関: ciclacillin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/02 07:54:14」(JST)

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Ciclacillin (INN) or cyclacillin (USAN), trade names Cyclapen, Cyclapen-W, Vastcillin, and others, is an aminopenicillin antibiotic. Its spectrum of activity is similar to that of ampicillin, although it is less susceptible to beta-lactamases than ampicillin and has much higher bioavailability.^[1] A large randomized, double-blind clinical trial published in 1978 also showed that ciclacillin is associated with significantly fewer and milder adverse effects than ampicillin;^[2] later studies seemed to confirm this improved tolerability, at least in children.^[3]^[4]

Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States.^[5]

References[edit]

^ Warren GH (1976). "Cyclacillin: microbiological and pharmacological properties and use in chemotherapy of infection - a critical appraisal". Chemotherapy 22 (3-4): 154–82. doi:10.1159/000221924. PMID 773605.
^ Gold JA, Hegarty CP, Deitch MW, Walker BR (January 1979). "Double-blind clinical trials of oral cyclacillin and ampicillin". Antimicrob Agents Chemother 15 (1): 55–8. PMC 352600. PMID 371540.
^ McLinn SE, Goldberg F, Kramer R, Saltstein E, Bomze JP, Deitch MW (October 1982). "Double-blind multicenter comparison of cyclacillin and amoxicillin for the treatment of acute otitis media". J Pediatr 101 (4): 617–21. doi:10.1016/S0022-3476(82)80724-5. PMID 6750067.
^ McLinn SE, Kaplan J, West N (1983). "Multicenter comparison of cyclacillin and amoxicillin in the treatment of acute streptococcal pharyngitis". Clin Ther 5 (3): 299–304. PMID 6342785.
^ Gorbach SL, Bartlett JG, Blacklow NR (2004). Infectious diseases (3rd ed.). Hagerstown, MD: Lippincott Williams & Wilkins. pp. p. 186. ISBN 0-7817-3371-5. Retrieved on September 7, 2008 through Google Book Search.

English Journal

Gender differences in kidney function.

Sabolić I1, Asif AR, Budach WE, Wanke C, Bahn A, Burckhardt G.
Pflügers Archiv : European journal of physiology.Pflugers Arch.2007 Dec;455(3):397-429. Epub 2007 Jul 19.
Sex hormones influence the development of female (F) and male (M) specific traits and primarily affect the structure and function of gender-specific organs. Recent studies also indicated their important roles in regulating structure and/or function of nearly every tissue and organ in the mammalian b
PMID 17638010

Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes.

Lin H1, King N.
Pflügers Archiv : European journal of physiology.Pflugers Arch.2007 Mar;453(6):915-22. Epub 2006 Nov 21.
The transporters PEPT1 and PEPT2 accept a broad spectrum of substrates including small, naturally occurring peptides and peptidomimetic drugs. This study aimed to investigate for the first time whether these transporters are expressed and active in isolated cardiomyocytes. PEPT1/PEPT2 expression in
PMID 17120020

Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives.

Tsuda M1, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K.
The Journal of pharmacology and experimental therapeutics.J Pharmacol Exp Ther.2006 Jul;318(1):455-60. Epub 2006 Apr 5.
Midodrine is an oral drug for orthostatic hypotension. This drug is almost completely absorbed after oral administration and converted into its active form, 1-(2',5'-dimethoxyphenyl)-2-aminoethanol) (DMAE), by the cleavage of a glycine residue. The intestinal H+-coupled peptide transporter 1 (PEPT1)
PMID 16597710

Japanese Journal

Determination of β-Lactam Antibiotics in Water by Fluorescence Quenching of Mercurochrome, and Application for Simple Investigation of Potency

森逸男,藤田芳一,生田絹子,北野尚子,川辺博司,中橋義弘,加藤圭司,稲森善彦
Chemical & pharmaceutical bulletin 37(7), 1827-1830, 1989-07-25
… The calibration graphs were linear over the ranges of about 0-6 μg/ml β-lactam antibiotics penicillins (AB-PC, penicillin G, sulbenicillin, amoxicillin, cyclacillin, oxacillin, hetacillin and piperacillin) and cepham antibiotics (CEX, cefazolin, cephaloglycin, cephaloridine and cefpyramide), and the relative standard deviation was 2.7% for 1.4 μg/ml of AB-PC(n=5).This fluorescence quenching reaction between mercurochrome and β-lactam antibiotics was applied in a survey of decomposition and remaining potency of β-lactam antibiotics. …
NAID 110003627868

Intestinal Absorption of Drugs in Rats with Glycerol-Induced Acute Renal Failure

木村聡城郎,小林享,小林美代子,沼田香苗,河合祐吉,黒崎勇二,中山太二,森将晏,粟井通泰
Chemical & pharmaceutical bulletin 36(5), 1847-1856, 1988-05-25
… Drugs examined were poorly-absorbable drugs (sulfanilic acid, procainamide ethobromide, cefazolin and sulfaguanidine), well-absorbable drugs (sulfisoxazole, quinine, salicyclic acid and impramine), actively-transported drugs (cefadroxil and cyclacillin) and water-soluble, high-molecular-weight compounds (polyethylene glycol (PEG) 1000,PEG 1500 and fluorescein isothiocyanate-conjugated dextran with a molecular weight of 4000). …
NAID 110003627001

エルシニアのβ-ラクタム系抗生物質に対する感受性

金城俊夫 [他],武藤照美,木原正子,源宜之
岐阜大学農学部研究報告 51, 219-225, 1987-01-10
エルシニアはY. pseudotuberculosisを除きβ-ラクタマーゼを産生する。このβ-ラクタマーゼ産生能に,エルシニアの菌種,生物型あるいは血清型によって,これらの分類の一助となりうるような差があるか否かを検討するため,各菌種のβ-ラクタム系抗生物質に対する感受性試験を行った。ヒト及び各種動物由来のY. enterocolitica B:1 81株,B:2 10株,B:3 30株,B:4 …
NAID 110000976529

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Cyclacillin
Systematic (IUPAC) name
	(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}- 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane- 2-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Routes	Oral
Pharmacokinetic data
Bioavailability	Moderate
Protein binding	<25%
Identifiers
CAS number	3485-14-1
ATC code	None
PubChem	CID 19003
DrugBank	DB01000
ChemSpider	17941
UNII	72ZJ154X86
KEGG	D01334
ChEBI	CHEBI:31444
ChEMBL	CHEMBL1200356
Chemical data
Formula	C15H23N3O4S
Mol. mass	341.425 g/mol
	SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)C1(N)CCCCC1)[C@H]3SC2(C)C;
	InChI InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1 ; Key:HGBLNBBNRORJKI-WCABBAIRSA-N ;
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英: cyclacillin、((欧州))ciclacillin

[1] Warren GH (1976). "Cyclacillin: microbiological and pharmacological properties and use in chemotherapy of infection - a critical appraisal". Chemotherapy 22 (3-4): 154–82. doi:10.1159/000221924. PMID 773605.

[2] Gold JA, Hegarty CP, Deitch MW, Walker BR (January 1979). "Double-blind clinical trials of oral cyclacillin and ampicillin". Antimicrob Agents Chemother 15 (1): 55–8. PMC 352600. PMID 371540.

[3] McLinn SE, Goldberg F, Kramer R, Saltstein E, Bomze JP, Deitch MW (October 1982). "Double-blind multicenter comparison of cyclacillin and amoxicillin for the treatment of acute otitis media". J Pediatr 101 (4): 617–21. doi:10.1016/S0022-3476(82)80724-5. PMID 6750067.

[4] McLinn SE, Kaplan J, West N (1983). "Multicenter comparison of cyclacillin and amoxicillin in the treatment of acute streptococcal pharyngitis". Clin Ther 5 (3): 299–304. PMID 6342785.

[5] Gorbach SL, Bartlett JG, Blacklow NR (2004). Infectious diseases (3rd ed.). Hagerstown, MD: Lippincott Williams & Wilkins. pp. p. 186. ISBN 0-7817-3371-5. Retrieved on September 7, 2008 through Google Book Search.

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cyclacillin