Bemotrizinol

Identification

Name
Bemotrizinol
Accession Number
DB11206
Type
Small Molecule
Groups
Approved
Description

Bemotrizinol, or bis-ethylhexyloxyphenol methoxyphenyl triazine, is an organic UV filter found in over-the-counter sunscreen products. It primarily absorbs UV-A rays. Compared to older broad-spectrum chemical agents, bemotrizinol is more more fat soluble (oil soluble in cosmetic oils) to aid in efficacy and broad-spectrum activity 2. It is claimed to be photostable, which increases its onset of action and its efficiency in providing protection against UV-rays upon topical application 2,3. Bemotrizinol is commonly marketed as Tinosorb S and Escalol S.

Structure
Thumb
Synonyms
  • Bemotrizinol
  • BEMT
External IDs
FAT 70'884 / FAT-70884
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
a.c. care Bees Sun ProtectionBemotrizinol (2.10000 g/70g) + Amiloxate (1.40000 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 50Bemotrizinol (2.10000 g/70g) + Amiloxate (1.40000 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
Anthelios SPF 45Bemotrizinol (0.5 %) + Avobenzone (3.0 %) + Drometrizole trisiloxane (0.5 %) + Ecamsule (1.0 %) + Octisalate (5.0 %) + Octocrylene (5.0 %) + Titanium dioxide (4.7 %)LotionTopicalLaboratoires La Roche Posay Canada2010-05-042015-08-07Canada
Anthelios Spray SPF 45Bemotrizinol (3.0 %) + Avobenzone (4.0 %) + Drometrizole trisiloxane (1.5 %) + Ecamsule (1.0 %) + Octisalate (5.0 %) + Octocrylene (3.5 %) + Titanium dioxide (2.6 %)SprayTopicalLaboratoires La Roche Posay Canada2010-05-042016-06-30Canada
Anthelios XL Melt-IN CreamBemotrizinol (5 %) + Avobenzone (4 %) + Drometrizole trisiloxane (3 %) + Ecamsule (0.5 %) + Octisalate (5 %) + Octocrylene (7 %) + Titanium dioxide (2.5 %)CreamTopicalLaboratoires La Roche Posay Canada2019-06-05Not applicableCanada
be Flat Daily Mild Flat Sun BlockBemotrizinol (2 g/100g) + Avobenzone (4.5 g/100g) + Homosalate (3.5 g/100g) + Octinoxate (6.5 g/100g) + Octisalate (5 g/100g)CreamTopicalLately Korea, Inc.2018-12-03Not applicableUs
Dpc Pink Aura Cushion No.21Bemotrizinol (1.5 g/100g) + Amiloxate (3 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.23Bemotrizinol (1.5 g/100g) + Amiloxate (3 g/100g) + Octinoxate (7 g/100g) + Octisalate (3 g/100g) + Titanium dioxide (12.7 g/100g)LiquidTopicalMsco2017-07-01Not applicableUs
Emulsion SPF 50+Bemotrizinol (2 %) + Avobenzone (3 %) + Bisoctrizole (4 %) + Octocrylene (9 %) + Titanium dioxide (3.4 %)EmulsionTopicalPierre Fabre Dermo Cosmetique Usa, Inc.2016-03-01Not applicableCanada
Hansai Beestox Sun Cream SPF 50Bemotrizinol (1.35000 g/45g) + Amiloxate (0.90000 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
Categories
UNII
PWZ1720CBH
CAS number
187393-00-6
Weight
Average: 627.826
Monoisotopic: 627.36722169
Chemical Formula
C38H49N3O5
InChI Key
XVAMCHGMPYWHNL-UHFFFAOYSA-N
InChI
InChI=1S/C38H49N3O5/c1-6-10-12-26(8-3)24-45-30-18-20-32(34(42)22-30)37-39-36(28-14-16-29(44-5)17-15-28)40-38(41-37)33-21-19-31(23-35(33)43)46-25-27(9-4)13-11-7-2/h14-23,26-27,42-43H,6-13,24-25H2,1-5H3
IUPAC Name
5-[(2-ethylhexyl)oxy]-2-(4-{4-[(2-ethylhexyl)oxy]-2-hydroxyphenyl}-6-(4-methoxyphenyl)-1,3,5-triazin-2-yl)phenol
SMILES
CCCCC(CC)COC1=CC(O)=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(OC)C=C1)C1=C(O)C=C(OCC(CC)CCCC)C=C1

Pharmacology

Indication

Indicated as an active sunscreen agent.

Associated Conditions
Pharmacodynamics

Findings from an immature rat uterotrophic competitive binding assay suggest that bemotrizinol does not display significant binding affinities towards estrogen and androgen receptors in vitro, thus lacking intrinsic estrogenic, antiestrogenic, androgenic and antiandrogenic activity 1. Bemotrizinol minimizes erythema and provides excellent anti-aging effects as well as protectant effects on the skin's antioxidant defense system 2. In a comparative study of individuals with a history of polymorphic light eruption (PLE) undergoing photoprovocation, treatment of bemotrinizol was effective in preventing the development of PLE 4.

Mechanism of action

By absorbing UV-A and UVB rays ranging from 280 to 400nm, bemotrizinol serves to prevent the formation of free radicals induced by UV radiation 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

No pharmacokinetic data available.

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 > 2000 mg/kg and dermal LD50 in rabbit is > 2000 mg/kg, respectively MSDS.

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

Interactions

Drug Interactions
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
Not Available

References

General References
  1. Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA: Lack of binding to isolated estrogen or androgen receptors, and inactivity in the immature rat uterotrophic assay, of the ultraviolet sunscreen filters Tinosorb M-active and Tinosorb S. Regul Toxicol Pharmacol. 2001 Dec;34(3):287-91. doi: 10.1006/rtph.2001.1511. [PubMed:11754532]
  2. Latha MS, Martis J, Shobha V, Sham Shinde R, Bangera S, Krishnankutty B, Bellary S, Varughese S, Rao P, Naveen Kumar BR: Sunscreening agents: a review. J Clin Aesthet Dermatol. 2013 Jan;6(1):16-26. [PubMed:23320122]
  3. Chatelain E, Gabard B: Photostabilization of butyl methoxydibenzoylmethane (Avobenzone) and ethylhexyl methoxycinnamate by bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter. Photochem Photobiol. 2001 Sep;74(3):401-6. [PubMed:11594052]
  4. Schleyer V, Weber O, Yazdi A, Benedix F, Dietz K, Rocken M, Berneburg M: Prevention of polymorphic light eruption with a sunscreen of very high protection level against UVB and UVA radiation under standardized photodiagnostic conditions. Acta Derm Venereol. 2008;88(6):555-60. doi: 10.2340/00015555-0509. [PubMed:19002338]
External Links
ChemSpider
10645286
RxNav
1306115
ChEBI
135857
ChEMBL
CHEMBL2104956
Wikipedia
Bemotrizinol
MSDS
Download (31.6 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)80.4MSDS
boiling point (°C)>400MSDS
water solubilityInsolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.000339 mg/mLALOGPS
logP8.26ALOGPS
logP11.62ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)0.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.82 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity216.4 m3·mol-1ChemAxon
Polarizability75.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on December 03, 2015 09:51 / Updated on March 01, 2020 20:49

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