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Dimesna

CAT: 0013-GTR19162961-01Size: 1 gDry Ice: NoHazardous: No
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CAT#:0013-GTR19162961-01Size:1 g
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Description
Dimesna is an uroprotective agent used to decrease urotoxicity.
CAS Number
16208-51-8
Product Name Alternative
Mesna disulfide. US brand name: Tavocept. Abbreviation: DIM. Code name: BNP7787
Purity
>98% (HPLC)
Solubility
Water: 65 mg/mL (199.17 mM) ; DMSO: 65 mg/mL (199.17 mM)
Smiles
O=S (CCSSCCS (=O) ([O-]) =O) ([O-]) =O.[Na+].[Na+]
Molecular Formula
C4H8Na2O6S4
Molecular Weight
326.34
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
Sodium 2,2'-disulfanediyldiethanesulfonate

Chemical Information

Dimesna

Dimesna is the disodium salt form of dithio-ethane sulfonate, a dimer of mesna and a disulfide bond disrupting agent (DDA), with uroprotective, nephroprotective, chemoprotective, chemosensitizing and chemo-enhancing activities. Upon administration, dimesna is able to modify cysteine on various proteins, such as the kinases EGFR, MET and ROS1, thereby disrupting extracellular disulfide bonds and modulating the activity of these proteins. This inhibits their signaling pathways and downregulates proliferative signaling in cancer cells in which these kinases are overexpressed. This may also enhance the activity of other kinase inhibitors targeting the same proteins. In the kidneys, dimesna undergoes reduction to the free thiol compound, mesna, which reacts chemically with the urotoxic ifosfamide metabolites acrolein and 4-hydroxy-ifosfamide, resulting in their detoxification. This agent also inhibits cyclophosphamide-induced hemorrhagic cystitis. In addition, dimesna reduces toxicities associated with taxanes and platinum-based chemotherapeutic agents.

CAS Number16208-51-8
PubChem CID65625
IUPAC Namedisodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate
Molecular FormulaC4H8Na2O6S4
Molecular Weight326.4
Topological Polar Surface Area182
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Heavy Atom Count16
Formal Charge0
Complexity268
SMILES
C(CS(=O)(=O)[O-])SSCCS(=O)(=O)[O-].[Na+].[Na+]
InChI
InChI=1S/C4H10O6S4.2Na/c5-13(6,7)3-1-11-12-2-4-14(8,9)10;;/h1-4H2,(H,5,6,7)(H,8,9,10);;/q;2*+1/p-2
InChIKey
KQYGMURBTJPBPQ-UHFFFAOYSA-L
Chemical Structure
2D Structure
2D structure of Dimesna
CAS: 16208-51-8
CID: 65625
Formula: C4H8Na2O6S4
MW: 326.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight326.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass325.89991123
Monoisotopic Mass325.89991123
Topological Polar Surface Area182 Ų
Heavy Atom Count16
Formal Charge0
Complexity268
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BUP16907-01Dimesna

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