Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
칸타리딘
칸타리딘 · (1R,2S)-헥사하이드로-1,2-다이메틸-3,6-에폭시프탈릭안하이드라이드 · (1R,2S)-헥사하이드로-1,2-다이메틸-3,6-에폭시프탈릭안하이드라이드(칸타리딘) · Cantharidine · Cantharone · cantharides · (1r,2s,3r,6s)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride · Canthari
식별자 및 물리적 특성
| CAS No. | 56-25-7 |
|---|---|
| 분자식 | C10H12O4 |
| 평균 분자량 | 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 |
| 현지명 | 칸타리딘 |
화학 및 물리적 성질
| XLogP | 0.6 |
|---|---|
| 극성 표면적 | 52.6 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 318 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| Color/Form | Orthorhombic plates, scales |
| 용해도 | 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), 아세톤(8 mg/ml), 에탄올(8 mg/ml), 클로로포름(1:65), 에테르(1:560) 및 에틸 아세테이트(1:150)에 용해됩니다. |
| Human Drugs | FDA approved drugs -> Active ingredient |
| 끓는 점 | 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. |
| 녹는점 | 424 °F (EPA, 1998)218 °C215-217 °C (lit.) |
| 증기압 | 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 Ų [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. |
| 밀도 | 1.0357 (rough estimate) |
| 굴절률 | 1.4699 (estimate) |
| 저장 조건 | 2-8°C |
| 물리적 상태 | 액체 |
| 색상 | 하얀색 |
| 생물학적 소스 | insect |
| 용해도 | 30mg/L(20℃) |
| Merck | 14,1752 |
| 안정성 | 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 2주 동안 보관할 수 있습니다. |
| 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(분배 계수) | -0.409 (est) |
| NIST | Cantharidin(56-25-7) |
| EPA | Cantharidin (56-25-7) |
화학적 성질
Cantharidin is a brown to black powder.
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | Cantharidin: HSNO Approval: HSR006361 Approved with controls |
| 운송 라벨(DOT) | Poison |
| 화재 위험 | When heated to decomposition it emits acrid smoke and irritating fumes. (EPA, 1998) |
| 건강 유해성 | 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 요건 | 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). |
| 반응성 그룹 | 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 보고 수량 | 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%) |
| 소화 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 응급 처치 | Signs and Symptoms of Acute Cantharidin Exposure: Acute exposure to cantharidin may produce the following signs and symptoms: salivation, difficulty in swallowing, thirst, severe vesication (blistering) of the upper gastrointestinal tract following ingestion, abdominal pain, vomiting and bloody diarrhea. Excessive, painful and bloody urination may be noted. Tachycardia (rapid heart beat) with normal blood pressure, hypotension (low blood pressure), and abnormal heart conduction are not uncommon. Eye contact may cause irritation with swelling of the lidsdermal contact may cause swelling followed by formation of blisters within 24 hours. Mental confusion, tetanic convulsions and fainting may be noted. Ataxia may progress to coma. |
| 비화재 누출 대응 | Avoid inhalation and skin contact. (EPA, 1998) |
| 처리 방법 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Protective Action Criteria (PAC) | 0.39 [mg/m3]4.3 [mg/m3]27 [mg/m3] |
| Personal Protective Equipment (PPE) | For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998) |
| 상호 작용 | CANTHARIDIN, IN THE INCUBATION MEDIUM CONTAINING SUCCINATE OR SODIUM D,L-BETA-HYDROXYBUTYRATE, CAUSES UNCOUPLING OF OXIDATIVE PHOSPHORYLATION IN MITOCHONDRIA FROM LIVER OF THE RAT. |
| Natural Pollution Sources | Cantharidin, the active ingredient in the crude drug cantharides, is obtained from the dried insects Cantharis vesicatoria. |
| Human Toxicity Excerpts | WHEN TAKEN ORALLY IT CAUSES VOMITING, PURGING, ABDOMINAL PAIN, AND SHOCK. ... /IT/ IRRITATES ENTIRE URINARY TRACT. IRRITATION OF BLADDER CAUSES URGENCY OF URINATION, AND IRRITATION OF URETHRA MAY RESULT IN PRIAPISM.DEATH MAY OCCUR RAPIDLY IN HYPOVOLEMIC SHOCK.... IN CONTACT WITH HUMAN ... EYES CAUSES CONJUNCTIVITIS, KERATITIS, AND IRITIS, WITH MUCH EDEMA OF THE LIDS.VESICANT CONTACTS SKIN WHEN BEETLE IS KILLED BY CRUSHING BLOW ... INITIAL TISSUE REACTION IS ERYTHEMA FOLLOWED BY VESICLE FORMATION WITHIN 24 HR.For more Human Toxicity Excerpts (Complete) data for CANTHARIDINE (12 total), please visit the HSDB record page. |
| Carcinogen Classification | CantharidinGroup 3: Not classifiable as to its carcinogenicity to humansVolume 10: (1976) Some Naturally Occurring Substances1987 |
| Non-Human Toxicity Excerpts | Toxic doses of cantharides are of the order of 15 g in the horse and ox, 4 g in the sheep and 2 g in the dog. When taken by mouth in large doses they produce severe irritation of the gastrointestinal tract and of the kidneys, inducing albuminuria and, later, nephritis. They also have a stimulant action and cause quickened respiration and excitement, followed by coma and collapse. /Cantharides/EXPERIMENTALLY INJECTED INTO ANTERIOR CHAMBER OF RABBITS, CANTHARIDES CAUSES FIBRINOUS EXUDATE, HYPEREMIA, ACCUMULATION OF LEUKOCYTES AND EXTENSIVE NECROSIS. INTRAOCULAR PRESSURE IS LOWERED ... . /CANTHARIDES/HAS BEEN SHOWN ... TO POISON MITOCHONDRIA AND TO CAUSE CHANGES IN CELL MEMBRANES, EPIDERMAL CELL DYSHESION, AND ACANTHOLYSIS.A GROUP OF HR/HR HAIRLESS MICE OF BOTH SEXES, 8-10 WK OLD, RECEIVED TWICE WEEKLY SKIN APPLICATIONS TO THE DORSAL SKIN OF A SOLUTION OF 0.016% CANTHARIDIN IN BENZENE FOR LIFESPAN. ... 32 MICE SURVIVED APPEARANCE OF FIRST TUMOR & 10 MICE DEVELOPED SKIN TUMORS, INCL 2 SQUAMOUS CELL CARCINOMAS. INTERNAL TUMORS WERE PRESENT IN 17 ANIMALS (51.6%) AND 9 MICE (28%) HAD RETICULUM CELL TUMORS ORMALIGNANT LYMPHOMAS. ... 7.3% OF /CONTROLS PAINTED WITH BENZENE/ ... DEVELOPED SKIN PAPILLOMAS AFTER 10-14 MO.For more Non-Human Toxicity Excerpts (Complete) data for CANTHARIDINE (10 total), please visit the HSDB record page. |
| Evidence for Carcinogenicity | Classification of carcinogenicity: 1) evidence in humans: No adequate data2) evidence in animals: Limited evidence. Overall summary evaluation of carcinogenic risk to humans is Group 3: The agent is not classifiable as to its carcinogenicity to humans. /From table/ |
| Antidote and Emergency Treatment | Basic Treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation at the first sign of upper airway obstruction may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/ |
| Non-Human Toxicity Values | TOXIC DOSES OF CANTHARIDES ARE ... 15 G IN HORSE AND OX ... 4 G IN SHEEP, & 2 G IN DOG.LD50 Mouse ip 1 mg/kg |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | RN8575000 |
| 운송 번호(UN) | UN 2811 6.1/PG 1 |
| 관세 코드 | 29329990 |
| 위험 문구(R) | 28-36/37/38-38-37-36-23/24/25 |
| 위험 표시 | T+,T |
| 안전 문구(S) | 53-45-36/37/39 |
| 포장분류 | I |
| 위험 등급 | 6.1(a)Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 유해 물질 데이터 | 56-25-7(Hazardous Substances Data) |
용도
용도
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.
일반 설명
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.