WordNet

a complex consisting of an organic base in association with hydrogen chloride

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/06 19:36:00」(JST)

wiki en

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).

This systemic antibacterial-related article is a stub. You can help Wikipedia by expanding it.

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. 過敏性腸症候群に対するアロセトロン塩酸塩（Lotronex） alosetron hydrochloride lotronex for irritable bowel syndrome
2. 変形性関節症の初回薬物療法 initial pharmacologic therapy of osteoarthritis
3. 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
4. クリンダマイシン：概要 clindamycin an overview
5. 成人における急性咽頭炎の対症療法 symptomatic treatment of acute pharyngitis in adults

English Journal

Antimicrobial drug use in primary healthcare clinics: a retrospective evaluation.

Shamsuddin S1, Akkawi ME2, Zaidi ST3, Ming LC4, Manan MM5.
International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases.Int J Infect Dis.2016 Nov;52:16-22. doi: 10.1016/j.ijid.2016.09.013. Epub 2016 Sep 14.
PMID 27639454

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

Buonomo A1, Nucera E, De Pasquale T, Pecora V, Lombardo C, Sabato V, Colagiovanni A, Rizzi A, Aruanno A, Pascolini L, Patriarca G, Schiavino D.
International archives of allergy and immunology.Int Arch Allergy Immunol.2011;155(2):155-9. doi: 10.1159/000318844. Epub 2010 Dec 22.
PMID 21196760

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

Oda M1, Fujimoto K, Kobayashi M, Saitoh H.
Biological & pharmaceutical bulletin.Biol Pharm Bull.2007 Jul;30(7):1344-9.
PMID 17603179

Japanese Journal

Studies on Sustained-Release Suppositories. II. Evaluation of Polymer Electrolyte Containing Acidic Groups for Prolonged Rectal Absorption of Bacampicillin in Rabbits

河島進,杉村美智代,野口たつ美,藤原洋
Chemical & pharmaceutical bulletin 37(7), 1899-1903, 1989-07-25
… Rectal absorption of bacampicillin hydrochloride (BAPC) was found to show the best bioavailability with Witepsol H-15 as suppository base among various Witepsol bases. … Bacampicillin reacts with acidic polymer electrolytes such as pectic acid (Pc), chondroitin sulfate (Cd) and precipitates as its adduct with the polymer in an aqueous solution. …
NAID 110003627885

Influence of Macrogol Bases on the Bioavailability of Bacampicillin after Rectal Administration in Rabbits

河島進,中沢勇人,藤原洋
Chemical & pharmaceutical bulletin 36(4), 1475-1482, 1988-04-25
… Rectal administration of bacampicillin hydrochloride (BAPC) in Witepsol H-15 base suppository provided a fairly good absorption in rabbits; …
NAID 110003626940

Rectal Absorption of Bacampicillin in Rabbits

河島進,広瀬由和,藪邦彦,藤原洋
Chemical & pharmaceutical bulletin 36(4), 1463-1468, 1988-04-25
… In this study, the rectal absorption of bacampicillin hydrochloride (BAPC) in rabbits as a model was investigated with the aim of preparing efficacious suppositories. …
NAID 110003626938

「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 ;
(what is this?) (verify)