ベンジルペニシリン
- 関
- benzathine benzylpenicillin、benzylpenicillin benzathine hydrate、benzylpenicillin potassium、penicillin G
- 関
- Penicillin G
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/02/03 04:41:18」(JST)
[Wiki en表示]
Penicillin G
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| Systematic (IUPAC) name |
| (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| Clinical data |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
| MedlinePlus |
a685013 |
| Pregnancy cat. |
B (US) |
| Legal status |
℞ Prescription only |
| Routes |
parenteral |
| Pharmacokinetic data |
| Protein binding |
60 % |
| Metabolism |
hepatic |
| Half-life |
30 min |
| Excretion |
renal |
| Identifiers |
| CAS number |
61-33-6 Y (free acid)
69-57-8 (sodium salt) |
| ATC code |
J01CE01 S01AA14 QJ51CE01 |
| PubChem |
CID 5904 |
| DrugBank |
DB01053 |
| ChemSpider |
5693 Y |
| UNII |
Q42T66VG0C Y |
| KEGG |
D02336 N |
| ChEBI |
CHEBI:18208 N |
| ChEMBL |
CHEMBL29 N |
| Chemical data |
| Formula |
C16H18N2O4S |
| Mol. mass |
334.4 g/mol |
SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
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InChI
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InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1 Y
Key:JGSARLDLIJGVTE-MBNYWOFBSA-N Y
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| N (what is this?) (verify) |
Benzylpenicillin, commonly known as penicillin G, is the gold standard type of penicillin.[citation needed] Penicillin G is typically given parenterally, bypassing the intestines, because it is unstable in the highly acidic stomach. Because the drug is given parenterally, higher tissue concentrations of penicillin G can be achieved than is possible with phenoxymethylpenicillin. These higher concentrations translate to increased antibacterial activity.
Contents
- 1 Antimicrobial Potency
- 2 Medical uses
- 3 Adverse effects
- 4 Toxicology
- 5 Compendial status
- 6 References
Antimicrobial Potency[edit]
As an antibiotic, Penicillin G is noted to possess effectiveness mainly against Gram-positive organisms. Some Gram-negative organisms such as Neisseria gonorrhoeae and Neisseria meningitidis are also reported to be susceptible to Penicillin G.[1]
Medical uses[edit]
Specific indications for benzylpenicillin include:[2]
- Cellulitis
- Infective endocarditis
- Gonorrhea
- Meningitis
- Aspiration pneumonia, lung abscess
- Community-acquired pneumonia
- Syphilis
- Septicemia in children
- Septic Arthritis
- Gangrene
- Diphtheria
Adverse effects[edit]
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This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (April 2011) |
Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely CNS toxicity including convulsions (especially with high doses or in severe renal impairment), interstitial nephritis, haemolytic anaemia, leucopenia, thrombocytopenia, and coagulation disorders. Also reported diarrhoea (including antibiotic-associated colitis).
Toxicology[edit]
Benzylpenicillin serum concentrations can be monitored either by traditional microbiological assay or by more modern chromatographic techniques. Such measurements can be useful to avoid central nervous system toxicity in any patient receiving large doses of the drug on a chronic basis, but they are especially relevant to patients with renal failure, who may accumulate the drug due to reduced urinary excretion rates.[3][4]
Compendial status[edit]
- British Pharmacopoeia [5]
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This section requires expansion. (March 2010) |
References[edit]
- ^ "Penicillin G" (pdf). Toku-E. 2010-10-10. Retrieved 2012-06-11.
- ^ Rossi S, editor, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3.
- ^ Fossieck B Jr, Parker RH. Neurotoxicity during intravenous infusion of penicillin. A review. J. Clin. Pharmacol. 14: 504- 512, 1974.
- ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1195-1196.
- ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)". Retrieved 26 March 2010.
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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) |
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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
- Isoniazid
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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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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- Safety and technological characterization of Staphylococcus equorum isolates from jeotgal, a Korean high-salt-fermented seafood, for starter development.
- Jeong DW1, Han S1, Lee JH2.
- International journal of food microbiology.Int J Food Microbiol.2014 Oct 1;188:108-15. doi: 10.1016/j.ijfoodmicro.2014.07.022. Epub 2014 Jul 26.
- To select starters for jeotgal, a traditional Korean high-salt-fermented seafood, the safety and technological properties of its predominant bacteria isolates, which were identified as Staphylococcus equorum, were assessed. Among the 185 S. equorum isolates from jeotgal, 126 ampicillin-sensitive str
- PMID 25106039
- Prevalence and antimicrobial susceptibility of Arcobacter species in cow milk, water buffalo milk and fresh village cheese.
- Yesilmen S1, Vural A2, Erkan ME3, Yildirim IH4.
- International journal of food microbiology.Int J Food Microbiol.2014 Oct 1;188:11-4. doi: 10.1016/j.ijfoodmicro.2014.07.006. Epub 2014 Jul 17.
- In this study, the presence of Arcobacter spp. was examined in cow milk (n=50), water buffalo (WB) milk (n=50) and fresh village cheese (n=50) samples. The 16S rDNA-RFLP method was used for the identification of Arcobacter spp. The disc diffusion method was used to investigate the susceptibility of
- PMID 25064812
- Serotype Distribution and Antimicrobial Resistance of Invasive and Noninvasive Pneumococcal Isolates in Tunisia.
- Marzouk M1, Ferjani A, Bouafia N, Harb H, Ben Salem Y, Boukadida J.
- Microbial drug resistance (Larchmont, N.Y.).Microb Drug Resist.2014 Sep 5. [Epub ahead of print]
- Pneumococcal conjugate vaccines have not yet been introduced into the national program for childhood vaccination in Tunisia. The aim of this 7-year study was to obtain local data about serotype distribution and antimicrobial resistance of Streptococcus pneumoniae. A total of 203 isolates of culture
- PMID 25191941
Japanese Journal
- Eikenella corrodens 感染症4症例の臨床細菌学的検討
- 正木 孝幸,松本 珠美
- 保健科学研究誌 9, 7-13, 2012-03-31
- … corrodens was susceptible to benzylpenicillin,ampicillin, third-generation cephems, tetracycline, minocyclin, clindamycin and new quinolones;and moderately susceptible to gentamicin; …
- NAID 110009537006
- Infectious Endocarditis Caused by Lactobacillus acidophilus in a Patient with Mistreated Dental Caries
- Nishijima Takeshi,Teruya Katsuji,Yanase Mikio,Tamori Yuiichi,Mezaki Kazuhisa,Oka Shinichi
- Internal Medicine 51(12), 1619-1621, 2012
- … In vitro susceptibility-guided antibiotics with benzylpenicillin plus clindamycin and successive mitral annuloplasty resulted in a favorable outcome. …
- NAID 130002062171
- 扁桃感染症と Eikenella corrodens
- 平木 信明,宇高 毅,塩盛 輝夫 [他],小泉 弘樹,門川 洋平,小野 頌子,鈴木 秀明
- 耳鼻咽喉科臨床 102(3), 207-212, 2009-03-01
- … and moderately susceptible to benzylpenicillin, ampicillin, cefotiam, and minocycline; …
- NAID 10024762644
Related Links
- Benzylpenicillin, commonly known as penicillin G, is the gold standard type of penicillin. Penicillin G is typically given parenterally, bypassing the intestines, because it is unstable in the highly acidic stomach. Because the drug is given ...
- Benzathine benzylpenicillin (rINN) is a form of penicillin also known as benzathine penicillin. It is slowly absorbed into the circulation, after intramuscular injection, and hydrolysed to benzylpenicillin in vivo. It is the drug-of-choice when ...
★リンクテーブル★
[★]
- 英
- penicillin G, PCG
- 同
- ベンジルペニシリン benzylpenicillin
- 英
- 注射用ペニシリンGカリウム
- 関
- ペニシリンG、肺炎球菌
特徴
構造
肺炎球菌
[★]
- 英
- benzylpenicillin、penicillin G、benzathine benzylpenicillin、benzylpenicillin potassium、benzylpenicillin benzathine hydrate
- ラ
- benzylpenicillinum
- 商
- バイシリン、バイシリンG、ピシバニール、ペニシリンGカリウム
- 関
- ペニシリンG penicillin G PCG、ベンジルペニシリンカリウム、ベンジルペニシリンベンザチン、ベンジルペニシリンベンザチン水和物
- ペニシリン
- 主としてグラム陽性菌に作用するもの
[★]
- 関
- benzathine benzylpenicillin、benzylpenicillin、benzylpenicillin benzathine hydrate、penicillin G
[★]
ベンジルペニシリンベンザチン
- 関
- benzathine penicillin G、benzylpenicillin、benzylpenicillin benzathine hydrate、benzylpenicillin potassium、penicillin G
[★]
- 関
- benzathine benzylpenicillin、benzylpenicillin、benzylpenicillin potassium、penicillin G
[★]
ベンジルペニシリン