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22071-15-4 分子结构
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2-(3-benzoylphenyl)propanoic acid

ChemBase编号:882
分子式:C16H14O3
平均质量:254.28056
单一同位素质量:254.09429431
SMILES和InChIs

SMILES:
OC(=O)C(c1cc(ccc1)C(=O)c1ccccc1)C
Canonical SMILES:
OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)C
InChI:
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
InChIKey:
DKYWVDODHFEZIM-UHFFFAOYSA-N

引用这个纪录

CBID:882 http://www.chembase.cn/molecule-882.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-(3-benzoylphenyl)propanoic acid
IUPAC传统名
2-(3-benzoylphenyl)propanoic acid
ketoprofen
商标名
Actron
Alrheumat
Alrheumun
Capisten
Dexal
Epatec
Fastum
Iso-K
Kefenid
Ketopron
Lertus
Menamin
Meprofen
Orudis
Orudis KT
Orugesic
Oruvail
Oscorel
Profenid
Toprec
Toprek
别名
2-(3-苯甲酰苯基)丙酸
酮洛芬
Alrheumat
2-(3-benzoylphenyl)propanoic acid
Orudis
Oruvail
Ketoflam
Orudis KT
m-Benzoylhydratropic acid
Ketoprofen
2-[3-Benzoylphenyl]propionic acid
Ketoprofen
2-(3-Benzoylphenyl)propionic acid
3-Benzoyl-α-methylbenzeneacetic Acid
RP-19583
Alreumat
Alrheumun
Capisten
Epatec
Fastum
Ketofen
Menamin
Toprec
rac Ketoprofen
CAS号
22071-15-4
EC号
244-759-8
MDL号
MFCD00055790
PubChem SID
160964345
24896217
24860779
24278504
46505715
PubChem CID
3825
CHEBI ID
6128
ATC码
M01AE03
M01AE17
M02AA10
CHEMBL
571
Chemspider ID
3693
DrugBank ID
DB01009
KEGG ID
D00132
美国药典/FDA物质标识码
90Y4QC304K
维基百科标题
Ketoprofen
Medline Plus
a686014

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 3.882609  质子受体
质子供体 LogD (pH = 5.5) 1.9908713 
LogD (pH = 7.4) 0.39084414  Log P 3.6133335 
摩尔折射率 72.5156 cm3 极化性 28.005615 Å3
极化表面积 54.37 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 3.29  LOG S -4.08 
溶解度 2.13e-02 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
51 mg/L expand 查看数据来源
Chloroform expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
75 - 78°C expand 查看数据来源
91-93°C expand 查看数据来源
94°C expand 查看数据来源
疏水性(logP)
2.761 expand 查看数据来源
3.2 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) expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
UE7570000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(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
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
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)
3 expand 查看数据来源
III expand 查看数据来源
澳大利亚Hazchem
2X expand 查看数据来源
危险公开号
25-36/37/38 expand 查看数据来源
R:25 expand 查看数据来源
安全公开号
26-45 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
false expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H301-H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P301 + P310-P305 + P351 + P338 expand 查看数据来源
个人保护装置
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 3 expand 查看数据来源
给药途径
Oral, topical, intravenous (veterinary use) expand 查看数据来源
半衰期
2-2.5 hours expand 查看数据来源
蛋白结合率
99% expand 查看数据来源
法定药品分级
Prescription-only medicine expand 查看数据来源
妊娠期药物分类
C (D in 3rd trimester) expand 查看数据来源
相关基因信息
human ... ALB(213), IL8RA(3577), PTGS1(5742), PTGS2(5743) expand 查看数据来源
生物活性机理
Bradykinin antagonist expand 查看数据来源
Leukotriene synthesis inhibitor expand 查看数据来源
Prostaglandin-antagonist expand 查看数据来源
纯度
≥98% (TLC) expand 查看数据来源
95% expand 查看数据来源
95+% expand 查看数据来源
级别
VETRANAL™, analytical standard 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
Analgesic expand 查看数据来源
Antiinflammatory expand 查看数据来源
Empirical Formula (Hill Notation)
C16H14O3 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 Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02155154 external link
(2-[3-Benzoylphenyl]propionic acid)
DrugBank -  DB01009 external link
Item Information
Drug Groups approved
Description Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.
Indication For symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain.
Pharmacology Ketoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.
Toxicity LD50=62.4 mg/kg (rat, oral).

Symptoms of overdose include drowsiness, vomiting and abdominal pain.


Side effects are usually mild and mainly involved the GI tract. Most common adverse GI effect is dyspepsia (11% of patients). May cause nausea, diarrhea, abdominal pain, constipation and flatulence in greater than 3% of patients.

Affected Organisms
Humans and other mammals
Biotransformation Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.
Absorption Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.
Half Life Conventional capsules: 1.1-4 hours

Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)

Protein Binding 99% bound, primarily to albumin
Elimination In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.
Clearance * Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 × 50 mg)]
* Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 × 200 mg)]
* 0.08 L/kg/h
* 0.7 L/kg/h [alcoholic cirrhosis patients]
References
Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. [Pubmed]
Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals -  S1645 external link
Research Area: Inflammation
Biological Activity:
Ketoprofen (Actron) is a non-selective NSAID exhibiting IC50 of 0.5 μM and 2.33 μM for human recombinant COX-1 and COX-2, respectively. [1] It is used for its antipyretic, analgesic, and anti-inflammatory properties by inhibiting cyclooxygenase-1 and -2 (COX-1 and COX-2) enzymes reversibly, which decreases production of pro-inflammatory prostaglandin precursors. [2] Based on in vitro IC(50) COX-1:IC(50) COX-2 ratios, robenacoxib was COX-2 selective (ratio=32.2), diclofenac (ratio=3.9) and meloxicam (ratio=2.7) were only weakly COX-2 preferential, and ketoprofen (ratio=0.049) was COX-1 selective. [3]References on Ketoprofen (Actron)[] J. vet. Pharmacol. Therap., 2010, 33, 444–452
Sigma Aldrich -  K1751 external link
Biochem/physiol Actions
非甾体抗炎药,对 COX-1 具有选择性。
Sigma Aldrich -  34016 external link
Biochem/physiol Actions
非甾体抗炎药,对 COX-1 具有选择性。
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Sigma Aldrich -  K2012 external link
Biochem/physiol Actions
非甾体抗炎药,对 COX-1 具有选择性。
Toronto Research Chemicals -  K200800 external link
Anti-inflammatory; analgesic.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. Pubmed
  • Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. Pubmed
  • http://en.wikipedia.org/wiki/Ketoprofen
  • Ueno, K., et al.: J. Med. Chem., 19, 941 (1976)
  • Liversidge, G.G., Anal. Profiles Drug Subs., 10, 443 (1976)
  • Jamali, F., et al.: Clin. Pharmacokinet., 19, 197 (1976)
  • Brogden, R.N. et al., Drugs, 1974, 8, 168, (rev, pharmacol)
  • Allais, A. et al., Eur. J. Med. Chem. (Chim. Ther.), 1974, 9, 381, (synth, pharmacol)
  • Pinna, G. et al., Farmaco, Ed. Sci., 1980, 35, 684, (synth)
  • Comisso, G. et al., Gazz. Chim. Ital., 1980, 110, 123, (synth, abs config)
  • Liversidge, G.G., Anal. Profiles Drug Subst., 1981, 10, 443, (rev)
  • Kim, J.W. et al., Arch. Pharmacal Res., 1987, 10, 25, (resoln, abs config)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3889
  • Mitra, R.B. et al., Synth. Commun., 1988, 18, 2259, (synth)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 21
  • Camps, P. et al., Synth. Commun., 1993, 23, 1739, (synth)
  • Sonawane, H.R. et al., Tetrahedron, 1994, 50, 1243, (synth)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BDU500
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