ペニシリンV
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Phenoxymethylpenicillin (Penicillin V)
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Systematic (IUPAC) name |
3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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Clinical data |
Trade names |
Veetids |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a685015 |
License data |
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Pregnancy
category |
- US: B (No risk in non-human studies)
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Routes of
administration |
oral |
Legal status |
Legal status |
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Pharmacokinetic data |
Bioavailability |
60% |
Protein binding |
80% |
Metabolism |
hepatic |
Biological half-life |
30–60 min |
Excretion |
renal |
Identifiers |
CAS Number |
87-08-1 Y , 132-98-9 (potassium), 147-48-8 (anhydrous calcium), 73368-74-8 (calcium dihydrate) |
ATC code |
J01CE02 |
PubChem |
CID 6869 |
DrugBank |
DB00417 Y |
ChemSpider |
6607 Y |
UNII |
Z61I075U2W Y |
KEGG |
D05411 Y |
ChEBI |
CHEBI:27446 Y |
ChEMBL |
CHEMBL615 Y |
Chemical data |
Formula |
C16H18N2O5S |
Molar mass |
350.39 g/mol |
SMILES
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CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
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InChI
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InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1 Y
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Key:BPLBGHOLXOTWMN-MBNYWOFBSA-N Y
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Physical data |
Melting point |
120–128 °C (248–262 °F) |
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Phenoxymethylpenicillin, commonly known as penicillin V, is an antibiotic useful for the treatment of a number of bacterial infections. It is a penicillin that is orally active. It is less active than benzylpenicillin (penicillin G) against Gram-negative bacteria.[1][2] Phenoxymethylpenicillin is more acid-stable than benzylpenicillin, which allows it to be given orally. It exerts a bactericidal action against penicillin-sensitive microorganisms during the stage of active multiplication. It acts by inhibiting the biosynthesis of cell-wall peptidoglycan. It is not active against beta-lactamase-producing bacteria, which include many strains of Staphylococci.[3]
Phenoxymethylpenicillin has a range of antimicrobial activity against Gram-positive bacteria that is similar to that of benzylpenicillin and a similar mode of action, but it is substantially less active than benzylpenicillin against Gram-negative bacteria.[1][2]
Phenoxymethylpenicillin is usually used only for the treatment of mild to moderate infections, and not for severe or deep-seated infections since absorption can be unpredictable. Except for the treatment or prevention of infection with Streptococcus pyogenes (which is uniformly sensitive to penicillin), therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response.[3] Patients treated initially with parenteral benzylpenicillin may continue oral treatment with phenoxymethylpenicillin once a satisfactory clinical response has been obtained.[4]
For prophylaxis against rheumatic fever, phenoxymethylpenicillin given by mouth twice a day is used as an alternative to injections of benzathine penicillin given every two weeks. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[5]
Contents
- 1 Medical uses
- 2 Adverse effects
- 3 Compendial status
- 4 References
Medical uses
Specific indications for phenoxymethylpenicillin include:[4][6]
- Infections caused by Streptococcus pyogenes
- Tonsillitis
- Pharyngitis
- Skin infections
- Anthrax (mild uncomplicated infections)
- Lyme disease (early stage in pregnant women or young children)
- Rheumatic fever (primary and secondary prophylaxis)
- Streptococcal skin infections
- Spleen disorders (pneumococcal infection prophylaxis)
- Initial treatment for Dental Abscesses
- Moderate-to-severe gingivitis (with metronidazole)
- Avulsion injuries of teeth (as an alternative to tetracycline)
- Blood infection prophylaxis in children with sickle cell disease.
Penicillin V is sometimes used in the treatment of odontogenic infections.
Adverse effects
Further information: Penicillin drug reaction
Phenoxymethylpenicillin is usually well tolerated but may occasionally cause transient nausea, vomiting, epigastric distress, diarrhea, constipation, acidic smell to urine and black hairy tongue. A previous hypersensitivity reaction to any penicillin is a contraindication.[3][4]
Compendial status
- British Pharmacopoeia [7]
References
- ^ a b Garrod, L. P. (1960). "Relative Antibacterial Activity of Three Penicillins". British Medical Journal (5172): 527–29.
- ^ a b Garrod, L. P. (1960). "The Relative Antibacterial Activity of Four Penicillins". British Medical Journal (5214): 1695–6.
- ^ a b c "Penicillin V Potassium tablet: Drug Label Sections". U.S. National Library of Medicine, Daily Med: Current Medication Information. December 2006. Retrieved 2009-08-02.
- ^ a b c Sweetman S., ed. (2002). Martindale: The complete drug reference (Electronic version ed.). London: Royal Pharmaceutical Society of Great Britain and the Pharmaceutical Press.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ Rossi S., ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3.
- ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Retrieved 26 March 2010.
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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Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- Antimicrobial liquid formulations: a blind taste comparison of three brands of penicillin VK and three brands of amoxicillin.
- Chan DS1, Demers DM, Bass JW.
- The Annals of pharmacotherapy.Ann Pharmacother.1996 Feb;30(2):130-2.
- OBJECTIVE: To rate the perception of taste, texture, smell and aftertaste of various brands of penicillin VK and amoxicillin.DESIGN: Oral, liquid formulations of three brands of penicillin VK (PenVee K, V-Cillin-K, VeeTids) and three brands of amoxicillin (Amoxil, Trimox, Wymox) were evaluated for s
- PMID 8835043
- Antimicrobial drug suspensions: a blinded comparison of taste of twelve common pediatric drugs including cefixime, cefpodoxime, cefprozil and loracarbef.
- Demers DM1, Chan DS, Bass JW.
- The Pediatric infectious disease journal.Pediatr Infect Dis J.1994 Feb;13(2):87-9.
- We conducted a blinded taste test evaluating 12 antimicrobial suspensions by smell, texture, taste, aftertaste and overall acceptance. Drugs received cumulative scores in each category as well as a total score ranking. Overall Lorabid scored highest but not significantly higher than Keflex, Suprax a
- PMID 8190556
- NTP Toxicology and Carcinogenesis Studies of Penicillin VK (CAS No. 132-98-9) in F344/N Rats and B6C3F1 Mice (Gavage Studies).
- National Toxicology Program.
- National Toxicology Program technical report series.Natl Toxicol Program Tech Rep Ser.1988 Jun;336:1-170.
- Penicillin VK, a widely used antibiotic for treatment of gram-positive coccal infections, was nominated for study by the National Cancer Institute because rodent carcinogenicity studies for this drug had not been performed. The chemical (94% or 98% pure, USP grade) was administered orally (by gavage
- PMID 12732900
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Related Pictures
★リンクテーブル★
[★]
- 英
- penicillin V PCV
- 同
- フェノキシメチルペニシリン phenoxymethylpenicillin
- 商
- Veetids
- first aid step1 2006 p.166(作用スペクトル)
抗菌スペクトル
動態
適応
- gram-positive cocci, gram-positive rods, gram-negative cocci, and spirochetes(first aid step1 2006 p.166)
副作用
- hypersensitivity, hemolytic anemia