Bisoctrizole

Chembox new
Name = Bisoctrizole
ImageFile = Bisoctrizole.svg
ImageName = Bisoctrizole
IUPACName = 2,2'-methylenebis [6-(2"H"-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]
Section1 = Chembox Identifiers
CASNo = 103597-45-l
Section2 = Chembox Properties
Formula = C₄₁H₅₀N₆O₂
MolarMass = 658.89 g/mol
MeltingPt = 195.7 °C

Bisoctrizole (INN [http://whqlibdoc.who.int/druginfo/18_4_2004_INN92.pdf] [http://whqlibdoc.who.int/druginfo/INN_2005_list54.pdf] /USAN [http://www.ama-assn.org/ama1/pub/upload/mm/365/bisoctrizol.doc] , marketed by Ciba Specialty Chemicals as Tinosorb M, INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is a benzotriazole based organic compound which is added to sunscreens to absorb UV rays.

Bisoctrizole is a broad spectrum ultraviolet radiation absorber, absorbing UVB as well as UVA rays. It also reflects and scatters UV. Bisoctrizole is a hybrid UV absorber, the first and only organic UV filter produced as microfine organic particles (< 200 nm), [ [http://www.ciba.com/index/ind-index/ind-per_car/skin_care___sun_care_actives/tinosorb-registered-_uv_filters/tinosorb-registered-_m-2.htm Ciba TINOSORB M] ] [ [http://www.blackwell-synergy.com/doi/abs/10.1046/j.1467-2494.2002.00137.x Blackwell Synergy - Int J Cosmet Sci, Volume 24 Issue 3 Page 170-185, June 2002 (Article Abstract) ] ] like microfine zinc oxide and titanium dioxide. Where other organic UV absorbers need to be dissolved in either the oil or water phase, bisoctrizole dissolves poorly in both.

Bisoctrizole is added to the water phase of a sunscreen as a 50% suspension, while mineral micropigments are usually added to the oil phase. The bisoctrizole particles are stabilized by the surfactant decyl glucoside.

Bisoctrizole shows very little photodegradation and has a stabilizing effect on other UV absorbers, octyl methoxycinnamate (octinoxate) in particular.

When formulated into a sunscreen bisoctrizole has minimal skin penetration. [cite journal| title=In vitro percutaneous absorption and in vivo stratum corneum distribution of an organic and a mineral sunscreen| year=2007| pmid=17035717| author=Mavon A, Miquel C, Lejeune O, Payre B, Moretto P| journal=Skin Pharmacol Physiol| volume=20(1)| pages=10–20| doi=10.1159/000096167] Unlike some other organic sunscreen actives, it shows no estrogenic effects in vitro. [cite journal| title=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| year=2001| month=Dec| pmid=11754532| author=Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA| journal= Regul Toxicol Pharmacol| volume=34(3)| pages=287–91| doi=10.1006/rtph.2001.1511]

Bisoctrizole is not approved by the FDA, but is approved in the EU and other parts of the world. [ [http://www.modernmedicine.com/modernmedicine/article/articleDetail.jsp?id=169626 Manage Account - Modern Medicine ] ] [ [http://eur-lex.europa.eu/LexUriServ/site/en/consleg/1976/L/01976L0768-20060809-en.pdf CL1976L0768EN0150010.0001 1..107 ] ] [ [http://www.tga.gov.au/docs/pdf/argom_10.pdf Australian Regulatory Guidelines for OTC Medicines - Chapter 10 ] ]

ee also

*Sunscreen
*Avobenzone
*Bemotrizinol
*Bisdisulizole disodium
*Ecamsule

References

External links

* http://www.cibasc.com/index/ind-index/ind-per_car/ind-pc-uv/ind-pc-uv-tinosorbm.htm
* http://www.dermatologytimes.com/dermatologytimes/article/articleDetail.jsp?id=159652
* http://pubs.acs.org/cen/coverstory/83/8315sunscreens.html
* http://www.fda.gov/ohrms/dockets/dockets/05n0446/05n-0446-bkg0001-03-Tab-01-vol2.pdf