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semisynthetic penicillin (trade names Principen and Polycillin and SK-Ampicillin) (同)Principen, Polycillin, SK-Ampicillin

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アンビシリン(ペニシリンに似た抗生物質)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/05 04:17:51」(JST)

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Ampicillin is a beta-lactam antibiotic that is part of the aminopenicillin family and is roughly equivalent to its successor, amoxicillin in terms of spectrum and level of activity.^[1] It can sometimes result in reactions that range in severity from a rash (in the case of patients that may unwittingly have mononucleosis) to potentially lethal allergic reactions such as anaphylaxis. However, as with other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only rarely.

Mechanism of action

Belonging to the penicillin group of beta-lactam antibiotics, ampicillin is able to penetrate Gram-positive and some Gram-negative bacteria. It differs from penicillin only by the presence of an amino group. That amino group helps the drug penetrate the outer membrane of gram-negative bacteria.

Ampicillin acts as a competitive inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their cell walls.^[1] It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis. Ampicillin has received FDA approval for its mechanism of action.

Effects on chloroplast division

Ampicillin, like other β-lactam antibiotics, not only blocks the division of bacteria, but also the division of chloroplasts of the Glaucophytes (called cyanelles) and chloroplasts of the moss Physcomitrella patens, a bryophyte. In contrast, it has no effect on the plastids of the higher developed vascular plant Lycopersicon esculentum L. (tomato).^[2]

Application

Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract infections, otitis media, Haemophilus influenzae, salmonellosis and Listeria meningitis. It is used with flucloxacillin in the combination antibiotic co-fluampicil for empiric treatment of cellulitis; providing cover against Group A streptococcal infection whilst the flucloxacillin acts against the Staphylococcus aureus bacterium. Of concern is the number of bacteria that become resistant to Ampicillin necessitating combination therapy or use of other antibiotics.

All Pseudomonas and most strains of Klebsiella and Aerobacter are considered resistant.^[3] Additionally, resistance to ampicillin is seen in enterobacter, citrobacter, serratia, indole-positive proteus species, and other hospital-acquired gram negative infections.^[4]

An ampicillin resistance gene (abbreviated ampR) is commonly used as a selectable marker in routine biotechnology. Due to concerns over horizontal gene transfer to pathogenic organisms in the wild, the European Food Safety Authority restricts use of this gene (among other resistance genes) in commercial genetically modified organisms. The enzyme responsible for degrading ampicillin is called beta-lactamase, in reference to the beta-lactam structure of ampicillin and related drugs.

History

Ampicillin has been used extensively to treat bacterial infections since 1961. Until the introduction of ampicillin by the British company Beecham, penicillin therapies had only been effective against Gram-positive organisms such as staphylococci and streptococci. Ampicillin (originally branded as 'Penbritin') also demonstrated activity against Gram-negative organisms such as H. influenzae, coliforms and Proteus spp. Ampicillin was the first of a number of so-called broad spectrum penicillins subsequently introduced by Beecham.

References

^ ^a ^b AHFS DRUG INFORMATION 2006 (2006 ed.). American Society of Health-System Pharmacists. 2006.
^ Britta Kasten und Ralf Reski (1997): β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum). Journal of Plant Physiology 150, 137-140. [1]
^ Mosby's Drug Consult 2006 (16 ed.). Mosby, Inc.. 2006.
^ Katzung, Bertram G. (2007). Basic and Clinical Pharmacology, 10th edition. New York, NY: McGraw Hill Medical. pp. 733. ISBN 978-0-07-145153-6.

External links

Ampicillin bound to proteins in the PDB

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 腸球菌における抗菌薬耐性の機構 mechanisms of antibiotic resistance in enterococci
2. サイクロスポーラ感染患者の臨床管理 clinical management of patients with cystoisospora infection
3. 小児および思春期における陰嚢損傷 scrotal trauma in children and adolescents
4. 成人における急性副鼻腔炎および鼻副鼻腔炎：治療 acute sinusitis and rhinosinusitis in adults treatment
5. 小児における急性肝不全：病因および評価 acute liver failure in children etiology and evaluation

English Journal

Molecular characterization of Salmonella enterica serovar Saintpaul isolated from imported seafood, pepper, environmental and clinical samples.

Akiyama T, Khan AA, Cheng CM, Stefanova R.SourceMicrobiology Division, US Food and Drug Administration, National Center for Toxicological Research, Jefferson, AR 72079, USA.
Food microbiology." abstractLink="yes" alsec="jour" alterm="Food Microbiol.2011 Sep;28(6):1124-8. Epub 2011 Mar 11.
A total of 39 Salmonella enterica serovar Saintpaul strains from imported seafood, pepper and from environmental and clinical samples were analyzed for the presence of virulence genes, antibiotic resistance, plasmid and plasmid replicon types. Pulsed-field gel electrophoresis (PFGE) fingerprinting u
PMID 21645810

Raman spectroscopic detection of physiology changes in plasmid-bearing Escherichia coli with and without antibiotic treatment.

Walter A, Reinicke M, Bocklitz T, Schumacher W, Rosch P, Kothe E, Popp J.SourceInstitut fur Physikalische Chemie, Friedrich-Schiller-Universitat, Helmholtzweg 4, 07743, Jena, Germany.
Analytical and bioanalytical chemistry." abstractLink="yes" alsec="jour" alterm="Anal Bioanal Chem.2011 Jul;400(9):2763-73. Epub 2011 Mar 20.
Bacterial resistances against antibiotics are increasingly problematic for medical treatment of pathogenic bacteria, e.g., in hospitals. Resistances are, among other genes, often encoded on plasmids which can be transmitted between bacteria not only within one species, but also between different spe
PMID 21424521

Analysis of PBP5 of Early U.S. Isolates of Enterococcus faecium: Sequence Variation Alone Does Not Explain Increasing Ampicillin Resistance over Time.

Galloway-Pena JR, Rice LB, Murray BE.SourceDivision of Infectious Disease, Center for the Study of Emerging and Re-emerging Pathogens, University of Texas Medical School, 6431 Fannin St., MSB 2.112, Houston, TX 77030. BEM.asst@uth.tmc.edu.
Antimicrobial agents and chemotherapy." abstractLink="yes" alsec="jour" alterm="Antimicrob Agents Chemother.2011 Jul;55(7):3272-7. Epub 2011 May 16.
Recent studies have shown that ampicillin resistance has increased steadily over the past 3 decades within U.S. Enterococcus faecium isolates. Analysis of the predicted PBP5 protein of 41 isolates showed a consensus PBP5 pattern for the 9 isolates with MICs of <4 μg/ml that is distinctly differe
PMID 21576454

Japanese Journal

国立病院機構DPC導入28施設における成人肺炎入院症例の施設間ベンチマークについて

川本俊治,富永春海,中野喜久雄 [他]
医療 65(2), 69-76, 2011-02
NAID 40018778696

Antimicrobial Susceptibility of Escherichia coli Isolates from Wild Mice in a Forest of Natural Park in Hokkaido, Japan

ISHIHARA Kanako,KANAMORI Kyoko,ASAI Tetsuo,KOJIMA Akemi,TAKAHASHI Toshio,UENO Hiroshi,MURAMATSU Yasukazu,TAMURA Yutaka
Journal of Veterinary Medical Science advpub(0), 1104210498, 2011
… coli isolate was resistant to ampicillin, dihydrostreptomycin, kanamycin, chloramphenicol and oxytetracycline. …
NAID 130000677181

The Prevalence of Antimicrobial-Resistant Escherichia coli in Two Species of Invasive Alien Mammals in Japan

NAKAMURA Ichiro,OBI Takeshi,SAKEMI Yoko,NAKAYAMA Ayano,MIYAZAKI Kei,OGURA Go,TAMAKI Masanobu,OKA Tatsuzo,TAKASE Kozo,MIYAMOTO Atsushi,KAWAMOTO Yasuhiro
Journal of Veterinary Medical Science advpub(0), 1103250475, 2011
… coli isolates between the SAM and JW, JW showed significantly higher prevalence of resistance against three drugs, ampicillin, chlortetracycline and nalidixic acid, compared with SAMs test results (P<0.05). … The blaTEM gene and the aph1 gene were detected in 35 subjects (91%) of ampicillin-resistant isolates and 6 subjects (100%) of kanamycin-resistant isolates, respectively. …
NAID 130000676929

Related Pictures

★リンクテーブル★

リンク元	「抗菌薬」「アンピシリン」「ペニシリン系抗菌薬」「anhydrous ampicillin」「ABPC」
拡張検索	「ampicillin hydrate」「metampicillin」「methampicillin」

「抗菌薬」

Ampicillin
Systematic (IUPAC) name
	(2S,5R,6R)-6-([(2R)-2-amino-2-phenylacetyl]amino); -3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-; carboxylic acid
Clinical data
Trade names	Principen
AHFS/Drugs.com	monograph
MedlinePlus	a685002
Pregnancy cat.	A (Au), B (U.S.)
Legal status	?
Routes	Oral, intravenous
Pharmacokinetic data
Bioavailability	40% (oral)
Protein binding	15 to 25%
Metabolism	12 to 50%
Half-life	approx 1 hour
Excretion	75 to 85% renal
Identifiers
CAS number	69-53-4
ATC code	J01CA01 S01AA19 QJ51CA01
PubChem	CID 6249
DrugBank	DB00415
ChemSpider	6013
UNII	7C782967RD
KEGG	D00204
ChEBI	CHEBI:28971
ChEMBL	CHEMBL174
Chemical data
Formula	C16H19N3O4S
Mol. mass	349.41 g·mol−1
	SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C;
	InChI 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 ; Key:AVKUERGKIZMTKX-NJBDSQKTSA-N ;
(what is this?) (verify);

　　[★]

英: antibacterial drug, antibacterial
関: 抗生剤、薬理学、抗菌薬一覧、抗細菌薬

first aid step 1 2006 p.165

定義

細菌/微生物に静菌作用、殺菌作用を示す物質。結果として、人において病原性を除去する目的で使用される。
このうち、微生物によって産生される物質を抗生物質と呼ぶ

作用機序による分類

細胞壁合成阻害：βラクタム系抗菌薬(ペニシリン系抗菌薬、セフェム系抗菌薬、モノバクタム系抗菌薬、カルバペネム系抗菌薬)
核酸合成阻害　：ニューキノロン系抗菌薬、メトロニダゾール
タンパク質合成阻害

30S：アミノグリコシド系抗菌薬、テトラサイクリン系抗菌薬
50S：マクロライド系抗菌薬、クリンダマイシン、クロラムフェニコール、ストレプトグラミン系抗菌薬、オキソゾリニドン系抗菌薬(リゾネリド)

代謝拮抗：サルファ剤(サルファメソキサゾール、トリメトプリム)

first aid step 1 2006 p.165

	Mechanism of action	Drugs
1	Block cell wall synthesis by inhibition of peptidoglycan cross-linking	penicillin, ampicillin, ticarcillin, piperacillin, imipenem, aztreonam, cephalosporins
2	Block peptidoglycan synthesis	bacitracin, vancomycin, cycloserine
3	Disrupt bacterial/fungal cell membranes	polymyxins
4	Disrupt fungal cell membranes	amphotericin B, nystatin, fluconazole/azoles
5	Block nucleotide synthesis	sulfonamides, trimethoprim
6	Block DNA topoisomerases	quinolones
7	Block mRNA synthesis	rifampin
8	Block protein synthesis at 50S ribosomal subunit	chloramphenicol, erythromycin/macrolides, lincomycin, clindamycin, streptogramins (quinupristin, dalfopristin), linezolid
9	Block protein synthesis at 30S ribosomal subunit	aminoglycosides, tetracyclines, spectinomycin 　ATuSi　→　あつし

薬物動態

濃度依存性：アミノグリコシド系抗菌薬、ニューロキノロン系抗菌薬
時間依存性：βラクタム系抗菌薬

治療期間

小児

尾内一信 ; 第 39 回日本小児感染症学会教育講演 2 小児感染症の抗菌薬療法 -耐性菌時代の適正使用-

感染臓器・臨床診断	原因菌	投与期間（抗菌薬）
髄膜炎	インフルエンザ菌	7-10日
	肺炎球菌	10-14日
	髄膜炎菌	7-10日
	GBS，腸内細菌，リステリア	21日
中耳炎	＜2 歳	10日
中耳炎	2 歳≦	5-7日
咽頭炎	A 群連鎖球菌	10日(ペニシリン系薬)
咽頭炎	A 群連鎖球菌	5日(セフェム系薬)
肺炎	肺炎球菌，インフルエンザ菌	解熱後3-4日
	黄色ブドウ球菌	3-4週間
	マイコプラズマ，クラミジア	10-21日
腎臓、膀胱炎、腎盂腎炎	大腸菌，プロテウス，腸球菌	3日
腎臓、膀胱炎、腎盂腎炎	大腸菌，プロテウス，腸球菌	14日
骨髄炎	黄色ブドウ球菌	21日
骨髄炎	連鎖球菌，インフルエンザ菌	14日

主要な感染症の抗菌薬投与期間

感染レジマニュ p.27

骨	骨髄炎		4-6週
耳鼻咽喉	中耳炎		5-7日
	副鼻腔炎		5-14日
	A群溶連菌咽頭炎		10日
肺	肺炎	肺炎球菌	7-10日 or 解熱後3日間
		インフルエンザ菌	10-14日
		マイコプラズマ	14日(7-10日)
		レジオネラ	21日
	肺化膿症		28-42日
心臓	感染性心内膜炎	α連鎖球菌	2-4週
		黄色ブドウ球菌	4-6週
消化管	腸炎	赤痢菌	3日
		チフス	14日(5-7日)
		パラチフス
	腹膜炎	特発性	5日
		二次性	10-14日
胆肝膵	肝膿瘍	細菌性	4-8週
		アメーバ性	10日
尿路	膀胱炎		3日
	急性腎盂腎炎		14日(7-10日)
	急性腎盂腎炎・再発		6週
	慢性前立腺炎		1-3ヶ月
髄腔	髄膜炎	インフルエンザ菌	7-10日
		髄膜炎菌
		肺炎球菌	10-14日
		リステリア	21日
敗血症	敗血症	コアグラーゼ陰性ブドウ球菌	5-7日
		黄色ブドウ球菌	28日(14日)
		グラム陰性桿菌	14日(7-14日)
		カンジダ	血液培養陰性化後, 14日