Amiloxate

Identification

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Name
Amiloxate
Accession Number
DB11207
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • 3-(4-Methoxyphenyl)-2-propenoic acid, 3-methylbutyl ester
  • Amiloxate
  • Isoamyl p-methoxycinnamate
  • Isoamyl-p-methoxycinnamate
External IDs
E-1000 / NSC-408332
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
a.c. care Bees Sun ProtectionAmiloxate (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)CreamTopicalDong Sung Pharm. Co., Ltd.2014-08-202015-11-30Us
a.c.care Bees Sun Protection UV Moisturizer SPF 50Amiloxate (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)CreamTopicalDong Sung Pharm. Co., Ltd.2011-12-202014-08-01Us
Cathycat Essence Sun BbAmiloxate (1 mL/100mL) + Octinoxate (7 mL/100mL) + Titanium dioxide (13.76176 mL/100mL) + Zinc oxide (3.92 mL/100mL)LiquidTopicalLg Household & Health Care Ltd.2011-04-15Not applicableUs
Daily Defense SunblockAmiloxate (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)CreamTopicalHumex,Inc.2013-04-222014-01-01Us
Dermafirm SunblockAmiloxate (2 g/100mL) + Octinoxate (7.5 g/100mL) + Octisalate (5 g/100mL) + Titanium dioxide (4.15 g/100mL) + Zinc oxide (4.9 g/100mL)CreamTopicalDermafirm Inc.2018-04-01Not applicableUs
Dpc Pink Aura Cushion No.21Amiloxate (3 g/100g) + Bemotrizinol (1.5 g/100g) + Octinoxate (7 g/100g) + Octisalate (3 g/100g) + Titanium dioxide (13.3 g/100g)LiquidTopicalMsco2017-07-01Not applicableUs
Dpc Pink Aura Cushion No.23Amiloxate (3 g/100g) + Bemotrizinol (1.5 g/100g) + Octinoxate (7 g/100g) + Octisalate (3 g/100g) + Titanium dioxide (12.7 g/100g)LiquidTopicalMsco2017-07-01Not applicableUs
Egf Uv ShieldAmiloxate (2 g/60g) + Octinoxate (7.5 g/60g) + Octisalate (5 g/60g) + Titanium dioxide (4.15 g/60g) + Zinc oxide (4.9 g/60g)CreamTopicalDermaesthetics Inc.2013-06-26Not applicableUs
Egf Uv ShieldAmiloxate (2 g/100mL) + Octinoxate (7.5 g/100mL) + Octisalate (5 g/100mL) + Titanium dioxide (4.15 g/100mL) + Zinc oxide (0.9 g/100mL)CreamTopicalDermaesthetics Inc.2018-07-07Not applicableUs
Hansai Beestox Sun Cream SPF 50Amiloxate (0.90000 g/45g) + Bemotrizinol (1.35000 g/45g) + Octinoxate (3.37500 g/45g) + Titanium dioxide (0.51381 g/45g) + Zinc oxide (1.12646 g/45g)CreamTopicalDong Sung Pharm. Co., Ltd.2014-06-062015-11-30Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Laser Block 100 sunblockAmiloxate (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)CreamTopicalUniversal Cosmetic Co., Ltd2010-08-04Not applicableUs
Categories
UNII
376KTP06K8
CAS number
71617-10-2
Weight
Average: 248.322
Monoisotopic: 248.141244504
Chemical Formula
C15H20O3
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

Pharmacology

Indication

Indicated as an active sunscreen agent.

Associated Conditions
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.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

Toxicity

Oral LD50 in rat is 9600 mg/kg MSDS.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:23284607]
  2. Sova M: Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini Rev Med Chem. 2012 Jul;12(8):749-67. [PubMed:22512578]
  3. Cutaneous Permeation and Penetration of Sunscreens: Formulation Strategies and In Vitro Methods [File]
External Links
ChemSpider
1266578
ChEMBL
CHEMBL1476782
Wikipedia
Amiloxate
MSDS
Download (76.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Not Yet RecruitingTreatmentFunctional Popliteal Artery Entrapment Syndrome / Popliteal artery entrapment syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidTopical
CreamTopical
SprayTopical
LotionTopical
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)< -30MSDS
boiling point (°C)170MSDS
water solubilityInsoluble MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00738 mg/mLALOGPS
logP4.27ALOGPS
logP3.97ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity72.71 m3·mol-1ChemAxon
Polarizability28.33 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Cinnamic acid ester / Phenoxy compound / Anisole / Methoxybenzene / Phenol ether / Styrene / Alkyl aryl ether / Fatty acid ester / Monocyclic benzene moiety / Fatty acyl
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on December 03, 2015 09:51 / Updated on August 14, 2019 11:09