スペクチノマイシン
スペクティノマイシン SULFATE · スペクチノマイシン · スペクタム · (2R,5aβ,9aα,10aβ)-デカヒドロ-4aβ,7β,9α-トリヒドロキシ-2α-メチル-6β,8β-ビス(メチルアミノ)-4H-ピラノ[2,3-b][1,4]ベンゾジオキシン-4-オン · (2R)-2,3,4a,5aβ,6,7,8,9,9aα,10aβ-デカヒドロ-4aβ,7β,9α-トリヒドロキシ-2α-メチル-6β,8β-ビス(メチルアミノ)-4H-ピラノ[2,3-b][1,4]ベンゾジオキシン-4-オン · アクチノスペクタシン · (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-トリヒドロキシ-5-メチル-11,13-ビス(メチルアミノ)-2,4,9-トリオキサトリシクロ[8.4.0.03,8]テトラデカン-7-オン · エスペクチノミシナ
識別子と物理属性
| CAS No. | 1695-77-8 |
|---|---|
| 分子式 | C14H24N2O7 |
| 平均分子量 | 332.35 g/mol |
| 単同位体質量 | 332.15835111 g/mol |
| SMILES | CN[C@@H]1[C@H](O)[C@H](NC)[C@H]2O[C@@]3(O)C(=O)C[C@@H](C)O[C@H]3O[C@@H]2[C@H]1O |
| InChIKey | UNFWWIHTNXNPBV-WXKVUWSESA-N |
| PubChem CID | 15541 |
| ChEMBL | CHEMBL1167 |
| ChEBI | CHEBI:9215 |
| EC No. | 216-911-3 |
| DTXSID | DTXSID9023592 |
| 現地名 | スペクチノマイシン |
化学・物理的性質
| XLogP | -3.1 |
|---|---|
| 極性表面積 | 130 |
| 水素結合供与体数 | 5 |
| 水素結合受容体数 | 9 |
| 回転可能結合数 | 2 |
| 重原子数 | 23 |
| 形式電荷 | 0 |
| 複雑度 | 478 |
| LogP（分配係数） | -2.3 |
| 溶解度 | Easily soluble in cold water1.50e+02 g/LDMSO/H2O, 1:1: soluble 100mg/mL |
| Physical Description | Solid |
| Dissociation Constants | 6.95 |
| Collision Cross Section | 176.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]183.5 Ų [M+Na]+ [CCS Type: TW175.51 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]171.79 Ų [M+Na]+ [CCS Type: TW166.15 Ų [M+H-H2O]+ [CCS Type: TW171.31 Ų [M+H]+ [CCS Type: TW |
| 融点 | 185 °C (decomp) |
| 沸点 | 583.1±50.0 °C(Predicted) |
| 比旋光度 | D25 -20° (water) |
| 密度 | 1.43±0.1 g/cm3(Predicted) |
| 貯蔵条件 | -20°C |
| 外観・状態 | solution |
| pKa（酸解離定数） | pKa1 6.95, pKa2 8.70(at 25℃) |
| 色 | colorless |
| 由来生物 | Streptomyces sp. |
| EPAの化学物質情報 | Spectinomycin (1695-77-8) |
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 5.6% (3 of 54) of reports.WarningH315 (90.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (92.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (92.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract 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 54 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 3 of 54 reports by companies.There are 4 notifications provided by 51 of 54 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Spectinomycin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| 有害性の概要 | Allergic contact dermatitis reported in veterinarian workers[Kanerva, p. 1171-2] |
| Hazard Classes and Categories | Skin Irrit. 2 (90.7%)Eye Irrit. 2 (92.6%)STOT SE 3 (92.6%)Not Classified |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| 水環境危害等級（WGK） | WGK 2 |
| 貯蔵分類 | 10 - Combustible liquids |
用途
用途
抗生物質，全身用抗菌薬。
説明
An unusual aminoglycoside antibiotic, spectinomycin is produced by fermentation of Streptomyces spectabil is and differs substantially in its clinical properties from the others. The diaminoinositol unit (spectinamine) contains two mono-N-methyl groups, and the hydroxyl between them has a stereochemistry opposite to that in streptomycin. The glycosidically attached sugar also is unusual in that it contains three consecutive carbonyl groups, either overt or masked, and is fused by two adjacent linkages to spectinamine to produce an unusual, fused, three-ring structure.
使用
Spectinomycin finds principal application in the treatment of gonorrhea. It should be noted that the antibiotic resistance among N. gonorrhoeae has caused a number of therapeutic problems. It has been found that only by escalating the antibiotic doses and using probenecid to retard the excretion of penicillin and ampicillin (the drugs of choice) has the continued effective use of penicillin, ampicillin, and tetracycline been possible. Even with modifications in the therapy, from 3 to 8% of cases fail to respond to the usual regimens for uncomplicated gonorrhea. Thus, the treatment of uncomplicated gonorrhea that fails to respond to the usual regimen is spectinomycin therapy.