ENZACAMENE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H22O
Molecular Weight	254.3667
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)\C=C2/[C@H]3CC[C@@](C)(C2=O)C3(C)C

InChI

InChIKey=HEOCBCNFKCOKBX-RELGSGGGSA-N

InChI=1S/C18H22O/c1-12-5-7-13(8-6-12)11-14-15-9-10-18(4,16(14)19)17(15,2)3/h5-8,11,15H,9-10H2,1-4H3/b14-11+/t15-,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H22O
Molecular Weight	254.3667
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15926546https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c | https://www.ncbi.nlm.nih.gov/pubmed/26888529
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25694030 | https://www.ncbi.nlm.nih.gov/pubmed/26888529

4-Methylbenzylidene-camphor (4-MBC, also known as ENZACAMENE) is an organic sunscreen components, that protects against UV radiation and may therefore help in the prevention of skin cancer. Recently was reveled, that 4-MBC was a teratogen and influenced muscular and neuronal development, which might result in developmental defects.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ultraviolet (UV) radiation 3 Target ID: ultraviolet (UV) radiation Sources: https://www.ncbi.nlm.nih.gov/pubmed/15926546	Inhibitor 8297
ultraviolet (UV) radiation 3 Target ID: ultraviolet (UV) radiation Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Sunburn 84 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c	Preventing	Approved 8429	Unknown Approved Use Unknown
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15926546	Preventing	Approved 8429	Unknown Approved Use Unknown
Sunburn 84 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aca12ac3-dc05-4f5b-a2b9-dae942bf856c	Preventing	Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Stereoisomer composition of the chiral UV filter 4-methylbenzylidene camphor in environmental samples.	2005 May 1	15926546
Comparison of effects of estradiol (E2) with those of octylmethoxycinnamate (OMC) and 4-methylbenzylidene camphor (4MBC)--2 filters of UV light - on several uterine, vaginal and bone parameters.	2006 Feb 1	15979666
Female sexual behavior, estrous cycle and gene expression in sexually dimorphic brain regions after pre- and postnatal exposure to endocrine active UV filters.	2009 Mar	19150460
Effects of in vivo exposure to UV filters (4-MBC, OMC, BP-3, 4-HB, OC, OD-PABA) on endocrine signaling genes in the insect Chironomus riparius.	2013 Jul 1	23591065
Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells.	2013 Jun	23397585
Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity.	2013 Oct 1	24004914
Mixtures of environmentally relevant endocrine disrupting chemicals affect mammary gland development in female and male rats.	2015 Jul	25305543

Patents

Sample Use Guides

In Vivo Use Guide

Apply liberally 15 minutes before sun exposure Reapply: immediately after towel drying. At least every 2 hours

Route of Administration: Topical

In Vitro Use Guide

Zebrafish embryos were exposed to various concentrations of 4-Methylbenzylidene camphor (4-MBC/ ENZACAMENE) in embryo medium for 3 days. A high concentration of 4-MBC was used for the purpose of phenotypic screening. Embryos exposed to 15 μM of 4-MBC displayed abnormal axial curvature and exhibited impaired motility. Exposure effects were found to be greatest during the segmentation period, when somite formation and innervation occur. Immunostaining of the muscle and axon markers F59, znp1, and zn5 revealed that 4-MBC exposure leads to a disorganized pattern of slow muscle fibers and axon pathfinding errors during the innervation of both primary and secondary motor neurons.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:44:18 GMT 2023` Edited by `admin` on `Fri Dec 15 18:44:18 GMT 2023`
Record UNII	8I3XWY40L9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENZACAMENE

Official Name

English

ENZACAMENE [USP MONOGRAPH]

Common Name

English

3-(4-Methylbenzylidene)camphor

Systematic Name

English

Enzacamene [WHO-DD]

Common Name

English

ENZACAMENE [USAN]

Common Name

English

ENZACAMENE [MART.]

Common Name

English

enzacamene [INN]

Common Name

English

BICYCLO(2.2.1)HEPTAN-2-ONE, 1,7,7-TRIMETHYL-3-((4-METHYLPHENYL)METHYLENE)-

Systematic Name

English

METHYL BENZYLIDENE CAMPHOR

Systematic Name

English

4-METHYLBENZYLIDENE CAMPHOR

Official Name

English

Enzacamene D-L form [WHO-DD]

Common Name

English

ENZACAMENE D-L FORM

Common Name

English

(±)-3-(P-METHYLBENZYLIDENE)CAMPHOR

Common Name

English

4-METHYLBENZYLIDENE CAMPHOR [INCI]

Common Name

English

4-METHYLBENZYLIDENE CAMPHOR [MI]

Common Name

English

METHYL BENZYLIDENE CAMPHOR [USP-RS]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C851