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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
- All
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- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antitubercular Agents
- Drug / Therapeutic Agent
- Human Data
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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
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/s1InChIKey
AEUTYOVWOVBAKS-UWVGGRQHSA-NSmiles
CC[C@@H](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.