Identification
- Summary
Bisoctrizole is an absorber of UVA and UVB radiation used in sunscreen.
- Generic Name
- Bisoctrizole
- DrugBank Accession Number
- DB11262
- Background
Bisoctrizole, or methylene bis-benzotriazolyl tetramethylbutylphenol, is a broad-spectrum organic UV filter that is marketed as Tinosorb M 1. It is a benzotriazole-based organic compound that absorbs, reflects, and scatters both UV-A and UV-B rays. Bisoctrizole is not approved by the FDA, but is approved in the EU and other parts of the world as a UV-filter in sunscreens, day care products and skin lightening products at a maximum concentration of 10% 2.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Bisoctrizole (DB11262)
- Weight
- Average: 658.891
Monoisotopic: 658.399524874 - Chemical Formula
- C41H50N6O2
- Synonyms
- Bisoctrizole
- MBBT
- External IDs
- FAT 75'634
- FAT-75634
Pharmacology
- Indication
Indicated for use as a sunscreen agent in cosmetic products.
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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
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Under the conditions of in vitro androgen competitive binding assay, bisoctrizole displayed no intrinsic androgenic, estrogenic, nor uterotrophic activity 2.
- Mechanism of action
Bisoctrizole is an organic UV-A filter that absorbs both UV-A and UV-B rays 2.
- Absorption
A rat and human dermal penetration study in vitro indicates that bisoctrizole displays minimal absorption through the skin, with only about 0.01% and 0.06 % of the applied dose penetration through the human and rat skin membrane, respectively 2. Despite low dermal uptake, potential bioaccumulation after repeated skin applications cannot be excluded 2.
- 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
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Both oral LD50 and dermal LD50 in rat is > 2000 mg/kg MSDS. In a developmental toxicity study of rats, the maternal and developmental no-observed-effect-level (NOEL) of bisoctrizole was the high dose level of 1000 mg/kg bw/day 2. Animal studies suggest that bisoctrizole mediates no phytotoxic effects 2.
- 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
- 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 Aqua-fluid Bisoctrizole (4 % w/w) + Avobenzone (3 % w/w) + Bemotrizinol (2 % w/w) + Octocrylene (9 % w/w) + Titanium dioxide (3.4 % w/w) Emulsion Topical Pierre Fabre Dermo Cosmetique Usa, Inc. 2022-06-02 Not applicable Canada 
Calming Days Vegan Sunscreen Bisoctrizole (2 g/100mL) + Diethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Iscotrizinol (1.2 g/100mL) + Octyl triazone (2.4 g/100mL) Gel Topical Merci Co. 2022-10-18 Not applicable US 
Emulsion SPF 50+ Bisoctrizole (4 % w/w) + Avobenzone (3 % w/w) + Bemotrizinol (2 % w/w) + Octocrylene (9 % w/w) + Titanium dioxide (3.4 % w/w) Emulsion Topical Pierre Fabre Dermo Cosmetique Usa, Inc. 2016-03-01 Not applicable Canada High Protection Emulsion Bisoctrizole (6.0 % w/w) + Bemotrizinol (4.5 % w/w) + Octinoxate (7.5 % w/w) Emulsion Topical Pierre Fabre Dermo Cosmetique Usa, Inc. 2010-05-26 2019-01-03 Canada High Protection Lotion Bisoctrizole (6.0 % w/w) + Bemotrizinol (3.5 % w/w) + Octinoxate (7.5 % w/w) Lotion Topical Pierre Fabre Dermo Cosmetique Usa, Inc. 2010-05-26 2018-01-04 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Calming Days Vegan Sunscreen Bisoctrizole (2 g/100mL) + Diethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Iscotrizinol (1.2 g/100mL) + Octyl triazone (2.4 g/100mL) Gel Topical Merci Co. 2022-10-18 Not applicable US iUNIK Centella Calming Daily Sunscreen Bisoctrizole (2 g/100mL) + Diethylamino hydroxybenzoyl hexyl benzoate (5 g/100mL) + Octyl triazone (4 g/100mL) Cream Topical IUNIK Co., Ltd. 2023-04-18 Not applicable US Sun Project Skin-relief Suncream Bisoctrizole (1 mg/50mL) + Diethylamino hydroxybenzoyl hexyl benzoate (1.5 mg/50mL) + Iscotrizinol (0.6 mg/50mL) + Octyl triazone (1.2 mg/50mL) Cream Topical Thank You Farmer Co., Ltd. 2022-05-30 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Phenyl-1,2,3-triazoles / Phenylpropanes / Benzotriazoles / Phenols / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- 1,2,3-triazole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzotriazole / Diphenylmethane / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 8NT850T0YS
- CAS number
- 103597-45-1
- InChI Key
- FQUNFJULCYSSOP-UHFFFAOYSA-N
- InChI
- InChI=1S/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21-29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3
- IUPAC Name
- 2-(2H-1,2,3-benzotriazol-2-yl)-6-{[3-(2H-1,2,3-benzotriazol-2-yl)-2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl}-4-(2,4,4-trimethylpentan-2-yl)phenol
- SMILES
- CC(C)(C)CC(C)(C)C1=CC(CC2=C(O)C(=CC(=C2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)=C(O)C(=C1)N1N=C2C=CC=CC2=N1
References
- General References
- 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. [Article]
- European Commission Scientific Committee on Consumer Safety (SCCS): Opinion on 2,2’-Methylene-bis-(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3- tetramethylbutyl)phenol) [File]
- External Links
- ChemSpider
- 2808671
- 1310510
- ChEBI
- 135865
- ChEMBL
- CHEMBL2104957
- ZINC
- ZINC000011677911
- Wikipedia
- Bisoctrizole
- MSDS
- Download (31.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Supportive Care Idiopathic Solar Urticaria 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel Topical Lotion Topical Emulsion Topical Powder Topical Cream Topical Spray Topical Cream Cutaneous; Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 195 MSDS water solubility < 5 ng/L at 25 °C European Commission Scientific Committee on Consumer Safety logP 12.7 MSDS - Predicted Properties
Property Value Source Water Solubility 0.000458 mg/mL ALOGPS logP 8.65 ALOGPS logP 11.84 Chemaxon logS -6.2 ALOGPS pKa (Strongest Acidic) 7.56 Chemaxon pKa (Strongest Basic) -0.54 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 101.88 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 220.17 m3·mol-1 Chemaxon Polarizability 75.8 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 286.6488065 predictedDarkChem Lite v0.1.0 [M-H]- 255.62552 predictedDeepCCS 1.0 (2019) [M+H]+ 288.2518065 predictedDarkChem Lite v0.1.0 [M+H]+ 257.45044 predictedDeepCCS 1.0 (2019) [M+Na]+ 288.0661065 predictedDarkChem Lite v0.1.0 [M+Na]+ 263.05627 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:53