Suprofen

HCID 5359CAS 40828-46-4

기본 정보

표준 SMILES
CC(C(=O)O)c1ccc(C(=O)c2cccs2)cc1
InChIKey
MDKGKXOCJGEUJW-UHFFFAOYSA-N
분자식
C14H12O3S
평균 분자량
260.31 g/mol
단동위원소 질량
260.05071524

개요

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.

이름 및 식별자

우선 이름
Suprofen
IUPAC
2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
영어명
Suprofen
분자식
C14H12O3S
분자량
260.31

이름 및 동의어

suprofen40828-46-4SutoprofenProfenalp-2-Thenoylhydratropic acidSulproltinSrendamSuprofeneTopalgicSuprofenumracemic suprofen2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
이름 더 보기
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

데이터베이스 식별자

CAS
40828-46-4
PubChem CID
5359
DTXSID
DTXSID5045469
ChEMBL
CHEMBL956
ChEBI
CHEBI:9362
UNII
988GU2F9PE
EC Number
255-096-9
Nikkaji
J16.410K

물성

구조 계산 물성

XLogP
3.3
극성 표면적
82.6 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
4
무거운 원자 수
18

실험 및 물리화학적 성질

LogP · 2건

2.2

2.83

Solubility · 2건

limited solubility

4.22e-02 g/L

Human Drugs · 3건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

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

4.3

3.91

물리화학적 성질

녹는점
278 °C · 278°C
끓는 점
373.57 °C · 373.57°C (rough estimate)
밀도
1.2959 · 1.2959 (rough estimate)
굴절률
1.505 · 1.5050 (estimate)
저장 조건
-20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
용해도
30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 0.5 mg/ml

화학적 성질

Off-White to Light-Brown

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 3 (100%)

안전 데이터

wgk
WGK 3
ridadr
3249
독성
LD50 (7 days post-drug) in mice, rats, guinea pigs, dogs (mg/kg): 590, 353, 280, 160 orally (Niemegeers)
HS 번호
2934990002
포장분류
III
위험 등급
6.1(b)

화학 및 산업

약리 정보

ATC Code · 2건

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein Binding20%
Pharmacodynamics · 1건

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 · 1건

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 · 2건

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 · 4건

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.

용도 및 제조

Use ClassificationPharmaceuticals

응용 분야

개요Suprofen 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.

용도Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.

공급사50 곳

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]

추가 설명

정의ChEBI: An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.

관련 반응

42건

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