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].

See full entry for Vancomycin

Accession Number

DBSALT000300

Structure

Similar Structures

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

Vancomycin hydrochlorideProduct ingredient for Vancomycin

Structure for Vancomycin hydrochloride (DBSALT000300)