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87-08-1 分子结构
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(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

ChemBase编号:300
分子式:C16H18N2O5S
平均质量:350.38952
单一同位素质量:350.09364269
SMILES和InChIs

SMILES:
S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)COc1ccccc1
Canonical SMILES:
O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)COc1ccccc1
InChI:
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
InChIKey:
BPLBGHOLXOTWMN-MBNYWOFBSA-N

引用这个纪录

CBID:300 http://www.chembase.cn/molecule-300.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
IUPAC传统名
penicillin V
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
商标名
Acipen V
Apopen
Beepen-Vk
Beromycin
Betapen-Vk
Calcipen
Compocillin V
Crystapen V
Distaquaine V
Eskacillian V
Eskacillin V
Fenacilin
Fenospen
Fenoxypen
Ledercillin Vk
Meropenin
Oracillin
Oratren
Ospen
Pen-Oral
Pen-V
Pen-Vee
Pen-Vee K
Penapar-Vk
Penicillin Vk
Penicillin-Vk
Pfizerpen Vk
Phenocillin
Phenomycilline
Phenopenicillin
Robicillin
Rocilin
Stabicillin
Uticillin Vk
V-Cil
V-Cillin
V-Cillin K
V-Cylina
V-Cyline
V-Tablopen
Vebecillin
Veetids
Veetids '125'
Veetids '250'
Veetids '500'
别名
Fenossimetilpenicillina [Dcit]
Fenoximetilpenicilina [INN-Spanish]
Penicillin Phenoxymethyl
Penicillin V Potassium
Phenoxymethylpenicillinic Acid
Phenoxymethylpenicillinic Acid Potassium Salt
Phenoxymethylpenicillin Potassium
Phenoxymethylenepenicillinic Acid
Phenoxymethyl Penicillin
Phenoximethylpenicillinum
Penicillin V
Apopen
Fenacillin
Fenocin
Fenospen
Fenoxypen
Meropenin
Oracillin
Oratren
Ospen
Pen-Vee
Phenocillin
Stabicillin
Vebecillin
Phenoxymethylpenicillin
CAS号
87-08-1
PubChem SID
46507164
160963763
PubChem CID
6869

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
InterBioScreen
Bio-0630 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 3.390268  质子受体
质子供体 LogD (pH = 5.5) -1.3336357 
LogD (pH = 7.4) -2.6421306  Log P 0.7632417 
摩尔折射率 85.768 cm3 极化性 34.069244 Å3
极化表面积 95.94 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.78  LOG S -2.89 
溶解度 4.54e-01 g/l 

分子性质

分子性质

理化性质 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
<0.1 g/100mL expand 查看数据来源
疏水性(logP)
1.4 expand 查看数据来源
生物活性机理
Binds penicillin binding protein 1Bs expand 查看数据来源
Binds penicillin binding protein 3 expand 查看数据来源
Cell-wall mucopeptide synthesis inhibitor expand 查看数据来源
应用领域
Orally absorbed antibiotic active against gram-positive bacteria expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00417 external link
Item Information
Drug Groups approved
Description Penicillin V is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V may also be used in some cases as prophylaxis against susceptible organisms.

Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
Indication For the treatment of mild to moderately severe infections (e.g. dental infection, infections in the heart, middle ear infections, rheumatic fever, scarlet fever, skin infections, upper and lower respiratory tract infections) due to microorganisms
Pharmacology Penicillin V is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin V has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Penicillin V results from the inhibition of cell wall synthesis and is mediated through Penicillin V binding to penicillin binding proteins (PBPs). Penicillin V is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Toxicity LD50 >1040 mg/kg (Orally in rats with Sodium salt); Nausea, vomiting, stomach pain, diarrhea, and, in rare cases, major motor seizures
Affected Organisms
Bacteria
Biotransformation About 35-70% of an oral dose is metabolized to penicilloic acid, an inactive metabolite. Small amounts of 6-aminopenicillanic acid have been recovered in the urine of patients on penicillin G. A small percentage of the drug appears to be hydroxylated into one or more active metabolites, which are also excreted via urine.
Absorption 25% of the dose given is absorbed, 50-60% bioavailable
Half Life 30 to 40 minutes
Protein Binding 80%
Elimination Mostly renal. A small percentage is eliminated by feces and the biliary route.
References
: Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9. [Pubmed]
Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • : Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9. Pubmed
  • Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. Pubmed
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  • Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 129
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专利

专利

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