Vancomycin hydrochlorideProduct ingredient for Vancomycin
- Name
- Vancomycin hydrochloride
- Drug Entry
- Vancomycin
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.
As of January 29 2018, CutisPharma's Firvanq is the only FDA approved vancomycin oral liquid treatment option available for the the treatment of Clostridium difficile associated diarrhea and enterocolitis caused by Staphylococcus aureus, including methicillin-resistant strains [LP1196]. Such an oral liquid formulation is expected to make Clostridium difficile associated diarrhea therapy more accessible in comparison to previously available specialty compounding products [LP1196].
- Accession Number
- DBSALT000300
- Structure
- Synonyms
- Vancomycin HCl / Vancomycin hydrochloride
- UNII
- 71WO621TJD
- CAS Number
- 1404-93-9
- Weight
- Average: 1485.715
Monoisotopic: 1483.406877526 - Chemical Formula
- C66H76Cl3N9O24
- InChI Key
- LCTORFDMHNKUSG-XTTLPDOESA-N
- InChI
- InChI=1S/C66H75Cl2N9O24.ClH/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);1H/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-;/m0./s1
- IUPAC Name
- (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 hydrochloride
- SMILES
- Cl.CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@H]4C[C@](C)(N)[C@H](O)[C@H](C)O4)C4=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]1C3=CC(=C(O)C=C3)C3=C(O)C=C(O)C=C3[C@H](NC(=O)[C@@H](NC1=O)[C@H](O)C1=CC(Cl)=C(O4)C=C1)C(O)=O)C(Cl)=C2
- External Links
- PubChem Compound
- 6420023
- ChemSpider
- 4925607
- ChEBI
- 774579
- ChEMBL
- CHEMBL1200628
- Wikipedia
- Vancomycin
- Predicted Properties
Property Value Source Water Solubility 0.225 mg/mL ALOGPS logP 1.11 ALOGPS logP -4.4 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 2.99 Chemaxon pKa (Strongest Basic) 9.89 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 24 Chemaxon Hydrogen Donor Count 19 Chemaxon Polar Surface Area 530.49 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 346.61 m3·mol-1 Chemaxon Polarizability 138.39 Å3 Chemaxon Number of Rings 10 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon