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

https://huagongshe.com/ja/chemical/6249

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)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
InChIKey	AVKUERGKIZMTKX-NJBDSQKTSA-N
PubChem CID	6249
ChEMBL	CHEMBL174
ChEBI	CHEBI:28971
EC No.	200-709-7
DTXSID	DTXSID4022602
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
物質分類	Other Uses -> Pharmaceuticals
医薬品	Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics (Penicillins)
LogP（分配係数）	1.35
臭い	Odorless or has a faint odor characteristic of the penicillins
Color/Form	White, crystalline powderWhite crystalline powder or as white, needle-like crystals
溶解度	SOL IN WATER, DIMETHYL SULFOXIDEDECOMP @ 199-202 °CSPECIFIC ROTATION: +287.9 DEG @ 23 °C/D (WATER) /ANHYDROUS FORM/CRYSTALS FROM WATERSPARINGLY SOL IN WATER @ ROOM TEMPERATUREDECOMP @ 202 °CSPECIFIC ROTATION: +281 DEG @ 21 °C/D (WATER) /MONOHYDRATE/1 Gm dissolves in about 90 ml of water, 20 ml of methanol, 250 ml of absolute ethanol, 13 ml of dimethylacetamide, and less than 10 ml of dimethylsulfoxidepractically insoluble in ether, ethyl acetate, petroleum ether, benzene, and chloroform.In water, 10.1X10+3 mg/l at 21 °C1.01E+004 mg/L (at 21 °C)NH4OH 1 M: 50 mg/mL、無色透明13.9g/L(25℃)
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsPenicillinsFDA approved drugs -> Active ingredientAccess group antibiotics
Animal Drugs	Active Ingredients (Ampicillin Anhydrous) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in TaiwanPharmaceuticals -> UK Veterinary Medicines Directorate List
融点	202 °C, with decomposition208 °C198-200 °C (dec.)(lit.)
Optical Rotation	Optical rotation = +287.9 deg at 20 °C (C=1 in H2O)
Physical Description	Solid
Stability/Shelf Life	The stability of ampicillin sodium in soln is concn dependent and decreased as the concn of the drug increases. Ampicillin sodium appears to be especially susceptible to inactivation in soln containing dextrose, which appears to have a catalytic effect on hydrolysis of the drug.... When stored @ room temperature (25 °C), ampicillin sodium soln containing 30 mg or less of ampicillin per ml in sterile water for injection, 0.9% sodium chloride injection, 1/6 M sodium lactate injection, or lactated Ringer's injection lose less than 10% of activity within 8 hr and soln containing 2 mg or less of ampicillin per ml in 5% dextrose, 5% dextrose and 0.45% sodium chloride, or 10% invert sugar lose less than 10% of activity within 4 hr. At concn of 10-20 mg/ml in 5% dextrose, ampicillin loses less than 10% of its activity within 2 hr @ room temperature.When refrigerated @ 4 °C, ampicillin sodium soln containing 30 mg of ampicillin per ml are stable for 48 hr in sterile water for injection or 0.9% sodium chloride injection and soln containing 30 mg or less per ml are stable for 24 hr in lactated Ringer's or 8 hr in 1/6 M sodium lactate injection. Soln of the drug containing 20 mg or less of ampicillin per ml are stable @ 4 °C for 72 hr in sterile water for injection or 0.9% sodium chloride injection, 4 hr in 5% dextrose, or 3 hr in 10% invert sugar and soln containing 10 mg or less per ml are stable for 4 hr @ 4 °C in 5% dextrose and 0.45% sodium chloride.Following reconstitution of the commercially available 10-g pharmacy bulk package of ampicillin sodium, soln containing 100 mg of ampicillin per ml should either be used or discarded within 2 hr if stored @ room temperature or within 4 hr if refrigerated.For more Stability/Shelf Life (Complete) data for AMPICILLIN (6 total), please visit the HSDB record page.
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
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

保管条件
GHS 分類	This chemical does not meet GHS hazard criteria for 0.6% (1 of 167) of reports.DangerH315 (26.3%): Causes skin irritation [Warning Skin corrosion/irritation]P233, P260, P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 167 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	Status: Active Update: 20-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/11498Ampicillin: 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 - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-: Environment tier I assessment
有害性の概要	Allergic contact dermatitis reported in a nurse[Kanerva, p. 1189] Asthma reported in pharmaceutical workers[Malo]
FDA 要件	Oral Dosage Form New Animal Drugs. Specifications and conditions of use for dogs and cats. /Ampicillin capsules/Oral Dosage Form New Animal Drugs. Specifications and conditions of use for dogs. /Ampicillin trihydrate tablets/Oral Dosage Form New Animal Drugs. Specifications and conditions of use for dogs and cats. /Ampicillin trihydrate capsules/Oral Dosage Form New Animal Drugs. Specifications and conditions of use for dogs and cats. /Ampicillin trihydrate for oral suspension/For more FDA Requirements (Complete) data for AMPICILLIN (11 total), please visit the HSDB record page.
Special Reports	DHHS/NTPToxicology & Carcinogenesis Studies of Ampicillin Trihydrate in F344/N Rats and B6C3F1 (Feed Studies) Mice Technical Report Series No. 318 (1987) NIH Publication No. 87-2574 /Ampicillin trihydrate/
Hazard Classes and Categories	Skin Irrit. 2 (26.3%)

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.