Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Vancomycin [USP:INN:BAN]
RN: 1404-90-6
UNII: 6Q205EH1VU
InChIKey: MYPYJXKWCTUITO-LYRMYLQWSA-N

Note

  • 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.

Molecular Formula

  • C66-H75-Cl2-N9-O24

Molecular Weight

  • 1449.2635
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Natural Product

Names and Synonyms

Name of Substance

  • Vancomycin
  • Vancomycin [USP:INN:BAN]

MeSH Heading

  • Vancomycin

Synonyms

  • (3S-(3R*,6S*(S*),7S*,22S*,23R*,26R*,36S*,38aS*))-3-(2-Amino-2-oxoethyl)-44-((2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-glucopyranosyl)oxy)-10,19-dichloro-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-((4-methyl-2-(methylamino)-1-oxopentyl)amino)-2,5,24,38,39-pentaoxo-22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-(1,6,9)oxadiazacyclohexadecino(4,5-m)(10,2,16)-benzoxadiazacyclotetracosine-26-carboxylic acid
  • (Sa)-(3S,6R,7R,22R,23S,26S,36R,38aR)-44-((2-O-(3-Amino-2,3,6-trideoxy-3-C-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-glucopyranosyl)oxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-((2R)-4-methyl-2-(methylamino)valeramido)-2,5,24,38,39-pentaoxo-22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-(1,6,9)oxadiazacyclohexadecino(4,5-m)(10,2,16)-benzoxadiazacyclotetracosine-26-carboxylic acid
  • EINECS 215-772-6
  • HSDB 3262
  • UNII-6Q205EH1VU
  • Vancocin
  • Vancoled
  • Vancomicina
  • Vancomicina [INN-Spanish]
  • Vancomycin
  • Vancomycine
  • Vancomycine [INN-French]
  • Vancomycinum
  • Vancomycinum [INN-Latin]

Systematic Name

  • Vancomycin

Registry Numbers

CAS Registry Number

  • 1404-90-6

FDA UNII

  • 6Q205EH1VU

Related Registry Numbers

  • 1404-93-9 (hydrochloride)
  • 64685-75-2 (sulfate)

System Generated Number

  • 0001404906

Structure Descriptors

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

Smiles

c12c3c(cc(O)cc3O)[C@H](NC(=O)[C@H]3NC(=O)[C@H](NC(=O)[C@H]4c5cc(Oc6c(Cl)cc([C@H]3O)cc6)c(O[C@H]3[C@H](O[C@@H]6O[C@@H](C)[C@@H](O)[C@](N)(C)C6)[C@@H](O)[C@H](O)[C@@H](CO)O3)c(Oc3c(Cl)cc([C@@H](O)[C@H](C(=O)N[C@@H](CC(=O)N)C(=O)N4)NC(=O)[C@@H](CC(C)C)NC)cc3)c5)c(ccc1O)c2)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo intravenous 30mg/kg/20M-C (30mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

CARDIAC: OTHER CHANGES
Archives of Disease in Childhood. Vol. 73, Pg. F123, 1995.
infant TDLo intravenous 119mg/kg (119mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Journal of Toxicology, Clinical Toxicology. Vol. 34, Pg. 83, 1996.
infant TDLo intravenous 295mg/kg/3D-I (295mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 285, 1992.
man TDLo intravenous 15mg/kg/2H-C (15mg/kg)   Annals of Pharmacotherpy. Vol. 33, Pg. 1043, 1999.
man TDLo intravenous 15mg/kg/2H-C (15mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annals of Pharmacotherpy. Vol. 33, Pg. 1043, 1999.
mouse LD50 intraperitoneal 1734mg/kg (1734mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 675, 1967.
mouse LD50 intravenous 430mg/kg (430mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 913, 1990.
mouse LD50 subcutaneous 5gm/kg (5000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 315, 1980.
women TDLo intravenous 15mg/kg/90M-C (15mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" New England Journal of Medicine. Vol. 313, Pg. 756, 1985.
women TDLo intravenous 170mg/kg/19D- (170mg/kg) BLOOD: AGRANULOCYTOSIS Canadian Medical Association Journal. Vol. 132, Pg. 39, 1985.
women TDLo multiple routes 30mg/kg/2D-I (30mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Annals of Internal Medicine. Vol. 115, Pg. 410, 1991.