CAS 112118-18-0 Diacerein (HCID 26248)

名称と識別子

優先名称: Diacerein
IUPAC: 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
現地名: ジアセレイン
英語名: Diacerein
分子式: C19H12O8
分子量: 368.29

名称と別名

Diacerein13739-02-1DiacetylrheinArtrodarDiacerheinFisiodar1,8-DIACETOXY-3-CARBOXYANTHRAQUINONEDiacereineSF-277DiacereinaVerborilZondar

名称をさらに表示

4,5-ジアセトキシ-9,10-ジオキソ-9,10-ジヒドロアントラセン-2-カルボン酸4,5-ジアセトキシ-9,10-ジオキソ-2-アントラセンカルボン酸ジアセチルレイン4,5-ビス(アセチルオキシ)-9,10-ジヒドロ-9,10-ジオキソアントラセン-2-カルボン酸4,5-ジアセチルレイン4,5-ジアセトキシ-9,10-ジヒドロ-9,10-ジオキソ-2-アントラセンカルボン酸ジアセレインフィシオダルアルトロダル4,5-ジアセトキシ-9,10-ジヒドロ-9,10-ジオキソアントラセン-2-カルボン酸4,5-ジアセトキシアントラキノン-2-カルボン酸1,8-ジアセトキシ-3-カルボキシアントラキノン4,5-ビス(アセチルオキシ)-9,10-ジオキソ-9,10-ジヒドロアントラセン-2-カルボン酸DARDiacerein 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

データベース識別子

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

物性

構造計算による物性

XLogP: 1.9
極性表面積: 124 Å²
水素結合供与体数: 1
水素結合受容体数: 8
回転可能結合数: 5
重原子数: 27
形式電荷: 0
複雑度: 683

実験および物理化学的性質

Collision Cross Section · 1 件

171.33 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；170.4 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；168.12 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；169.49 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 217 · 217-2180C
沸点: 631.5 · 631.5±55.0 °C(Predicted)
比重(密度): 1.491 · 1.491±0.06 g/cm3(Predicted)
貯蔵温度: Sealed in dry,Room Temperature
溶解性: DMSO（少量）、メタノール（少量）
外見: Solid
酸解離定数(Pka): 3.01 · 3.01±0.20(Predicted)
色: 薄黄色～黄色
水溶解度: 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)
CAS データベース: 13739 · 13739-02-1(CAS DataBase Reference)

化学的性質

化学的特性Yellow Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

Regulatory Information · 2 件

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 · 2 件

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

Not Classified

毒性情報

Drug Induced Liver Injury · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Diacerein

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

法規制情報

Regulatory Information · 2 件

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

安全データ

wgk: 3
rtecs: CB8781000
毒性: rat,LD50,unreported,7500mg/kg (7500mg/kg),Drugs of the Future. Vol. 4, Pg. 445, 1979.
hs_code: 29146990
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 2 件

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 · 1 件

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.

用途と製造

Use ClassificationPharmaceuticals

応用分野 · 2 件

説明Diacerein 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.

使用Diacerein 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.

上流・下流製品情報

上流原料

9,10-ジヒドロ-4,5-ジヒドロキシ-9,10-ジオキソアントラセン-2-カルボン酸

サプライヤー100 社

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]

化合物ノート

読み込み中…

ジアセレイン

基本情報