基本情報
- 標準SMILES
CC(C(=O)O)c1ccc(C(=O)c2cccs2)cc1- InChIKey
MDKGKXOCJGEUJW-UHFFFAOYSA-N- 分子式
- C14H12O3S
- 平均分子量
- 260.31 g/mol
- 単同位体質量
- 260.05071524
概要
Suprofen is an aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antirheumatic drug, a peripheral nervous system drug and a drug allergen. It is a monocarboxylic acid, a member of thiophenes and an aromatic ketone.
名称と識別子
- 優先名称
- Suprofen
- IUPAC
- 2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
- 現地名
- スプロフェン
- 英語名
- Suprofen
- 分子式
- C14H12O3S
- 分子量
- 260.31
名称と別名
名称をさらに表示
データベース識別子
- CAS
40828-46-4- PubChem CID
- 5359
- DTXSID
DTXSID5045469- ChEMBL
CHEMBL956- ChEBI
CHEBI:9362- UNII
- 988GU2F9PE
- EC Number
- 255-096-9
- Nikkaji
- J16.410K
物性
構造計算による物性
- XLogP
- 3.3
- 極性表面積
- 82.6 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 4
- 回転可能結合数
- 4
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 321
実験および物理化学的性質
LogP
2.2
2.83
Solubility
limited solubility
4.22e-02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Dissociation Constants
4.3
3.91
Collision Cross Section
157.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
156.15 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 278 °C · 278°C
- 沸点
- 373.57 °C · 373.57°C (rough estimate)
- 比重(密度)
- 1.2959 · 1.2959 (rough estimate)
- 屈折率
- 1.505 · 1.5050 (estimate)
- 貯蔵温度
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- 溶解性
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 0.5 mg/ml
- 酸解離定数(Pka)
- 3.91 · 3.91(at 25℃)
- 外見
- Powder
- 色
- White to off-white
- 水溶解度
- 溶ける
- InChI
- InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)
- InChIKey
- MDKGKXOCJGEUJW-UHFFFAOYSA-N
- SMILES
- C1(=CC=C(C(C)C(=O)O)C=C1)C(=O)C1SC=CC=1
- CAS データベース
- 40828 · 40828-46-4(CAS DataBase Reference)
化学的性質
化学的特性Off-White to Light-Brown
安全と法規制
GHS分類
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
安全データ
- wgk
- WGK 3
- ridadr
- 3249
- 毒性
- LD50 (7 days post-drug) in mice, rats, guinea pigs, dogs (mg/kg): 590, 353, 280, 160 orally (Niemegeers)
- hs_code
- 2934990002
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 Oral
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Pharmacodynamics
Suprofen is a non-steroidal anti-inflammatory analgesic and antipyretic. Ophthalmic anti-inflammatory medicines are used in the eye to lessen problems that can occur during or after some kinds of eye surgery. Sometimes, the pupil of the eye gets smaller during an operation (pupil constriction), making it more difficult for the surgeon to reach some areas of the eye. Suprofen is used to help prevent this.
Mechanism of Action
Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A<sub>2</sub>). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.
Metabolism/Metabolites
Primarily hepatic (mainly via cytochrome P450 isozyme 2C9).
Suprofen has known human metabolites that include Suprofen -sulfoxide, Thiophene-4,5-epoxide, and (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-[4-(thiophene-2-carbonyl)phenyl]propanoyloxy]oxane-2-carboxylic acid.
MeSH Pharmacological Classification
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
用途と製造
応用分野
説明Suprofen is an arylpropionic acid analgesic/antiinflammatory agent with close structural resemblance to ketoprofen. It is more potent in many assays than indomethacin and ketoprofen and appears better tolerated.
使用Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
定義ChEBI: An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.
関連反応
関連ノート
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