(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 449
• 分子式: C16H17N3O4S
• 平均质量: 347.38888
• 单一同位素质量: 347.09397704
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)c2ccccc2)C(=C(C1)C)C(=O)O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
• InChIKey: ZAIPMKNFIOOWCQ-UEKVPHQBSA-N

名称和登记号

名称

• IUPAC标准名: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: cephalexin
• 商标名: Alcephin; Alexin; Alsporin; Biocef; Carnosporin; Cefa-iskia; Cefablan; Cefadal; Cefadin; Cefadina; Cefaleksin; Cefalin; Cefaloto; Cefaseptin; Cefax; Ceforal; Cefovit; Celexin; Cepastar; Cepexin; Cephacillin; Cephanasten; Cephaxin; Cephin; Cepol; Ceporex; Ceporex Forte; Ceporexin; Ceporexin-E; Ceporexine; Check; Cophalexin; Durantel; Durantel DS; Ed A-Ceph; Erocetin; Factagard; Felexin; Fexin; Ibilex; Ibrexin; Inphalex; Kefalospes; Keflet; Keflex; Kefolan; Keforal; Keftab; Kekrinal; Kidolex; L-Keflex; Lafarine; Larixin; Lenocef; Lexibiotico; Lonflex; Lopilexin; Madlexin; Mamalexin; Mamlexin; Medoxine; Neokef; Neolexina; Novolexin; Nufex; Oracef; Oriphex; Oroxin; Ortisporina; Ospexin; Palitrex; Panixine Disperdose; Pectril; Pyassan; Roceph; Sanaxin; Sartosona; Sencephalin; Sepexin; Servispor; Sialexin; Sinthecillin; Sporicef; Sporidex; Syncl; Syncle; Synecl; Tepaxin; Tokiolexin; Uphalexin; Voxxim; Winlex; Zozarine
• 别名: 头孢氨苄; Cefalessina [DCIT]; Cefalexin Sodium; Cefalexina [INN-Spanish]; Cefalexine [INN-French]; Cefalexinum [INN-Latin]; Cefalexin; Cephalexin 1-hydrate; Cephalexin hydrate; Cephalexin monohydrate; Cephalexinum; Cephalexine; CEX; Cephalexin; Cefalexin; 7-(D-α-amino-phenylacetamido)-3-methyl-3-cepheme-4-carboxylic acid; Cefalexin; Alcephin; Cefablan; keflex; Cefadin; Tepaxin

登记号

• CAS号: 15686-71-2
• EC号: 239-773-6
• MDL号: MFCD00056877
• PubChem SID: 160963912; 24860698; 46506749
• PubChem CID: 27447; 2666
• CHEBI ID: 3534
• ATC码: QJ51DB01; J01DB01
• CHEMBL: 1727
• Chemspider ID: 25541
• DrugBank ID: DB00567
• KEGG ID: D00263
• 美国药典/FDA物质标识码: 5SFF1W6677
• 维基百科标题: Cefalexin
• Medline Plus: a682733

理论计算性质

JChem

• 摩尔折射率: 88.9736 cm^3
• 极化性: 34.625595 Å^3
• 极化表面积: 112.73 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true
• Acid pKa: 3.4520106
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.1413963
• LogD (pH = 7.4): -2.3951817
• Log P: -2.145041

ALOGPS 2.1

• 溶解度: 2.97e-01 g/l
• Log P: 0.55
• LOG S: -3.07

分子性质

理化性质

• 溶解度: 1789 mg/L
• 疏水性(logP): 0

安全信息

• 保存条件: -20°C
• RTECS编号: XI0350000
• 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: 22-36/37-45
• 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

药理学性质

• 给药途径: Oral
• 生物利用度: Well absorbed
• 排泄: Renal
• 半衰期: For an adult with normal renal function, the serum half-life is 0.5-1.2 hours
• 代谢: 80% excreted unchanged in urine within 6 hours of administration
• 蛋白结合率: 15%
• 法定药品分级: POM (UK); Rx-only (US); S4 (Australia)
• 妊娠期药物分类: A (Australia); B (US)
• 美国（FDA）药品许可证: Keflex

产品相关信息

• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C16H17N3O4S

详细说明

DrugBank - DB00567

• Drug Groups: approved
• Description: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of cephaloridine or cephalothin, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms. [PubChem]
• Indication: For the treatment of respiratory tract infections caused by Streptococcus pneumoniae and Streptococcus pyogenes; otitis media due to Streptococcus pneumoniae, Haemophilus influenzae, Staphylococcus aureus, Streptococcus pyogenes, and Moraxella catarrhalis; skin and skin structure infections caused by Staphylococcus aureus and/or Streptococcus pyogenes; bone infections caused by Staphylococcus aureus and/or Proteus mirabilis; genitourinary tract infections, including acute prostatitis, caused by Escherichia coli, Proteus mirabilis, and Klebsiella pneumoniae.
• Pharmacology: Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic. It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations. It is effective against most gram-positive bacteria.
• Toxicity: Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting. The oral median lethal dose of cephalexin in rats is >5000 mg/kg.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: No appreciable biotransformation in the liver (90% of the drug is excreted unchanged in the urine).
• Absorption: Well absorbed from the gastrointestinal tract
• Half Life: 1 hour
• Protein Binding: 14%
• Elimination: Cephalexin is excreted in the urine by glomerular filtration and tubular secretion. Studies showed that over 90% of the drug was excreted unchanged in the urine within 8 hours.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1502

Research Area: Infection
Biological Activity:
Cefalexin or cephalexin is a first-generation cephalosporin antibiotic. It is an orally administered agent with a similar antimicrobial spectrum to the intravenous agents cefalotin and cefazolin. Cefalexin is used to treat urinary tract infections, respiratory tract infections, and skin and soft tissue infections. It is also sometimes used to treat acne. [1]

Sigma Aldrich - 33989

Application
欧洲委员会 (EU) 2009 年 12 月 22 日 第 37/2010 号关于动物源食品药理活性物质及其最大残留限值分类的规定。
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

参考文献

• http://en.wikipedia.org/wiki/Cefalexin