カンタリジン

exo-1,2-cis-ジメチル-3,6-エポキシヘキサヒドロフタル酸無水物 · カンタリデスカンファー · カンタロン · (1β,4β)-2α,3α-ジメチル-7-オキサビシクロ[2.2.1]ヘプタン-2,3-ジカルボン酸無水物 · 3a,4,5,6,7,7a-ヘキサヒドロ-3aα,7aα-ジメチル-4β,7β-エポキシイソベンゾフラン-1,3-ジオン · カンタリジン · (1R,2S,6R,7S)-2,6-ジメチル-4,10-ジオキサトリシクロ[5.2.1.02,6]デカン-3,5-ジオン · Cantharidine

https://huagongshe.com/ja/chemical/5944

識別子と物理属性

CAS No.	56-25-7
分子式	C10H12O4
平均分子量	196.2 g/mol
SMILES	C[C@@]12C(=O)OC(=O)[C@]1(C)[C@H]1CC[C@@H]2O1
InChIKey	DHZBEENLJMYSHQ-XCVPVQRUSA-N
PubChem CID	5944
ChEMBL	CHEMBL48449
ChEBI	CHEBI:64213
EC No.	200-263-3
現地名	カンタリジン

化学・物理的性質

XLogP	0.6
極性表面積	52.6
水素結合供与体数	0
水素結合受容体数	4
回転可能結合数	0
重原子数	14
形式電荷	0
複雑度	318
医薬品	Pharmaceuticals -> Listed in ZINC15
Color/Form	Orthorhombic plates, scales
溶解度	Insol in cold watersomewhat sol in hot water1 g dissolves in 40 ml acetone, 65 ml chloroform1 g dissolves in 560 ml ether, 150 ml ethyl acetatesol in oils.SOL IN CONCN SULFURIC ACID, ACETIC ACIDSLIGHTLY SOL IN BENZENE, ALCOHOLIn water, 31 mg/l @ 20 °C.DMSO (25 mg/ml 加熱)、アセトン (8 mg/ml)、エタノール (8 mg/ml 加熱)、クロロホルム (1:65)、エーテル (1:560)、酢酸エチル (1:150) に可溶。30mg/L(20℃)
Human Drugs	FDA approved drugs -> Active ingredient
沸点	Sublimes at 230 °F (EPA, 1998)Sublimes @ 84 °C253.08°C (rough estimate)
Decomposition	When heated to decomposition it emits acrid smoke and irritating fumes.
融点	424 °F (EPA, 1998)218 °C215-217 °C (lit.)
蒸気圧	0.02 [mm Hg] @25 °C
Physical Description	Cantharidin appears as brown to black powder or plates or scales. Formerly used as a counterirritant and vesicant. Used for the removal of warts. Used as an experimental anti tumor agent. Active ingredient in spanish fly, a reputed aphrodisiac. (EPA, 1998)
Collision Cross Section	137.27 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental Properties	Sublimes at about 110 °C (12 mm Hg, 3-5 mm distance)Hydrolyzed to cantharinic acid.
密度	1.0357 (rough estimate)
屈折率	1.4699 (estimate)
貯蔵条件	2-8°C
外観・状態	解決
色	白い
由来生物	insect
Merck	14,1752
安定性	購入日から2年間安定です。この DMSO またはエタノール溶液は、-20°C で 2 週間保存できます。
InChI	1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9+,10-
InChIKey	DHZBEENLJMYSHQ-XCVPVQRUSA-N
SMILES	C[C@]12C3CCC(O3)[C@@]1(C)C(=O)OC2=O
LogP（分配係数）	-0.409 (est)
CAS データベース	56-25-7(CAS DataBase Reference)
NISTの化学物質情報	Cantharidin(56-25-7)
EPAの化学物質情報	Cantharidin (56-25-7)

化学的特性

Cantharidin is a brown to black powder.

安全性と法規制

GHS 分類	DangerH300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	Cantharidin: HSNO Approval: HSR006361 Approved with controls
輸送ラベル（DOT）	Poison
火災危険	When heated to decomposition it emits acrid smoke and irritating fumes. (EPA, 1998)
健康有害性	It is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste of less than 7 drops for a 70 kg (150 lb.) person. It is very toxic by absorption through skin. (EPA, 1998)
FDA 要件	Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).
反応性グループ	Anhydrides
Reactivity Profile	Organic anhydrides, such as CANTHARIDIN, are incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
Air and Water Reactions	No rapid reaction with air. No rapid reaction with water.
CERCLA 報告数量	Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Cantharidin is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100/10,000 lbs.
Hazard Classes and Categories	Acute Tox. 2 (100%)
消火	Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

用途

解説

化学式はC1(/0)H12O4。カンタリジンは，ツチハンミョウ，マメハンミョウなどの甲虫が分泌する無水酸。人に触れると皮膚内に浸透し，種々の刺激作用を呈し，排出に際して強く尿路を刺激し腎炎を起こすこともある。日本薬局方のカンタリスは0.6％以上のカンタリジンを含み，皮膚刺激剤，発泡剤として用いられる。→関連項目ツチハンミョウ｜マメハンミョウ株式会社平凡社百科事典マイペディアについて情報

使用

Cantharidin is a natural toxin produced by blister beetles that moderately inhibits protein phosphatases 1 (PP1) (IC50 = 1.7 μM) and PP2A (IC50 = 0.2 μM) and only weakly inhibits the activity of PP2B (IC50 = 1 mM). It has been shown to stimulate cell cycle progression and induce premature mitosis, used topically (0.7%) as an anti-wart treatment, and has been shown to be active in cervical, tongue, neuroblastoma, bone, leukemia, ovarian, colon, and various other cancer cell lines.

一般的な説明

Brown to black powder or plates or scales. Formerly used as a counterirritant and vesicant. Used for the removal of warts. Used as an experimental anti tumor agent. Active ingredient in spanish fly, a reputed aphrodisiac.