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Substance Name: Vancomycin hydrochloride [USP:JAN]
RN: 1404-93-9
UNII: 71WO621TJD
InChIKey: LCTORFDMHNKUSG-XTTLPDOESA-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.Cl-H

Molecular Weight

  • 1485.7244
 

Classification Codes

  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Vancomycin hydrochloride [USP:JAN]

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, monohydrochloride
  • AeroVanc
  • NSC 757377
  • UNII-71WO621TJD
  • Vancocin hydrochloride
  • Vancocin hydrochloride in plastic container
  • Vancocine hydrochloride
  • Vancoled
  • Vancomycin HCl
  • Vancomycin hydrochloride
  • Vancomycin hydrochloride in a plastic container
  • Vancomycin monohydrochloride
  • Vancor

Systematic Names

  • Vancomycin, hydrochloride
  • Vancomycin, monohydrochloride

Registry Numbers

CAS Registry Number

  • 1404-93-9

FDA UNII

  • 71WO621TJD

Related Registry Number

  • 1404-90-6 (Parent)

System Generated Number

  • 0001404939

Molecular Formulas

Molecular Formula

  • C66-H75-Cl2-N9-O24.Cl-H

Molecular Formula Fragments

  • C66-H75-Cl2-N9-O24
  • Cl-H
  • COMPONENT

Structure Descriptors

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

InChIKey

LCTORFDMHNKUSG-XTTLPDOESA-N

Smiles

Cl.CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O)[C@@H]6NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC1=O)c7ccc(O)c(c7)c8c(O)cc(O)cc8[C@H](NC6=O)C(=O)O)c3O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O[C@H]%10C[C@](C)(N)[C@H](O)[C@H](C)O%10)c(Cl)c2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 27500ug/kg/10 (27.5mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Clinical Pediatrics Vol. 23, Pg. 416, 1984.
guinea pig LD50 intraperitoneal 737mg/kg (737mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA Antibiotics Annual. Vol. 4, Pg. 75, 1956/1957.
man LDLo intravenous 43mg/kg/2W-I (43mg/kg) BLOOD: AGRANULOCYTOSIS American Journal of Medicine. Vol. 81, Pg. 1059, 1986.
man TDLo intravenous 1429ug/kg/10- (1.429mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Mayo Clinic Proceedings. Vol. 61, Pg. 721, 1986.
mouse LD50 intraperitoneal 1734mg/kg (1734mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 933, 1981.
mouse LD50 intravenous 489mg/kg (489mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 933, 1981.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Antibiotics Annual. Vol. 4, Pg. 75, 1956/1957.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Antibiotics Annual. Vol. 4, Pg. 75, 1956/1957.
rat LD50 intraperitoneal 2218mg/kg (2218mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 933, 1981.
rat LD50 intravenous 319mg/kg (319mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 933, 1981.
rat LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 597, 1982.
women TDLo intraperitoneal 40mg/kg (40mg/kg) BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT

GASTROINTESTINAL: PERITONITIS		 American Journal of Kidney Diseases. Vol. 17, Pg. 76, 1991.
women TDLo intravenous 20mg/kg (20mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Annals of Internal Medicine. Vol. 101, Pg. 880, 1984.