(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 1082
• 分子式: C18H18N8O7S3
• 平均质量: 554.57992
• 单一同位素质量: 554.04605796
• SMILES: [C@@H]12N(C(=C(CS1)CSc1nc(=O)c(=O)[nH]n1C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nc(=O)c(=O)[nH]n1C
• InChI: InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1
• InChIKey: VAAUVRVFOQPIGI-SPQHTLEESA-N

名称和登记号

名称

• IUPAC标准名: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: @ceftriaxone; ceftriaxone
• 商标名: Biotrakson; Rocephine
• 别名: Ceftriaxona [INN-Spanish]; Ceftriaxonum [INN-Latin]; Cefatriaxone; Ceftriazone; Ceftriaxone; (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt Hydrate; Ro-13-9904/001; Rocefin; Rocephine; Ceftriaxone Disodium Salt Hemiheptahydrate

登记号

• CAS号: 104376-79-6; 73384-59-5
• PubChem SID: 160964545; 46506458
• PubChem CID: 5479530

理论计算性质

JChem

• Acid pKa: 3.1880236
• 质子受体: 12
• 质子供体: 4
• LogD (pH = 5.5): -3.2965198
• LogD (pH = 7.4): -4.674165
• Log P: -2.2233887
• 摩尔折射率: 128.4667 cm^3
• 极化性: 48.594624 Å^3
• 极化表面积: 208.98 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -0.01
• LOG S: -3.72
• 溶解度: 1.05e-01 g/l

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White to Off White Solid
• 熔点: >190°C (dec.)
• 疏水性(logP): -1.7

安全信息

• 保存条件: -20°C Freezer

详细说明

DrugBank - DB01212

• Drug Groups: approved
• Description: A broad-spectrum cephalosporin antibiotic with a very long half-life and high penetrability to meninges, eyes and inner ears. [PubChem]
• Indication: For the treatment of the infections (respiratory, skin, soft tissue, UTI, ENT) caused by S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph
• Pharmacology: Ceftriaxone is a cephalosporin/cephamycin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. Ceftriaxone has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ceftriaxone results from the inhibition of cell wall synthesis and is mediated through Ceftriaxone binding to penicillin binding proteins (PBPs). Ceftriaxone is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: 5.8-8.7 hours
• Protein Binding: 95%
• Elimination: Thirty-three percent to 67% of a ceftriaxone dose was excreted in the urine as unchanged drug and the remainder was secreted in the bile and ultimately found in the feces as microbiologically inactive compounds.
• Distribution: * 5.78 to 13.5 L
• Clearance: * 0.58 - 1.45 L/h [healthy adults receiving 0.15-3 g of CEFTRIAXONE]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C245000

An antibacterial, a third-generation cephalosporin.

参考文献

• Reiner, R., et al.: J. Antibiot., 33, 783 (1980)