Identification
- Generic Name
- Amiloxate
- DrugBank Accession Number
- DB11207
- Background
Amiloxate is an EMA-approved chemical UV-filter found in over-the-counter sunscreen products at concentrations up to 10%m 3. It is often referred to as isoamyl 4-methoxycinnamate or isoamyl p-methoxycinnamate. Amiloxate is a cinnamic acid derivative with an anti-inflammatory activity 1.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Amiloxate (DB11207)
- Weight
- Average: 248.322
Monoisotopic: 248.141244504 - Chemical Formula
- C15H20O3
- Synonyms
- 3-(4-Methoxyphenyl)-2-propenoic acid, 3-methylbutyl ester
- Amiloxate
- Isoamyl p-methoxycinnamate
- Isoamyl-p-methoxycinnamate
- External IDs
- E-1000
- NSC-408332
Pharmacology
- Indication
Indicated as an active sunscreen agent.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for prophylaxis of Sunburn ••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
In a mouse study, amiloxate exerted a dose-dependent anti-inflammatory action and inhibited edema by about 70% even at a low dose 1. Due to structural similarities, amiloxate may also display antioxidant and antimicrobial properties of cinnamic acid 2.
- Mechanism of action
Amiloxate is a UV-B filter that selectively absorbs UV-B rays 3. It is proposed that amiloxate mediates an antioxidant action by acting as a free radical scavenger 2.
- Absorption
According to in vitro studies of amiloxate-containing tape strips on porcine ear, there was no detection of amiloxate undergoing skin penetration 3.
- Volume of distribution
No pharmacokinetic data available.
- Protein binding
No pharmacokinetic data available.
- Metabolism
No pharmacokinetic data available.
- Route of elimination
No pharmacokinetic data available.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral LD50 in rat is 9600 mg/kg MSDS.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image a.c. care Bees Sun Protection Amiloxate (1.40000 g/70g) + Bemotrizinol (2.10000 g/70g) + Octinoxate (5.25000 g/70g) + Titanium dioxide (0.79100 g/70g) + Zinc oxide (1.75000 g/70g) Cream Topical Dong Sung Pharm. Co., Ltd. 2014-08-20 2015-11-30 US 
a.c.care Bees Sun Protection UV Moisturizer SPF 50 Amiloxate (1.40000 g/70g) + Bemotrizinol (2.10000 g/70g) + Octinoxate (5.25000 g/70g) + Titanium dioxide (0.79100 g/70g) + Zinc oxide (1.75000 g/70g) Cream Topical Dong Sung Pharm. Co., Ltd. 2011-12-20 2014-08-01 US Carecella Sun Cream Amiloxate (7.49 g/100mL) + Octyl triazone (4.5 g/100mL) Cream Topical General Bio Co., Ltd. 2023-07-19 Not applicable US Cathycat Essence Sun Bb Amiloxate (1 mL/100mL) + Octinoxate (7 mL/100mL) + Titanium dioxide (13.76176 mL/100mL) + Zinc oxide (3.92 mL/100mL) Liquid Topical Lg Household & Health Care Ltd. 2011-04-15 Not applicable US Daily Defense Sunblock Amiloxate (2 g/100mL) + Avobenzone (0.5 g/100mL) + Enzacamene (3 g/100mL) + Octinoxate (7.5 g/100mL) + Titanium dioxide (2 g/100mL) + Zinc oxide (5 g/100mL) Cream Topical Humex,Inc. 2013-04-22 2014-01-01 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Carecella Sun Cream Amiloxate (7.49 g/100mL) + Octyl triazone (4.5 g/100mL) Cream Topical General Bio Co., Ltd. 2023-07-19 Not applicable US Laser Block 100 sunblock Amiloxate (0.02 mL/1mL) + Avobenzone (0.005 mL/1mL) + Enzacamene (0.03 mL/1mL) + Octinoxate (0.07 mL/1mL) + Titanium dioxide (0.02 mL/1mL) + Zinc oxide (0.05 mL/1mL) Cream Topical Universal Cosmetic Co., Ltd 2010-08-04 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Cinnamic acids and derivatives
- Sub Class
- Cinnamic acid esters
- Direct Parent
- Cinnamic acid esters
- Alternative Parents
- Styrenes / Phenoxy compounds / Methoxybenzenes / Anisoles / Fatty acid esters / Alkyl aryl ethers / Enoate esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Alkyl aryl ether / Alpha,beta-unsaturated carboxylic ester / Anisole / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cinnamic acid ester / Enoate ester show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 376KTP06K8
- CAS number
- 71617-10-2
- InChI Key
- UBNYRXMKIIGMKK-RMKNXTFCSA-N
- InChI
- InChI=1S/C15H20O3/c1-12(2)10-11-18-15(16)9-6-13-4-7-14(17-3)8-5-13/h4-9,12H,10-11H2,1-3H3/b9-6+
- IUPAC Name
- 3-methylbutyl (2E)-3-(4-methoxyphenyl)prop-2-enoate
- SMILES
- COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1
References
- General References
- Couteau C, Chauvet C, Paparis E, Coiffard L: UV filters, ingredients with a recognized anti-inflammatory effect. PLoS One. 2012;7(12):e46187. doi: 10.1371/journal.pone.0046187. Epub 2012 Dec 20. [Article]
- Sova M: Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini Rev Med Chem. 2012 Jul;12(8):749-67. [Article]
- Cutaneous Permeation and Penetration of Sunscreens: Formulation Strategies and In Vitro Methods [File]
- External Links
- ChemSpider
- 1266578
- 1426854
- ChEMBL
- CHEMBL1476782
- ZINC
- ZINC000001600509
- Wikipedia
- Amiloxate
- MSDS
- Download (76.2 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count Not Available Completed Diagnostic Dermatitis, Photocontact 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical Cream Topical Spray Topical Lotion Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) < -30 MSDS boiling point (°C) 170 MSDS water solubility Insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.00738 mg/mL ALOGPS logP 4.27 ALOGPS logP 3.97 Chemaxon logS -4.5 ALOGPS pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 35.53 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 72.71 m3·mol-1 Chemaxon Polarizability 28.33 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03ec-6910000000-074f5497491c5e262b4a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-02ft-5960000000-179c87d408337c7b549c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000j-5910000000-04591b60619ad0b8ed0e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-4910000000-2f8ff5044e3eb6f475fc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f89-4900000000-4a7c375c5af9638a824f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0900000000-b182c57432e58d2d5bf0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0zfr-8900000000-5847eba449d2c9e5424f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.50606 predictedDeepCCS 1.0 (2019) [M+H]+ 168.86407 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.95721 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:53