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- carindacillin sodium
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/08/10 23:13:53」(JST)
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Carindacillin
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Systematic (IUPAC) name |
(2S,5R,6R)-6-([3-(2,3-dihydro-1H-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]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 |
℞ Prescription only |
Routes |
Oral |
Identifiers |
CAS number |
26605-69-6 |
ATC code |
J01CA05 |
PubChem |
CID 93184 |
ChemSpider |
391995 |
UNII |
5V278481KE Y |
Chemical data |
Formula |
C26H26N2O6S |
Mol. mass |
494.55 g/mol |
SMILES
- [Na+].O=C([O-])[C@@H]4N5C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)Oc2cc3c(cc2)CCC3)[C@H]5SC4(C)C
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Carindacillin (INN), also known as Carbenicillin indanyl (USAN) is a penicillin antibiotic. It is a prodrug of carbenicillin.[1]
It is administered orally, as the sodium salt. It is marketed by Pfizer under the brand name Geocillin.
References
- ^ English AR, Retsema JA, Ray VA, Lynch JE (March 1972). "Carbenicillin indanyl sodium, an orally active derivative of carbenicillin". Antimicrob. Agents Chemother. 1 (3): 185–91. PMC 444190. PMID 4558137. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=4558137.
Antibacterials: cell envelope antibiotics (J01C-J01D)
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Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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|
Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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UpToDate Contents
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English Journal
- Use of lavage fluids in arthroplasty to prevent postoperative infections.
- Kruckenhauser EM1, Nogler M1, Coraça-Huber D1.
- Drug research.Drug Res (Stuttg).2014 Mar;64(3):166-8. doi: 10.1055/s-0033-1354367. Epub 2013 Aug 28.
- OBJECTIVE: Lavage techniques are used every day all over the world to clean wounds and surgical approaches. The solutions used vary depending on the application range; there are, for instance, normal saline, antibiotic or antiseptic solutions. This review describes the lavage solutions actually used
- PMID 23986306
- Carinatumins A-C, new alkaloids from Lycopodium carinatum inhibiting acetylcholinesterase.
- Choo CY1, Hirasawa Y, Karimata C, Koyama K, Sekiguchi M, Kobayashi J, Morita H.
- Bioorganic & medicinal chemistry.Bioorg Med Chem.2007 Feb 15;15(4):1703-7. Epub 2006 Dec 15.
- Three new Lycopodium alkaloids, carinatumins A-C (1-3), have been isolated from the club moss Lycopodium carinatum. Structures and stereochemistry of 1-3 were elucidated on the basis of 2D NMR correlations. Carinatumins A (1) and B (2) exhibited a potent inhibitory activity against acetylcholinester
- PMID 17188496
- Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model.
- Li YH1, Tanno M, Itoh T, Yamada H.
- International journal of pharmaceutics.Int J Pharm.1999 Nov 30;191(2):151-9.
- Transport of carbenicillin (CBPC) and its orally active prodrug (carindacillin, CIPC) was studied with rat intestinal brush border membrane vesicles (BBMV). CIPC was transported uphill into BBMV in the presence of a H(+) gradient, indicating that CIPC absorption is carrier-mediated. Indeed, CIPC was
- PMID 10564841
Japanese Journal
- Mechanism of intestinal absorption of an orally active β-lactam prodrug : uptake and transport of carindacillin in Caco-2 cells
- 緑膿菌性複雑性尿路感染症に対するcarindacillinの再評価
- 日本化学療法学会雜誌 = Japanese journal of chemotherapy 43(1), 89-95, 1995-01-25
- NAID 10005861767
- 緑膿菌性複雑性尿路感染症に対するcarindacillinの再評価
Related Links
- The Merck Index* Online | Carindacillin | Monograph containing literature references, physical and biological properties and relevant information ... You are able to perform searches and obtain result sets but do not currently have ...
- Carindacillin | C26H26N2O6S | CID 93184 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. ... NIH NLM U.S. National Library of Medicine ...
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