スプロフェン

Suprofen

HCID 5359CAS 40828-46-4

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

suprofen40828-46-4SutoprofenProfenalp-2-Thenoylhydratropic acidSulproltinSrendamSuprofeneTopalgicSuprofenumracemic suprofen2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
名称をさらに表示
(±)-スプロフェンrac-(R*)-2-[4-(2-チエニルカルボニル)フェニル]プロパン酸スプロフェンスプロフェン (JAN)ストプロフェン2-[4-(2-チエニルカルボニル)フェニル]プロピオン酸2-(4-(2-チエニルカルボニル)フェニル)プロピオン酸α-メチル-4-(2-チエニルカルボニル)ベンゼン酢酸2-[4-(2-チエニルカルボニル)フェニル]プロパン酸2-[4-(チオフェン-2-カルボニル)フェニル]プロパン酸トパルジックスルプロチン2-[p-(2-テノイル)フェニル]プロピオン酸2-[4-[(2-チエニル)カルボニル]フェニル]プロパン酸スレンダムProfenolSuprolr25061AnemetSuprocilmaldocil
TN-7624-(2-Thenoyl)hydratropsaeureR-25061p-(2-thenoyl)hydratropic acidTN 7622-(4-(thiophene-2-carbonyl)phenyl)propanoic acid2-(4-(2-Thenoyl)phenyl)propionsaeureR-25,061

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

実験および物理化学的性質

LogP · 2 件

2.2

2.83

Solubility · 2 件

limited solubility

4.22e-02 g/L

Human Drugs · 3 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point124.3 °C
Physical DescriptionSolid
Dissociation Constants · 2 件

4.3

3.91

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

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 · 4 件

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

Hazard Classes and CategoriesAcute Tox. 3 (100%)

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

化学と産業

薬理情報

ATC Code · 2 件

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein Binding20%
Pharmacodynamics · 1 件

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 · 1 件

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 · 2 件

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 · 4 件

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

Use ClassificationPharmaceuticals

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.

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

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

42 件

関連ノート

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