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スルファチアゾール
2-(スルファニリルアミノ)チアゾール · N-(チアゾール-2-イル)-4-アミノベンゼンスルホンアミド · ノルスルファゾール · チバゾール · 4-[(2-チアゾリル)アミノスルホニル]アニリン · 2-スルファニルアミドチアゾール · 4-アミノ-N-(2-チアゾリル)ベンゼンスルホンアミド · 4-アミノ-N-(チアゾール-2-イル)ベンゼンスルホンアミド
識別子と物理属性
| CAS No. | 72-14-0 |
|---|---|
| 分子式 | C9H9N3O2S2 |
| 平均分子量 | 255.3 g/mol |
| 単同位体質量 | 255.01361853 g/mol |
| SMILES | Nc1ccc(S(=O)(=O)Nc2nccs2)cc1 |
| InChIKey | JNMRHUJNCSQMMB-UHFFFAOYSA-N |
| PubChem CID | 5340 |
| ChEMBL | CHEMBL437 |
| ChEBI | CHEBI:9337 |
| EC No. | 200-771-5 |
| DTXSID | DTXSID8026068 |
| 現地名 | スルファチアゾール |
化学・物理的性質
| XLogP | 0.1 |
|---|---|
| 極性表面積 | 122 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 3 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 320 |
| 物質分類 | Other Uses -> Pharmaceuticals |
| 医薬品 | Pharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Sulfonamide)Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Crystal structure |
| LogP（分配係数） | log Kow = 0.050.43 |
| Color/Form | Brown plates, rods or powder from 45% alcoholYellowish-white prismatic rods and six sided plates and prisms |
| 溶解度 | Insoluble (<1 mg/ml at 70 °F) (NTP, 1992)Amorphous powder. Practically insol in water /Polymer with formaldehyde/Soly at 26 °C (mg/100 mL): water 60 (pH 6.03)alcohol 525. Sol in acetone, dil mineral acids, KOH and NaOH solns, ammonia water. Sparingly soluble in ethanol. Practically insoluble in chloroform, ether.Slightly soluble in dimethyl sulfoxide.In water, 373 mg/L at 25 °C0.5g/l不溶性 (<0.1 g/100 mL at 21 ºC) |
| Human Drugs | Pharmaceuticals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits very toxic fumes of /nitrogen and sulfur oxides/. |
| 融点 | 396.5 °F (Form I)347 °F (Form II) (NTP, 1992)175 °C (form a)202 °C (form b)189 °C200-202 °C (lit.) |
| Physical Description | Sulfathiazole is a white crystalline powder. Is dimorphous: form I is consists of prismatic rods and form II of six-sided plates and prisms. Insoluble in water and soluble in dil aqueous acid and aqueous base.White solid[HSDB] |
| Stability/Shelf Life | The stability of sulfamethazine (sulfadimidine) sulfathiazole, sulfameter (sulfamethoxydiazine), and sulfacetamide during acid hydrolysis in one mol/L of hydrochloric acid under increased temperature was examined using high pressure liquid chromatography. Kinetic characteristics of the process of decomposition were calculated from the found values of the concentration of undecomposed sulfonamide in relation to time. The calculated values of activation energy for the individual sulfonamides are given. The paper stresses the illustrativeness of HPLC in the examination of decomposition products. |
| 沸点 | 479.5±47.0 °C(Predicted) |
| 密度 | 1.4629 (rough estimate) |
| 屈折率 | 1.6560 (estimate) |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 7.2(at 25℃) |
| 外観・状態 | Solid |
| 色 | 白い |
| Merck | 14,8943 |
| BRN | 226178 |
| ヘンリー定数 | 1.7×108 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 主な用途 | 臨床検査 |
| InChI | 1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12) |
| InChIKey | JNMRHUJNCSQMMB-UHFFFAOYSA-N |
| SMILES | Nc1ccc(cc1)S(=O)(=O)Nc2nccs2 |
| CAS データベース | 72-14-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Sulfathiazole(72-14-0) |
| EPAの化学物質情報 | Sulfathiazole (72-14-0) |
化学的特性
white to cream powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 5.8% (5 of 86) of reports.WarningH315 (91.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 86 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Sulphathiazole: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Benzenesulfonamide, 4-amino-N-2-thiazolyl-: Human health tier I assessment |
| 火災危険 | Flash point data for this compound are not available, but it is probably combustible. (NTP, 1992) |
| 有害性の概要 | Liver necrosis has been rarely reported during therapy[HSDB] Occupational asthma confirmed in two hospital workers[Malo] |
| FDA 要件 | A tolerance of 0.1 part per million is established for negligible residues of sulfathiazole in the uncooked edible tissues of swine.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Sulfathiazole is included on this list.The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Sulfathiazole is included on this list.The following drug products were withdrawn or removed from the market because such drug products or components of such drug products were found to be unsafe or not effective. The following drug products may not be compounded under the exemptions provided by section 503A(a) of the Federal Food, Drug, and Cosmetic Act: All drug products containing sulfathiazole (except those formulated for vaginal use).New animal drugs for use in animal feeds. Chlortetracycline, sulfathiazole, penicillin. Type A medicated articles: (1) 20 grams of chlortetracycline hydrochloride, 4.4 percent (20 grams) sulfathiazole, and procaine penicillin equivalent to 10 grams of penicillin per pound to No. 046573 in section 510.600(c) of this chapter. (2) 40 grams of chlortetracycline hydrochloride, 8.8 percent (40 grams) sulfathiazole and procaine penicillin equivalent in activity to 20 grams of penicillin per pound to No. 046573 in section 510.600(c) of this chapter. ... Indications for use: For reduction of incidence of cervical abscesses. Treatment of bacterial enteritis (salmonellosis or necrotic enteritis caused by Salmonella choleraesuis and vibrionic dysentery). Maintenance of weight gains in the presence of atrophic rhinitis. Swine 10 pounds of body weight to 6 weeks post-weaning: Increased rate of weight gain and improved feed efficiency. Swine 6 to 16 weeks post-weaning: Increased rate of weight gain. ... Limitations: For swine raised in confinement (dry-lot) or on limited pasture. Feed as sole ration. Withdraw 7 days prior to slaughter. |
用途
解説
スルファチアゾール,融点200～204 ℃(柱状晶)，175 ℃(六角板状晶)．pKa1 2.1，pKa2 7.43(20 ℃)．効力は強いが全身的な毒性もやや強く，使用法が制限されている．森北出版「化学辞典（第2版）
使用
Sulfonamide antibacterial.
一般的な説明
White crystalline powder. Is dimorphous: form I is consists of prismatic rods and form II of six-sided plates and prisms. Insoluble in water and soluble in dil aqueous acid and aqueous base.