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Chemistry

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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
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 Weight 317.27 g/mol
Molecular Formula C13H20NO6P
XLogP30.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass317.10282436 g/mol
Monoisotopic Mass317.10282436 g/mol
Topological Polar Surface Area96.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity503
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

ABOUT THIS PAGE

Fosciclopirox Manufacturers

A Fosciclopirox manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Fosciclopirox, including repackagers and relabelers. The FDA regulates Fosciclopirox manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Fosciclopirox API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Fosciclopirox Suppliers

A Fosciclopirox supplier is an individual or a company that provides Fosciclopirox active pharmaceutical ingredient (API) or Fosciclopirox finished formulations upon request. The Fosciclopirox suppliers may include Fosciclopirox API manufacturers, exporters, distributors and traders.

Fosciclopirox GMP

Fosciclopirox Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Fosciclopirox GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Fosciclopirox GMP manufacturer or Fosciclopirox GMP API supplier for your needs.

Fosciclopirox CoA

A Fosciclopirox CoA (Certificate of Analysis) is a formal document that attests to Fosciclopirox's compliance with Fosciclopirox specifications and serves as a tool for batch-level quality control.

Fosciclopirox CoA mostly includes findings from lab analyses of a specific batch. For each Fosciclopirox CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Fosciclopirox may be tested according to a variety of international standards, such as European Pharmacopoeia (Fosciclopirox EP), Fosciclopirox JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Fosciclopirox USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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