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2 Drugs in Development

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Also known as: Ciclopirox-pom, Fosciclopirox [inn], 1380539-06-9, G8fr269qpq, 2(1h)-pyridinone, 6-cyclohexyl-4-methyl-1-((phosphonooxy)methoxy)-, 6-cyclohexyl-4-methyl-1-((phosphonooxy)methoxy)-2(1h)-pyridinone

Molecular Formula

C₁₃H₂₀NO₆P

Molecular Weight

317.27 g/mol

InChI Key

NTKBXPWLNROYPE-UHFFFAOYSA-N

FDA UNII

G8FR269QPQ

Fosciclopirox is a phosphoryloxymethyl (POM) ester-based prodrug of ciclopirox (CPX), a synthetic, broad-spectrum antifungal agent with antibacterial, anti-inflammatory and potential antineoplastic activities. Upon intravenous administration of fosciclopirox, the POM moiety is cleaved off by phosphatases and the active metabolite CPX is released. Although its exact anticancer mechanism is not yet fully elucidated, CPX has been shown to inhibit tumor cell proliferation, induce apoptosis, and reduce tumor cell mobility in certain cancer types. CPX inhibits Notch1 activation and inhibits the Notch1-mediated signaling pathway, which is upregulated in many cancer cell types. This inhibits Notch downstream target proteins, inhibits the expression of gamma-secretase complex proteins, and prevents proliferation in susceptible cancer cells. CPX inhibits the iron-containing enzymes, catalase and peroxidase, which facilitate the decomposition of hydrogen peroxide, a reactive oxygen species (ROS) involved in oxidative stress. CPX also inhibits the iron-dependent enzyme ribonucleotide reductase, which is essential in DNA synthesis. CPX downregulates protein expression of cyclin D1 and cyclin E1, as well as their enzymatic counterparts cyclin-dependent kinases 4 and 2 (CDK4 and CDK2), which may inhibit tumor cell proliferation by slowing cell cycle progression from G1/G0 to S phase. Further, CPX may induce apoptosis by downregulating the expression of anti-apoptotic proteins, Bcl-xL and survivin, and increasing cleavage of Bcl-2. Additionally, CPX may inhibit tumor cell proliferation, survival and motility by inhibiting the phosphorylation of p70 S6 kinase 1 (S6K1) and eukaryotic initiation factor 4E binding protein 1 (4E-BP1), two downstream effector molecules of the mammalian target of rapamycin complex 1 (mTORC1). The CPX-POM prodrug improves the solubility of CPX and increases systemic efficacy.

1 2D Structure

Fosciclopirox

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2-cyclohexyl-4-methyl-6-oxopyridin-1-yl)oxymethyl dihydrogen phosphate

2.1.2 InChI

InChI=1S/C13H20NO6P/c1-10-7-12(11-5-3-2-4-6-11)14(13(15)8-10)19-9-20-21(16,17)18/h7-8,11H,2-6,9H2,1H3,(H2,16,17,18)

2.1.3 InChI Key

NTKBXPWLNROYPE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=O)N(C(=C1)C2CCCCC2)OCOP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

G8FR269QPQ

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Ciclopirox-pom

2. Fosciclopirox [inn]

3. 1380539-06-9

4. G8fr269qpq

5. 2(1h)-pyridinone, 6-cyclohexyl-4-methyl-1-((phosphonooxy)methoxy)-

6. 6-cyclohexyl-4-methyl-1-((phosphonooxy)methoxy)-2(1h)-pyridinone

7. (2-cyclohexyl-4-methyl-6-oxopyridin-1-yl)oxymethyl Dihydrogen Phosphate

8. ((6-cyclohexyl-4-methyl-2-oxopyridin-1(2h)-yl)oxy)methyl Dihydrogen Phosphate

9. Unii-g8fr269qpq

10. Fosciclopirox [who-dd]

11. Schembl9103427

12. Chembl4802149

13. Ex-a5502

14. Hy-109174

15. Cs-0116368

2.4 Create Date

2012-11-30

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₂₀NO₆P
Molecular Weight	317.27 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	317.10282436 g/mol
Monoisotopic Mass	317.10282436 g/mol
Topological Polar Surface Area	96.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	503
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1