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Odafosfamide

CAT: 0931-T211703-02Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0931-T211703-02Size:50 mg
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CAS Number
2097713-69-2
Target
Dehydrogenase
Related Pathways
Metabolism
Bioactivity
Odafosfamide ((S) -OBI-3424) is a highly selective prodrug bi-alkylating agent activated by aldo-keto reductase 1C3 (AKR1C3) . It exhibits potent cytotoxicity in cell lines with high AKR1C3 expression. Odafosfamide demonstrates antitumor activity in various tumors with elevated AKR1C3 expression, such as liver cancer, non-small cell lung cancer, and leukemia. It is applicable for cancer research.
Smiles
P(O[C@@H](C)C1=CC(OC2=CC(C(N(C)C)=O)=CC=C2)=C(N(=O)=O)C=C1)(=O)(N3CC3)N4CC4
Molecular Formula
C21H25N4O6P
Molecular Weight
460.42
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

3-[5-[(1S)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide

Odafosfamide is the S-isoform of odafosfamide, a small-molecule nitro-benzene, aldo-keto reductase 1C3 (AKR1C3)-activated prodrug of N,N'-bisethylenephosphoramidate, a DNA bis-alkylating agent, with potential antineoplastic activity. Upon intravenous administration, odafosfamide is converted to its active form by AKR1C3, which is upregulated in certain tumor cell types while not expressed in normal healthy cells. The active metabolite selectively binds to and alkylates DNA in AKR1C3-overexpressing tumor cells, resulting in DNA base pair mismatching, interstrand crosslinking and inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis. As the expression of AKR1C3 is restricted to tumors, Odafosfamide is selectively converted to its active metabolite in tumor cells only while its conversion in normal, healthy tissue is absent; this allows for an increased cytotoxic effect of the alkylating agent in tumor cells while decreasing its toxicity.

CAS Number2097713-69-2
PubChem CID134817236
IUPAC Name3-[5-[(1S)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
Molecular FormulaC21H25N4O6P
Molecular Weight460.4
XLogP2.2
Topological Polar Surface Area108
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Heavy Atom Count32
Formal Charge0
Complexity737
SMILES
C[C@@H](C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
InChI
InChI=1S/C21H25N4O6P/c1-15(31-32(29,23-9-10-23)24-11-12-24)16-7-8-19(25(27)28)20(14-16)30-18-6-4-5-17(13-18)21(26)22(2)3/h4-8,13-15H,9-12H2,1-3H3/t15-/m0/s1
InChIKey
NWGZZGNICQFUHV-HNNXBMFYSA-N
Chemical Structure
2D Structure
2D structure of 3-[5-[(1S)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
CAS: 2097713-69-2
CID: 134817236
Formula: C21H25N4O6P
MW: 460.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight460.4
XLogP32.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass460.15117153
Monoisotopic Mass460.15117153
Topological Polar Surface Area108 Ų
Heavy Atom Count32
Formal Charge0
Complexity737
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
GTR19264050-01Odafosfamide
HY-124573-01(R) -Odafosfamide

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