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    Chemistry

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    Also known as: 3-(4'-methylbenzylidene)camphor, 4-methylbenzylidene camphor, 38102-62-4, 36861-47-9, 3-(4-methylbenzylidene)camphor, Parsol 5000
    Molecular Formula
    C18H22O
    Molecular Weight
    254.4  g/mol
    InChI Key
    HEOCBCNFKCOKBX-SDNWHVSQSA-N
    Enzacamene
    Commonly known as 4-methylbenzylidene-camphor (4-MBC), enzacamene is a camphor derivative and an organic chemical UV-B filter. It is used in cosmetic products such as sunscreen to provide skin protection against UV rays. While its effects on the human reproductive system as an endocrine disruptor are being investigated, its use in over-the-counter and cosmetic products is approved by Health Canada. Its tradenames include Eusolex 6300 (Merck) and Parsol 5000 (DSM).
    1 2D Structure

    Enzacamene

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3E)-1,7,7-trimethyl-3-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-2-one
    2.1.2 InChI
    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+
    2.1.3 InChI Key
    HEOCBCNFKCOKBX-SDNWHVSQSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)C=C2C3CCC(C2=O)(C3(C)C)C
    2.1.5 Isomeric SMILES
    CC1=CC=C(C=C1)/C=C/2\C3CCC(C2=O)(C3(C)C)C
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 3-(4'-methylbenzylidene)camphor

    2. 3-(4-methylbenzylidene)camphor

    3. 4-mbc Cpd

    4. 4-methylbenzylidene Camphor

    5. Eusolex 6300

    6. Eusolex-6300

    2.2.2 Depositor-Supplied Synonyms

    1. 3-(4'-methylbenzylidene)camphor

    2. 4-methylbenzylidene Camphor

    3. 38102-62-4

    4. 36861-47-9

    5. 3-(4-methylbenzylidene)camphor

    6. Parsol 5000

    7. 4-methylbenzylidenecamphor

    8. 3-(4-methylbenzyliden)camphor

    9. 3-(4-methylbenzylidene)-camphor

    10. 3-(p-methylbenzylidene)-dl-camphor

    11. 4-mbc

    12. 1782069-81-1

    13. Methyl Benzylidene Camphor

    14. Enzacamene D-l Form

    15. (e)-1,7,7-trimethyl-3-(4-methylbenzylidene)bicyclo[2.2.1]heptan-2-one

    16. (e)-enzacamene

    17. (+/-)-3-(p-methylbenzylidene)camphor

    18. Schembl83245

    19. Chembl2104261

    20. Chebi:135937

    21. Dtxsid201348972

    22. Bdbm50103609

    23. Akos015865884

    24. Akos025310897

    25. Ac-8477

    26. Db11219

    27. Ncgc00167419-02

    28. Ls-14659

    29. Q4637174

    30. 1,7,7-trimethyl-3-[(e)-4-methylbenzylidene]bicyclo[2.2.1]heptane-2-one

    31. (e)-rac-1,7,7-trimethyl-3-(4-methyl-benzylidene)-bicyclo-[2.2.1]-heptan-2-one

    2.3 Create Date
    2006-04-28
    3 Chemical and Physical Properties
    Molecular Weight 254.4 g/mol
    Molecular Formula C18H22O
    XLogP34.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count1
    Exact Mass254.167065321 g/mol
    Monoisotopic Mass254.167065321 g/mol
    Topological Polar Surface Area17.1 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity423
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated for use as an active sunscreen agent.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Several studies suggest that enzacamene elicit estrogen-like effects. In prepubertal male rats exposed to enzacamene during embryonic and fetal development, decrease in testicular weight with decreased levels of LH, GnRH, and glutamate were observed; in comparison, there was an increase in LH, GnRH, and aspartate levels in peripubertal rats. These findings suggest that high concentrations of enzacamene during embryonic and fetal stage inhibits the testicular axis in male rats during the prepubertal stage and stimulates it during peripubertad stage. In a study of zebrafish (Danio rerio) embryo, exposure to enzacamene during early vertebrate development was associated with muscular and neuronal defects that may result in developmental defects, including a reduction in AChE activity, disorganized pattern of slow muscle fibers, and axon pathfinding errors during motor neuron innervation. Enzacamene displays a weak binding activity in receptors binding assays using the mammalian estrogen receptor (ER).

    5.2 Absorption, Distribution and Excretion

    Absorption

    The maximum plasma concentration of enzacamene was 16ng/mL in healthy female volunteers following daily whole-body topical application of 2mg/cm^2 of sunscreen formulation at 10% (weight/weight) for four days. Blood concentration of enzacamene (4-MBC) and its main metabolite, 3-(4-carboxybenzylidene)camphor, peaked within 10 h after oral administration of enzacamene.

    Route of Elimination

    The urine concentration of 4 ng/mL and 4 ng/mL of enzacamene were observed in female and male volunteers, respectively. In a rat pharmacokinetic study, most of orally administered enzacamene was recovered in in feces as 3-(4-carboxybenzylidene)camphor and, to a smaller extent, as 3-(4-carboxybenzylidene)-6-hydroxycamphor. Glucuronides of both metabolites were also detectable in faces. In urine, one isomer of 3-(4-carboxybenzylidene)hydroxycamphor was the predominant metabolite [3-(4-carboxybenzylidene)-6-hydroxycamphor], the other isomers and 3-(4-carboxybenzylidene)camphor were only minor metabolites excreted with urine. Enterohepatic circulation of glucuronides derived from the two major 4-MBC metabolites may explain the slow excretion of 4-MBC metabolites with urine and the small percentage of the administered doses recovered in urine.

    Volume of Distribution

    No pharmacokinetic data available.

    Clearance

    No pharmacokinetic data available.

    5.3 Metabolism/Metabolites

    Based on the findings of a rat pharmacokinetic study, it is proposed that absorbed enzacamene following oral administration undergo extensive first-pass hepatic metabolism. Following oral administration of enzacamene (4-MBC) in rats, detected metabolites in the plasma and urine were 3-(4-carboxybenzylidene)camphor and as four isomers of 3-(4-carboxybenzylidene)hydroxycamphor containing the hydroxyl group located in the camphor ring system with 3-(4-carboxybenzylidene)-6-hydroxycamphor as the major metabolite. However the blood concentrations of 3-(4-carboxybenzylidene)-6-hydroxycamphor were below the limit of detection following peak concentration. Via hydroxylation mediated by cytochrome P450 system, 3-(4-hydroxymethylbenzylidene)camphor is formed. This metabolite is further oxidized to 3-(4-carboxybenzylidene)camphor via oxidation of alcohol dehydrogenase and aldehyde dehydrogenase, and may be further hydroxylated to form 3-(4-carboxybenzylidene)-6-hydroxycamphor mediated by CYP450 system.

    5.4 Biological Half-Life

    The half life of enzacamene (4-MBC) and its main metabolite, 3-(4-carboxybenzylidene)camphor, displayed half-lives of approximately 15 h after reaching peak plasma concentrations after oral administration in rats.

    5.5 Mechanism of Action

    Enzacamene absorbs UV-B rays. It is proposed that enzacamene exerts estrogen-like activities in the same direction as endogenous estrogens via nonclassical estrogen signaling mechanisms that do not involve gene regulation by the nuclear ER. It binds to cytosolic estradiol binding sites of estrogen receptors with low to moderate affinity compared to that of the endogenous agonist. Based on the findings of a study with _Xenopus_ hepatocytes in culture, enzacamene has a potential to induce the ER gene only at higher concentrations (10100 mol/L). While enzacamene was not shown to activate estrogen-dependent gene transcription when tested in an ER reporter gene assay in yeast cells, it was demonstrated in _Xenopus_ hepatocytes cultures that activate ER-dependent signaling mechanisms leading to altered gene expression. In micromolar concentrations, enzacamene accelerates cell proliferation rate in MCF-7 human breast cancer cells.

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    Regulatory Info : Allowed

    Registration Country : Switzerland

    Garlic Onion Extract; Hyoscyamus Oil; Allantoin; Heparin Sodium; Avobenzone; Enzacamen

    Brand Name : Keli-med

    Dosage Form : Cream

    Dosage Strength :

    Packaging :

    Approval Date : 05/11/1986

    Application Number : 47456

    Regulatory Info : Allowed

    Registration Country : Switzerland

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    Regulatory Info : Allowed

    Registration Country : Switzerland

    Garlic Onion Extract; Hyoscyamus Oil; Allantoin; Heparin Sodium; Avobenzone; Enzacamen

    Brand Name : Keli-med

    Dosage Form : Cream

    Dosage Strength :

    Packaging :

    Approval Date : 05/11/1986

    Application Number : 47456

    Regulatory Info : Allowed

    Registration Country : Switzerland

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    Looking for 36861-47-9 / Enzacamene API manufacturers, exporters & distributors?

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    Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Enzacamene manufacturer or Enzacamene supplier.

    PharmaCompass also assists you with knowing the Enzacamene API Price utilized in the formulation of products. Enzacamene API Price is not always fixed or binding as the Enzacamene Price is obtained through a variety of data sources. The Enzacamene Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

    API | Excipient name

    Enzacamene

    Synonyms

    3-(4'-methylbenzylidene)camphor, 4-methylbenzylidene camphor, 38102-62-4, 36861-47-9, 3-(4-methylbenzylidene)camphor, Parsol 5000

    Cas Number

    36861-47-9

    About Enzacamene

    Commonly known as 4-methylbenzylidene-camphor (4-MBC), enzacamene is a camphor derivative and an organic chemical UV-B filter. It is used in cosmetic products such as sunscreen to provide skin protection against UV rays. While its effects on the human reproductive system as an endocrine disruptor are being investigated, its use in over-the-counter and cosmetic products is approved by Health Canada. Its tradenames include Eusolex 6300 (Merck) and Parsol 5000 (DSM).

    Enzacamene Manufacturers

    A Enzacamene manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Enzacamene, including repackagers and relabelers. The FDA regulates Enzacamene manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Enzacamene API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    Enzacamene Suppliers

    A Enzacamene supplier is an individual or a company that provides Enzacamene active pharmaceutical ingredient (API) or Enzacamene finished formulations upon request. The Enzacamene suppliers may include Enzacamene API manufacturers, exporters, distributors and traders.

    Enzacamene GMP

    Enzacamene Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Enzacamene GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Enzacamene GMP manufacturer or Enzacamene GMP API supplier for your needs.

    Enzacamene CoA

    A Enzacamene CoA (Certificate of Analysis) is a formal document that attests to Enzacamene's compliance with Enzacamene specifications and serves as a tool for batch-level quality control.

    Enzacamene CoA mostly includes findings from lab analyses of a specific batch. For each Enzacamene CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Enzacamene may be tested according to a variety of international standards, such as European Pharmacopoeia (Enzacamene EP), Enzacamene JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Enzacamene USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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