General
Preferred name
Coenzyme M
Synonyms
MESNA ()
Mesnex tabs ()
2-MERCAPTOETHANE ()
ARGIMESNA ()
Mesnum ()
Sodium 2-mercaptoethanesulfonate ()
Mesnex ()
Uromitexan ()
Mitexan ()
2-MERCAPTOETHANESULFONIC ACID ()
Coenzyme M Sodium ()
D 7093 ()
D-7093 ()
Mistabron ()
Coenzyme m sodium salt ()
NSC-113891 ()
Mesna ()
Mesna free acid ()
Mesna ()
P&D ID
PD014327
CAS
19767-45-4
3375-50-6
Tags
available
drug
Approved by
FDA
First approval
1988
Drug Status
approved
investigational
Max Phase
4.0
Drug indication
Detoxifying Agent
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA 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.[A18570] In addition, Mesna binds to and detoxifies a urotoxic ifosfamide metabolite called 4-hydroxy-ifosfamide.
INDICATION Mesna is a uroprotective agent and is used prophylactically to reduce ifosfamide and cyclophosphamide induced hemorrhagic cystitis.[A18572]
DESCRIPTION Mesna is converted to a free thiol compound in the kidney, where it binds to and inactivates acrolein and other urotoxic metabolites of ifosfamide and cyclophosphamide, thereby reducing their toxic effects on the urinary tract during urinary excretion. (BOC Sciences Bioactive Compounds)
Compound Sets
22
Axon Medchem Screening Library
3246
BOC Sciences Bioactive Compounds
mesna-cas-19767-45-4-item-84-62194
Cayman Chemical Bioactives
21238
ChEMBL Approved Drugs
CHEMBL975
CHEMBL1098319
ChEMBL Drugs
CHEMBL975
CHEMBL1098319
Drug Repurposing Hub
DrugBank
DB09110
DrugBank Approved Drugs
DB09110
DrugCentral
1711
DrugCentral Approved Drugs
1711
DrugMatrix
Enamine BioReference Compounds
MedChem Express Bioactive Compound Library
HY-13679
NCATS Inxight Approved Drugs
VHD28S0H7F
NIH Clinical Collections (NCC)
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Mesna(Uromitexan)
TargetMol Bioactive Compound Library
T1414
The Spectrum Collection
External IDs
80
Properties
(calculated by RDKit )
Molecular Weight
141.98
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
2
Ring Count
0
Aromatic Ring Count
0
cLogP
-0.2
TPSA
54.37
Fraction CSP3
1.0
Chiral centers
0.0
Largest ring
0.0
QED
0.41
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Indication
hemorrhagic cystitis
MOA
Antioxidant
Target
Chemoprotective agent
Source data