기본 정보
- CAS
1143-38-0- 표준 SMILES
O=C1c2c(O)cccc2Cc2cccc(O)c21- InChIKey
NUZWLKWWNNJHPT-UHFFFAOYSA-N- 분자식
- C14H10O3
- 평균 분자량
- 226.23 g/mol
- 단동위원소 질량
- 226.06299418
이름 및 식별자
- 우선 이름
- Anthralin
- IUPAC
- 1,8-dihydroxy-10H-anthracen-9-one
- 현지명
- 안트랄린
- 영어명
- ANTHRALIN
- 분자식
- C14H10O3
- 분자량
- 226.23
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
1143-38-0- PubChem CID
- 2202
- DTXSID
DTXSID7024538- ChEMBL
CHEMBL46469- ChEBI
CHEBI:37510- UNII
- U8CJK0JH5M
- EC Number
- 214-538-0
- Nikkaji
- J5.224H
물성
구조 계산 물성
- XLogP
- 3.2
- 극성 표면적
- 57.5 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 17
- 형식 전하
- 0
- 복잡도
- 287
실험 및 물리화학적 성질
Solubility
less than 1 mg/mL at 68 °F (NTP, 1992)
not soluble in water
Melting Point
349 to 358 °F (NTP, 1992)
178-182 °C
Collision Cross Section
142.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
142.24 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];142.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];151.92 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 178 · 178-181 °C (lit.)
- 끓는 점
- 464.1 · 464.1±45.0 °C(Predicted)
- 밀도
- 1.419 · 1.419±0.06 g/cm3(Predicted)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 물에 거의 녹지 않고, 염화메틸렌에 녹고, 아세톤에 조금 녹고, 에탄올에 약간 녹습니다(96%). 알칼리 수산화물의 묽은 용액에 용해됩니다.
- 물리적 상태
- Solid
- 산도 계수 (pKa)
- 7.16 · 7.16±0.20(Predicted)
- 색상
- 노란색에서 주황색, 진한 노란색까지
- 수용성
- 물에 불용성. 아세트산, 클로로포름(20 mg/mL), 아세톤, 벤젠, 알칼리 수산화물 용액, 고정 오일에 용해됩니다. 95% 에탄올, 알코올, 에테르 및 빙초산에 약간 용해됩니다.
- Merck
- 14 · 14,684
- BRN
- 2054360 · 2054360
- 안정성
- 안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
- InChI
- 1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2
- InChIKey
- NUZWLKWWNNJHPT-UHFFFAOYSA-N
- SMILES
- Oc1cccc2Cc3cccc(O)c3C(=O)c12
- EPA
- Dithranol (1143-38-0)
화학적 성질
Yellow Crystalline Solid
안전 및 규제
GHS 분류
GHS Classification
Warning
H315 (98.3%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (98.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (96.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
Regulatory Information
Chemical: 9(10H)-Anthracenone,1,8-dihydroxy-
Anthralin: Does not have an individual approval but may be used under an appropriate group standard
안전 및 보호
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should protect this material from light and moisture, and store it in a refrigerator. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
독성 정보
Carcinogen Classification
Dithranol
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 13: (1977) Some Miscellaneous Pharmaceutical Substances;Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)
1987
1987
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Topical anthralin has not been studied during breastfeeding. Anthralin has suspected mutagenic properties, so it should only be used if the potential benefit to the mother justifies potential risk to the infant. If anthralin is used, ensure that the infant's skin does not come into direct contact with the areas of maternal skin that have been treated and the infant does not ingest the product from the mother's skin.;◉ 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.
규제 정보
Regulatory Information
Chemical: 9(10H)-Anthracenone,1,8-dihydroxy-
Anthralin: Does not have an individual approval but may be used under an appropriate group standard
안전 데이터
- wgk
- 3
- rtecs
- CB8927000
- HS 번호
- 29144000
- risk_code
- 36/37/38-45
- hazard_code
- Xi,T
- safety_code
- 26-53-45
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
D - Dermatologicals;D05 - Antipsoriatics;D05A - Antipsoriatics for topical use;D05AC - Antracen derivatives;D05AC01 - Dithranol
QD - Dermatologicals;QD05 - Drugs for keratoseborrheic disorders (atc human: antipsoriatics);QD05A - Drugs for keratoseborrheic disorders, topical use (atc human: antipsoriatics for topical use);QD05AC - Antracen derivatives;QD05AC01 - Dithranol
Pharmacodynamics
Anthralin is a natural anthraquinone derivative, anti-psoriatic and anti-inflammatory agent. It controls skin growth by reducing the synthesis of DNA and the mitotic activity in the hyperplastic epidermis, normalizing the rate of cell proliferation and keratinization.
Mechanism of Action
Anthralin inhibits the proliferation of keratinocytes (epidermal skin cells), prevents the action of T-cells, and promotes cell differentiation, likely through mitochondrial dysfunction. In addition, the production of free radicals may contribute to its anti-psoriatic effect. In vitro studies demonstrate that anthralin prolongs the prophase component of mitosis for keratinocytes and leukocytes. Prophase is the first step of mitosis, the process separating the duplicated genetic material carried in the nucleus of a parent cell into two identical daughter cells. In vivo studies demonstrate that anthralin blocks DNA synthesis and can increase the release of reactive oxygen species. Anthralin is believed to normalize the rate of epidermal cell proliferation and keratinization by reducing the mitotic activity of the epidermal hyperplasia in psoriasis. Anti-proliferative and anti-inflammatory effects of anthralin have been demonstrated on both psoriatic and healthy skin. The anti-proliferative effects of anthralin are thought to be due to a combination of inhibition of DNA synthesis and its strong reducing properties. The effectiveness of anthralin as an anti-psoriatic agent is partly owed to its ability to promote lipid peroxidation and reduce the concentration of endothelial adhesion molecules, which are found to be elevated in psoriatic patients,. Recent studies suggest that its ability to prevent T-lymphocyte activation and normalize keratinocyte differentiation may occur by a direct effect on mitochondria.
Metabolism/Metabolites
Anthralin is administered topically. Although the extent of systemic absorption after topical application has not been determined, no traces of anthraquinone metabolites were detected in the urine of treated subjects in a limited clinical study of anthralin cream,. Anthralin does not inhibit hepatic microsomal enzyme activity.
용도 및 제조
Uses
Synthetic Polymer MALDI Matrix Compounds
Use (kg; approx.) in Germany (2009): >10;Consumption (g per capita; approx.) in Germany (2009): 0.000122;Calculated removal (%): 80.4
응용 분야
개요Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation. It increases apoptosis and inhibits proliferation of normal human keratinocytes (NHKs) when used at a concentration of 2.5 μM. It also decreases the mitochondrial membrane potential, increases cytochrome c release, and induces perinuclear mitochondrial clustering in NHKs when used at a concentration of 5 μM. Anthralin (0.25 μM) decreases the expression of β-defensin-2 and S100 calcium-binding protein A9 (S100A9) and increases the expression of IL-6 and IL-8 in IL-17A- and IL-22-stimulated NHKs. It also inhibits leukotriene B4 (LTB4; ) production, stimulated by the calcium ionophore A23187 , from human neutrophils (IC50 = 7 μM). Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.
용도Antipsoriatic
일반 설명Lemon yellow leaflets or plates or an orange powder. Melting point 176-181°C. No odor or taste. Insoluble in water. Moderately toxic by ingestion, inhalation and skin absorption. Used as a treatment for psoriasis.
상·하류 제품 정보
하류 제품
공급사100 곳
추가 설명
정의ChEBI: An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.
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