posaconazole   Click here for help

GtoPdb Ligand ID: 11428

Synonyms: Noxafil® | SCH-56592 | SCH56592 | Schering 56592
Approved drug PDB Ligand
posaconazole is an approved drug (EMA (2005), FDA (2006))
Compound class: Synthetic organic
Comment: Posaconazole is a broad-spectrum, second generation, antifungal drug. It inhibits the fungal lanosterol 14α-demethylase, which reduces production of ergosterol (an important component of the fungal cell wall).

posaconazole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 115.18
Molecular weight 700.33
XLogP 5.72
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC[C@H](n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@@H]1CO[C@@](C1)(Cn1cncn1)c1ccc(cc1F)F)[C@@H](O)C
Isomeric SMILES CC[C@H](n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@@H]1CO[C@@](C1)(Cn1cncn1)c1ccc(cc1F)F)[C@@H](O)C
InChI InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1
InChI Key RAGOYPUPXAKGKH-XAKZXMRKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EMA (2005)  |  FDA (2006)
IUPAC Name Click here for help
4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypentan-3-yl]-1,2,4-triazol-3-one
International Nonproprietary Names Click here for help
INN number INN
7713 posaconazole
Synonyms Click here for help
Noxafil® | SCH-56592 | SCH56592 | Schering 56592
Database Links Click here for help
BindingDB Ligand 50181473
CAS Registry No. 171228-49-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL1397
DrugBank Ligand DB01263
GtoPdb PubChem SID 440816797
PubChem CID 468595
RCSB PDB Ligand X2N
Search Google for chemical match using the InChIKey RAGOYPUPXAKGKH-XAKZXMRKSA-N
Search Google for chemicals with the same backbone RAGOYPUPXAKGKH
Search PubMed clinical trials posaconazole
Search PubMed titles posaconazole
Search PubMed titles/abstracts posaconazole
UniChem Compound Search for chemical match using the InChIKey RAGOYPUPXAKGKH-XAKZXMRKSA-N
UniChem Connectivity Search for chemical match using the InChIKey RAGOYPUPXAKGKH-XAKZXMRKSA-N

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MedChemExpress
Posaconazole (links to external site)
Cat. No. HY-17373
Posaconazole (Standard) (links to external site)
Cat. No. HY-17373R