スペクチノマイシン

Spectinomycin

HCID 15541CAS 1695-77-8
部分構造検索類似構造を探す

基本情報

標準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
分子式
C14H24N2O7
平均分子量
332.35 g/mol
単同位体質量
332.15835111

名称と識別子

優先名称
Spectinomycin
IUPAC
(1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one
現地名
スペクチノマイシン
英語名
Spectinomycin
分子式
C14H24N2O7
分子量
332.35

名称と別名

SpectinomycinEspectinomicina1695-77-8TogamycinAntibiotic 2233wpSpectinomycineSpectinomycinumProspecAdspecM-141U 18409 E93AKI1U6QF
名称をさらに表示
スペクティノマイシン SULFATEスペクチノマイシン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(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trobicinspectamSpectacinmacromycinpectinomycin
SpectinomicinaCHX-3101U-18409ECHEBI:9215DTXSID90235924H-Pyrano(2,3-b)(1,4)benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4H-Pyrano(2,3-b)(1,4)benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4H-Pyrano[2,3-b][1,4]benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-

データベース識別子

CAS
1695-77-8、22189-32-8
PubChem CID
15541
DTXSID
DTXSID9023592
ChEMBL
CHEMBL1167
ChEBI
CHEBI:9215
UNII
93AKI1U6QF
EC Number
216-911-3、606-950-8
Nikkaji
J7.562K

物性

構造計算による物性

XLogP
-3.1
極性表面積
130 Ų
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

実験および物理化学的性質

LogP · 2 件

-2.3

-2.3

Solubility · 2 件

Easily soluble in cold water

1.50e+02 g/L

Physical DescriptionSolid
Dissociation Constants6.95
Collision Cross Section · 2 件

176.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]；183.5 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

175.51 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；171.79 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；166.15 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；171.31 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
185 °C · 185 °C (decomp)
沸点
583.1 · 583.1±50.0 °C(Predicted)
比旋光度
25 · D25 -20° (water)
比重(密度)
1.43 · 1.43±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
2 O, · DMSO/H2O, 1:1: soluble 100mg/mL

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 5.6% (3 of 54) of reports.

Warning

H315 (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 exposure; Respiratory 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.

危険有害性情報

Regulatory InformationSpectinomycin: 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.
Hazards SummaryAllergic contact dermatitis reported in veterinarian workers; [Kanerva, p. 1171-2]
Hazard Classes and Categories · 2 件

Skin Irrit. 2 (90.7%)；Eye Irrit. 2 (92.6%)；STOT SE 3 (92.6%)

Not Classified

毒性情報

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

法規制情報

Regulatory InformationSpectinomycin: 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.

安全データ

wgk
WGK 2
ストレージクラス
10 - Combustible liquids

化学と産業

薬理情報

ATC Code · 3 件

J - Antiinfectives for systemic use；J01 - Antibacterials for systemic use；J01X - Other antibacterials；J01XX - Other antibacterials；J01XX04 - Spectinomycin

QJ - Antiinfectives for systemic use；QJ01 - Antibacterials for systemic use；QJ01X - Other antibacterials；QJ01XX - Other antibacterials；QJ01XX04 - Spectinomycin

J01XX04

Protein BindingNot significant
Pharmacodynamics · 1 件

Spectinomycin is an aminocyclitol antibiotic produced by a species of soil microorganism designated as S<i>treptomyces spectabilis</i>. In vitro studies have shown spectinomycin to be active against most strains of <i>Neisseria gonorrhoeae</i> (minimum inhibitory concentration <7.5 to 20 mcg/mL). Footprint studies indicate that spectinomycin exerts regional effects on ribosomal structure.

Mechanism of ActionSpectinomycin is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. It is bactericidal in its action.
Biological Half-Life1 to 3 hours in patients with normal renal function and 10 to 30 hours in patients with impaired renal function with a creatinine clearance &lt; 20 mL per minute.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.

用途と製造

Use Classification · 6 件

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

応用分野 · 3 件

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.

上流・下流製品情報

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd+86-13119157289 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

補足説明

定義ChEBI: An organic heterotricyclic antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis.

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