スルタミシリン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/03/05 23:09:58」(JST)
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This article needs more medical references for verification or relies too heavily on primary sources. Please review the contents of the article and add the appropriate references if you can. Unsourced or poorly sourced material may be removed. (September 2014) |
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Sultamicillin
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| Systematic (IUPAC) name |
| [(2R)-3,3-Dimethyl-4,4,7-trioxy-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl(2R)-6-{[(2S)-2-amino-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| Legal status |
?
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| Routes |
Oral |
| Identifiers |
| CAS number |
76497-13-7 N |
| ATC code |
J01CR04 |
| PubChem |
CID 444022 |
| ChemSpider |
392048 Y |
| UNII |
65DT0ML581 Y |
| KEGG |
D05972 Y |
| ChEBI |
CHEBI:51770 Y |
| ChEMBL |
CHEMBL506110 Y |
| Chemical data |
| Formula |
C25H30N4O9S2 |
| Molecular mass |
594.659 g/mol |
SMILES
- O=C(OCOC(=O)[C@@H]2N1C(=O)C[C@H]1S(=O)(=O)C2(C)C)[C@@H]4N5C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]5SC4(C)C
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InChI
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InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1 Y
Key:OPYGFNJSCUDTBT-PMLPCWDUSA-N Y
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| N (what is this?) (verify) |
Sultamicillin is an oral form of the antibiotic combination (codrug or mutual prodrug) ampicillin/sulbactam. It contains esterified ampicillin and sulbactam and is marketed under a number of trade names, including Saltum from Morepen Lab and Unasyn from Pfizer.
The pharmacokinetic properties of sultamicillin are improved compared to a combination of ampicillin and sulbactam. Sultamicillin increases the absorption and decreases the chances of diarrhea and dysentery. The inclusion of sulbactam extends ampicillin's spectrum of action to beta-lactamase producing strains of bacteria. Oral sulbactam with parenteral form provides a regimen of continuous sulbactam therapy throughout the treatment, resulting in better clinical results.
Contents
- 1 Chemical evaluation
- 2 Mechanism of action
- 3 Indications
- 4 References
§Chemical evaluation
Sultamicillin is a mutual prodrug of ampicillin and sulbactam. Ampicillin, a semi-synthetic orally active broad spectrum antibiotic, is linked via a methylene group with a beta-lactamase inhibitor. Sultamicillin is chemically oxymethyl penicillinate sulfone ester of ampicillin.
§Mechanism of action
After absorption, sultamicillin releases ampicillin and sulbactam into the system, so all the antibacterial efficacy of sultamicillin is due to ampicillin and sulbactam. Ampicillin exerts antibacterial activity against sensitive organisms by inhibiting biosynthesis of cell wall mucopeptide where as sulbactam irreversibly inhibits most important beta-lactamases that occur in resistant strains.
§Indications
Indications for sultamicillin include:
- Skin and soft tissue infections - furuncles, carbuncles, cellulitis, paronychia, impetigo contagiosa, diabetic foot ulcers and abscesses caused by Staphylococcus aureus and Streptococcus pyogenes.
- Upper respiratory tract infections - pharyngitis and tonsillitis caused by S. pyogenes and S. aureus. Acute and chronic sinusitis caused by S. aureus, S. pneumoniae, H. influenzae and S. progenies. Otis media, particularly suppurative otis media, with or without mastoiditis antrum.
- Lower respiratory tract infections - bacterial pneumonias, bronchitis, bronchiestasis caused by S. pneumoniae, H. influenzae, Staphylococcus aureus and S. progenies. Acute exacerbations of COPD.
- Urinary tract infections - pyelonephritis, cystitis caused by Escherichia coli, Proteus mirabilis, Klebsiella, Enterobacter and Staphylococcus aureus.
- Surgical infections - prophylaxis and treatment of surgical site infections, peri-operative prophylaxis in orthopaedic and cardiovascular surgery.
- Gynecological infections - Caused by beta-lactamase producing strains of E. coli and Bacteroides sp. (including B. fragilis).
- Infections of the gastrointestinal tract - Bacterial esophagitis, treatment of H. pylori infections as a part of MDT in ulcer management.
§References
- Singh, G.S. (2004). "Beta-lactams in the new millennium. Part-II: Cephems, oxacephems, penams and sulbactam". Mini Reviews in Medicinal Chemistry 4 (1): 93–109. doi:10.2174/1389557043487547. PMID 14754446.
English Journal
- Perioperative antibiotic prophylaxis in renal transplantation: a single-center comparison between two regimens and a brief survey among the Eurotransplant renal transplantation centers.
- Bachmann F, Adam T, Friedersdorff F, Liefeldt L, Slowinski T, Budde K, Waiser J.
- World journal of urology. 2019 May;37(5)957-967.
- Perioperative antibiotic prophylaxis (PAP) is an integral part of kidney transplantation to prevent surgical site infections (SSI). In July 2015, we changed our standard from a multiple-dose to a single-dose (SD) prophylaxis. Here, we report on results with both regimens and a related survey among E
- PMID 30109484
- Antibiotic use in children with Kawasaki disease.
- Han SB, Lee SY.
- World journal of pediatrics : WJP. 2018 Dec;14(6)621-622.
- PMID 29713927
- Effectiveness of Outpatient Antibiotics After Surgical Drainage of Abscesses in Reducing Treatment Failure.
- Pulia MS, Schwei RJ, Patterson BW, Repplinger MD, Smith MA, Shah MN.
- The Journal of emergency medicine. 2018 10;55(4)512-521.
- The optimal approach to outpatient antibiotic use after surgical drainage of abscesses is unclear given conflicting clinical trial results. Our primary objective was to evaluate the real-world effectiveness of outpatient antibiotic prescribing after surgical drainage of cutaneous abscesses on reduci
- PMID 30149998
Japanese Journal
- 蜂刺症後にAlcaligenes faecalisによる皮下膿瘍を形成した一例
- 出血を伴う多発性転移性脳腫瘍の像を示した皮膚原発悪性黒色腫の一例
- 高知赤十字病院医学雑誌 = Medical Journal of Kochi Red Cross Hospital 18(1), 5-9, 2014-03
- NAID 120005675209
- 新規に生じた心雑音により心炎の合併を同定し得た高齢発症リウマチ熱の1例
- 日本臨床免疫学会会誌 = Japanese journal of clinical immunology 35(3), 194-198, 2012-06-30
- NAID 10030832745
Related Links
- Sultamicillin [SBTPC] スルタミシリン, ペニシリン系 1. 商品名 先発品 ユナシン細粒小児用10％ 【ファイザー】 ユナシン錠375mg 【ファイザー】 2. 日本における発売年 1987（昭和62）年 3. 特長 世界初のミューチュアルプロドラッグの経口 ...
- Synopsis Sultamicillin is the tosylate salt of the double ester of sulbactam plus ampicillin. Sulbactam is a semisynthetic β-lactamase inhibitor which, in combination with ampicillin, ... Various sections of the manuscript reviewed by: S.C. Aronoff ...
Related Pictures
★リンクテーブル★
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- 英
- sultamicillin
- 同
- SBTPC
- 化
- トシル酸スルタミシリン sultamicillin tosilate
- 商
- ユナシン
- 関
- 抗菌薬
薬効薬理
抗菌作用
- (1) 本薬はブドウ球菌属、レンサ球菌属、腸球菌、肺炎球菌などのグラム陽性菌から淋菌、大腸菌、プロテウス・ミラビリス、インフルエンザ菌などのグラム陰性菌まで広い抗菌スペクトルを有し、殺菌的に作用する。
- (2) アンピシリン感性菌はもとより耐性菌にも強い抗菌力を発揮し、Rプラスミドを有する大腸菌やプロテウス・ブルガリスの本薬による形態変化を観察するとアンピシリンのMIC濃度ではみられないスフェロプラスト化や溶菌が本薬のMIC濃度で顕著にみられる。
- (3) β-ラクタマーゼ産生菌を含む複数菌による混合感染に対してスルバクタムのβ-ラクタマーゼ阻害作用によりアンピシリンの生体内での安定性を高めて本来の抗菌力を発揮させるので、本薬はアンピシリン単独投与時より強い感染防御効果が認められている（マウス）。
作用機序
- 生体内で遊離したスルバクタムはβ-ラクタマーゼのIc、II、III及びIV型を強く、Ia及びV型を軽度に不可逆的に不活性化する25)。従って本薬ではβ-ラクタマーゼによるアンピシリンの加水分解が阻害され、アンピシリン本来の広く、強い抗菌力が発揮される。
添付文書
- http://www.info.pmda.go.jp/go/pack/6131008F1030_1_02/6131008F1030_1_02?view=body
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- 関
- sultamicillin