スルフィンピラゾン
(4α)-1,2-ジフェニル-4-[2-(フェニルスルフィニル)エチル]-3,5-ピラゾリジンジオン · アンツラン · (4β)-1,2-ジフェニル-4-[2-(フェニルスルフィニル)エチル]-3,5-ピラゾリジンジオン · 1,2-ジフェニル-4-[2-(フェニルスルフィニル)エチル]-3,5-ピラゾリジンジオン · エンツレン · スルフィンピラゾン · 1,2-ジフェニル-4-[2-(フェニルスルフィニル)エチル]ピラゾリジン-3,5-ジオン · スルホキシフェニルピラゾリジン
識別子と物理属性
| CAS No. | 57-96-5 |
|---|---|
| 分子式 | C23H20N2O3S |
| 平均分子量 | 404.5 g/mol |
| 単同位体質量 | 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 |
| 現地名 | スルフィンピラゾン |
化学・物理的性質
| XLogP | 2.3 |
|---|---|
| 極性表面積 | 76.9 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 6 |
| 重原子数 | 29 |
| 形式電荷 | 0 |
| 複雑度 | 571 |
| LogP（分配係数） | 2.4 |
| Color/Form | WHITE TO OFF-WHITE |
| 溶解度 | 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.水に極めて溶けにくく、エタノール（96%）に溶けにくい。アルカリ溶液に溶けます。2.601g/L(22℃) |
| Human Drugs | FDA approved drugs -> Active ingredient |
| 融点 | 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-/ |
| 沸点 | 590.8±42.0 °C(Predicted) |
| 密度 | 1.1890 (rough estimate) |
| 屈折率 | 1.6360 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | Solid |
| pKa（酸解離定数） | pKa 2.8(H2O t = RT I undefined) (Uncertain) |
| 色 | オフホワイトからライトブラウン |
| 主な用途 | 洗浄剤化粧品食品および飲料法医学と毒物学パーソナルケア医薬品（低分子化合物）獣医 |
| 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 |
| CAS データベース | 57-96-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Sulfinpyrazone(57-96-5) |
化学的特性
White or almost white powder.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| その他の安全情報 | 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%) |
| 相互作用 | ...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. |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | UQ8575000 |
| 税関コード | 2933194350 |
| 危険文句（R） | 22 |
| 危険表示 | Xn |
| 安全措置（S） | 36 |
| 危険等級 | Acute Tox. 4 Oral |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 57-96-5(Hazardous Substances Data) |
用途
説明
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.
使用
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.
一般的な説明
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.