oxymetazoline   Click here for help

GtoPdb Ligand ID: 124

Synonyms: Afrin® | oxymethazoline | SCH-9384 | Upneeq® (opthalmic solution) | Vicks Sinex®
Approved drug PDB Ligand
oxymetazoline is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Oxymetazoline is a selective α1-adrenoceptor agonist and α2-adrenoceptor partial agonist with vasoconstricting properties.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
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 2
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 44.62
Molecular weight 260.19
XLogP 3.36
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 Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C
Isomeric SMILES Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C
InChI InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
InChI Key WYWIFABBXFUGLM-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. da Silva Junior ED, Sato M, Merlin J, Broxton N, Hutchinson DS, Ventura S, Evans BA, Summers RJ. (2017)
Factors influencing biased agonism in recombinant cells expressing the human α1A -adrenoceptor.
Br J Pharmacol, 174 (14): 2318-2333. [PMID:28444738]
2. Evans BA, Broxton N, Merlin J, Sato M, Hutchinson DS, Christopoulos A, Summers RJ. (2011)
Quantification of functional selectivity at the human α(1A)-adrenoceptor.
Mol Pharmacol, 79 (2): 298-307. [PMID:20978120]
3. Fitzgerald LW, Conklin DS, Krause CM, Marshall AP, Patterson JP, Tran DP, Iyer G, Kostich WA, Largent BL, Hartig PR. (1999)
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.
J Neurochem, 72 (5): 2127-34. [PMID:10217294]
4. Horie K, Obika K, Foglar R, Tsujimoto G. (1995)
Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes.
Br J Pharmacol, 116 (1): 1611-8. [PMID:8564227]
5. Jasper JR, Lesnick JD, Chang LK, Yamanishi SS, Chang TK, Hsu SA, Daunt DA, Bonhaus DW, Eglen RM. (1998)
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.
Biochem Pharmacol, 55 (7): 1035-43. [PMID:9605427]
6. Kurko D, Kapui Z, Nagy J, Lendvai B, Kolok S. (2014)
Analysis of functional selectivity through G protein-dependent and -independent signaling pathways at the adrenergic α(2C) receptor.
Brain Res Bull, 107: 89-101. [PMID:25080296]
7. Law H, Dukat M, Teitler M, Lee DK, Mazzocco L, Kamboj R, Rampersad V, Prisinzano T, Glennon RA. (1998)
Benzylimidazolines as h5-HT1B/1D serotonin receptor ligands: a structure-affinity investigation.
J Med Chem, 41 (13): 2243-51. [PMID:9632357]
8. MacDonald E, Kobilka BK, Scheinin M. (1997)
Gene targeting--homing in on alpha 2-adrenoceptor-subtype function.
Trends Pharmacol Sci, 18 (6): 211-9. [PMID:9227000]
9. Minneman KP, Theroux TL, Hollinger S, Han C, Esbenshade TA. (1994)
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
Mol Pharmacol, 46 (5): 929-36. [PMID:7969082]
10. Obika K, Shibata K, Horie K, Foglar R, Kimura K, Tsujimoto G. (1995)
NS-49, a novel alpha 1a-adrenoceptor-selective agonist characterization using recombinant human alpha 1-adrenoceptors.
Eur J Pharmacol, 291 (3): 327-34. [PMID:8719417]
11. Proudman RGW, Akinaga J, Baker JG. (2022)
The signaling and selectivity of α-adrenoceptor agonists for the human α2A, α2B and α2C-adrenoceptors and comparison with human α1 and β-adrenoceptors.
Pharmacol Res Perspect, 10 (5): e01003. [PMID:36101495]
12. Proudman RGW, Baker JG. (2021)
The selectivity of α-adrenoceptor agonists for the human α1A, α1B, and α1D-adrenoceptors.
Pharmacol Res Perspect, 9 (4): e00799. [PMID:34355529]
13. Schwinn DA, Johnston GI, Page SO, Mosley MJ, Wilson KH, Worman NP, Campbell S, Fidock MD, Furness LM, Parry-Smith DJ et al.. (1995)
Cloning and pharmacological characterization of human alpha-1 adrenergic receptors: sequence corrections and direct comparison with other species homologues.
J Pharmacol Exp Ther, 272 (1): 134-42. [PMID:7815325]
14. Shibata K, Foglar R, Horie K, Obika K, Sakamoto A, Ogawa S, Tsujimoto G. (1995)
KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues.
Mol Pharmacol, 48 (2): 250-8. [PMID:7651358]
15. Taniguchi T, Inagaki R, Murata S, Akiba I, Muramatsu I. (1999)
Microphysiometric analysis of human alpha1a-adrenoceptor expressed in Chinese hamster ovary cells.
Br J Pharmacol, 127 (4): 962-8. [PMID:10433504]
16. Uhlén S, Porter AC, Neubig RR. (1994)
The novel alpha-2 adrenergic radioligand [3H]-MK912 is alpha-2C selective among human alpha-2A, alpha-2B and alpha-2C adrenoceptors.
J Pharmacol Exp Ther, 271 (3): 1558-65. [PMID:7996470]