avanafil   Click here for help

GtoPdb Ligand ID: 7448

Synonyms: Spedra® | Stendra® | TA-1790
Approved drug PDB Ligand
avanafil is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Avanafil is a phosphodiesterase type 5 inhibitor.
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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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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 9
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 125.39
Molecular weight 483.18
XLogP 2.58
No. Lipinski's rules broken 0

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 OCC1CCCN1c1ncc(c(n1)NCc1ccc(c(c1)Cl)OC)C(=O)NCc1ncccn1
Isomeric SMILES OC[C@@H]1CCCN1c1ncc(c(n1)NCc1ccc(c(c1)Cl)OC)C(=O)NCc1ncccn1
InChI InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
InChI Key WEAJZXNPAWBCOA-INIZCTEOSA-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. FDA (2012)  |  EMA (2013)
IUPAC Name Click here for help
4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
International Nonproprietary Names Click here for help
INN number INN
8572 avanafil
Synonyms Click here for help
Spedra® | Stendra® | TA-1790
Database Links Click here for help
CAS Registry No. 330784-47-9
ChEBI CHEBI:66876
ChEMBL Ligand CHEMBL1963681
DrugBank Ligand DB06237
DrugCentral Ligand 4305
GtoPdb PubChem SID 178104020
PubChem CID 9869929
RCSB PDB Ligand E6L
Search Google for chemical match using the InChIKey WEAJZXNPAWBCOA-INIZCTEOSA-N
Search Google for chemicals with the same backbone WEAJZXNPAWBCOA
Search PubMed clinical trials avanafil
Search PubMed titles avanafil
Search PubMed titles/abstracts avanafil
UniChem Compound Search for chemical match using the InChIKey WEAJZXNPAWBCOA-INIZCTEOSA-N
UniChem Connectivity Search for chemical match using the InChIKey WEAJZXNPAWBCOA-INIZCTEOSA-N
Wikipedia Avanafil

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MedChemExpress
Avanafil (links to external site)
Cat. No. HY-18252