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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/22 00:01:34」(JST)
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Hetacillin
|
Systematic (IUPAC) name |
(2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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Clinical data |
Trade names |
Hetacin |
AHFS/Drugs.com |
Veterinary Use |
Legal status |
|
Routes of
administration |
Intramammary injection |
Identifiers |
CAS Number |
3511-16-8 Y |
ATC code |
J01CA18 |
PubChem |
CID: 193260 |
DrugBank |
DB00739 Y |
ChemSpider |
167708 Y |
UNII |
TN4JSC48CV Y |
KEGG |
D01074 N |
ChEMBL |
CHEMBL1201116 N |
Chemical data |
Formula |
C19H23N3O4S |
Molecular mass |
389.469 g/mol |
SMILES
-
O=C(O)[C@@H]3N4C(=O)[C@@H](N2C(=O)C(c1ccccc1)NC2(C)C)[C@H]4SC3(C)C
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InChI
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InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11?,12-,13+,16-/m1/s1 Y
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Key:DXVUYOAEDJXBPY-XQERAMJGSA-N Y
|
N (what is this?) (verify) |
Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself,[1] but quickly splits of acetone in the human body to form ampicillin,[2] which is active against a variety of bacteria.
Administration
Hetacillin can be administered orally.[2] The potassium salt, hetacillin potassium, is administered by injection, either intravenously or intramuscularly.[citation needed] It is sold under the trade name Hetacin for intramammary injection in veterinary use.[3]
Hetacillin was removed from the market for human use when the discovery was made that it is actually cleaved in the gastrointestinal tract to formaldehyde and had no advantages over ampicillin.[citation needed]
Chemistry
Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at 37 °C (99 °F) and pH 7, quickly releasing acetone again.[1][4]
As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro.[4]
References
- ^ a b Drugbank: Hetacillin
- ^ a b Sutherland, R.; Robinson, O. P. (1967). "Laboratory and pharmacological studies in man with hetacillin and ampicillin". British Medical Journal 2 (5555): 804–808. doi:10.1136/bmj.2.5555.804. PMC 1843140. PMID 5182358.
- ^ Hetacin-K Intramammary Infusion for Veterinary Use
- ^ a b Faine, S.; Harper, M. (1973). "Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods". Antimicrobial agents and chemotherapy 3 (1): 15–18. doi:10.1128/aac.3.1.15. PMC 444353. PMID 4597707.
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) |
|
|
Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of bacterial disease
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|
Description |
|
|
Disease |
- Gram-positive firmicutes
- Gram-positive actinobacteria
- Gram-negative proteobacteria
- Gram-negative non-proteobacteria
- Cholera
- Tuberculosis
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|
Treatment |
- Antibiotics
- cell wall
- nucleic acid
- mycobacteria
- protein synthesis
- other
- Antibodies
|
|
|
English Journal
- Short communication: Pharmacokinetics of intramammary hetacillin in dairy cattle milked 3 times per day.
- Lindquist DA1, Baynes RE1, Smith GW2.
- Journal of dairy science.J Dairy Sci.2015 Mar;98(3):1856-61. doi: 10.3168/jds.2014-8715. Epub 2014 Dec 26.
- Mastitis remains a critical disease in the dairy industry and the use of intramammary antibiotics plays a critical role in mastitis treatment. Hetacillin is currently approved as an intramammary antibiotic that is used to treat mastitis in dairy cows. It is approved for once a day administration and
- PMID 25547305
- Treatments of clinical mastitis occurring in cows on 51 large dairy herds in Wisconsin.
- Oliveira L1, Ruegg PL2.
- Journal of dairy science.J Dairy Sci.2014 Sep;97(9):5426-36. doi: 10.3168/jds.2013-7756. Epub 2014 Jul 3.
- Antimicrobials are frequently used for treatment of bovine mastitis and few studies have examined modern treatment strategies on large US dairy farms. The objective of this study was to describe treatment practices for clinical mastitis occurring in cows on large dairy herds in Wisconsin. Treatments
- PMID 24997660
- Comparison of seven antibiotic treatments with no treatment for bacteriological efficacy against bovine mastitis pathogens.
- Wilson DJ1, Gonzalez RN, Case KL, Garrison LL, Gröhn YT.
- Journal of dairy science.J Dairy Sci.1999 Aug;82(8):1664-70.
- Milk culture results were retrospectively reviewed from 9007 cases of subclinical mastitis affecting cows housed in dairy herds located in New York and northern Pennsylvania. Cases included in this analysis had at least one mastitis pathogen isolated from the initial milk sample, were recultured wit
- PMID 10480091
Japanese Journal
- Determination of β-Lactam Antibiotics in Water by Fluorescence Quenching of Mercurochrome, and Application for Simple Investigation of Potency
- 森 逸男,藤田 芳一,生田 絹子,北野 尚子,川辺 博司,中橋 義弘,加藤 圭司,稲森 善彦
- Chemical & pharmaceutical bulletin 37(7), 1827-1830, 1989-07-25
- … The calibration graphs were linear over the ranges of about 0-6 μg/ml β-lactam antibiotics penicillins (AB-PC, penicillin G, sulbenicillin, amoxicillin, cyclacillin, oxacillin, hetacillin and piperacillin) and cepham antibiotics (CEX, cefazolin, cephaloglycin, cephaloridine and cefpyramide), and the relative standard deviation was 2.7% for 1.4 μg/ml of AB-PC(n=5).This fluorescence quenching reaction between mercurochrome and β-lactam antibiotics was applied in a survey of decomposition and remaining potency of β-lactam antibiotics. …
- NAID 110003627868
- Synthesis and Oral Absorption of Hetacillin and Hetamoxicillin Labile Esters(Medicinal Chemistry,Chemical)
- GUBERT SANTIAGO,PALACIN CELIA,SACRISTAN AURELIO,ORTIZ JOSE A.
- Chemical & pharmaceutical bulletin 35(6), 2366-2372, 1987-06-25
- … Nine esters of hetacillin or hetamoxicillin were synthesized as ampicillin and amoxicillin derivatives with the aim of obtaining improved plasma levels after oral administration. … Out of these esters, which are devoid of apparent toxic effects, the benzyloxymethyl ester of hetacillin(FI-5204) gave the best result and was chosen for subsequent studies. …
- NAID 80003459844
Related Links
- hetacillin [het″ah-sil´in] a semisynthetic penicillin that is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. hetacillin a semisynthetic penicillin, which is converted in the body to ampicillin, and ...
- Read more about the pharmacogenomics of hetacillin on PharmGKB. ... Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms.
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