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Also known as: Tp-1287, 2044686-42-0, 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5-hydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-7-(phosphonooxy)-, Alvocidib phosphate, Unii-7mpp85iij3, Alvocidib prodrug tp-1287

Molecular Formula

C₂₁H₂₁ClNO₈P

Molecular Weight

481.8 g/mol

InChI Key

YRNFLVUMZIRYKY-BLLLJJGKSA-N

FDA UNII

7MPP85IIJ3

Alvocidib Prodrug TP-1287 is an orally bioavailable, highly soluble phosphate prodrug of alvocidib, a potent inhibitor of cyclin-dependent kinase-9 (CDK9), with potential antineoplastic activity. Upon administration of the phosphate prodrug TP-1287, the prodrug is enzymatically cleaved at the tumor site and the active moiety alvocidib is released. Alvocidib targets and binds to CDK9, thereby reducing the expression of CDK9 target genes such as the anti-apoptotic protein MCL-1, and inducing G1 cell cycle arrest and apoptosis in CDK9-overexpressing cancer cells.

1 2D Structure

TP-1287

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-(2-chlorophenyl)-5-hydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl] dihydrogen phosphate

2.1.2 InChI

InChI=1S/C21H21ClNO8P/c1-23-7-6-12(16(26)10-23)19-18(31-32(27,28)29)9-15(25)20-14(24)8-17(30-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,16,25-26H,6-7,10H2,1H3,(H2,27,28,29)/t12-,16+/m0/s1

2.1.3 InChI Key

YRNFLVUMZIRYKY-BLLLJJGKSA-N

2.1.4 Canonical SMILES

CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)OP(=O)(O)O

2.1.5 Isomeric SMILES

CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)OP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

7MPP85IIJ3

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Tp-1287

2. 2044686-42-0

3. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5-hydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-7-(phosphonooxy)-

4. Alvocidib Phosphate

5. Unii-7mpp85iij3

6. Alvocidib Prodrug Tp-1287

7. Chembl4594423

8. Schembl18251861

9. Tp-1287 [who-dd]

10. Bdbm50553482

11. Tp1287

2.4 Create Date

2017-02-18

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₁ClNO₈P
Molecular Weight	481.8 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	4
Exact Mass	481.0693313 g/mol
Monoisotopic Mass	481.0693313 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	790
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1