raltegravir   Click here for help

GtoPdb Ligand ID: 11571

Synonyms: Isentress® | MK-0518 | MK0518
Approved drug PDB Ligand
raltegravir is an approved drug (EMA & FDA (2007))
Compound class: Synthetic organic
Comment: Raltegravir (MK-0518) is an HIV integrase inhibitor (integrase strand transfer inhibitor) [1].
2D Structure
Click here for help

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.

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

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.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 152.24
Molecular weight 444.16
XLogP 3.73
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
Click here for help

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/)

✖
Canonical SMILES Fc1ccc(cc1)CNC(=O)c1nc(n(c(=O)c1O)C)C(NC(=O)c1nnc(o1)C)(C)C
Isomeric SMILES Fc1ccc(cc1)CNC(=O)c1nc(n(c(=O)c1O)C)C(NC(=O)c1nnc(o1)C)(C)C
InChI InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)
InChI Key CZFFBEXEKNGXKS-UHFFFAOYSA-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 & FDA (2007))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
International Nonproprietary Names Click here for help
INN number INN
8842 raltegravir
Synonyms Click here for help
Isentress® | MK-0518 | MK0518
Database Links Click here for help
BindingDB Ligand 25351
CAS Registry No. 518048-05-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL254316
DrugBank Ligand DB06817
GtoPdb PubChem SID 441604943
PubChem CID 54671008
RCSB PDB Ligand RLT
Search Google for chemical match using the InChIKey CZFFBEXEKNGXKS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CZFFBEXEKNGXKS
Search PubMed clinical trials raltegravir
Search PubMed titles raltegravir
Search PubMed titles/abstracts raltegravir
UniChem Compound Search for chemical match using the InChIKey CZFFBEXEKNGXKS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CZFFBEXEKNGXKS-UHFFFAOYSA-N