기본 정보
- CAS
112118-18-0- 표준 SMILES
CC(=O)Oc1cccc2c1C(=O)c1c(OC(C)=O)cc(C(=O)O)cc1C2=O- InChIKey
TYNLGDBUJLVSMA-UHFFFAOYSA-N- 분자식
- C19H12O8
- 평균 분자량
- 368.3 g/mol
- 단동위원소 질량
- 368.05321734
이름 및 식별자
- 우선 이름
- Diacerein
- IUPAC
- 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
- 현지명
- 디아세레인
- 영어명
- Diacerein
- 분자식
- C19H12O8
- 분자량
- 368.29
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
112118-18-0、13739-02-1- PubChem CID
- 26248
- DTXSID
DTXSID4045636- ChEMBL
CHEMBL41286- ChEBI
CHEBI:94708- UNII
- 4HU6J11EL5
- EC Number
- 237-310-2、839-256-0
- Nikkaji
- J14.479G
물성
구조 계산 물성
- XLogP
- 1.9
- 극성 표면적
- 124 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 27
- 형식 전하
- 0
- 복잡도
- 683
실험 및 물리화학적 성질
Collision Cross Section
171.33 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];170.4 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];168.12 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];169.49 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 217 · 217-2180C
- 끓는 점
- 631.5 · 631.5±55.0 °C(Predicted)
- 밀도
- 1.491 · 1.491±0.06 g/cm3(Predicted)
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- DMSO(적게), 메탄올(약간)에 용해됨
- 물리적 상태
- Solid
- 산도 계수 (pKa)
- 3.01 · 3.01±0.20(Predicted)
- 색상
- 밝은 노란색에서 노란색까지
- 수용성
- 240 μg/L · 240μg/L at 25℃
- Merck
- 14 · 14,2960
- InChI
- InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)
- InChIKey
- TYNLGDBUJLVSMA-UHFFFAOYSA-N
- SMILES
- C1=C2C(C(=O)C3=C(C2=O)C=CC=C3OC(C)=O)=C(OC(C)=O)C=C1C(O)=O
- LogP
- 3.126 · 3.126 (est)
화학적 성질
Yellow Crystalline Solid
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 3.3% (2 of 60) of reports.
Warning
H315 (96.7%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (96.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (95%): 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 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 2 of 60 reports by companies.;There are 6 notifications provided by 58 of 60 reports by companies with hazard statement code(s).;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
Status: Active Update: 27-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23352
Status: Active Update: 30-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31372
Hazard Classes and Categories
Skin Irrit. 2 (96.7%);Eye Irrit. 2 (96.7%);STOT SE 3 (95%)
Not Classified
독성 정보
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Diacerein
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
규제 정보
Regulatory Information
Status: Active Update: 27-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23352
Status: Active Update: 30-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31372
안전 데이터
- wgk
- 3
- rtecs
- CB8781000
- 독성
- rat,LD50,unreported,7500mg/kg (7500mg/kg),Drugs of the Future. Vol. 4, Pg. 445, 1979.
- HS 번호
- 29146990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
M - Musculo-skeletal system;M01 - Antiinflammatory and antirheumatic products;M01A - Antiinflammatory and antirheumatic products, non-steroids;M01AX - Other antiinflammatory and antirheumatic agents, non-steroids;M01AX21 - Diacerein
QM - Musculo-skeletal system;QM01 - Antiinflammatory and antirheumatic products;QM01A - Antiinflammatory and antirheumatic products, non-steroids;QM01AX - Other antiinflammatory and antirheumatic agents, non-steroids;QM01AX21 - Diacerein
Mechanism of Action
Diacerein's active metabolite rhein [DB13174] reduces cartilage destruction by decreasing expression of matrix metalloproteinase (MMP)-1 and -3 as well as upregulating tissue inhibitor of matrix metalloproteinases which serve to reduce the activity of several MMPs. The anti-inflammatory action of rhein reduces the level of interleukin-1beta activity which plays a large role in reduction of extracellular matrix production, MMP activity, and continued inflammation. Rhein reduces abnormal osteoblast synthetic activity through an unknown mechanism.
Absorption, Distribution and Excretion
Bioavailability of 50-60%. Entirely converted to the active metabolite rhein [DB13174] before reaching systemic circulation.
37% excreted in urine and 53% in feces as estimated in rats.
15-60L.
Total CL is 1.5L/h and renal CL is 0.1L/h.
용도 및 제조
응용 분야
개요Diacerein is a disease-modifying antirheumatic drug (DMARD), reported to be useful in the treatment of various inflammatory conditions, including osteoarthritis. It forms water soluble chelates with calcium and copper, acting ultimately to reduce the activity of lysosomal enzymes and decrease the formation of rheumatoid factor.
용도Diacerein is a diacetyl precursor of rhein, an anthraquinone found in plants. Rhein, at 10 μM, inhibits IL-1β signaling, suppressing signaling through NF-κB and AP-1, and reduces the expression of the matrix metalloproteases MMP-1 and MMP-13. Diacerein, presumably after conversion to rhein, down-regulates the expression of the IL-1β receptor on articular chondrocytes, enhances the expression of TGF-β, and increases collagen and aggrecan. It does not alter COX activity. It is mildly effective in ameliorating osteoarthritis.
상·하류 제품 정보
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공급사100 곳
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