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Substance Name: Monensin [USAN:USP:INN:BAN]
RN: 17090-79-8
UNII: 906O0YJ6ZP
InChIKey: GAOZTHIDHYLHMS-KEOBGNEYSA-N

Note

  • An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.

Molecular Formula

  • C36-H62-O11

Molecular Weight

  • 670.8748
 

Classification Codes

  • Anti-Infective Agents
  • Antibacterial
  • Antifungal
  • Antifungal Agents
  • Antiparasitic Agents
  • Antiprotozoal
  • Antiprotozoal Agents
  • Coccidiostats
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Ionophores
  • Membrane Transport Modulators
  • Mutation Data
  • Natural Product
  • Proton Ionophores
  • Skin / Eye Irritant
  • Sodium Ionophores
  • Uncoupling Agents

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Monensin

Synonyms

  • 67314
  • A 3823A
  • ATCC 15413
  • Coban
  • Coban (as sodium salt)
  • EINECS 241-154-0
  • Elancoban
  • HSDB 7031
  • Lilly 673140
  • Monelan
  • Monensic acid
  • Monensin
  • Monensin A
  • Monensina
  • Monensina [INN-Spanish]
  • Monensinum
  • Monensinum [INN-Latin]
  • Rumensin
  • Rumensin (as sodium salt)
  • Rumensin 90
  • Stereoisomer of 2-(2-ethyloctahydro-3'-methyl-5'-(tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl)(2,2'-bifuran-5-yl))-9-hydroxy-beta-methoxy-alpha,gamma,2,8-tetramethyl-1,6-dioxaspiro(4.5)decan-7-butanoic acid
  • UNII-906O0YJ6ZP

Systematic Names

  • 1,6-Dioxaspiro(4.5)decane-7-butyric acid, 2-(5-ethyltetrahydro-5-(tetrahydro-3-methyl-5-(tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl)-2-furyl)-2-furyl)-9-hydroxy-beta-methoxy-alpha,gamma,2,8-tetramethyl-
  • Monensin

Registry Numbers

CAS Registry Number

  • 17090-79-8

FDA UNII

  • 906O0YJ6ZP

Other Registry Numbers

  • 1174269-36-3
  • 1192273-30-5
  • 1392-52-5
  • 802902-12-1

Related Registry Number

  • 22373-78-0 (sodium salt)

System Generated Number

  • 0017090798

Structure Descriptors

InChI

1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1

InChIKey

GAOZTHIDHYLHMS-KEOBGNEYSA-N

Smiles

CC[C@]1(CC[C@@H](O1)[C@]2(C)CC[C@]3(C[C@H](O)[C@@H](C)[C@H](O3)[C@@H](C)[C@@H](OC)[C@H](C)C(=O)O)O2)[C@@H]4O[C@H](C[C@@H]4C)[C@H]5O[C@@](O)(CO)[C@H](C)C[C@@H]5C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LD50 oral 12mg/kg (12mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: STIFFNESS
American Journal of Veterinary Research. Vol. 45, Pg. 1142, 1984.
horse/donkey LD50 oral 2mg/kg (2mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
American Journal of Veterinary Research. Vol. 42, Pg. 456, 1981.
mouse LD50 intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
mouse LD50 oral 43800ug/kg (43.8mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 472, 1981.
rat LD50 intraperitoneal 15mg/kg (15mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 oral 100mg/kg (100mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 5.430 (none)   EST
Water Solubility 3.00E-03 mg/L 25 EST
Vapor Pressure 3.20E-23 mm Hg 25 EST
Henry's Law Constant 2.00E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.95E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.