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Substance Name: Ivermectin [USAN:USP:INN:BAN]
RN: 70288-86-7
UNII: 8883YP2R6D
InChIKey: SPBDXSGPUHCETR-VHJJIYNUSA-N

Note

  • A mixture of mostly avermectin H2B1a (RN 71827-03-7) with some avermectin H2B1b (RN 70209-81-3), which are macrolides from STREPTOMYCES avermitilis. It binds glutamate-gated chloride channel to cause increased permeability and hyperpolarization of nerve and muscle cells. It also interacts with other CHLORIDE CHANNELS. It is a broad spectrum antiparasitic that is active against microfilariae of ONCHOCERCA VOLVULUS but not the adult form.

Molecular Formula

  • C48-H74-O14.C47-H72-O14

Molecular Weight

  • 1736.1704
 

Classification Codes

  • Anti-Infective Agents
  • Antiparasitic
  • Antiparasitic Agents
  • Drug / Therapeutic Agent
  • Insecticides
  • Natural Product
  • Pesticides
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Ivermectin
  • Ivermectin [USAN:USP:INN:BAN]

MeSH Heading

  • Ivermectin

Synonyms

  • (2aE,4E,8E)-(5'S,6S,6'R,7S,11R,13R,15S,17aR,20R,20aR,20bS)-3',4',5',6,6',7,10,11,-oxospiro(11,15-methano-2H,13H,17H-furo(4,3,2-pg)(2,6)benzodioxacyclooctadecin-13,2'(2H)pyran)-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)-3-O-methyl-alpha-L-arabino-hexopyranoside
  • 22,23-Dihydroavermectin B1
  • Acarexx
  • Agri-Mectin
  • Alverin Plus for Cattle
  • Avermectin A1a, 5-O-demethyl-25-de(1-methylpropyl)-22,23-dihydro-25-(1-methylethyl)-
  • Bimectin
  • Bimectin pour-on
  • Cardomec
  • Cardotek-30
  • CCRIS 8839
  • EINECS 274-536-0
  • Endo-Mectin for Cattle and Swine
  • Endo-Mectin Plus for Cattle
  • Equimectrin
  • Eqvalan
  • Heartgard
  • Heartgard-30
  • Hyvermectin
  • Ivermax
  • Ivermectin
  • Ivermectine
  • Ivermectine [INN-French]
  • Ivermectino
  • Ivermectino [INN-Spanish]
  • Ivermectinum
  • Ivermectinum [INN-Latin]
  • Ivomec
  • L 640471
  • Mectizan
  • MK 933
  • MK-0933
  • Noromectin
  • Noromectin for cattle and swine
  • Oramec
  • Pandex
  • Phoenectin
  • Sklice
  • Soolantra
  • Stromectol
  • UNII-8883YP2R6D
  • Uvemec
  • Vermic
  • Vetmec
  • Zimecterin

Systematic Names

  • 22,23-Dihydroavermectin B1
  • A mixture of Ivermectin component B(sub 1a) and Ivermectin component B(sub 1b).
  • Ivermectin

Mixture Names

  • Heartgard-30 Plus
  • Ivomec Plus
  • Ivomec-F

Registry Numbers

CAS Registry Number

  • 70288-86-7

FDA UNII

  • 8883YP2R6D

Other Registry Numbers

  • 1014990-52-3
  • 118710-50-2
  • 74564-75-3

System Generated Number

  • 0070288867

Molecular Formulas

Molecular Formula

  • C48-H74-O14.C47-H72-O14

Molecular Formula Fragments

  • C47-H72-O14
  • C48-H74-O14
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C48H74O14.C47H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38;1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3;11-14,18,24-25,27,29-30,32-44,48-49,51H,15-17,19-23H2,1-10H3/b13-12+,27-15+,32-14+;12-11+,26-14+,31-13+/t25?,26-,28-,30-,31-,33+,34?,35-,36-,37-,38?,39-,40+,41-,42-,43+,44-,45+,47+,48+;25-,27-,29-,30-,32+,33?,34-,35-,36-,37?,38-,39+,40-,41+,42-,43-,44+,46+,47+/m00/s1

InChIKey

SPBDXSGPUHCETR-VHJJIYNUSA-N

Smiles

CCC(C)[C@H]1O[C@]2(CC[C@@H]1C)CC3C[C@@H](C\C=C(/C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](OC5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C\6/CO[C@@H]7[C@H](O)C(=C[C@@H](C(=O)O3)[C@]67O)C)O2.CO[C@H]8CC(O[C@H]9[C@H](C)O[C@H](C[C@@H]9OC)O[C@H]%10[C@@H](C)\C=C\C=C\%11/CO[C@@H]%12[C@H](O)C(=C[C@@H](C(=O)OC%13C[C@@H](C\C=C\%10/C)O[C@@]%14(CC[C@H](C)[C@H](O%14)C(C)C)C%13)[C@]%11%12O)C)O[C@@H](C)[C@@H]8O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cattle LDLo subcutaneous 8mg/kg (8mg/kg)   Science. Vol. 221, Pg. 823, 1983.
dog LD50 oral 80mg/kg (80mg/kg)   Japanese Journal of Toxicology. Vol. 12, Pg. 227, 1999.
man TDLo intravenous 571ug/kg (0.571mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS Japanese Journal of Toxicology. Vol. 12, Pg. 227, 1999.
monkey LD50 oral > 24mg/kg (24mg/kg)   Japanese Journal of Toxicology. Vol. 12, Pg. 227, 1999.
mouse LD50 intraperitoneal 30mg/kg (30mg/kg)   Japanese Journal of Toxicology. Vol. 12, Pg. 227, 1999.
mouse LD50 oral 25mg/kg (25mg/kg)   Japanese Journal of Toxicology. Vol. 12, Pg. 227, 1999.
rat LD50 intraperitoneal 55mg/kg (55mg/kg)   Japanese Journal of Toxicology. Vol. 12, Pg. 227, 1999.
rat LD50 oral 10mg/kg (10mg/kg)   United States Patent Document. Vol. #5006545,