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Glufosfamide

CAT: 0804-HY-16232-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-16232-02Size:10 mM - 1 mL
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Description
Glufosfamide is a glucose-conjugated alkylating cytotoxic agent and a derivative of Ifosfamide. Glufosfamide induces apoptosis frequency and increase the expression of caspase-9 and caspase-3 in cancer cells. Glufosfamide shows great anti-tumor activity in MiaPaCa-2-RFP mouse model. Glufosfamide can be used for the study of hepatocellular carcinoma, prostate cancer and pancreatic carcinoma[1][2][3].
CAS Number
132682-98-5
Product Name Alternative
D 19575; Glucosylifosfamide mustard
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Bcl-2 Family; Caspase
Type
Reference compound
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/GLUFOSFAMIDE.html
Purity
98.0
Solubility
H2O : 125 mg/mL (ultrasonic)
Smiles
O[C@@H]1[C@@H](O)[C@H](OP(NCCCl)(NCCCl)=O)O[C@H](CO)[C@H]1O
Molecular Formula
C10H21Cl2N2O7P
Molecular Weight
383.16
Precautions
H302, H315, H319, H335
References & Citations
[1]Ahmed DE, et al. An in vitro cytotoxicity of glufosfamide in HepG2 cells relative to its nonconjugated counterpart. J Egypt Natl Canc Inst. 2021 Aug 23;33 (1) :22. |[2]Ammons WS, et al. A novel alkylating agent, glufosfamide, enhances the activity of gemcitabine in vitro and in vivo. Neoplasia. 2007 Aug;9 (8) :625-33. |[3]Attia RT, et al. The chemomodulatory effects of glufosfamide on docetaxel cytotoxicity in prostate cancer cells. PeerJ. 2016 Jun 29;4:e2168.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 3

Chemical Information

Glufosfamide

Glufosfamide is a compound consisting of the mustard agent ifosforamide conjugated to glucose, with potential alkylating activity. Glufosfamide is cleaved by glucosidases in tumor cells and forms ifosforamide. In turn, ifosforamide alkylates and forms DNA crosslinks, thereby inhibiting DNA replication and subsequent cell growth. The glucose moiety may enhance this agent's uptake by tumor cells.

CAS Number132682-98-5
PubChem CID123628
IUPAC Name(2S,3R,4S,5S,6R)-2-bis(2-chloroethylamino)phosphoryloxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC10H21Cl2N2O7P
Molecular Weight383.16
XLogP-2
Topological Polar Surface Area141
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count9
Heavy Atom Count22
Formal Charge0
Complexity369
SMILES
C(CCl)NP(=O)(NCCCl)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChI
InChI=1S/C10H21Cl2N2O7P/c11-1-3-13-22(19,14-4-2-12)21-10-9(18)8(17)7(16)6(5-15)20-10/h6-10,15-18H,1-5H2,(H2,13,14,19)/t6-,7-,8+,9-,10+/m1/s1
InChIKey
PSVUJBVBCOISSP-SPFKKGSWSA-N
Chemical Structure
2D Structure
2D structure of Glufosfamide
CAS: 132682-98-5
CID: 123628
Formula: C10H21Cl2N2O7P
MW: 383.16
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight383.16
XLogP3-2
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count9
Exact Mass382.0463434
Monoisotopic Mass382.0463434
Topological Polar Surface Area141 Ų
Heavy Atom Count22
Formal Charge0
Complexity369
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
sc-506131Glufosfamide
A20874-1GLUFOSFAMIDE 1mg
A20874-50GLUFOSFAMIDE 50mg
A20874-10GLUFOSFAMIDE 10mg
A20874-5GLUFOSFAMIDE 5mg
A20874-100GLUFOSFAMIDE 100mg
A20874-25GLUFOSFAMIDE 25mg

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