Cyclodisone
Basic information
- CAS
99591-73-8- Standard SMILES
O=S1(=O)CS(=O)(=O)OCCO1- InChIKey
RYIRMSRYCSMGJA-UHFFFAOYSA-N- Molecular formula
- C3H6O6S2
- Average molar mass
- 202.2 g/mol
- Monoisotopic mass
- 201.96058025
Overview
Cyclodisone is a cyclic sulfonate ester with potential antineoplastic activity. As an alkylating agent, clyclodisone induces the formation of DNA interstrand crosslinks, DNA strand breaks, and alkali-labile lesions in the DNA of some tumor cell lines. Alkylating agents exert cytotoxic and chemotherapeutic effects by transferring alkyl groups to DNA, thereby damaging DNA and interfering with DNA synthesis and cell division. (NCI04)
Names & identifiers
- Preferred name
- Cyclodisone
- IUPAC
- 1,5,2,4-dioxadithiepane 2,2,4,4-tetraoxide
- English name
- cyclodisone
- Molecular formula
- C3H6O6S2
- Molecular weight
- 202.21
Names & synonyms
Cyclodisone99591-73-8NSC-3489487YFV4WN79INSC 3489481,5,2,4-Dioxadithiepane, 2,2,4,4-tetraoxideNSC3489481,5,2,4-DIOXADITHIEPANE-2,2,4,4-TETRAOXIDEDTXSID80244147RefChem:129444DTXCID801666381,5,2,4-dioxadithiepane 2,2,4,4-tetraoxide
Show more names
NSC-348949
Cyclic-sosoethylene methanedisulfonateUNII-7YFV4WN79ISCHEMBL576075orb2815772CHEMBL1994476NCI60_003099NS00125187
Database identifiers
- CAS
99591-73-8- PubChem CID
- 57513
- DTXSID
DTXSID80244147- ChEMBL
CHEMBL1994476- UNII
- 7YFV4WN79I
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 278
Experimental & physicochemical properties
Solubility
Water < 1 (mg/mL)
Acetate buffer, pH 4 < 1 (mg/mL)
Carbonate buffer, pH 9 < 1 (mg/mL)
0.1 N HCl < 1 (mg/mL)
0.1 N NaOH 10-13 (mg/mL)
Ethanol (95%) < 1 (mg/mL)
Stability/Shelf Life
Bulk: Cyclodisone stored for 90 days at room temperature and at 50 °C under both dark and light conditions was stable (HPLC). Samples stored at 50 °C turned a light tan color. Solution: 180 mg of Cyclodisone was dissolved in 60 mL of DMSO/water (50/50, v/v). Aliquots of this solution (5 mL) were diluted to 10 mL with internal standard solution (5 mL, phenol 1.8 mg/mL in CH3CN/water, 20/80, v /v) and the concentration was determined over a 4 hour period using the HPLC system described below. The t90 was 320 min.
Physicochemical properties
- Density
- 1.693 · 1.693
- FDA UNII
- 7 YFV4WN79I · 7YFV4WN79I
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Related reactions
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Compound notes
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