디아세레인

Diacerein

HCID 26248

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

Diacerein13739-02-1DiacetylrheinArtrodarDiacerheinFisiodar1,8-DIACETOXY-3-CARBOXYANTHRAQUINONEDiacereineSF-277DiacereinaVerborilZondar
이름 더 보기
디아세레인DARDiacerein impurity mixture CRSDiacetineSF 277ICN17261ICN 17261
Diora4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acidDiacereinumRhein diacetate2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-M01AX214,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic AcidAC-201

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

실험 및 물리화학적 성질

Collision Cross Section · 1건

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

화학적 성질

Yellow Crystalline Solid

안전 및 규제

GHS 분류

GHS Classification · 6건

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 · 2건

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 · 2건

Skin Irrit. 2 (96.7%);Eye Irrit. 2 (96.7%);STOT SE 3 (95%)

Not Classified

독성 정보

Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Diacerein

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

규제 정보

Regulatory Information · 2건

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

화학 및 산업

약리 정보

ATC Code · 2건

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

Protein Binding99% of rhein is bound to plasma proteins.
PharmacodynamicsDecreases inflammation and cartilage destruction and also corrects altered osteoblast acitivity.
Mechanism of Action · 1건

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.

Biological Half-Life4-10h.
Metabolism/MetabolitesEntirely converted to rhien [DB13174] through double deacetylation before reaching systemic circulation. Rhein [DB13174] is further metabolized to rhein glucuronide and rhein sulfate.

용도 및 제조

Use ClassificationPharmaceuticals
응용 분야 · 2건

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

상류 원료

공급사100 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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4건

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