(1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-5,47-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^{3,6}.2^{14,17}.1^{8,12}.1^{29,33}.0^{10,25}.0^{34,39}]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid

• ChemBase编号: 394
• 分子式: C66H75Cl2N9O24
• 平均质量: 1449.2536
• 单一同位素质量: 1447.43019969
• SMILES: c1(c2cc3cc1Oc1c(Cl)cc([C@@H](O)[C@@H]4NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@@H](NC(=O)[C@@H]([C@@H](c3cc(c(O2)cc3)Cl)O)NC(=O)[C@@H](CC(C)C)NC)CC(=O)N)c2cc(c(cc2)O)c2c([C@@H](C(=O)O)NC4=O)cc(cc2O)O)cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]1C[C@@]([C@@H]([C@@H](O1)C)O)(N)C
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c(O)cc(cc3[C@H](NC2=O)C(=O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@](C1)(C)N)O
• InChI: InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
• InChIKey: MYPYJXKWCTUITO-LYRMYLQWSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-5,47-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^{3,6}.2^{14,17}.1^{8,12}.1^{29,33}.0^{10,25}.0^{34,39}]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid; (1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^3,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8(48),9,11,14,16,29,31,33(45),34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• IUPAC传统名: vancomycin
• 商标名: Vancocin; Vancocin HCL; Vancoled; Vancor
• 别名: Vancomycin HCL; Vancomycin

登记号

• CAS号: 1404-90-6
• PubChem SID: 46505261; 160963857
• PubChem CID: 14969
• CHEBI ID: 28001
• ATC码: J01XA01; A07AA09
• CHEMBL: 262777
• Chemspider ID: 14253
• DrugBank ID: DB00512
• KEGG ID: D00212
• 美国药典/FDA物质标识码: 6Q205EH1VU
• 维基百科标题: Vancomycin
• Medline Plus: a604038

理论计算性质

JChem

• Acid pKa: 2.9872115
• 质子受体: 24
• 质子供体: 19
• LogD (pH = 5.5): -6.39765
• LogD (pH = 7.4): -4.8581004
• Log P: -4.406618
• 摩尔折射率: 346.6085 cm^3
• 极化性: 138.79524 Å^3
• 极化表面积: 530.49 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 1.11
• LOG S: -3.81
• 溶解度: 2.25e-01 g/l

分子性质

理化性质

• 疏水性(logP): -3.1

药理学性质

• 给药途径: IV, oral
• 生物利用度: Negligible (oral)
• 排泄: Renal
• 半衰期: 4–11 hours (adults); 6-10 days (adults, impaired renal function)
• 代谢: Excreted unchanged
• 法定药品分级: POM (UK); Rx-only (US); S4 (Australia)
• 妊娠期药物分类: B2 (Au), B (PO) / C (IV)(U.S.)
• 美国（FDA）药品许可证: Vancocin

详细说明

DrugBank - DB00512

• Drug Groups: approved
• Description: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. [PubChem]
• Indication: For the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci.
• Pharmacology: Vancomycin is a branched tricyclic glycosylated nonribosomal peptide produced by the fermentation of the Actinobacteria species Amycolatopsis orientalis (formerly Nocardia orientalis). It is often reserved as the "drug of last resort", used only after treatment with other antibiotics had failed. Vancomycin has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae (including penicillin-resistant strains), Streptococcus agalactiae, Actinomyces species, and Lactobacillus species. The combination of vancomycin and an aminoglycoside acts synergistically in vitro against many strains of Staphylococcus aureus, Streptococcus bovis, enterococci, and the viridans group streptococci.
• Toxicity: The oral LD₅₀ in mice is 5000 mg/kg. The median lethal intravenous dose is 319 mg/kg in rats and 400 mg/kg in mice.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Poorly absorbed from gastrointestinal tract, however systemic absorption (up to 60%) may occur following intraperitoneal administration.
• Half Life: Half-life in normal renal patients is approximately 6 hours (range 4 to 11 hours). In anephric patients, the average half-life of elimination is 7.5 days.
• Protein Binding: Approximately 55% serum protein bound.
• Elimination: In the first 24 hours, about 75% of an administered dose of vancomycin is excreted in urine by glomerular filtration.
• Clearance: * 0.06 L/kg/h
• References: Sch?fer, Martina, Thomas R Schneider, and George M Sheldrick. 1996. Crystal structure of vancomycin. Structure 4, no. 12 (December 15): 1509-1515. "DOI:10.1016/S0969-2126(96)00156-6":http://dx.doi.org/10.1016/S0969-2126(96)00156-6.; Levine DP: Vancomycin: a history. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S5-12. [Pubmed] ; Small PM, Chambers HF: Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob Agents Chemother. 1990 Jun;34(6):1227-31. [Pubmed] ; Gonzalez C, Rubio M, Romero-Vivas J, Gonzalez M, Picazo JJ: Bacteremic pneumonia due to Staphylococcus aureus: A comparison of disease caused by methicillin-resistant and methicillin-susceptible organisms. Clin Infect Dis. 1999 Nov;29(5):1171-7. [Pubmed] ; Sivagnanam S, Deleu D: Red man syndrome. Crit Care. 2003 Apr;7(2):119-20. Epub 2002 Dec 23. [Pubmed] ; Cantu TG, Yamanaka-Yuen NA, Lietman PS: Serum vancomycin concentrations: reappraisal of their clinical value. Clin Infect Dis. 1994 Apr;18(4):533-43. [Pubmed] ; Boger DL. Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Small PM, Chambers HF: Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob Agents Chemother. 1990 Jun;34(6):1227-31. Pubmed
• Gonzalez C, Rubio M, Romero-Vivas J, Gonzalez M, Picazo JJ: Bacteremic pneumonia due to Staphylococcus aureus: A comparison of disease caused by methicillin-resistant and methicillin-susceptible organisms. Clin Infect Dis. 1999 Nov;29(5):1171-7. Pubmed
• Cantu TG, Yamanaka-Yuen NA, Lietman PS: Serum vancomycin concentrations: reappraisal of their clinical value. Clin Infect Dis. 1994 Apr;18(4):533-43. PubmedBoger DL. Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. Pubmed
• Sch?fer, Martina, Thomas R Schneider, and George M Sheldrick. 1996. Crystal structure of vancomycin. Structure 4, no. 12 (December 15): 1509-1515. "DOI:10.1016/S0969-2126(96)00156-6":http://dx.doi.org/10.1016/S0969-2126(96)00156-6.
• Levine DP: Vancomycin: a history. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S5-12. Pubmed
• Sivagnanam S, Deleu D: Red man syndrome. Crit Care. 2003 Apr;7(2):119-20. Epub 2002 Dec 23. Pubmed