기본 정보
- 표준 SMILES
CN(Cc1ccc(C(C)(C)C)cc1)Cc1cccc2ccccc12- InChIKey
ABJKWBDEJIDSJZ-UHFFFAOYSA-N- 분자식
- C23H27N
- 평균 분자량
- 317.5 g/mol
- 단동위원소 질량
- 317.21434987
이름 및 식별자
- 우선 이름
- Butenafine
- IUPAC
- 1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine
- 영어명
- Butenafine
- 분자식
- C23H27N
- 분자량
- 317.47
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
101828-21-1- PubChem CID
- 2484
- DTXSID
DTXSID7040657- ChEMBL
CHEMBL990- ChEBI
CHEBI:3238- UNII
- 91Y494NL0X
- Nikkaji
- J276.436I
물성
구조 계산 물성
- XLogP
- 6.3
- 극성 표면적
- 3.2 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 1
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 24
- 형식 전하
- 0
- 복잡도
- 374
실험 및 물리화학적 성질
LogP
6.6
6.6
Solubility
Slightly soluble (HCl salt)
7.56e-05 g/L
물리화학적 성질
- 녹는점
- 200 · 200-202 °C
- 끓는 점
- 426.1 · 426.1±14.0 °C(Predicted)
- 밀도
- 1.032 · 1.032±0.06 g/cm3(Predicted)
- 저장 조건
- -20 °C · Store at -20°C
- 용해도
- 63 mg/mL · DMSO: 63 mg/mL (198.44 mM);Ethanol: 63 mg/mL (198.44 mM)
- 산도 계수 (pKa)
- 7.87 · 7.87±0.50(Predicted)
- 수용성
- Water: Insoluble
- LogP
- 6.77 · 6.770 (est)
안전 및 규제
독성 정보
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Topical butenafine has not been studied during breastfeeding. Because it is poorly absorbed after topical application, it is not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants. Ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
화학 및 산업
약리 정보
ATC Code
D - Dermatologicals;D01 - Antifungals for dermatological use;D01A - Antifungals for topical use;D01AE - Other antifungals for topical use;D01AE23 - Butenafine
QD - Dermatologicals;QD01 - Antifungals for dermatological use;QD01A - Antifungals for topical use;QD01AE - Other antifungals for topical use;QD01AE23 - Butenafine
Pharmacodynamics
Butenafine is a synthetic antifungal agent that is structurally and pharmacologically related to allylamine antifungals. The exact mechanism of action has not been established, but it is suggested that butenafine's antifungal activity is exerted through the alteration of cellular membranes, which results in increased membrane permeability, and growth inhibition. Butenafine is mainly active against dermatophytes and has superior fungicidal activity against this group of fungi when compared to that of terbinafine, naftifine, tolnaftate, clotrimazole, and bifonazole. It is also active against <i>Candida albicans</i> and this activity is superior to that of terbinafine and naftifine. Butenafine also generates low MICs for <i>Cryptococcus neoformans</i> and <i>Aspergillus spp.</i> as well.
Mechanism of Action
Although the mechanism of action has not been fully established, it has been suggested that butenafine, like allylamines, interferes with sterol biosynthesis (especially ergosterol) by inhibiting squalene monooxygenase, an enzyme responsible for converting squalene to 2,3-oxydo squalene. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Blockage of squalene monooxygenase also leads to a subsequent accumulation of squalene. When a high concentration of squalene is reached, it is thought to have an effect of directly kill fungal cells.
FDA Pharmacological Classification
91Y494NL0X
BUTENAFINE
Established Pharmacologic Class [EPC] - Benzylamine Antifungal
Chemical Structure [CS] - Benzylamines
Butenafine is a Benzylamine Antifungal.
응용 분야
용도Butenafine (Mentax) is a synthetic benzylamine antifungal agent, related structurally and pharmacologically to terbinafine. It is thought to act by inhibiting the enzyme squalene 2,3-epoxidase, resulting in decreased ergosterol and corresponding increase in squalene, with subsequent cell membrane permeability alteration and cell death. It is active against dermatophytes, yeast, and Sporothrix.
공급사50 곳
추가 설명
정의ChEBI: Trimethylamine in which hydrogen atoms attached to different methyl groups are substituted by 1-naphthyl and 4-tert-butylphenyl groups. It is an inhibitor of squalene epoxidase, an enzyme responsible for the creation of sterols needed in funga cell membranes, and is used as its hydrochloride salt for treatment of dermatological fungal infections.
관련 반응
연결된 노트
불러오는 중…