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
Thumb
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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

Hover over products below to view reaction partners

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
Medicalerrors
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Toxicity

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

Products
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Product Ingredients
IngredientUNIICASInChI Key
MesnaNR7O1405Q919767-45-4XOGTZOOQQBDUSI-UHFFFAOYSA-M
International/Other Brands
Mistabron / Mistabronco
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MesnaInjection, solution100 mg/1mLIntravenousBaxter Healthcare Corporation1988-12-30Not applicableUS flag
MesnaInjection, solution100 mg/1mLIntravenousBaxter Healthcare Corporation1988-12-30Not applicableUS flag
Mesna for InjectionSolution100 mg / mLIntravenousFresenius Kabi2002-08-22Not applicableCanada flag
MesnexTablet, film coated400 mg/1OralBaxter Healthcare Corporation2002-03-21Not applicableUS flag
MesnexInjection, solution100 mg/1mLIntravenousBaxter Healthcare Corporation1988-12-30Not applicableUS flag
UromitexanSolution100 mg / mLIntravenous; OralBaxter Laboratories2001-03-06Not applicableCanada flag
UromitexanSolution100 mg / mLIntravenousBaxter Laboratories2012-04-13Not applicableCanada flag
Uromitexan Inj 100mg/mlLiquid100 mg / ampIntravenous; OralBristol Labs Division Of Bristol Myers Squibb1989-12-312001-06-12Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MesnaInjection, solution100 mg/1mLIntravenousAGILA SPECIALTIES PRIVATE LIMITED2014-07-192017-09-01US flag
MesnaInjection, solution100 mg/1mLIntravenousBedford Pharmaceuticals2004-02-232012-07-31US flag
MesnaInjection, solution100 mg/1mLIntravenousSagent Pharmaceuticals2013-04-30Not applicableUS flag
MesnaInjection, solution100 mg/1mLIntravenousAlvogen Inc.2018-03-29Not applicableUS flag
MesnaInjection, solution100 mg/1mLIntravenousMylan Institutional2012-04-032016-09-30US flag
MesnaInjection, solution100 mg/1mLIntravenousBedford Pharmaceuticals2008-03-032012-07-31US flag
MesnaInjection, solution100 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2002-05-012020-10-31US flag
MesnaInjection, solution100 mg/1mLIntravenousFresenius Kabi USA, LLC2001-09-05Not applicableUS flag
MesnaInjection, solution100 mg/1mLIntravenousBedford Pharmaceuticals2004-01-092012-07-31US flag
MesnaSolution100 mg/1mLIntravenousGland Pharma Limited2017-12-20Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
IFEX and MESNEXMesna (100 mg/1mL) + Ifosfamide (1 g/20mL)KitIntravenousE.R. Squibb & Sons, L.L.C.2009-06-012010-06-30US flag
IFEX and MESNEXMesna (100 mg/1mL) + Ifosfamide (3 g/60mL)KitIntravenousE.R. Squibb & Sons, L.L.C.2009-06-012010-03-31US flag
IFEX and MESNEXMesna (100 mg/1mL) + Ifosfamide (1 g/20mL)KitIntravenousE.R. Squibb & Sons, L.L.C.2009-06-012010-06-30US flag
Ifosfamide and MesnaMesna (100 mg/1mL) + Ifosfamide (1 g/20mL)KitIntravenousTeva Parenteral Medicines, Inc.2012-09-262012-09-26US flag
Ifosfamide and MesnaMesna (100 mg/1mL) + Ifosfamide (3 g/60mL)KitIntravenousTeva Parenteral Medicines, Inc.2012-09-262012-09-26US flag
Ifosfamide and MesnaMesna (100 mg/1mL) + Ifosfamide (1 g/20mL)KitIntravenousTeva Parenteral Medicines, Inc.2002-05-012011-07-31US flag

Categories

ATC Codes
R05CB05 — MesnaV03AF01 — Mesna
Drug Categories
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
  1. 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]
  2. 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]
  3. DynaMed [Link]
Human Metabolome Database
HMDB0003745
KEGG Compound
C03576
PubChem Compound
598
PubChem Substance
310265029
ChemSpider
578
RxNav
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
AHFS Codes
  • 92:56.00 — Protective Agents
PDB Entries
1e6v / 1e6y / 1hbn / 1hbo / 1hbu / 1mro / 2c3c / 2c3d / 3m1v / 3m2r
show 25 more
FDA label
Download (3.61 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentMultiple Myeloma (MM)1
4Unknown StatusTreatmentNasal and Nasal-type NK/T-cell Lymphoma1
4Unknown StatusTreatmentPleural Effusions1
3CompletedTreatmentBreast Cancer1
3CompletedTreatmentLeukemias1
3CompletedTreatmentLung Cancers1
3CompletedTreatmentLymphoma, Large-Cell, Diffuse1
3CompletedTreatmentMalignant Lymphomas1
3CompletedTreatmentNeoplasms, Brain / Tumors of the Central Nervous System1
3CompletedTreatmentNeuroblastomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitIntravenous
Injection, solutionIntravenous100 mg/1mL
SolutionIntravenous100 mg/1mL
Tablet, film coatedOral400 mg/1
Spray
SolutionNasal; Respiratory (inhalation)
Injection, solutionIntravenous; Parenteral
SolutionIntravenous100 mg / mL
SolutionIntravenous; Oral100 mg / mL
Tablet, coated
InjectionIntravenous
SolutionIntravenous
Tablet, film coatedOral
Solution100 mg/1ml
Injection, solutionIntravenous
LiquidIntravenous; Oral100 mg / amp
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.7 mg/mLALOGPS
logP-1.5ALOGPS
logP-0.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.13 m3·mol-1ChemAxon
Polarizability12.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00e9-7960000000-d0e9fc5f5629ba893d57
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-00e9-7960000000-d0e9fc5f5629ba893d57
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-052u-2900000000-51cd7c5f2497db0c7a15
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004m-7970000000-a5c3c33a78b251bdd12c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-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
  1. 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 May 14, 2021 11:41