Coenzyme M
Identification
- Summary
Coenzyme M is a uroprotective agent used for the reduction and prophylaxis of oxazaphosphorine-induced toxicity in the urinary tract.
- Brand Names
- Uromitexan
- Generic Name
- Coenzyme M
- DrugBank Accession Number
- DB09110
- Background
Coenzyme M (commonly known by its salt form, Mesna) is a synthetic sulfhydryl (thiol) compound and is used for prophylaxis of Ifosfamide and cyclophosphamide induced hemorrhagic cystitis.2
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Coenzyme M (DB09110)
- Weight
- Average: 142.197
Monoisotopic: 141.975835438 - Chemical Formula
- C2H6O3S2
- Synonyms
- 2-Mercaptoethane
- 2-Mercaptoethanesulfonate
- 2-mercaptoethanesulfonic acid
- 2-mercaptoethanesulphonic acid
- 2-mercaptoethylsulfonate
- 2-sulfanylethylsulfonate
- Coenzima M
- Coenzym M
- CoM
- HS-CoM
- reduced coenzyme M
- reduced CoM
- β-mercaptoethanesulfonic acid
Pharmacology
- Indication
Mesna is a uroprotective agent and is used prophylactically to reduce ifosfamide and cyclophosphamide induced hemorrhagic cystitis.2
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- Contraindications & Blackbox Warnings
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Mesna binds to and inactivates acrolein there by preventing or reducing bladder problems
- Mechanism of action
A metabolite called acrolein is produced when ifosfamide and cyclophosphamide are metabolized. This metabolite concentrates in the bladder and causes cell death via upregulation of reactive oxygen species (ROS), and activates inducible nitric oxide synthase (iNOS) which leads to production of nitric oxide (NO). Both ROS and NO produce products which are detrimental to lipids, proteins and DNA strands. Furthermore, ROS stimulate gene expression of pro-inflammatory cytokines such as TNF-α AND IL-1β. Acrolein may also lead to ulceration of the bladder urothelium. Mesna protects against cyclophosphamide and ifosfamide induced hemorrhagic cystitis by binding to their toxic metabolites. Mesna is metabolized to dimesna and excreted by the kidneys. Glutathione dihydrogenase acts on the reabsorbed portion and produces free sulfhydryl groups. These free sulfhydryl groups bind acrolein in the bladder, allowing effective excretion and prevention of toxic effects.1 In addition, Mesna binds to and detoxifies a urotoxic ifosfamide metabolite called 4-hydroxy-ifosfamide.
- Absorption
Peak plasma concentrations were reached within 1.5-4 hours for free mesna, and 3-7 hours for total mesna following oral administration. The average oral bioavailability is 58% for free mesna and 89% for total mesna. Food has no effect on the urinary availability of mesna.
- Volume of distribution
Vd = 0.652 ± 0.242 L/Kg after intravenous administration of mesna.
- Protein binding
Total plasma mesna is 28% protein bound.3
- Metabolism
Mesna undergoes rapid oxidation to mesna disulfide (dimesna) which is its major metabolite.
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- Route of elimination
Within 24 hours, approximately 32% of administered dose is eliminated in the urine as mesna while 33% is eliminated as dimesna.
- Half-life
The elimination half-life is 0.36 hours for mesna and 1.17 hours for dimesna.
- Clearance
Plasma clearance of mesna = 1.23 L/h/kg
- Adverse Effects
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The following adverse events were most common (>10%) when mesna was administered with ifosfamide: nausea, vomiting, fatigue, fever, abdominal pain, constipation, diarrhea, leukopenia, anorexia, thrombocytopenia, anemia, granulocytopenia, asthenia, headache, alopecia, and somnolence. Hypersensitivity reactions and dermatologic toxicity may occur in patients taking mesna; therefore, if either reaction occurs, mesna should be discontinued and patient should be provided with supportive care.
- 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.Not Available
- Food Interactions
- No food interactions are expected.
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 Mesna NR7O1405Q9 19767-45-4 XOGTZOOQQBDUSI-UHFFFAOYSA-M - International/Other Brands
- Mistabron / Mistabronco
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mesna Injection, solution 100 mg/1mL Intravenous Baxter Healthcare Corporation 1988-12-30 Not applicable US 
Mesna Injection, solution 100 mg/1mL Intravenous Baxter Healthcare Corporation 1988-12-30 Not applicable US Mesna for Injection Solution 100 mg / mL Intravenous Fresenius Kabi 2002-08-22 Not applicable Canada 
Mesnex Injection, solution 100 mg/1mL Intravenous Baxter Healthcare Corporation 1988-12-30 Not applicable US Mesnex Tablet, film coated 400 mg/1 Oral Baxter Healthcare Corporation 2002-03-21 Not applicable US Uromitexan Solution 100 mg / mL Intravenous; Oral Baxter Laboratories 2001-03-06 Not applicable Canada Uromitexan Solution 100 mg / mL Intravenous Baxter Laboratories 2012-04-13 Not applicable Canada Uromitexan Inj 100mg/ml Liquid 100 mg / amp Intravenous; Oral Bristol Labs Division Of Bristol Myers Squibb 1989-12-31 2001-06-12 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mesna Injection, solution 100 mg/1mL Intravenous Bedford Pharmaceuticals 2008-03-03 2012-07-31 US Mesna Injection, solution 100 mg/1mL Intravenous Mylan Institutional 2012-04-03 2016-09-30 US Mesna Solution 100 mg/1mL Intravenous Gland Pharma Limited 2017-12-20 Not applicable US Mesna Injection, solution 100 mg/1mL Intravenous Fresenius Kabi USA, LLC 2001-09-05 Not applicable US Mesna Injection, solution 100 mg/1mL Intravenous Bedford Pharmaceuticals 2004-01-09 2012-07-31 US Mesna Injection, solution 100 mg/1mL Intravenous AGILA SPECIALTIES PRIVATE LIMITED 2014-07-19 2017-09-01 US Mesna Injection, solution 100 mg/1mL Intravenous Alvogen Inc. 2018-03-29 Not applicable US Mesna Injection, solution 100 mg/1mL Intravenous Athenex Pharmaceutical Division, Llc. 2018-02-28 Not applicable US Mesna Injection, solution 100 mg/1mL Intravenous Bedford Pharmaceuticals 2004-02-23 2012-07-31 US Mesna Injection, solution 100 mg/1mL Intravenous Teva Parenteral Medicines, Inc. 2002-05-01 2020-10-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image IFEX and MESNEX Mesna (100 mg/1mL) + Ifosfamide (3 g/60mL) Kit Intravenous E.R. Squibb & Sons, L.L.C. 2009-06-01 2010-03-31 US IFEX and MESNEX Mesna (100 mg/1mL) + Ifosfamide (1 g/20mL) Kit Intravenous E.R. Squibb & Sons, L.L.C. 2009-06-01 2010-06-30 US IFEX and MESNEX Mesna (100 mg/1mL) + Ifosfamide (1 g/20mL) Kit Intravenous E.R. Squibb & Sons, L.L.C. 2009-06-01 2010-06-30 US Ifosfamide and Mesna Mesna (100 mg/1mL) + Ifosfamide (3 g/60mL) Kit Intravenous Teva Parenteral Medicines, Inc. 2012-09-26 2012-09-26 US Ifosfamide and Mesna Mesna (100 mg/1mL) + Ifosfamide (1 g/20mL) Kit Intravenous Teva Parenteral Medicines, Inc. 2012-09-26 2012-09-26 US Ifosfamide and Mesna Mesna (100 mg/1mL) + Ifosfamide (1 g/20mL) Kit Intravenous Teva Parenteral Medicines, Inc. 2002-05-01 2011-07-31 US
Categories
- ATC Codes
- R05CB05 — Mesna
- R05CB — Mucolytics
- R05C — EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
- R05 — COUGH AND COLD PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Acids
- Acids, Noncarboxylic
- Alkanes
- Alkanesulfonates
- Alkanesulfonic Acids
- Compounds used in a research, industrial, or household setting
- Cough and Cold Preparations
- Cytoprotective Agent
- Detoxifying Agents for Antineoplastic Treatment
- Expectorants
- Hydrocarbons, Acyclic
- Mesna
- Protective Agents
- Sulfhydryl Compounds
- Sulfonic Acids
- Sulfur Acids
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as organosulfonic acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic sulfonic acids and derivatives
- Sub Class
- Organosulfonic acids and derivatives
- Direct Parent
- Organosulfonic acids
- Alternative Parents
- Sulfonyls / Alkanesulfonic acids / Alkylthiols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alkanesulfonic acid / Alkylthiol / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organosulfonic acid / Organosulfur compound / Sulfonyl
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- thiol, organosulfonic acid (CHEBI:17905)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- VHD28S0H7F
- CAS number
- 3375-50-6
- InChI Key
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N
- InChI
- InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)
- IUPAC Name
- 2-sulfanylethane-1-sulfonic acid
- SMILES
- OS(=O)(=O)CCS
References
- General References
- Matz EL, Hsieh MH: Review of Advances in Uroprotective Agents for Cyclophosphamide and Ifosfamide-Induced Hemorrhagic Cystitis. Urology. 2016 Aug 23. pii: S0090-4295(16)30458-7. doi: 10.1016/j.urology.2016.07.030. [Article]
- Cutler MJ, Urquhart BL, Velenosi TJ, Meyer Zu Schwabedissen HE, Dresser GK, Leake BF, Tirona RG, Kim RB, Freeman DJ: In vitro and in vivo assessment of renal drug transporters in the disposition of mesna and dimesna. J Clin Pharmacol. 2012 Apr;52(4):530-42. doi: 10.1177/0091270011400414. Epub 2011 Apr 19. [Article]
- DynaMed [Link]
- External Links
- Human Metabolome Database
- HMDB0003745
- KEGG Compound
- C03576
- PubChem Compound
- 598
- PubChem Substance
- 310265029
- ChemSpider
- 578
- 1546354
- ChEBI
- 17905
- ChEMBL
- CHEMBL1098319
- ZINC
- ZINC000003831040
- PDBe Ligand
- COM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Coenzyme_M
- PDB Entries
- 1e6v / 1e6y / 1hbn / 1hbo / 1hbu / 1mro / 2c3c / 2c3d / 3m1v / 3m2r … show 31 more
- FDA label
- Download (3.61 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Multiple Myeloma (MM) 1 4 Unknown Status Treatment Nasal and Nasal-type NK/T-cell Lymphoma 1 4 Unknown Status Treatment Pleural Effusions 1 3 Completed Treatment Breast Cancer 1 3 Completed Treatment Diffuse Large Cell Diffuse Lymphoma 1 3 Completed Treatment Leukemias 1 3 Completed Treatment Lung Cancers 1 3 Completed Treatment Malignant Lymphomas 1 3 Completed Treatment Neoplasms, Brain / Tumors of the Central Nervous System 1 3 Completed Treatment Neuroblastoma (NB) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Intravenous Injection, solution Intravenous 100 mg/1mL Solution Intravenous 100 mg/1mL Solution Intravenous 100 mg Solution Intravenous 400 mg Tablet, film coated Oral 400 mg/1 Spray Solution Nasal; Respiratory (inhalation) 5 g Injection, solution Intravenous; Parenteral 400 MG/4ML Solution Intravenous 1 g/10ml Solution Intravenous 100 mg / mL Solution Intravenous 5 g/50ml Solution Intravenous; Oral 100 mg / mL Tablet, coated 400 MG Tablet, coated 600 MG Tablet, film coated Oral 400 mg Tablet, film coated Oral 600 mg Injection Intravenous Solution Intravenous Tablet, film coated Oral Solution 100 mg/1ml Injection, solution Intravenous Liquid Intravenous; Oral 100 mg / amp - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 12.7 mg/mL ALOGPS logP -1.5 ALOGPS logP -0.4 ChemAxon logS -1 ALOGPS pKa (Strongest Acidic) -1.2 ChemAxon pKa (Strongest Basic) -9.6 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 54.37 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 29.13 m3·mol-1 ChemAxon Polarizability 12.54 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-MS (2 TMS) GC-MS splash10-00e9-7960000000-d0e9fc5f5629ba893d57 Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - GC-MS GC-MS splash10-00e9-7960000000-d0e9fc5f5629ba893d57 GC-MS Spectrum - GC-EI-TOF GC-MS splash10-052u-2900000000-51cd7c5f2497db0c7a15 GC-MS Spectrum - GC-EI-TOF GC-MS splash10-004m-7970000000-a5c3c33a78b251bdd12c 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 LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-001i-9400000000-f69174f630c88b6e6c0b
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Substrate
- General Function
- Nadp binding
- Specific Function
- Maintains high levels of reduced glutathione in the cytosol.
- Gene Name
- GSR
- Uniprot ID
- P00390
- Uniprot Name
- Glutathione reductase, mitochondrial
- Molecular Weight
- 56256.565 Da
References
- Ormstad K, Orrenius S, Lastbom T, Uehara N, Pohl J, Stekar J, Brock N: Pharmacokinetics and metabolism of sodium 2-mercaptoethanesulfonate in the rat. Cancer Res. 1983 Jan;43(1):333-8. [Article]
Drug created on September 17, 2015 21:16 / Updated on September 18, 2021 03:34