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Also known as: Obi-3424, X6sh5t8h76, Th-3424, 2097713-68-1, 3-(5-((1r)-1-(bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-n,n-dimethylbenzamide, Unii-x6sh5t8h76

Molecular Formula

C₂₁H₂₅N₄O₆P

Molecular Weight

460.4 g/mol

InChI Key

NWGZZGNICQFUHV-OAHLLOKOSA-N

FDA UNII

X6SH5T8H76

AKR1C3-activated Prodrug OBI-3424 is 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, AKR1C3-activated prodrug OBI-3424 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, OBI-3424 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.

1 2D Structure

OBI-3424

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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-/m1/s1

2.1.3 InChI Key

NWGZZGNICQFUHV-OAHLLOKOSA-N

2.1.4 Canonical SMILES

CC(C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

X6SH5T8H76

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Obi-3424

2. X6sh5t8h76

3. Th-3424

4. 2097713-68-1

5. 3-(5-((1r)-1-(bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-n,n-dimethylbenzamide

6. Unii-x6sh5t8h76

7. Chembl4297474

8. Schembl20870529

9. Obi3424

10. Obi-3424 [who-dd]

11. Hy-124573

12. Cs-0086947

2.4 Create Date

2017-05-06

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅N₄O₆P
Molecular Weight	460.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	8
Exact Mass	460.15117153 g/mol
Monoisotopic Mass	460.15117153 g/mol
Topological Polar Surface Area	108 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	737
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1