remifentanil   Click here for help

GtoPdb Ligand ID: 7292

Synonyms: GI-87084B | Ultiva®
Approved drug
remifentanil is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Remifentanil is a synthetic opioid analgesic drug.
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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 7
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 76.15
Molecular weight 376.2
XLogP 1.38
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 COC(=O)C1(CCN(CC1)CCC(=O)OC)N(c1ccccc1)C(=O)CC
Isomeric SMILES COC(=O)C1(CCN(CC1)CCC(=O)OC)N(c1ccccc1)C(=O)CC
InChI InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3
InChI Key ZTVQQQVZCWLTDF-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 (FDA (1996))
IUPAC Name Click here for help
methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
International Nonproprietary Names Click here for help
INN number INN
6924 remifentanil
Synonyms Click here for help
GI-87084B | Ultiva®
Database Links Click here for help
CAS Registry No. 132875-61-7
ChEMBL Ligand CHEMBL1005
DrugBank Ligand DB00899
DrugCentral Ligand 2363
GtoPdb PubChem SID 178103866
PubChem CID 60815
Search Google for chemical match using the InChIKey ZTVQQQVZCWLTDF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZTVQQQVZCWLTDF
Search PubMed clinical trials remifentanil
Search PubMed titles remifentanil
Search PubMed titles/abstracts remifentanil
UniChem Compound Search for chemical match using the InChIKey ZTVQQQVZCWLTDF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZTVQQQVZCWLTDF-UHFFFAOYSA-N
Wikipedia Remifentanil