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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/15 00:57:35」(JST)

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Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.^[1]

It is sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).

Synthesis

Semi-synthetic antibiotic related to penicillin.

The relatively small chemical difference between ampicillin and benzylpenicillin not only allows for substantial oral activity but also results in a substantial broadening of antimicrobial spectrum so as to allow for use against many Gram-negative bacteria. Many devices have been employed in order to enhance still further the oral absorption of ampicillin. Bacampicillin is a prodrug of ampicillin designed for this purpose.

Bacampicillin synthesis:^[2]^[3]

An azidopenicillin sodium salt (1) is reacted with mixed carbonate ester 2 (itself prepared from acetaldehyde and ethyl chloroformate) to give ester 3. Reduction of the azido linkage witrh hydrogen and a suitable catalyst produces bacampillin (4). Both enantiomers are active. The drug is rapidly absorbed from the gastrointestinal tract and is quickly cleaved by serum esterases to bioactive ampicillin, acetaldehyde, CO2 and ethanol.

References

^ Bodin NO; Ekström B; Forsgren U; et al. (November 1975). "Bacampicillin: a New Orally Well-Absorbed Derivative of Ampicillin". Antimicrob Agents Chemother 8 (5): 518–25. PMC 429411. PMID 1211909.
^ B. A. Ekstrom, O. K. J. Kovacs, and B. O. H. Sjoberg, DE 2311328 (1973). Chem. Abstr., 80, 14921q(1974).
^ B. A. Ekstrom, B. O. H. Sjoberg, DE 2144457 ; eidem, U.S. Patent 3,873,521 and U.S. Patent 3,939,270 (1972, 1975 and 1976 all to Astra).

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UpToDate Contents

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1. セファロスポリン-アレルギー患者：セファロスポリンおよび関連抗菌薬のその後の使用 cephalosporin allergic patients subsequent use of cephalosporins and related antibiotics

English Journal

Tolerability of aztreonam in patients with cell-mediated allergy to β-lactams.

Buonomo A, Nucera E, De Pasquale T, Pecora V, Lombardo C, Sabato V, Colagiovanni A, Rizzi A, Aruanno A, Pascolini L, Patriarca G, Schiavino D.SourceDepartment of Allergology, Catholic University of the Sacred Heart, Rome, Italy.
International archives of allergy and immunology.Int Arch Allergy Immunol.2011;155(2):155-9. doi: 10.1159/000318844. Epub 2010 Dec 22.
BACKGROUND: Cross-reactivity between aztreonam and β-lactams is poor, but tolerability of aztreonam has been assessed in a few groups of patients suffering from IgE-mediated allergy to β-lactams. The aim of this study was to assess the cross-reactivity of aztreonam with other β-lactams and its to
PMID 21196760

Bacampicillin uptake is shared with thiamine in Caco-2 cells.

Oda M, Fujimoto K, Kobayashi M, Saitoh H.SourceDepartment of Pharmaceutics, Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido, Japan.
Biological & pharmaceutical bulletin.Biol Pharm Bull.2007 Jul;30(7):1344-9.
Bacampicillin was developed as a prodrug to improve the intestinal absorption of its metabolite ampicillin. This study was undertaken to characterize bacampicillin transport in Caco-2 cells. The uptake of bacampicillin in Caco-2 cells was significantly greater than those of ampicillin and pivampicil
PMID 17603179

Localized bacillary angiomatosis in the oral cavity: observations about a neoplasm with atypical behavior. Description of a case and review of the literature.

Tucci E, Della Rocca C, Santilli F.SourceDepartment of Dentistry and Stomatology, Faculty of Medicine and Surgery I, La Sapienza University, Rome, Italy.
Minerva stomatologica.Minerva Stomatol.2006 Jan-Feb;55(1-2):67-75.
Bacillary angiomatosis is a rather frequent infectious pathology appearing mainly in the skin but can also affect the liver, spleen, heart, bones, lungs, muscles, central nervous system and other organs. The localization of the lesion in the oral cavity is rather rare, as it is evident in the litera
PMID 16495874

Japanese Journal

咀嚼異常ラットにおける抗菌薬および非ステロイド性抗炎症薬の薬物動態に関する研究

小児歯科学雑誌 52(1), 38-46, 2014
NAID 130005073791

Bacampicillin Uptake Is Shared with Thiamine in Caco-2 Cells(Biopharmacy)

Biological & pharmaceutical bulletin 30(7), 1344-1349, 2007-07-01
NAID 110006342758

麻酔導入後に投与した抗菌薬によるアナフィラキシーショックが強く疑われた1症例

麻酔 55(10), 1270-1272, 2006-10
NAID 40015125958

Related Pictures

★リンクテーブル★

リンク元	「バカンピシリン」「BAPC」
拡張検索	「bacampicillin hydrochloride」

「バカンピシリン」

Bacampicillin
Systematic (IUPAC) name
	1-Ethoxycarbonyloxyethyl (2S,5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Oral
Pharmacokinetic data
Metabolism	Rapidly hydrolyzed to ampicillin
Identifiers
CAS Registry Number	37661-08-8
ATC code	J01CA06
PubChem	CID: 39849
DrugBank	DB01602
ChemSpider	390135
UNII	8GM2J22278
ChEBI	CHEBI:2968
ChEMBL	CHEMBL1583
Chemical data
Formula	C21H27N3O7S
Molecular mass	465.519 g/mol
	InChI InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1 ; Key:PFOLLRNADZZWEX-FFGRCDKISA-N ;
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