基本情報
- CAS
3902-71-4- 標準SMILES
Cc1cc2cc3c(C)cc(=O)oc3c(C)c2o1- InChIKey
FMHHVULEAZTJMA-UHFFFAOYSA-N- 分子式
- C14H12O3
- 平均分子量
- 228.24 g/mol
- 単同位体質量
- 228.07864424
概要
Trioxsalen is 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis. It has a role as a photosensitizing agent and a dermatologic drug.
名称と識別子
- 優先名称
- Trimethylpsoralen
- IUPAC
- 2,5,9-trimethylfuro[3,2-g]chromen-7-one
- 現地名
- トリオキシサレン
- 英語名
- TRIOXSALEN
- 分子式
- C14H12O3
- 分子量
- 228.24
名称と別名
trioxsalen3902-71-4TrioxysalenTrimethylpsoralen4,5',8-TrimethylpsoralenTrioxisalenoTrioxysalene2',4,8-TrimethylpsoralenTrioxysalenumNSC710472,5,9-trimethylfuro[3,2-g]chromen-7-oneTmp (psoralen)
名称をさらに表示
トリオキシサレントリメチルプソラレン2,5,9-トリメチル-7H-フロ[3,2-g][1]ベンゾピラン-7-オン4,5',8-トリメチルプソラレントリメチルソラレントリソラレントリオキスサレン4,2',8-トリメチルプソラレン４，５´，８－トリメチルプソラーレントリオキシサレン 4,5',8-トリメチルソラレン4,5,8-トリメチルプソラレン４，５，８トリメチルプソラレン4,5',8-トリメチルソラレン2,5,9-トリメチルフロ[3,2-g]ベンゾピラン-7-オン4,5,8‐トリメチルプソラレントリオキサレン4,8,5'-トリメチルソラレントリオキシサレン (JAN)2,5,9-トリメチル-7H-フロ[3,2-g]クロメン-7-オン4,5′,8-トリメチルプソラレンLACTONENSC-71047TrioxalenTrioxsaleTrixsalen
物性
構造計算による物性
- XLogP
- 3
- 極性表面積
- 39.4 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 17
- 形式電荷
- 0
- 複雑度
- 374
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP3.25
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
Collision Cross Section
147.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
146.69 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 229 · 229-231 °C(lit.)
- 沸点
- 310.05 °C · 310.05°C (rough estimate)
- 比重(密度)
- 1.2196 · 1.2196 (rough estimate)
- 屈折率
- 1.5557 · 1.5557 (estimate)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- DMSO：可溶
- 外見
- 粉
- 色
- 白い
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P203, P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Other Safety InformationIMAP assessments - 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: Human health tier I assessment
Hazard Classes and CategoriesSkin Corr. 1B (100%)
毒性情報
Carcinogen Classification
4,5',8-Trimethylpsoralen
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 40: (1986) Some Naturally Occurring and Synthetic Food Components, Furocoumarins and Ultraviolet Radiation
1987
1987
安全データ
- F
- 8-10
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- LV1576000
- ridadr
- UN 1759 8/PG 1
- hs_code
- 29322985
- risk_code
- 34-40
- hazard_code
- C
- safety_code
- 26-36/37/39-45
化学と産業
薬理情報
ATC Code
D - Dermatologicals
D - Dermatologicals
QD - Dermatologicals
QD - Dermatologicals
PharmacodynamicsTrioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.
Mechanism of ActionAfter photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.
FDA Pharmacological Classification
Y6UY8OV51T
TRIOXSALEN
Established Pharmacologic Class [EPC] - Psoralen
Chemical Structure [CS] - Psoralens
Trioxsalen is a Psoralen.
MeSH Pharmacological Classification
Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
Cellular LocationsCytoplasm
用途と製造
General Manufacturing Information7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: INACTIVE
応用分野
解説エステルの官能基－CO－O－を環内に含む化合物で，環状エステルの性質をもつ．ふつうのラクトンは五員環・六員環の構造をもつγ-ラクトン，δ-ラクトンであるが，四員環のβ-ラクトン，七員環またはそれ以上の大環状ラクトンもある．
用途薬理研究用、ソラレン光反応による核酸の2次構造と機能研究用。
関連反応
2 件
化合物ノート
読み込み中…