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etilefrine   Click here for help

GtoPdb Ligand ID: 14324

Synonyms: Effortil® | ethylnorphenylephrine | ethylphenephrine
Approved drug
etilefrine is an approved drug
Compound class: Synthetic organic
Comment: Etilefrine is a sympathomimetic, non-selective α1-adrenoceptor agonist [2,4,7].
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 3
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 52.49
Molecular weight 181.23
XLogP 0.02
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 CCNCC(C1=CC=CC(=C1)O)O
Isomeric SMILES CCNCC(C1=CC(=CC=C1)O)O
InChI InChI=1S/C10H15NO2/c1-2-11-7-10(13)8-4-3-5-9(12)6-8/h3-6,10-13H,2,7H2,1H3
InChI Key SQVIAVUSQAWMKL-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/)
References
1. Chinegwundoh FI, Smith S, Anie KA. (2017)
Treatments for priapism in boys and men with sickle cell disease.
Cochrane Database Syst Rev, 9 (9): CD004198. [PMID:28926088]
2. Coleman AJ, Leary WP, Asmal AC. (1975)
The cardiovascular effects of etilefrine.
Eur J Clin Pharmacol, 8 (1): 41-5. [PMID:9293]
3. Drugs,com. 
Etilefrine (International).
Accessed on 14/01/2026. Modified on 14/01/2026. www.drugs.com, https://www.drugs.com/international/etilefrine.html
4. Frost BR, Frewin DB, Gerke DC. (1977)
The effects of etilefrine on blood vessels in the rat tail.
J Pharm Pharmacol, 29 (5): 272-5. [PMID:17689]
5. Miller E, Wiener L, Bloomfield D. (1973)
Etilefrine in the treatment of levodopa-induced orthostatic hypotension.
Arch Neurol, 29 (2): 99-103. [PMID:4577820]
6. Radwan H, Ibrahim O, Badra G, El-Said H, El-Haggar S. (2022)
Effects of adding hypertonic saline solutions and/or etilefrine to standard diuretics therapy in cirrhotic patients with ascites.
Eur Rev Med Pharmacol Sci, 26 (18): 6608-6619. [PMID:36196711]
7. Skylynn T, Abel T, Christopher L, Suliman G, Dominic R, Joel V, Yu Z, Pemminati S. (2024)
Benefits and Risks of Medications Used in the Management of Hypotension: A Review.
Cureus, 16 (1): e51608. [PMID:38313995]
8. Thulesius O, Gjöres JE, Berlin E. (1979)
Vasoconstrictor effect of midodrine, ST 1059, noradrenaline, etilefrine and dihydroergotamine on isolated human veins.
Eur J Clin Pharmacol, 16 (6): 423-4. [PMID:93544]