설핀피라존
설핀피라존 · SULFINPYRAZONE · g28315 · anturan · anturen · enturan · enturen · g28,315
식별자 및 물리적 특성
| CAS No. | 57-96-5 |
|---|---|
| 분자식 | C23H20N2O3S |
| 평균 분자량 | 404.5 g/mol |
| 단동위원소 질량 | 404.1194635 g/mol |
| SMILES | O=C1C(CCS(=O)c2ccccc2)C(=O)N(c2ccccc2)N1c1ccccc1 |
| InChIKey | MBGGBVCUIVRRBF-UHFFFAOYSA-N |
| PubChem CID | 5342 |
| ChEMBL | CHEMBL832 |
| ChEBI | CHEBI:9342 |
| EC No. | 200-357-4 |
| DTXSID | DTXSID0023618 |
| 현지명 | 설핀피라존 |
화학 및 물리적 성질
| XLogP | 2.3 |
|---|---|
| 극성 표면적 | 76.9 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 6 |
| 무거운 원자 수 | 29 |
| 형식 전하 | 0 |
| 복잡도 | 571 |
| LogP(분배 계수) | 2.4 |
| Color/Form | WHITE TO OFF-WHITE |
| 용해도 | SOL IN ETHYL ACETATE, CHLOROFORMSLIGHTLY SOL IN WATER, ALC, ETHER, MINERAL OILSSLIGHTLY SOL IN FATS1 G SOL IN 10 ML ACETONE & 10 ML 0.5 N NAOHFor more Solubility (Complete) data for SULFINPYRAZONE (6 total), please visit the HSDB record page.물에는 매우 약간 용해되며, 에탄올에는 거의 용해되지 않습니다(96%). 알칼리 수산화물의 묽은 용액에 용해됩니다. |
| Human Drugs | FDA approved drugs -> Active ingredient |
| 녹는점 | 136-137 °CMELTING POINT: 130-133 °C /D-FORM, L-FORM/136 - 137 °C136-137° |
| Physical Description | Solid |
| Stability/Shelf Life | STABLE TO LIGHT & AIR |
| Dissociation Constants | 3.25PKA: 2.8 |
| Collision Cross Section | 193.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]199.9 Ų [M+K]+ [CCS Type: TW |
| Other Experimental Properties | CRYSTALS FROM CHLOROFORM & HEPTANECRYSTALS FROM ETHANOL /D-FORM/CRYSTALS /L-FORM/SPECIFIC OPTICAL ROTATION: +67.1 DEG @ 22 °C/D (C= 2.04 IN ETHANOL)+109.3 DEG @ 25 °C/D (C= 0.5 IN CHLOROFORM) /D-/SPECIFIC OPTICAL ROTATION: -64.2 DEG @ 23 °C/D (C= 2.14 IN ETHANOL)-104.5 DEG @ 26 °C/D (C= 0.5 IN CHLOROFORM) /L-/ |
| 끓는 점 | 590.8±42.0 °C(Predicted) |
| 밀도 | 1.1890 (rough estimate) |
| 굴절률 | 1.6360 (estimate) |
| 저장 조건 | Sealed in dry,Room Temperature |
| 물리적 상태 | Solid |
| pKa(산도 계수) | pKa 2.8(H2O t = RT I undefined) (Uncertain) |
| 색상 | 황백색부터 연한 갈색까지 |
| 용해도 | 2.601g/L(22 ºC) |
| 주요 응용 | 청소용품화장품음식 및 음료법의학 및 독성학개인 위생 관리의약품(소분자)수의사 |
| InChI | 1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2 |
| InChIKey | MBGGBVCUIVRRBF-UHFFFAOYSA-N |
| SMILES | O=C1C(CCS(=O)c2ccccc2)C(=O)N(N1c3ccccc3)c4ccccc4 |
| NIST | Sulfinpyrazone(57-96-5) |
화학적 성질
White or almost white powder.
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 70 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| 기타 안전 정보 | IMAP assessments - 3,5-Pyrazolidinedione, 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]-: Human health tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 상호 작용 | ...URICOSURIC ACTION /OF SULFINPYRAZONE/ IS ADDITIVE TO THAT OF PROBENECID & PHENYLBUTAZONE BUT IS MUTUALLY ANTAGONISTIC TO THAT OF SALICYLATES. ... POSSESSES ABILITY TO DISPLACE OTHER ORG ANIONS THAT ARE BOUND EXTENSIVELY TO PLASMA PROTEINS...THUS ALTERING THEIR DISTRIBUTION TO TISSUES & THEIR RENAL EXCRETION......SULFINPYRAZONE MAY POTENTIATE ACTIONS OF INSULIN & ORAL HYPOGLYCEMIC AGENTS...SULFINPYRAZONE MAY DISPLACE SULFONAMIDES FROM PLASMA PROTEIN BINDING SITES... |
| Human Toxicity Excerpts | HYPERSENSITIVITY REACTIONS, USUALLY A RASH WITH FEVER, DO OCCUR.../OCCASIONALLY/SIDE EFFECTS INCL UPPER GI DISTURBANCES...&, RARELY, ANEMIA, LEUKOPENIA, AGRANULOCYTOSIS, & THROMBOCYTOPENIA. |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UQ8575000 |
| 관세 코드 | 2933194350 |
| 위험 문구(R) | 22 |
| 위험 표시 | Xn |
| 안전 문구(S) | 36 |
| 위험 등급 | Acute Tox. 4 Oral |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 57-96-5(Hazardous Substances Data) |
용도
개요
Sulfinpyrazone is soluble in alkaline solutions. Its synthesis is similar to that of phenylbutazone (Fig. 36.33). It produces its uricosuric effect in a manner similar to that of probenecid. A dose of 35 mg produces a uricosuric effect equivalent to that produced by 100 mg of probenecid, whereas 400 mg/day of sulfinpyrazone produces an effect comparable to that obtained with doses of 1.5 to 2 g of probenecid. It also possesses, not surprisingly, some of the properties of phenylbutazone. It is an inhibitor of human platelet prostaglandin synthesis at the cyclooxygenase step, resulting in a decrease in platelet release and a reduction in platelet aggregation. This antiplatelet effect suggests a role for sulfinpyrazone in reducing the incidence of sudden death, which can occur in the first year following a myocardial infarction; however, it lacks the analgetic and anti-inflammatory effects of phenylbutazone.
용도
As an anti-inflammatory and uricosuric agent, its side effects were severe enough to preclude its continuous use in the treatment of chronic gout. Evaluation of several chemical congeners indicated that the phenylthioethyl analog of phenylbutazone had promising anti-inflammatory and uricosuric activity. A metabolite, the sulfoxide pyrazone, exhibited enhanced uricosuric activity. Interestingly, the corresponding sulfone does not appear to be a metabolite. Sulfinpyrazone lacks the clinically striking anti-inflammatory and analgesic properties of phenylbutazone.
일반 설명
Sulfinpyrazone (Anturane) produces its uricosuric action ina similar manner to that of probenecid and is indicated forthe treatment of chronic and recurrent gouty arthritis. It iswell absorbed with approximately 50% of the administereddose excreted as unchanged drug into the renal tubules. Therest of the drug is primarily metabolized via CYP2C9 intothe corresponding sulfide and sulfone metabolites, thus itcan potentiate the anticoagulant effect of warfarin.