アンピシリン
アルペン · 6α-[[(R)-アミノ(フェニル)アセチル]アミノ]ペニシラン酸 · (アミノフェニルメチル)ペニシリン · ペントレックス · 6α-[(D-フェニルグリシル)アミノ]ペニシラン酸 · アミペニックス · アミノベンジルペニシリン · オムニペン
識別子と物理属性
| CAS No. | 69-53-4 |
|---|---|
| 分子式 | C16H19N3O4S |
| 平均分子量 | 349.4 g/mol |
| 単同位体質量 | 349.10962709 g/mol |
| SMILES | CC1(C)SC2C(NC(=O)C(N)c3ccccc3)C(=O)N2C1C(=O)O |
| InChIKey | AVKUERGKIZMTKX-UHFFFAOYSA-N |
| PubChem CID | 2174 |
| ChEMBL | CHEMBL1617921 |
| ChEBI | CHEBI:94334 |
| DTXSID | DTXSID20859077 |
| 現地名 | アンピシリン |
化学・物理的性質
| XLogP | -1.1 |
|---|---|
| 極性表面積 | 138 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 4 |
| 重原子数 | 24 |
| 形式電荷 | 0 |
| 複雑度 | 562 |
| 融点 | 198-200 °C (dec.)(lit.) |
| 比旋光度 | D23 +287.9° (c = 1 in water) |
| 沸点 | 201.8°C (rough estimate) |
| 密度 | 1.2794 (rough estimate) |
| 屈折率 | 1.6320 (estimate) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | NH4OH 1 M: 50 mg/mL、無色透明13.9g/L(25℃) |
| 外観・状態 | 個体 |
| 色 | 白色～淡黄色 |
| pKa（酸解離定数） | 2.5 (COOH)(at 25℃) |
| 由来生物 | microbial |
| JECFA Number | 85 |
| Merck | 13,591 |
| BRN | 1090925 |
| 安定性 | 安定していますが、湿気に敏感な場合があります。強力な酸化剤とは相容れない。 |
| 主な用途 | 臨床検査 |
| InChI | 1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1 |
| InChIKey | AVKUERGKIZMTKX-NJBDSQKTSA-N |
| SMILES | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3)C(O)=O |
| CAS データベース | 69-53-4(CAS DataBase Reference) |
| EPAの化学物質情報 | Ampicillin (69-53-4) |
化学的特性
Ampicillin in anhydrous form occurs as crystals.
安全性と法規制
| F | 10-23 |
|---|---|
| 水環境危害等級（WGK） | 2 |
| RTECS 番号 | XH8425000 |
| 毒性 | LD50 oral in mouse: > 5gm/kg |
| 税関コード | 29212900 |
| 危険文句（R） | 36/37/38-42/43-61 |
| 危険表示 | Xn,T |
| 安全措置（S） | 22-26-36/37-45-53 |
| 自然発火温度 | 301°C |
| 危険等級 | Resp. Sens. 1Skin Sens. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 69-53-4(Hazardous Substances Data) |
用途
解説
アンピシリンは，抗生物質の一つ．ペニシリングループの一種で，グラム陽性菌にも陰性菌にも広い抗菌効果を示す．
用途
アンピシリン（Ampicillin）とは、1961年から感染症の治療に用いられているβ-ラクタム系抗生物質の1種である。アミノペニシリングループに属し、抗菌スペクトルや活性はアモキシシリンとほぼ同じである。
説明
Ampicillin is an antibacterial antibiotic from the α-aminobenzyl penicillin group, which differs from penicillin by the presence of an amino group that facilitates penetration through the outer membrane of some gram-negative bacteria. Ampicillin is Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin acts by interfering directly with the biosynthesis of peptidoglycan, which constitutes the major component of the bacterial cell wall, leading to structural instability and death of bacteria. Ampicillin is a β-lactam antibiotic within the penicillin family. As a member of this family, Ampicillin is susceptible to β-lactamase, which hydrolyzes the β-lactam ring. This broad spectrum antibiotic is effective against gram-positive, gram-negative bacteria and anaerobic bacteria. Ampicillin is widely used in cell culture as a selective agent. As an antibiotic, Ampicillin binds to penicillin binding proteins (PBPs) on a susceptible organism and Inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. After binding to the PBPs, Ampicilin acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and thereby prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium. Ampicillin sodium can be used as a selective agent in several types of isolation media. Ampicillin sodium is routinely used to select for cells containing the pcDNA3.1 and pEAK10 resistance plasmids in cell line A904L at an effective concentration of 50 μg/ml.
使用
Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.
一般的な説明
Ampicillin was synthesized by Beecham Research Laboratories in 1961 and evaluated for its anti-gram-negative activity by Rolinson et al.. It was the first semisynthetic penicillin showing strong activity against gramnegative bacilli. Although it is hydrolyzed by bacterial penicillinase, it is active against Escherichia coli, Shigella, Proteus mirabilis, and Haemophilus influenzae and is used very widely as an oral antibiotic. Ampicillin also is used by injection for serious infections.