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Enzacamene

HCID 6434217
노트반응

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기본 정보이름 및 식별자물성화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1782069-81-1
표준 SMILES
Cc1ccc(/C=C2/C(=O)C3(C)CCC2C3(C)C)cc1
InChIKey
HEOCBCNFKCOKBX-SDNWHVSQSA-N
분자식
C18H22O
평균 분자량
254.4 g/mol
단동위원소 질량
254.16706532

이름 및 식별자

우선 이름
Enzacamene
IUPAC
(3E)-1,7,7-trimethyl-3-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-2-one
영어명
Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-3-[(4-methylphenyl)methylene]-, (3E)-
분자식
C18H22O
분자량
254.37

이름 및 동의어

Enzacamene4-Methylbenzylidene camphorEnzacamenoMETHYL BENZYLIDENE CAMPHOR3-(4-Methylbenzylidene)camphor(3E)-1,7,7-trimethyl-3-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-2-oneDTXSID8047896enzacamenum(3E)-1,7,7-trimethyl-3-((4-methylphenyl)methylidene)bicyclo(2.2.1)heptan-2-oneEusolex-63004-MBC cpdRefChem:920992
이름 더 보기
Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-3-[(4-methylphenyl)methylene]-, (3E)-
DTXCID308142588I3XWY40L91782069-81-1Enzacamene D-L form4-MethylbenzylidenecamphorParsol 50003-(p-Methylbenzylidene)-DL-camphor3-(4-METHYLBENZYLIDENE)-CAMPHOR

데이터베이스 식별자

CAS
1782069-81-1、36861-47-9
PubChem CID
6434217
DTXSID
DTXSID201348972
ChEMBL
CHEMBL2104261
ChEBI
CHEBI:135937
Nikkaji
J2.361.347F、J475.334H

물성

구조 계산 물성보충 중

XLogP
4.5
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
19
형식 전하
0
복잡도
423

실험 및 물리화학적 성질

LogP5.14
SolubilityPoorly soluble
Melting Point66-69

물리화학적 성질

끓는 점
357 · 357-358℃ at 101.3kPa
밀도
1.108 at · 1.108 at 20℃
증기압
0 · 0-0.029Pa at 20-50℃
물리적 상태
Solid:crystalline
LogP
5.1 · 5.1-5.6 at 23℃ and pH7

화학 및 산업

약리 정보

Protein BindingNo pharmacokinetic data available.
Pharmacodynamics · 1건

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).

Mechanism of Action · 1건

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 (10–100 μmol/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.

Biological Half-LifeThe 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.

관련 반응

2건
반응 기록 만들기
HRID 130276 반응식
HRID 130276반응물로uspto-grants-2008_06
HRID 1743094 반응식
HRID 1743094반응물로uspto-grants-2006_03

화합물 노트

불러오는 중…

이 페이지에서기본 정보이름 및 식별자물성화학 및 산업관련 반응화합물 노트
Metabolism/Metabolites · 1건

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.

Absorption, Distribution and Excretion · 4건

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.

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.

No pharmacokinetic data available.

No pharmacokinetic data available.

용도 및 제조

Use ClassificationCosmetics -> Uv filter; Uv absorber

공급사2 곳

TLC梯尔希(南京)药物研发有限公司18012923235 · [email protected]
TLC梯尔希(南京)药物研发有限公司18012923235 · [email protected]