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53-86-1 分子结构
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2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid

ChemBase编号:213
分子式:C19H16ClNO4
平均质量:357.78764
单一同位素质量:357.07678568
SMILES和InChIs

SMILES:
Clc1ccc(C(=O)n2c3c(c(c2C)CC(=O)O)cc(OC)cc3)cc1
Canonical SMILES:
COc1ccc2c(c1)c(CC(=O)O)c(n2C(=O)c1ccc(cc1)Cl)C
InChI:
InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
InChIKey:
CGIGDMFJXJATDK-UHFFFAOYSA-N

引用这个纪录

CBID:213 http://www.chembase.cn/molecule-213.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
IUPAC传统名
indomethacin
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
商标名
Amuno
Apo-Indomethacin
Argun
Arthrexin
Artracin
Artrinovo
Artrivia
Bonidin
Bonidon
Bonidon Gel
Catlep
Chibro-Amuno
Chrono-Indicid
Chrono-Indocid
Confortid
Dolcidium
Dolcidium Pl
Dolovin
Durametacin
Elmetacin
Flexin Continus
Hicin
Idomethine
Imbrilon
Inacid
Indacin
Indameth
Indmethacine
Indo-Lemmon
Indo-Phlogont
Indo-Rectolmin
Indo-Spray
Indo-Tablinen
Indocid
Indocid Pda
Indocid Sr
Indocin
Indocin I.V
Indocin I.V.
Indocin Sr
Indolar Sr
Indomecol
Indomed
Indomee
Indomethegan
Indomo
Indomod
Indoptic
Indoptol
Indorektal
Indoxen
Inflazon
Infrocin
Inteban Sp
Lausit
Liometacen
Metacen
Metartril
Methazine
Metindol
Miametan
Mikametan
Mobilan
Novo-Methacin
Novomethacin
Nu-Indo
Reumacide
Rhemacin La
Rheumacin La
Sadoreum
Tannex
Vonum
Indaflex
别名
1-(4-氯苯甲酰基)-5-甲氧基-2-甲基-3-吲哚乙酸
吲哚美辛
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid
Indomethacin
1-[p-Chlorobenzoyl]-5-methoxy-2-methylindole-3-acetic acid
IMN
Indomethacinum
Indomethacine
Indometacyna
Indometacine
Indomethancin
Indomethazine
Indomethine
Indometicina
indomethacin
Indomethacin
Indochron E-R
Indocin-SR
Artracin
Flexin
Imbrilon
Indocid
Indocin
Indomed
Mobilan
Indometacin
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic Acid
CAS号
53-86-1
53-86-1
EC号
200-186-5
MDL号
MFCD00057095
Beilstein号
497341
默克索引号
144968
PubChem SID
24896136
46508291
24278173
160963676
PubChem CID
3715

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 3.802744  质子受体
质子供体 LogD (pH = 5.5) 1.8301284 
LogD (pH = 7.4) 0.2685538  Log P 3.5296743 
摩尔折射率 94.8106 cm3 极化性 37.338837 Å3
极化表面积 68.53 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 4.25  LOG S -5.17 
溶解度 2.40e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
0.937 mg/L expand 查看数据来源
Acetone expand 查看数据来源
Ethanol expand 查看数据来源
ethanol: soluble50 mg/mL, clear, yellow-green expand 查看数据来源
Ether expand 查看数据来源
外观
Off-White Solid expand 查看数据来源
熔点
155°C expand 查看数据来源
155°C Polymorphism expand 查看数据来源
155-162 °C expand 查看数据来源
158-161°C expand 查看数据来源
疏水性(logP)
3.4 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
Room Temperature (15-30°C), Protect from light expand 查看数据来源
RTECS编号
NL3500000 expand 查看数据来源
欧盟危险性物质标志
剧毒(Highly toxic) 剧毒(Highly toxic) (T+) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
UN2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
1 expand 查看数据来源
I expand 查看数据来源
澳大利亚Hazchem
2XE expand 查看数据来源
危险公开号
28 expand 查看数据来源
28-68 expand 查看数据来源
R:28 expand 查看数据来源
安全公开号
20-28-36/37-45 expand 查看数据来源
28-36/37-45 expand 查看数据来源
S:28-29-36/37/39-45 expand 查看数据来源
欧盟危险货物分类
T2 expand 查看数据来源
欧盟危险识别号(EUHIN)
6.1B expand 查看数据来源
美国ERG指导号
154 expand 查看数据来源
TSCA收录
expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H300 expand 查看数据来源
H300-H341 expand 查看数据来源
GHS警示性声明
P264-P301 + P310 expand 查看数据来源
P281-P301+P310-P321-P308+P313-P405-P501A expand 查看数据来源
个人保护装置
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 1 expand 查看数据来源
相关基因信息
human ... ALB(213), ALOX5(240), ELA2(1991), GPR44(11251), IL1A(3552), PLA2G1B(5319), PTGDR(5729), PTGS1(5742), PTGS2(5743)mouse ... Alox5(11689), Ptgdr(19214), Ptger1(19216), Ptger2(19217), Ptger3(19218), Ptger4(19219), Ptgs1(19224), Ptgs2(19225)rat ... Alox5(25290), Ptgs1(24693), Ptgs2(29527) expand 查看数据来源
human ... ALB(213), ALOX5(240), ELA2(1991), GPR44(11251), IL1A(3552), PLA2G1B(5319), PTGDR(5729), PTGS1(5742), PTGS2(5743)mouse ... Alox5(11689), Ptgdr(19214), Ptger1(19216), Ptger2(19217), Ptger3(19218), Ptger4(19219), Ptgs1(19224)rat ... Alox5(25290), Ptgs1(24693), Ptgs2(29527) expand 查看数据来源
生物活性机理
Possible cyclooxygenase-inhibitor. expand 查看数据来源
Prostaglandin-antagonist expand 查看数据来源
Prostaglandin-synthesis-inhibitor expand 查看数据来源
纯度
≥99% (TLC) expand 查看数据来源
≥99.0% (TLC) expand 查看数据来源
98% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
应用领域
Antiinflammatories expand 查看数据来源
Antipyretics expand 查看数据来源
Antirheumatics expand 查看数据来源
Empirical Formula (Hill Notation)
C19H16ClNO4 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02190217 external link
Crystalline
Inhibitor of cyclooxygenase.
DrugBank -  DB00328 external link
Item Information
Drug Groups approved; investigational
Description Indomethacin is a non-steroidal antiinflammatory agent (NSAIA) with antiinflammatory, analgesic and antipyretic activity. Its pharmacological effect is thought to be mediated through inhibition of the enzyme cyclooxygenase (COX), the enzyme responsible for catalyzes the rate-limiting step in prostaglandin synthesis via the arachidonic acid pathway.
Indication For moderate to severe rheumatoid arthritis including acute flares of chronic disease, ankylosing spondylitis, osteoarthritis, acute painful shoulder (bursitis and/or tendinitis) and acute gouty arthritis.
Pharmacology Indomethacin, a NSAIA, with analgesic and antipyretic properties exerts its pharmacological effects by inhibiting the synthesis of prostaglandins involved in pain, fever, and inflammation. Indomethacin inhibits the catalytic activity of the COX enzymes, the enzymes responsible for catalyzing the rate-limiting step in prostaglandin synthesis via the arachidonic acid pathway. Indomethacin is known to inhibit two well-characterized isoforms of COX, COX-1 and COX-2, with greater selectivity for COX-1. COX-1 is a constitutively expressed enzyme that is involved in gastric mucosal protection, platelet and kidney function. It catalyzes the conversion of arachidonic acid to prostaglandin (PG) G2 and PGG2 to PGH2. COX-1 is involved in the synthesis pathways of PGE2, PGD2, PDF2a, PGI2 (also known as prostacyclin) and thromboxane A2 (TXA2). COX-2 is constitutively expressed and highly inducible by inflammatory stimuli. It is found in the central nervous system, kidneys, uterus and other organs. It also catalyzes the conversion of arachidonic acid to PGG2 and PGG2 to PGH2. In the COX-2-mediated pathway, PGH2 is subsequently converted to PGE2 and PGI2 (also known as prostacyclin). PGE2 is involved in mediating inflammation, pain and fever. Decreasing levels of PGE2 leads to decreased inflammation.
Toxicity The following symptoms may be observed following overdosage: nausea, vomiting, intense headache, dizziness, mental confusion, disorientation, or lethargy. There have been reports of paresthesias, numbness, and convulsions. The oral LD50 of indomethacin in mice and rats (based on 14 day mortality response) was 50 and 12 mg/kg, respectively.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Bioavailability is approximately 100% following oral administration and 80–90% following rectal administration.
Half Life 4.5 hours
Protein Binding 97%
Elimination Indomethacin is eliminated via renal excretion, metabolism, and biliary excretion.
References
Akbarpour F, Afrasiabi A, Vaziri ND: Severe hyperkalemia caused by indomethacin and potassium supplementation. South Med J. 1985 Jun;78(6):756-7. [Pubmed]
HART FD, BOARDMAN PL: INDOMETHACIN: A NEW NON-STEROID ANTI-INFLAMMATORY AGENT. Br Med J. 1963 Oct 19;2(5363):965-70. [Pubmed]
Lum GM, Aisenbrey GA, Dunn MJ, Berl T, Schrier RW, McDonald KM: In vivo effect of indomethacin to potentiate the renal medullary cyclic AMP response to vasopressin. J Clin Invest. 1977 Jan;59(1):8-13. [Pubmed]
Phelan KM, Mosholder AD, Lu S: Lithium interaction with the cyclooxygenase 2 inhibitors rofecoxib and celecoxib and other nonsteroidal anti-inflammatory drugs. J Clin Psychiatry. 2003 Nov;64(11):1328-34. [Pubmed]
Ragheb M: The clinical significance of lithium-nonsteroidal anti-inflammatory drug interactions. J Clin Psychopharmacol. 1990 Oct;10(5):350-4. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1723 external link
Research Area: Inflammation
Biological Activity:
Indomethacin(Indocid, Indocin) is a non-steroidal anti-inflammatory drug commonly used to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms. It is marketed under many trade names, including Indocin, Indocid, Indochron E-R, and Indocin-SR. 
Sigma Aldrich -  I8280 external link
Biochem/physiol Actions
Used as a non-selective inhibitor of cyclooxygenases, COX1 and COX2, leading to reduced prostaglandin biosynthesis from arachidonic acid.
环加氧酶 (COX) 抑制剂,对 COX-1 的选择性相对较高。
Sigma Aldrich -  I7378 external link
Biochem/physiol Actions
环加氧酶 (COX) 抑制剂,对 COX-1 的选择性相对较高。
Sigma Aldrich -  57413 external link
Biochem/physiol Actions
环加氧酶 (COX) 抑制剂,对 COX-1 的选择性相对较高。
Other Notes
Blocks prostaglandin biosynthesis.; Topography of prostaglandin H synthase1; Cyclooxygenase inhibitor2
Toronto Research Chemicals -  I641000 external link
Inhibits cyclooxygenase (IC50=0.1uM) selectively over liposygenases (IC50=100uM for 5-,12- and 15-LO). A clinically useful NAISD.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Akbarpour F, Afrasiabi A, Vaziri ND: Severe hyperkalemia caused by indomethacin and potassium supplementation. South Med J. 1985 Jun;78(6):756-7. Pubmed
  • HART FD, BOARDMAN PL: INDOMETHACIN: A NEW NON-STEROID ANTI-INFLAMMATORY AGENT. Br Med J. 1963 Oct 19;2(5363):965-70. Pubmed
  • Lum GM, Aisenbrey GA, Dunn MJ, Berl T, Schrier RW, McDonald KM: In vivo effect of indomethacin to potentiate the renal medullary cyclic AMP response to vasopressin. J Clin Invest. 1977 Jan;59(1):8-13. Pubmed
  • Phelan KM, Mosholder AD, Lu S: Lithium interaction with the cyclooxygenase 2 inhibitors rofecoxib and celecoxib and other nonsteroidal anti-inflammatory drugs. J Clin Psychiatry. 2003 Nov;64(11):1328-34. Pubmed
  • Ragheb M: The clinical significance of lithium-nonsteroidal anti-inflammatory drug interactions. J Clin Psychopharmacol. 1990 Oct;10(5):350-4. Pubmed
  • Salari, H., et al.: Prostagland. Leukotrienes Med., 13, 53 (1984)
  • Lehmann, J.M., et al.: J. Biol. Chem., 272, 3406 (1997)
  • Shen, T.Y. et al., J.A.C.S., 1963, 85, 488
  • Yamamato, H., Chem. Pharm. Bull., 1968, 16, 17, (synth)
  • Bertazzoni, D. et al., Boll. Chim. Farm., 1970, 109, 60, (synth)
  • Kistenmacher, T.J. et al., J.A.C.S., 1972, 94, 1340, (cryst struct)
  • Shen, T.Y. et al., Adv. Drug Res., 1977, 12, 89, (rev)
  • Singh, S.P. et al., J. Het. Chem., 1978, 15, 13, (pmr)
  • Helleberg, L., Clin. Pharmacokinet., 1981, 6, 245, (metab)
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  • Kaneniwa, N. et al., Chem. Pharm. Bull., 1985, 33, 3447, (synth, struct)
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