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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 321
실험 및 물리화학적 성질
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]
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
- 산도 계수 (pKa)
- 3.91 · 3.91(at 25℃)
- 물리적 상태
- 가루
- 색상
- White to off-white
- 수용성
- 녹는
- 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
화학적 성질
Off-White to Light-Brown
안전 및 규제
GHS 분류
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.
유해성 정보
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)
- Hazard Classifications
- Acute Tox. 3 Oral
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
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.
용도 및 제조
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.
상·하류 제품 정보
상류 원료
공급사50 곳
추가 설명
정의ChEBI: An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.
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