日
関

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/02/16 15:15:07」(JST)

wiki en

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Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States.^[5]

Synthesis

In an attempt to form orally active penicillins unrelated to ampicillin, use was made of the fact that certain spiro α-amino acids, such as Cycloleucine, are well absorbed orally and transported like normal amino acids.

Cyclacillin synthesis:^[6]

Reaction of cyclohexanone with ammonium carbonate and KCN under the conditions of the Bucherer-Bergs reaction led to hydantoin 1. On acid hydrolysis, α-amino acid 2 resulted. Treatment with phosgene both protected the amino group and activated the carboxyl group toward amide formation (as 3) and reaction with 6-aminopenicillanic acid (6-APA) gave cyclacillin (4).

Interestingly, this artifice seems to have worked, since cyclacillin is more active in vivo than its in vitro spectrum suggests would be likely.

References

^ 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. doi:10.1128/aac.15.1.55. 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. p. 186. ISBN 0-7817-3371-5. Retrieved on September 7, 2008 through Google Book Search.
^ Alburn, H. E.; Clark, R. E.; Fletcher h, 3rd; Grant, N. H. (1967). "Synthesis of new broad-spectrum aminoalicyclic penicillins". Antimicrobial Agents and Chemotherapy. 7: 586–9. PMID 5596194.

English Journal

Gender differences in kidney function.

Sabolić I, Asif AR, Budach WE, Wanke C, Bahn A, Burckhardt G.
Pflugers Archiv : European journal of physiology. 2007 Dec;455(3)397-429.
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 H, King N.
Pflugers Archiv : European journal of physiology. 2007 Mar;453(6)915-22.
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 M, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K.
The Journal of pharmacology and experimental therapeutics. 2006 Jul;318(1)455-60.
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

上顎洞内貯留液よりみた副鼻腔炎検出菌の検討

足立光朗,古田茂,鈴木慎也,前田太郎
日本耳鼻咽喉科學會會報 105(9), 925-930, 2002-09-20
… Ciclacillin was effective against 64.7% of all pathogens isolated in this study, cefpodoxime proxetil effective against 6.5%, and cefixime effective against 2.4%.4. …
NAID 10010307772

Ciclacillin(Vastcillin),Ampicillin(Solcillin)の血中濃度および扁桃内濃度にかんする臨床的研究

松本和彦
The Japanese journal of antibiotics 32(11), 1196-1202, 1979-11
NAID 40000016649

実験的肺炎ラットにおける抗生物質の体内動態に関する研究-1-CiclacillinとSerratiopeptidase併用のばあい

荒谷春恵,建石英樹,称宜田純子
The Japanese journal of antibiotics 32(8), 806-811, 1979-08
NAID 40000016613

Related Pictures

Beta-lactam resistance 와이비탈캡슐250mg (Wyvital Cap. 250mg) - KMLE 약품/의약품 검색 클래팍신정500mg(클래리트로마이신) 일양약품(주) 오메타졸캡슐(오메프라졸) 익수제약(주) Peptiase - Serratiopeptidase : The Miracle Enzyme IHES40 The Life Extension Blog: Serrapeptase Enzyme Fights Germs and Helps with Pain Ciclacillina

★リンクテーブル★

リンク元	「cyclacillin」

「cyclacillin」

Ciclacillin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Pharmacokinetic data
Bioavailability	Moderate
Protein binding	<25%
Identifiers
	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;
CAS Number	3485-14-1 ;
PubChem CID	19003;
IUPHAR/BPS	4817;
DrugBank	DB01000 ;
ChemSpider	17941 ;
UNII	72ZJ154X86;
KEGG	D01334 ;
ChEBI	CHEBI:31444 ;
ChEMBL	CHEMBL1200356 ;
ECHA InfoCard	100.020.429
Chemical and physical data
Formula	C15H23N3O4S
Molar mass	341.425 g/mol
3D model (JSmol)	Interactive image;
	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 ;
(what is this?) (verify)

　　[★]

シクラシリン

関: 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. doi:10.1128/aac.15.1.55. 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. p. 186. ISBN 0-7817-3371-5. Retrieved on September 7, 2008 through Google Book Search.

[6] Alburn, H. E.; Clark, R. E.; Fletcher h, 3rd; Grant, N. H. (1967). "Synthesis of new broad-spectrum aminoalicyclic penicillins". Antimicrobial Agents and Chemotherapy. 7: 586–9. PMID 5596194.

匿名

検索

案内

案内

ciclacillin