(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase编号: 931
• 分子式: C16H19N3O5S
• 平均质量: 365.40416
• 单一同位素质量: 365.10454172
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c1ccc(O)cc1
• Canonical SMILES: O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
• InChIKey: LSQZJLSUYDQPKJ-NJBDSQKTSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC传统名: amoxicillin
• 商标名: Imacillin; Lamoxy; Metafarma capsules; Metifarma capsules; Moxacin; Moxal; Ospamox; Pamoxicillin; Piramox; Polymox; Robamox; Sawamox PM; Sumox; Tolodina; Trimox; Unicillin; Utimox; Vetramox; Wymox; Zimox; AMPC; Actimoxi; Amoclen; Amolin; Amopen; Amopenixin; Amoxi; Amoxi-Mast; Amoxibiotic; Amoxiden; Amoxil; Amoxivet; Anemolin; Aspenil; Biomox; Bristamox; Cemoxin; Clamoxyl; Delacillin; Dispermox; Efpenix; Flemoxin; Hiconcil; Histocillin; Ibiamox; Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others
• 别名: 阿莫西林; Amoxicillin; Amoxicilina [INN-Spanish]; Amoxicillin anhydrous; Amoxicillin Trihydrate; Amoxicilline [INN-French]; Amoxicillinum [INN-Latin]; AMC; Amoxycillin Trihydrate; Amoxycillin; D-Amoxicillin; p-Hydroxyampicillin; Amoxicillin; (2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid-d4; AMPC-d4; Amoxycillin-d4; Helvamox-d4; Pasetocin-d4; Penimox-d4; Zamocillin-d4; Amoxicillin-d4; (2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; Amoxillat; Ardine; Helvamox; Pasetocin; Penimox; Zamocillin; Amoxicillin Trihydrate; AMPC; Amolin; Amoxi; (2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

登记号

• CAS号: 61336-70-7; 26787-78-0
• EC号: 248-003-8
• MDL号: MFCD00056860
• Beilstein号: 7507120
• PubChem SID: 46507578; 160964394
• PubChem CID: 33613
• CHEBI ID: 2676
• ATC码: J01CA04; QG51AA03
• CHEMBL: 1082
• Chemspider ID: 31006
• DrugBank ID: DB01060
• KEGG ID: D07452
• 美国药典/FDA物质标识码: 9EM05410Q9
• 维基百科标题: Amoxicillin
• Medline Plus: a685001

理论计算性质

JChem

• Acid pKa: 3.2314606
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -2.3092988
• LogD (pH = 7.4): -2.5697672
• Log P: -2.3101761
• 摩尔折射率: 89.5044 cm^3
• 极化性: 35.524654 Å^3
• 极化表面积: 132.96 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.75
• LOG S: -2.58
• 溶解度: 9.58e-01 g/l

分子性质

理化性质

• 溶解度: 3430 mg/L; Do you have solubility information on this product that you would like to share?; Water
• 外观: Off-White to Pale Yellow Solid; White to Off-White Solid
• 熔点: >200°C (dec.); 209-210°C
• 疏水性(logP): 0; -1.872

安全信息

• 保存条件: -20°C Freezer; -20°C Freezer, Under Inert Atmosphere; 2-8°C
• RTECS编号: XH8300000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 42/43
• 安全公开号: 22-36/37
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H317-H334
• GHS警示性声明: P261-P280-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral, intravenous
• 生物利用度: 95% oral
• 排泄: renal
• 半衰期: 61.3 minutes
• 代谢: less than 30% biotransformed in liver
• 法定药品分级: POM (UK); Rx-only (US)
• 妊娠期药物分类: A (Australia); B (US)

产品相关信息

• 纯度: ≥97.0% (dried material, NT); 95%
• 药效: ≥900 μg per mg
• 杂质: ~15% water
• Empirical Formula (Hill Notation): C16H19N3O5S

详细说明

MP Biomedicals - 02190145

Crystalline

DrugBank - DB01060

• Drug Groups: approved
• Description: A broad-spectrum semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration. Amoxicillin is commonly prescribed with clauvanic acid (a beta lactamase inhibitor) as it is susceptible to beta-lacatamase degradation. [PubChem]
• Indication: For the treatment of infections of the ear, nose, and throat, the genitourinary tract, the skin and skin structure, and the lower respiratory tract due to susceptible (only b-lactamase-negative) strains of Streptococcus spp. (a- and b-hemolytic strains only), S. pneumoniae, Staphylococcus spp., H. influenzae, E. coli, P. mirabilis, or E. faecalis. Also for the treatment of acute, uncomplicated gonorrhea (ano-genital and urethral infections) due to N. gonorrhoeae (males and females).
• Pharmacology: Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptability. The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin is sometimes combined with clavulanic acid, a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production.
• Toxicity: Serious toxicity is unlikely following large doses of amoxicillin. Acute ingestion of large doses of amoxicillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins
• Absorption: Rapidly absorbed after oral administration.
• Half Life: 61.3 minutes
• Protein Binding: In blood serum, amoxicillin is approximately 20% protein-bound
• Elimination: Most of the amoxicillin is excreted unchanged in the urine; its excretion can be delayed by concurrent administration of probenecid.
• References: Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A8523

Application
Do you have application information on this product that you would like to share?
Amoxicillin is a moderate-spectrum, β-lactam antibiotic . Amoxicillin is one of the most common antibiotics prescribed for children. It is used to study the oxygen dependent antimicrobial systems of polymorphonuclear leukocytes (PMNLs), the risk of resistance development in Helicobacter pylor, and various dosing strategies against Streptococcus pneumoniae and Pneumococcal pneumonia 1,2,3,4. It is also used to study the synthesis of bacterial cell walls at the level of peptidoglycan polymer chain cross-linking involving bacterial transpeptidase.
Amoxicillin is used to study the synthesis of bacterial cell walls at the level of peptidoglycan polymer chain cross-linking involving bacterial transpeptidase.
Biochem/physiol Actions
Amoxicillin inhibits the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive and Gram-negative bacteria.

Toronto Research Chemicals - A634238

Labelled semi-synthetic antibiotic related to Penicillin. Antibacterial.

Toronto Research Chemicals - A634235

Semi-synthetic antibiotic related to Penicillin. Antibacterial.

参考文献

• Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. Pubmed
• Brogden, R.N., et al.: Drugs, 18, 169 (1979)
• Bird, A.E., et al.: Anal. Profiles Drug Subs. Excip., 23, 1 (1979)
• Brogden, R.N., et al.: Drugs, 18, 169 (1979)
• Bird, A.E., et al.: Anal. Profiles Drug Subs. Excip., 23, 1 (1979)