ファロペネムナトリウム
WordNet
- a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11
PrepTutorEJDIC
- ソジウム,ナトリウム(金属元素;化学記号はNa)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/11/06 20:15:06」(JST)
[Wiki en表示]
Faropenem
|
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
?
|
Routes |
Oral |
Identifiers |
CAS number |
106560-14-9 N |
ATC code |
J01DI03 |
PubChem |
CID 65894 |
ChemSpider |
59303 Y |
UNII |
F52Y83BGH3 Y |
ChEBI |
CHEBI:51257 Y |
ChEMBL |
CHEMBL556262 Y |
Chemical data |
Formula |
C12H15NO5S |
Mol. mass |
285.317 g/mol |
SMILES
- O=C2N1/C(=C(\S[C@@H]1[C@H]2[C@H](O)C)[C@@H]3OCCC3)C(=O)O
|
InChI
-
InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1 Y
Key:HGGAKXAHAYOLDJ-FHZUQPTBSA-N Y
|
N (what is this?) (verify) |
Faropenem is an orally active beta-lactam antibiotic belonging to the penem group.[1] It is resistant to some forms of extended-spectrum beta-lactamase.[2] It is available for oral use.[3]
Contents
- 1 Forms
- 2 Clinical use
- 3 History
- 4 References
- 5 External links
Forms
Faropenem was developed by Daiichi Asubio Pharma, which markets it in two forms.
- The sodium salt faropenem sodium, available under the trade name Farom, has been marketed in Japan since 1997. (PubChem 636379)
- The prodrug form faropenem medoxomil[4] (also known as faropenem daloxate) has been licensed from Daiichi Asubio Pharma by Replidyne, which plans to market it in conjunction with Forest Pharmaceuticals. The trade name proposed for the product was Orapem, but company officials recently announced this name was rejected by the FDA.[5]
Clinical use
Faropenem has yet to receive marketing approval in the United States, and was submitted for consideration by the United States Food and Drug Administration (FDA) on 20 December 2005. The new drug application dossier submitted included these proposed indications:
- acute bacterial sinusitis
- community-acquired pneumonia
- acute exacerbations of chronic bronchitis
- uncomplicated skin and skin structure infections
- urinary tract infections
History
The FDA refused to approve faropenem, an antibiotic manufactured by Louisville-based Replidyne. The FDA said the drug was “nonapprovable”, but did not refer to specific safety concerns about the product. The company will have to conduct new studies and clinical trials, lasting an estimated two more years, to prove the drug treats community-acquired pneumonia, bacterial sinusitis, chronic bronchitis, and skin infections.
References
- ^ Critchley IA, Brown SD, Traczewski MM, Tillotson GS, Janjic N (December 2007). "National and regional assessment of antimicrobial resistance among community-acquired respiratory tract pathogens identified in a 2005-2006 U.S. Faropenem surveillance study". Antimicrob. Agents Chemother. 51 (12): 4382–9. doi:10.1128/AAC.00971-07. PMC 2168020. PMID 17908940.
- ^ Mushtaq S, Hope R, Warner M, Livermore DM (May 2007). "Activity of faropenem against cephalosporin-resistant Enterobacteriaceae". J. Antimicrob. Chemother. 59 (5): 1025–30. doi:10.1093/jac/dkm063. PMID 17353220.
- ^ Milazzo I, Blandino G, Caccamo F, Musumeci R, Nicoletti G, Speciale A (March 2003). "Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates". J. Antimicrob. Chemother. 51 (3): 721–5. doi:10.1093/jac/dkg120. PMID 12615878.
- ^ Gettig JP, Crank CW, Philbrick AH (January 2008). "Faropenem medoxomil". Ann Pharmacother 42 (1): 80–90. doi:10.1345/aph.1G232. PMID 18094341.
- ^ (Q1 06 Investor Conf Call)(PubChem 6918218)
External links
- Replidyne website
- Daiichi Asubio Pharma products page
Antibacterials: cell envelope antibiotics (J01C-J01D)
|
|
Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
|
|
Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
|
|
β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
|
Extended sp.
|
- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
|
|
Narrow sp.
|
β-lactamase sensitive
|
- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
|
|
β-lactamase resistant
|
- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
|
|
|
|
Penems
|
|
|
Carbapenems
|
- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
|
|
Cephalosporins/Cephamycins
(cephems)
|
1st (PEcK)
|
- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
|
|
2nd (HEN)
|
- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
|
|
3rd
|
- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
|
|
4th (antipseudomonal)
|
- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
|
|
5th
|
- Ceftobiprole
- Ceftaroline fosamil
- Ceftolozane
|
|
Veterinary
|
- Ceftiofur
- Cefquinome
- Cefovecin
|
|
|
Monobactams
|
- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
|
|
β-lactamase inh.
|
- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
|
|
Combinations
|
- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
|
|
|
Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (lysozyme)
- Gramicidin
- Isoniazid
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
gr+f/gr+a (t)/gr-p (c)/gr-o
|
drug (J1p, w, n, m, vacc)
|
|
|
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UpToDate Contents
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English Journal
- Synthesis, characterization and antibacterial activities of some new ferrocene-containing penems.
- Long B, He C, Yang Y, Xiang J.SourceCollege of Chemistry and Chemical Engineering, and Biomedical Engineering Center, State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.
- European journal of medicinal chemistry.Eur J Med Chem.2010 Mar;45(3):1181-8. Epub 2009 Dec 28.
- The synthesis and structure-activity relationships of a series of new penems bearing ferrocenyl group attached to the C-2 position of the penem nucleus were described. The beta-lactanic derivatives obtained had been characterized as sodium salts, through (1)H NMR and IR, as well as through element a
- PMID 20053481
- Gateways to clinical trials.
- Tomillero A, Moral MA.AbstractGateways to clinical trials is a guide to the most recent trials in current literature and congresses. The data in the following tables has been retrieved from the Clinical Trials Knowledge Area of Prous Science Integrity(R), the drug discovery and development portal, http://integrity.prous.com. This issue focuses on the following selection of drugs: (+)-Dapoxetine hydrochloride, (S)-Tenatoprazole sodium salt monohydrate 19-28z, Acotiamide hydrochloride hydrate, ADV-TK, AE-37, Aflibercept, Albinterferon alfa-2b, Aliskiren fumarate, Asenapine maleate, Axitinib; Bavituximab, Becatecarin, beta-1,3/1,6-Glucan, Bevacizumab, Bremelanotide; Calcipotriol/betamethasone dipropionate, Casopitant mesylate, Catumaxomab, CDX-110, Cediranib, CMD-193, Cositecan; Darinaparsin, Denosumab, DP-b99, Duloxetine hydrochloride; E75, Ecogramostim, Elacytarabine, EMD-273063, EndoTAG-1, Enzastaurin hydrochloride, Eplerenone, Eribulin mesilate, Esomeprazole magnesium, Etravirine, Everolimus, Ezetimibe; Faropenem daloxate, Febuxostat, Fenretinide; Ghrelin (human); I-131 ch-TNT-1/B, I-131-3F8, Iclaprim, Iguratimod, Iloperidone, Imatinib mesylate, Inalimarev/Falimarev, Indacaterol, Ipilimumab, Iratumumab, Ispinesib mesylate, Ixabepilone; Lapatinib ditosylate, Laquinimod sodium, Larotaxel dehydrate, Linezolid, LOR-2040; Mapatumumab, MKC-1, Motesanib diphosphate, Mycophenolic acid sodium salt; NK-012; Olanzapine pamoate, Oncolytic HSV, Ortataxel; Paclitaxel nanoparticles, Paclitaxel poliglumex, Paliperidone palmitate, Panitumumab, Patupilone, PCV-9, Pegfilgrastim, Peginterferon alfa-2a, Peginterferon alfa-2b, Pertuzumab, Picoplatin, Pimavanserin tartrate, Pimecrolimus, Plerixafor hydrochloride, PM-02734, Poly I:CLC, PR1, Prasugrel, Pregabalin, Progesterone caproate, Prucalopride, Pumosetrag hydrochloride; RAV-12, RB-006, RB-007, Recombinant human erythropoietin alfa, Rimonabant, Romidepsin; SAR-109659, Satraplatin, Sodium butyrate; Tadalafil, Talampanel, Tanespimycin, Tarenflurbil, Tariquidar, Taurine, Tecovirimat, Telatinib, Telavancin hydrochloride, Telcagepant, Terameprocol, Tesofensine, Tetrodotoxin, Tezampanel, Tipifarnib, TPI-287, Tremelimumab; Valspodar, Vatalanib succinate, VCL-CB01, vCP1452, Vorinostat; XL-228; Ziprasidone hydrochloride.
- Methods and findings in experimental and clinical pharmacology.Methods Find Exp Clin Pharmacol.2008 Oct;30(8):643-72.
- Gateways to clinical trials is a guide to the most recent trials in current literature and congresses. The data in the following tables has been retrieved from the Clinical Trials Knowledge Area of Prous Science Integrity(R), the drug discovery and development portal, http://integrity.prous.com. Thi
- PMID 19088949
Japanese Journal
- 小児伝染性膿痂疹に対するファロペネムナトリウム(ファロム^【○!R】ドライシロップ小児用)の臨床的有用性の検討
- 野崎 誠,幸田 太,佐々木 りか子
- 日本小児皮膚科学会雑誌 = Journal of pediatric dermatology 27(1), 35-39, 2008-05-31
- NAID 10024137666
- 高齢者におけるfaropenem sodiumの体内動態ならびに安全性の検討
- 柴 孝也,加治木 章,原田 泰子,原田 進,高本 正祇,宮崎 三弘,小山 優,山田 陽介,千田 守,山本 俊信,鈴木 幹三,谷川原 祐介
- 日本化学療法学会雜誌 = Japanese journal of chemotherapy 50(10), 640-645, 2002-10-25
- NAID 10010298991
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