicylic acid is unknown, but appears exert its anti-inflammatory effects locally (in the GI tract) rather than systemically. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways (catalyzes the formation of prostaglandin precursors from arachidonic acid), and through the lipoxygenase pathways (catalyzes the formation of leukotrienes and hydroxyeicosatetraenoic acids from arachidonic acid and its metabolites), is increased in patients with chronic inflammatory bowel disease. Therefore, it is possible that 5-aminosalicylic acid diminishes inflammation by blocking production of arachidonic acid metabolites in the colon through both the inhibition of cyclooxygenase and lipoxygenase.
Target Actions Organism APeroxisome proliferator-activated receptor gamma agonistHumans AProstaglandin G/H synthase 2 inhibitorHumans AProstaglandin G/H synthase 1 inhibitorHumans AArachidonate 5-lipoxygenase inhibitorHumans - Absorption
Low and variable, intact balsalazide is poorly absorbed systemically.
- Volume of distribution
Not Available
- Protein binding
≥99%
- Metabolism
Cleaved in the colon via bacterial azoreduction to 5–aminosalicylic acid (5–ASA) and 4–aminobenzoyl-beta-alanine, the inactive carrier moiety.
Hover over products below to view reaction partners
- Route of elimination
The products of the azoreduction of this compound, 5-ASA and 4-aminobenzoyl-ß-alanine, and their N-acetylated metabolites have been identified in plasma, urine and feces. Following single-dose administration of 2.25 g COLAZAL (three 750 mg capsules) under fasting conditions in healthy subjects, mean urinary recovery of balsalazide, 5-ASA, and N-Ac-5-ASA was 0.20%, 0.22% and 10.2%, respectively.
- Half-life
Half-life could not be determined.
- Clearance
Not Available
- Adverse Effects
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- Toxicity
A single oral dose of balsalazide disodium at 5 grams/kg or 4-aminobenzoyl-(beta)-alanine, a metabolite of balsalazide disodium, at 1 gram/kg was non-lethal in mice and rats. No symptoms of acute toxicity were seen at these doses.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Balsalazide 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 Balsalazide is combined with Abciximab. Acarbose Balsalazide may increase the hypoglycemic activities of Acarbose. Acebutolol Balsalazide may decrease the antihypertensive activities of Acebutolol. Aceclofenac The therapeutic efficacy of Balsalazide can be decreased when used in combination with Aceclofenac. - Food Interactions
- Take with or without food.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Balsalazide disodium 1XL6BJI034 150399-21-6 XDCNKOBSQURQOZ-MVIJUDHYSA-L - Product Images
- International/Other Brands
- Colazide
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Colazal Capsule 750 mg/1 Oral Cardinal Health 2000-07-18 2010-02-28 US Colazal Capsule 750 mg/1 Oral Salix Pharmaceuticals, Inc 2000-07-18 Not applicable US Colazal Capsule 750 mg/1 Oral Physicians Total Care, Inc. 2005-06-09 2011-06-30 US Giazo Tablet, film coated 1.1 g/1 Oral Salix Pharmaceuticals, Inc 2012-02-03 2020-08-31 US - Generic Prescription Products
Categories
- ATC Codes
- A07EC04 — Balsalazide
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Alimentary Tract and Metabolism
- Aminobenzoates
- Aminosalicylate
- Aminosalicylic Acids
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Benzene Derivatives
- Benzoates
- Colitis, Ulcerative
- Gastrointestinal Agents
- Hydrazines
- Hydroxy Acids
- Hydroxybenzoates
- Inflammatory Bowel Diseases
- Intestinal Antiinflammatory Agents
- meta-Aminobenzoates
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Phenols
- Prodrugs
- 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
- Beta amino acids and derivatives / Salicylic acids / Benzamides / Benzoic acids / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / Dicarboxylic acids and derivatives / Vinylogous acids / Secondary carboxylic acid amides / Azo compounds show 6 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Azo compound / Azobenzene / Benzamide / Benzenoid / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Beta amino acid or derivatives show 21 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monohydroxybenzoic acid (CHEBI:267413)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- P80AL8J7ZP
- CAS number
- 80573-04-2
- InChI Key
- IPOKCKJONYRRHP-FMQUCBEESA-N
- InChI
- InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+
- IUPAC Name
- 5-[(1E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid
- SMILES
- OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O
References
- Synthesis Reference
Eckardt C. G. Wolf, Nageib Mohamed, Bhaskar Reddy Guntoori, "Safe process for the preparation of balsalazide." U.S. Patent US07271253, issued September 18, 2007.
US07271253- General References
- Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [Article]
- Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [Article]
- FDA Approved Drug Products: Colazal (basalazide disodium) capsules for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0015149
- KEGG Drug
- D07488
- PubChem Compound
- 6335412
- PubChem Substance
- 46505592
- ChemSpider
- 10662422
- 18747
- ChEBI
- 267413
- ChEMBL
- CHEMBL1201346
- ZINC
- ZINC000003952881
- Therapeutic Targets Database
- DAP000733
- PharmGKB
- PA448536
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Balsalazide
- FDA label
- Download (44.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Supportive Care Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis 1 3 Completed Treatment Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis 1 1 Completed Not Available Healthy Subjects (HS) 2 Not Available Completed Treatment Ulcerative Colitis 2
Pharmacoeconomics
- Manufacturers
- Apotex inc etobicoke site
- Mylan pharmaceuticals inc
- Roxane laboratories inc
- Salix pharmaceuticals inc
- Packagers
- Apotex Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Physicians Total Care Inc.
- Resource Optimization and Innovation LLC
- Roxane Labs
- Salix Pharmaceuticals
- Dosage Forms
Form Route Strength Capsule Oral 750 mg/1 Tablet Oral 1.1 g/1 Capsule Oral 750 MG Capsule Oral Tablet, film coated Oral 1.1 g/1 - Prices
Unit description Cost Unit Colazal 750 mg capsule 2.82USD capsule Balsalazide disodium 750 mg capsule 1.54USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7452872 Yes 2008-11-18 2027-02-24 US US7625884 Yes 2009-12-01 2027-02-24 US US6197341 No 2001-03-06 2018-03-13 US US8497256 No 2013-07-30 2031-06-23 US US9192616 No 2015-11-24 2026-08-02 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Freely soluble as disodium salt Not Available logP 1.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0621 mg/mL ALOGPS logP 3.37 ALOGPS logP 3.17 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 3.06 Chemaxon pKa (Strongest Basic) -0.033 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 148.65 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 94.37 m3·mol-1 Chemaxon Polarizability 35.98 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 + 0.8947 Blood Brain Barrier + 0.7807 Caco-2 permeable - 0.6455 P-glycoprotein substrate Non-substrate 0.6247 P-glycoprotein inhibitor I Non-inhibitor 0.7877 P-glycoprotein inhibitor II Non-inhibitor 0.7615 Renal organic cation transporter Non-inhibitor 0.8312 CYP450 2C9 substrate Non-substrate 0.7932 CYP450 2D6 substrate Non-substrate 0.8255 CYP450 3A4 substrate Non-substrate 0.5523 CYP450 1A2 substrate Non-inhibitor 0.7689 CYP450 2C9 inhibitor Non-inhibitor 0.7883 CYP450 2D6 inhibitor Non-inhibitor 0.8726 CYP450 2C19 inhibitor Non-inhibitor 0.8153 CYP450 3A4 inhibitor Non-inhibitor 0.9537 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9196 Ames test Non AMES toxic 0.5593 Carcinogenicity Non-carcinogens 0.75 Biodegradation Not ready biodegradable 0.5575 Rat acute toxicity 1.9986 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9148 hERG inhibition (predictor II) Non-inhibitor 0.7772
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0ldi-1393000000-af92622c6ce32e802a99 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0090000000-3efeb84ef93c25381028 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4r-0019000000-4402ebfff105ce6e520d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-75df5afb51977a88b7ec Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1092000000-e949a91a57799829c879 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0391000000-f293b03350c3d35e0aa4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1290000000-b9b4baedb768cdf2e34c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.7574324 predictedDarkChem Lite v0.1.0 [M-H]- 195.7941324 predictedDarkChem Lite v0.1.0 [M-H]- 183.05284 predictedDeepCCS 1.0 (2019) [M+H]+ 191.2576324 predictedDarkChem Lite v0.1.0 [M+H]+ 191.7883324 predictedDarkChem Lite v0.1.0 [M+H]+ 185.41084 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.4727324 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.13875 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 Da
References
- Tursi A: Balsalazide in treating colonic diseases. Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1555-63. doi: 10.1517/17425250903228842. [Article]
- Iacucci M, de Silva S, Ghosh S: Mesalazine in inflammatory bowel disease: a trendy topic once again? Can J Gastroenterol. 2010 Feb;24(2):127-33. [Article]
- Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [Article]
- Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [Article]
- Stolfi C, Fina D, Caruso R, Caprioli F, Sarra M, Fantini MC, Rizzo A, Pallone F, Monteleone G: Cyclooxygenase-2-dependent and -independent inhibition of proliferation of colon cancer cells by 5-aminosalicylic acid. Biochem Pharmacol. 2008 Feb 1;75(3):668-76. Epub 2007 Sep 29. [Article]
- Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [Article]
- Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Iron ion binding
- Specific Function
- Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
- Gene Name
- ALOX5
- Uniprot ID
- P09917
- Uniprot Name
- Arachidonate 5-lipoxygenase
- Molecular Weight
- 77982.595 Da
References
- Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [Article]
- Rask-Madsen J, Bukhave K, Laursen LS, Lauritsen K: 5-Lipoxygenase inhibitors for the treatment of inflammatory bowel disease. Agents Actions. 1992;Spec No:C37-46. [Article]
Enzymes
- Kind
- Protein
- Organism
- Bacillus sp. (strain OY1-2)
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Azobenzene reductase activity
- Specific Function
- Catalyzes the reductive cleavage of azo bond in aromatic azo compounds to the corresponding amines. Requires NADPH as an electron donor for its activity. Compounds with paired naphthalene groups co...
- Gene Name
- azr
- Uniprot ID
- Q9FAW5
- Uniprot Name
- NADPH azoreductase
- Molecular Weight
- 19293.155 Da
References
- Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [Article]
- Ryan A, Laurieri N, Westwood I, Wang CJ, Lowe E, Sim E: A novel mechanism for azoreduction. J Mol Biol. 2010 Jul 2;400(1):24-37. doi: 10.1016/j.jmb.2010.04.023. Epub 2010 Apr 24. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:47