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Substance Name: Ethambutol [INN:BAN]
RN: 74-55-5
UNII: 8G167061QZ
InChIKey: AEUTYOVWOVBAKS-UWVGGRQHSA-N

Note

  • An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863).

Molecular Formula

  • C10-H24-N2-O2

Molecular Weight

  • 204.3116
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antitubercular Agents
  • Drug / Therapeutic Agent
  • Human Data

Names and Synonyms

Name of Substance

  • Ethambutol
  • Ethambutol [INN:BAN]

MeSH Heading

  • Ethambutol

Synonyms

  • (+)-2,2'-(Ethylenediimino)di-1-butanol
  • (+)-N,N'-Bis(1-(hydroxymethyl)propyl)ethylenediamine
  • (+)-S,S-Ethambutol
  • (R)-2,2'-(1,2-Ethanediyldiimino)bis-1-butanol
  • 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (R-(R*,R*))-
  • 1-Butanol, 2,2'-(ethylenediimino)di-, (+)-
  • Aethambutolum
  • d,N,N'-Bis(1-hydroxymethylpropyl)ethylenediamine
  • D-2,2'-(Ethylenediimino)bis(1-butanol)
  • D-2,2'-(Ethylenediimino)di-1-butanol
  • d-Ethambutol
  • D-N,N'-Bis(1-hydroxymethylpropyl)ethylenediamine
  • Diambutol
  • EINECS 200-810-6
  • EMB
  • Etambutol
  • Etambutol [INN-Spanish]
  • Etambutolo
  • Etambutolo [DCIT]
  • Ethambutol
  • Ethambutolum
  • Ethambutolum [INN-Latin]
  • HSDB 3078
  • Purderal
  • Tibutol
  • UNII-8G167061QZ

Systematic Names

  • 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (R)-
  • 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (S-(R*,R*))-
  • Ethambutol

Registry Numbers

CAS Registry Number

  • 74-55-5

FDA UNII

  • 8G167061QZ

System Generated Number

  • 0000074555

Structure Descriptors

InChI

InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1

InChIKey

AEUTYOVWOVBAKS-UWVGGRQHSA-N

Smiles

CC[C@@H](CO)NCCN[C@@H](CC)CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 1410mg/kg/11W (1410mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE New Zealand Medical Journal. Vol. 111, Pg. 428, 1998.
mammal (species unspecified) LD50 intravenous 350mg/kg (350mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63(3), Pg. 114S, 1967.
mammal (species unspecified) LD50 subcutaneous 890mg/kg (890mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63(3), Pg. 114S, 1967.
man TDLo oral 332mg/kg/31D- (332mg/kg)   Journal of Allergy and Clinical Immunology. Vol. 100, Pg. 712, 1997.
man TDLo oral 332mg/kg/31D- (332mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

BLOOD: EOSINOPHILIA		 Journal of Allergy and Clinical Immunology. Vol. 100, Pg. 712, 1997.
man TDLo oral 600mg/kg (600mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

PERIPHERAL NERVE AND SENSATION: STRUCTURAL CHANGE IN NERVE OR SHEATH		 British Medical Journal. Vol. 2, Pg. 1105, 1976.
man TDLo oral 1200mg/kg (1200mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 2, Pg. 1105, 1976.
mouse LD50 intraperitoneal 1075mg/kg (1075mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 463, 1971.
mouse LD50 intravenous 240mg/kg (240mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 463, 1971.
mouse LD50 oral 8700mg/kg (8700mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 463, 1971.
rat LD50 oral 998mg/kg (998mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
women TDLo oral 900mg/kg/60D- (900mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" British Medical Journal. Vol. 292, Pg. 866, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 88 deg C   EXP
log P (octanol-water) -0.410 (none)   EST
Atmospheric OH Rate Constant 2.13E-10 cm3/molecule-sec 25 EST

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