(1S,2R,18R,22S,25R,28R,40R)-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-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid

Base Information

• Chemical Name: (1S,2R,18R,22S,25R,28R,40R)-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-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• CAS No.: 1404-90-6
• Molecular Formula: C66H75Cl2N9O24
• Molecular Weight: 1449.27
• Hs Code.: 3004209090
• European Community (EC) Number: 215-772-6
• Wikipedia: Vancomycin
• Wikidata: Q105175096
• Mol file: 1404-90-6.mol

Synonyms:1404-90-6;SCHEMBL589609;LMPK14000004;AKOS037653246;GS-6039

Chemical Property of (1S,2R,18R,22S,25R,28R,40R)-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-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid

Chemical Property:

• Appearance/Colour: Almost white powder
• Refractive Index: 1.7350 (estimate)
• PKA: pKa 2.18±0.08(H2O t = 25.0±0.1 I = 0.2 (NaCl) N2 atmosphere) (Uncertain);7.75±0.02(H2O t = 25.0±0.1 I = 0.2 (NaCl) N2 atmosphere) (Uncertain);8.89±0.01(H2O t = 25.0±0.1 I = 0.2 (NaCl) N2 atmosphere) (Uncertain)
• PSA: 530.49000
• Density: 1.657 g/cm³
• LogP: 4.73460
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly)
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 19
• Hydrogen Bond Acceptor Count: 26
• Rotatable Bond Count: 13
• Exact Mass: 1447.4301997
• Heavy Atom Count: 101
• Complexity: 2960

Purity/Quality:

99%, ^*data from raw suppliers

Vancomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
• Isomeric SMILES: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H](C(C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
• Recent EU Clinical Trials: A Multicenter, Open-Label, Evaluator-Blinded, Randomized Study to Evaluate the Safety and Tolerability of Single-Dose IV Oritavancin Versus Standard of Care for the Treatment of Pediatric Subjects with Acute Bacterial Skin And Skin Structure Infections
• Description: Vancomycin is produced by fermentation of Amycol atopsis orientalis (formerly Nocardi a orientalis). It has been available for approximately 40 years, but its popularity has increased significantly with the emergence of MRSA in the early 1980s. Chemically, vancomycin has a glycosy lated hexapeptide chain that is rich in unusual amino acids, many of which contain aromatic rings cross-linked by aryl ether bonds into a rigid molecular framework.
• Uses: Antibacterial. Vancomycin is used for serious bacterial infections caused by microorganisms sensitive to this drug when penicillins and cephalosporins are ineffective for diseases such as sepsis, endocarditis, pneumonia, pulmonary abscess, osteomyelitis, meningitis, and enterocolitis, or when penicillins and cephalosporins cannot be tolerated by patients. Vancomycin is the drug of choice for infections caused by methicillin-resistant forms of S. aureus, S. epidermidus, and other coagulase-negative staphylococci, as well as for endocarditis, diphtherioid infections, and for patients very sick with colitis caused by C. difficile. A synonym of this drug is vancocin.
• Therapeutic Function: Antibacterial
• Clinical Use: Although a number of adverse effects can result from IV infusion, vancomycin has negligible oral activity. It can be used orally for action in the GI tract, especially in cases of Cl ostri di um difficile overgrowth. The useful spectrum is restricted to Gram-positive pathogens, with particular utility against multiply-resistant, coagulase-negative staphylococci and MRSA, which causes septicemias, endocarditis, skin and soft-tissue infections, and infections associated with venous catheters. Vancomycin was discovered, developed, and approved by the US Food and Drug Administration in the 1950s. In 1956, it was introduced in the USA as a possible treatment for infections due to penicillinresistant S. aureus, but it was not used widely because of toxicity and the nearly simultaneous development of semisynthetic antibiotics and cephalosporins. Thus, its main indication was the treatment of serious Gram-positive infections in penicillin-allergic patients. In clinical practice, however, nafcillin remained the treatment of choice for staphylococcal bacteremia, largely because it had failure rates of only 4%. With the appearance of methicillin-resistant S. aureus and coagulase-negative staphylococci, vancomycin became the drug of choice for these infections. With the recognition and/or emergence of S. aureus strains (generally MRSA isolates) with reduced susceptibility to vancomycin 586 Glycopeptides and Lipopeptides, vancomycin efficacy may be less in some clinical situations than previously reported – especially in serious deep-seated infections, such as endocarditis and prosthetic device infections. This is demonstrated by increased mortality seen in patients with MRSA infection and markedly attenuated vancomycin efficacy caused by vancomycin heteroresistance in S. aureus. Resistance of S. aureus to vancomycin can be a continuous phenomenon, rather than a categorical one. Thus, this has resulted in some clinical microbiology laboratories having difficulty identifying S. aureus strains that have reduced vancomycin susceptibility based on standard laboratory susceptibility testing methodology. A better understanding is still needed of the pharmacodynamic relationship between vancomycin and MRSA as relates to optimal dosing strategies, including consideration of loading doses.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of nephrotoxicity and ototoxicity with aminoglycosides, capreomycin or colismethate sodium; increased risk of nephrotoxicity with polymyxins. Ciclosporin: variable response; increased risk of nephrotoxicity. Diuretics: increased risk of ototoxicity with loop diuretics. Muscle relaxants: enhanced effects of suxamethonium. Tacrolimus: possible increased risk of nephrotoxicity

Technology Process of (1S,2R,18R,22S,25R,28R,40R)-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-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid

There total 8 articles about (1S,2R,18R,22S,25R,28R,40R)-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-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

UDP-vancosamine + desvancosaminyl vancomycin (101485-50-1) → vancomycin (1404-90-6)

Guidance literature:

With tris(2-carboxyethyl)phosphine; glycosyltransferase GtfD; bovine serum albumin; In glycerol; at 37 ℃; for 1.5h; Enzymatic reaction;

DOI:10.1021/ol501568t

Reference yield: 81.0%

C82H87Cl2N9O28 → vancomycin (1404-90-6)

Guidance literature:

With ammonium bicarbonate; palladium on activated charcoal; In acetic acid; at 23 ℃; for 4h;

DOI:10.1002/(SICI)1521-3773(20000317)39:6<1084::AID-ANIE1084>3.0.CO;2-O

Reference yield: 78.0%

N,N'-dialloc-tri-O-allyl vancomycin allyl ester (216668-88-1) → vancomycin (1404-90-6)

Guidance literature:

With bis(triphenylphosphine)palladium(II) dichloride; tri-n-butyl-tin hydride; In acetic acid; N,N-dimethyl-formamide; for 0.166667h; Ambient temperature;

DOI:10.1021/ja983504u

upstream raw materials:

N,N'-dialloc-tri-O-allyl vancomycin allyl ester

desvancosaminyl vancomycin

thymidine 5'-(3-amino-2,3,6-trideoxy-3C-methyl-β-L-lyxo-hexopyranosyl diphosphate)

Refernces

• 1、 Nakayama, Atsushi,Okano, Akinori,Feng, Yiqing,Collins, James C.,Collins, Karen C.,Walsh, Christopher T.,Boger, Dale L.. "Enzymatic glycosylation of vancomycin aglycon: Completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate". supporting information. p. 3572 - 3575. Retrieved 2014/07/21.
• 2、 Nicolaou,Cho, Suk Young,Hughes, Robert,Winssinger, Nicolas,Smethurst, Christian,Labischinski, Harald,Endermann, Rainer. "Solid- and solution-phase synthesis of vancomycin and vancomycin analogues with activity against vancomycin-resistant bacteria". . p. 3798 - 3823. Retrieved 2007/10/03.