Bisoctrizole

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{{expert needed | chemistry | reason = article lacks clear, believable chemical explanations, and a firm basis in good secondary sources | date = July 2022}}

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{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477373238

| Name = Bisoctrizole

| OtherNames = UV-360

| ImageFile = Bisoctrizole.svg

| ImageSize = 260

| ImageAlt = Skeletal formula of bisoctrizole

| ImageFile1 = Bisoctrizole-3D-spacefill.png

| ImageSize1 = 235

| ImageAlt1 = Space-filling model of the bisoctrizole molecule

| PIN = 2,2′-Methylenebis[6-(2H-1,2,3-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol]

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2808671

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FQUNFJULCYSSOP-UHFFFAOYSA-N

| PubChem = 3571576

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104957

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8NT850T0YS

| InChIKey = FQUNFJULCYSSOP-UHFFFAOYAP

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 103597-45-1

| SMILES = n1c6ccccc6nn1c2cc(cc(c2O)Cc5cc(cc(n3nc4ccccc4n3)c5O)C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C

| InChI = 1/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}}

| Section2 = {{Chembox Properties

| Formula = C₄₁H₅₀N₆O₂

| MolarMass = 658.88 g/mol

| MeltingPtC = 195.7

| MeltingPt_notes =

}}}}

Bisoctrizole (INN{{Cite journal |last=WHO Staff |date=2005 |title=Recommended International Nonproprietary Names: List 54, International Nonproprietary Names for Pharmaceutical Substances (INN) [Entry 'bisoctrizolum'] |url=http://apps.who.int/medicinedocs/en/d/Js7918e/8.html |url-status=dead |journal=WHO Drug Information |volume=19 |issue=3 |archive-url=https://web.archive.org/web/20091019164225/http://apps.who.int/medicinedocs/en/d/Js7918e/8.html |archive-date=October 19, 2009 |access-date=July 5, 2022}}/USAN,{{Cite web |last=National Library of Medicine Staff |date=July 5, 2022 |title=Bisoctrizole |url=https://chem.nlm.nih.gov/chemidplus/rn/103597-45-1 |access-date=July 5, 2022 |website=Chem.NLM.NIH.gov}} marketed by BASF as Tinosorb M, by DSM Nutritional Products as Parsol Max , by Everlight Chemical as Eversorb M, and by MPI as Milestab 360, INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is a phenolic benzotriazole that is added to sunscreens to absorb UV rays.{{Cite journal |last=Latha |first=MS |last2=Martis |first2=Jacintha |last3=Shobha |first3=V |last4=Shinde |first4=Rutuja Sham |last5=Bangera |first5=Sudhakar |last6=Krishnankutty |first6=Binny |last7=Bellary |first7=Shantala |last8=Varughese |first8=Sunoj |last9=Rao |first9=Prabhakar |last10=Naveen Kumar |first10=B.R. |date=January 2013 |title=Sunscreening Agents A Review |journal=Journal of Clinical and Aesthetic Dermatology |volume=6 |issue=1 |pages=16–26 |pmc=3543289 |pmid=23320122}} It is a broad-spectrum ultraviolet radiation absorber, absorbing UVB as well as UVA rays. It also reflects and scatters UV.{{fact|date = July 2022|reason=Organic compounds used as sunscreens, are usually so used because they absorb UVA and UVB. Typically do not "reflect and scatter" UV.}}

Bisoctrizole is what is termed is a hybrid UV absorber, which has been described as an organic UV filter produced in microfine organic particles (< 200 nm),{{verification needed|date = July 2022}}{{Cite web |last=Ciba Staff |date=July 5, 2022 |title=TINOSORB® M, Broad-spectrum UV Filter for the Water Phase |url=https://www.carecreations.basf.com/products-formulation/products/products-detail/TINOSORB%20M/30482916 |access-date=July 5, 2022 |website=BASF.com}}{{better source | date = July 2022}}{{Cite journal |last=Herzog |first=B. |last2=Mongiat |first2=S. |last3=Deshayes |first3=C. |last4=Neuhaus |first4=M. |last5=Sommer |first5=K. |last6=Mantler |first6=A. |year=2002 |title=In vivo and in vitro assessment of UVA protection by sunscreen formulations containing either butyl methoxy dibenzoyl methane, methylene bis-benzotriazolyl tetramethylbutylphenol, or microfine ZnO |journal=International Journal of Cosmetic Science |volume=24 |issue=3 |pages=170–85 |doi=10.1046/j.1467-2494.2002.00137.x |pmid=18498509 |s2cid=37553401}}{{primary source inline|date = July 2022}}{{primary source inline|date = July 2022}} like microfine zinc oxide and titanium dioxide.{{dubious|date = July 2022}}{{fact | date = July 2022}} Where other organic UV absorbers dissolved in either the oily or aqueous phases, bisoctrizole dissolves poorly in both.{{fact|date = July 2022}}

Hence, bisoctrizole is formulated in sunscreen preparations as a 50% suspension, the absorber added to the water phase,{{Contradict-inline|date = July 2022}} and mineral micropigments usually added to the oil phase.{{fact|date = July 2022}} The bisoctrizole particles are stabilized by the surfactant decyl glucoside.{{fact|date = July 2022}} The compound shows very little photodegradation, and has a stabilizing effect on other UV absorbers, octyl methoxycinnamate (octinoxate) in particular.{{fact|date = July 2022}}

In primary research reports, bisoctrizole has been reported to minimally penetrate skin,{{Cite journal |vauthors=Mavon A, Miquel C, Lejeune O, Payre B, Moretto P |year=2007 |title=In vitro percutaneous absorption and in vivo stratum corneum distribution of an organic and a mineral sunscreen |journal=Skin Pharmacol Physiol |volume=20 |issue=1 |pages=10–20 |doi=10.1159/000096167 |pmid=17035717 |s2cid=22041398}}{{primary source inline|date = July 2022}}{{primary source inline|date = July 2022}} and has been described as lacking estrogenic effects in vitro.{{Cite journal |vauthors=Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA |date=December 2001 |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 |journal=Regul Toxicol Pharmacol |volume=34 |issue=3 |pages=287–91 |doi=10.1006/rtph.2001.1511 |pmid=11754532}}{{primary source inline|date = July 2022}}{{primary source inline|date = July 2022}}

Bisoctrizole has not yet been approved by the U.S. Food and Drug Administration (FDA),{{fact|date = July 2022}} but is approved in the EU and other parts of the world.{{Cite web |last=Kapes, Beth |date=July 1, 2005 |title=Docs Rally for Better Sun Protection |url=http://www.modernmedicine.com/modernmedicine/article/articleDetail.jsp?id=169626 |url-access=registration |url-status=dead |archive-url=https://web.archive.org/web/20071009095100/http://www.modernmedicine.com/modernmedicine/article/articleDetail.jsp?id=169626 |archive-date=October 9, 2007 |access-date=July 5, 2022 |website=ModernMedicine.com}}{{better source |date = July 2022}}{{Cite web |title=Eur-Lex.Europa.eu PDF |url=http://eur-lex.europa.eu/LexUriServ/site/en/consleg/1976/L/01976L0768-20060809-en.pdf |url-status=dead |archive-url=https://web.archive.org/web/20080814155936/http://eur-lex.europa.eu/LexUriServ/site/en/consleg/1976/L/01976L0768-20060809-en.pdf |archive-date=2008-08-14 |access-date=2007-08-19}}[https://web.archive.org/web/20070831075404/http://tga.gov.au/docs/pdf/argom_10.pdf Australian Regulatory Guidelines for OTC Medicines, Chapter 10.]{{full | date = July 2022}}{{full | date = July 2022}}