Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01309)
Name
Oxymetazoline
Synonyms    Click to Show/Hide the Synonyms of This API
oxymetazoline; Oxymethazoline; 1491-59-4; Hazol; Oximetazolinum; Oxylazine; Rhinofrenol; Iliadin; Sinerol; Nafrine; Navisin; Nezeril; Oxymetozoline; Rhinolitan; Oxymetazolinum; Afrin; 6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol; 6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol; 2-(4-tert-Butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline; HSDB 3143; UNII-8VLN5B44ZY; H 990; 6-tert-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol; 3-[(4,5-Dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol; Phenol, 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl-; 8VLN5B44ZY; Phenol, 3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-6-(1,1-dimethylethyl)-2,4-dimethyl-; CHEBI:7862; Navasin; Phenol, 3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl-; Vicks Sinex; NCGC00015766-08; Oximetazolina; oxymeta zoline; Phenol, 6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl-; DSSTox_CID_20691; DSSTox_RID_79545; DSSTox_GSID_40691; Oxymetazoline [INN:BAN]; Oxymetazolinum [INN-Latin]; Oximetazolina [INN-Spanish]; CAS-1491-59-4; Operil (TN); SCH-9384; Oxymetazoline (INN); EINECS 216-079-1; oxymetazoline hydrochloride crystalline; BRN 0886303; oxymetazolina; 1262053-60-0; Nasivine (Salt/Mix); Spectrum_001051; Tocris-1142; 6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol;hydrochloride; Prestwick0_000224; Prestwick1_000224; Prestwick2_000224; Prestwick3_000224; Spectrum2_000998; Spectrum3_000533; Spectrum4_000464; Spectrum5_001114; Lopac-O-2378; Biomol-NT_000161; CHEMBL762; Upneeq (opthalmic solution); Lopac0_000903; SCHEMBL24301; BSPBio_000267; BSPBio_002145; GTPL124; KBioGR_000908; KBioSS_001531; cid_66259; DivK1c_000567; SPBio_001095; SPBio_002188; BPBio1_000295; BPBio1_000419; DTXSID3040691; BDBM30712; KBio1_000567; KBio2_001531; KBio2_004099; KBio2_006667; KBio3_001645; ZINC57435; Oxymetazoline-d4(imidazoline-d4); NINDS_000567; HMS2089G03; Tox21_110217; STK075254; 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-6-tert-butyl-phenol; AKOS007930348; Tox21_110217_1; AC-6370; CAS-151615; CCG-204985; DB00935; MCULE-8690625159; SDCCGSBI-0050878.P005; IDI1_000567; NCGC00015766-01; NCGC00015766-02; NCGC00015766-03; NCGC00015766-04; NCGC00015766-05; NCGC00015766-06; NCGC00015766-07; NCGC00015766-09; NCGC00015766-10; NCGC00015766-11; NCGC00015766-13; NCGC00015766-16; NCGC00015766-21; NCGC00022345-02; NCGC00022345-04; NCGC00022345-05; NCGC00022345-06; SBI-0050878.P004; FT-0601532; H-990; C07363; D08322; AB00053513-12; AB00053513-13; AB00053513_14; AB00053513_15; L000459; Q417813; BRD-K16195444-001-01-7; BRD-K16195444-003-16-1; 6-tert-butyl-3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-2,4-dimethylphenol; 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl-phenol;hydrochloride; 6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol #; 6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-phenol;hydrochloride; Phenol, 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl- (7CI,8CI); Phenol,3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl-; Phenol, 3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl- (9CI)
Clinical Status
Approved
PubChem CID
4636
Formula
C16H24N2O
Canonical SMILES
CC1=CC(=C(C(=C1CC2=NCCN2)C)O)C(C)(C)C
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)
InChIKey
WYWIFABBXFUGLM-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=4636"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 260.37 Topological Polar Surface Area 44.6
XlogP 2.9 Complexity 345
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Oxymetazoline 1% cream Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium Citrate Dihydrate; Citric Acid Anhydrous; Disodium Edetate Dihydrate; Butylated Hydroxytoluene; Anhydrous Lanolin; Medium Chain Triglycerides; Diisopropyl Adipate; Oleyl Alcohol; Polyethylene Glycol 300; Peg-6 Stearate; Glycol Stearate; Peg-32 Stearate; Cetostearyl Alcohol; Ceteareth-6; Stearyl Alcohol; Ceteareth-25; Methylparaben; Propylparaben; Phenoxyethanol; Purified Water
                   Dosage Form Cream
                   Company Epi Hlth
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [1]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [2]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [3]
Oleyl alcohol DIG Info Squalene monooxygenase (IC50 = 4000 nM) [4]
Propylparaben sodium DIG Info Estrogen receptor alpha (EC50 = 38200 nM) [5]
Diisopropyl adipate DIG Info Cholesterol 25-hydroxylase (IC50 = 110000 nM) [6]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [7]
Polyethylene glycol 300 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 54 %) [8]
          Oxymetazoline 0.1% solution Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Calcium Chloride; Hydrochloric Acid; Hypromellose; Magnesium Chloride; Potassium Chloride; Sodium Acetate; Sodium Chloride; Sodium Citrate; Water
                   Dosage Form Solution
                   Company Rvl Pharms
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [9]
Sodium acetate DIG Info Carbonic anhydrase I (Ki = 10800 nM) [10]
Potassium chloride DIG Info Carbonic anhydrase IV (Ki = 90000 nM) [11]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [12]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [13]
          Oxymetazoline 0.1mg/spray spray Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Citric Acid; Sodium Citrate; Hydroxyethylcellulose; Benzylalcohol; Water; Sodium Hydroxide; Hydrochloric Acid
                   Dosage Form Spray
                   Company St Renatus
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [9]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [14]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [3]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [12]
          Oxymetazoline 6mg/spray spray Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Citric Acid; Sodium Citrate; Hydroxyethylcellulose; Benzylalcohol; Water; Sodium Hydroxide; Hydrochloric Acid
                   Dosage Form Spray
                   Company St Renatus
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [9]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [14]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [3]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [12]
References
1 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
2 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
3 PubChem BioAssay data set.
4 Inhibition of vertebrate squalene epoxidase by extended and truncated analogues of trisnorsqualene alcohol. J Med Chem. 1990 Jun; 33(6):1698-701.
5 Discovery of natural estrogen receptor modulators with structure-based virtual screening. Bioorg Med Chem Lett. 2013 Jun 1; 23(11):3329-33.
6 Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2; 48(11):3808-15.
7 Interactions between human multidrug resistance related protein (MRP2; ABCC2) and excipients commonly used in self-emulsifying drug delivery systems (SEDDS). Int J Pharm. 2013 Apr 15;447(1-2):192-8.
8 The effect of polyoxyethylene polymers on the transport of ranitidine in Caco-2 cell monolayers. Int J Pharm. 2011 May 16;409(1-2):164-8.
9 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
10 Carbonic anhydrase inhibitors. Inhibition of the -class enzymes from the fungal pathogens Candida albicans and Cryptococcus neoformans with branched aliphatic/aromatic carboxylates and their derivatives. Bioorg Med Chem Lett. 2011 Apr 15; 21(8):2521-6.
11 Characterization and anions inhibition studies of an -carbonic anhydrase from the teleost fish Dicentrarchus labrax. Bioorg Med Chem. 2011 Jan 15; 19(2):744-8.
12 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
13 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
14 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.

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