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Ethambutol
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Name

Ethambutol

 EINECS 200-810-6
CAS No. 74-55-5 Density 0.987 g/cm3
PSA 64.52000 LogP 0.48920
Solubility Soluble in water. Also soluble in chloroform and methylene chloride Melting Point 199 - 204oC
Formula C10H24N2O2 Boiling Point 345.342 °C at 760 mmHg
Molecular Weight 204.313 Flash Point 113.661 °C
Transport Information N/A Appearance white crystalline hygroscopic powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 74-55-5 (Ethambutol) Hazard Symbols N/A
Synonyms

1-Butanol,2,2'-(1,2-ethanediyldiimino)bis-, [S-(R*,R*)]-;1-Butanol,2,2'-(ethylenediimino)di-, (+)- (8CI);(+)-Ethambutol;(+)-N,N'-Bis[1-(hydroxymethyl)propyl]ethylenediamine;(+)-S,S-Ethambutol;(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diol;(S,S)-Ethambutol;Diambutol;EMB;Purderal;d-2,2'-(Ethylenediimino)bis(1-butanol);d-2,2'-(Ethylenediimino)di-1-butanol;d-Ethambutol;d-N,N'-Bis(1-hydroxymethylpropyl)ethylenediamine;

Article Data 11

Ethambutol Synthetic route

5856-62-2

(S)-2-aminobutan-1-ol

107-06-2

1,2-dichloro-ethane

74-55-5

ethambutol

Conditions
ConditionsYield
In ethanol at 78 - 80℃; for 9.5h; Solvent; Temperature;98.01%
(heating);

C12H20N2O4

74-55-5

ethambutol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 10h; Reflux;91%
909567-52-8

(S,S)-N1,N2-bis(1-tert-butyldimethylsilyloxybutan-3-yl)oxamide

74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating;80%

(S,S)-2-[[[1-(methoxycarbonyl)propylamino]oxalyl]amino]butyric acid methyl ester

74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;75%
Stage #1: (S,S)-2-[[[1-(methoxycarbonyl)propylamino]oxalyl]amino]butyric acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating / reflux;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; for 0.5h;		36%
36697-75-3

2,2'-bis(4-ethyloxazoline)

74-55-5

ethambutol

Conditions
ConditionsYield
With hydrogen; rhodium(IV) oxide; platinum In ethanol Ambient temperature;
5856-62-2

(S)-2-aminobutan-1-ol

106-93-4

ethylene dibromide

74-55-5

ethambutol

Conditions
ConditionsYield
With potassium hydroxide

(4S,4'S)-4,4'-Diethyl-[2,2']bioxazolidinyl

74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether Heating;
61051-11-4

(-)-(S)-N,N'-Bis-(2-hydroxy-1-aethyl-aethyl)-oxalsaeurediamid

74-55-5

ethambutol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether
Multi-step reaction with 3 steps
1: SOCl2
2: NaOH / methanol / 1 h / Heating
3: H2 / Pt-RhO2 / ethanol / Ambient temperature
View Scheme

N,N'-bis-(1-benzyloxymethyl-propyl)-ethane-1,2-diamine

74-55-5

ethambutol

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; 3percent Pd/C In methanol at 20℃; under 760.051 Torr; for 48h; Hydrogenolysis;
147315-16-0

(S,S)-2-[[[1-(methoxycarbonyl)-3-(methylsulfanyl)propylamino]oxalyl]amino]-4-(methylsulfanyl)butyric acid methyl ester

74-55-5

ethambutol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 64 percent / W-4 Raney nickel / methanol; H2O / Heating
2: 75 percent / lithium aluminum hydride / tetrahydrofuran / Heating
View Scheme

Ethambutol Chemical Properties

IUPAC Name: (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol
Synonyms: Ethambutol;(+)-2,2-(Ethylenediimino)di-1-butanol ; (+)-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 ; 2,2’-(1,2-Ethanediyldiimino)bis-,(r-(r*,r*))-1-butano ; 2’-(1,2-Ethanediyldiimino)bis-(r)-1-butano
CAS: 74-55-5
MF: C10H24N2O2
MW: 204.31
MS:
EINECS: 200-810-6
Mol File: 74-55-5.mol
Surface Tension: 38 dyne/cm 
Density: 0.987 g/cm3 
Flash Point: 113.7 °C 
Enthalpy of Vaporization: 68.26 kJ/mol 
Boiling Point: 345.3 °C at 760 mmHg
Flash Point: 95°C  
Vapour Pressure: 3.9E-06 mmHg at 25°C
eat Of Vaporization:49.0 kJ/mol
Refractive Index:1.5738 (20 C)

Ethambutol Uses

Tibutol (74-55-5) has anti-tuberculosis effect on the common tuberculos iof anti-TB drug resistance . the product can still have inhibitation,but It's inhibitory effect is weaker than the small isoniazid,  approximation with streptomycin.no effect on other bacteria and fungi.

Ethambutol Toxicity Data With Reference

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)

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)

peripheral nerve and sensation: structural change in nerve or sheath
behavioral: changes in motor activity (specific assay)
kidney, ureter, and bladder: other changes in urine composition

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.

Ethambutol Safety Profile

http://www.chemicalbook.com/

http://www.chemspider.com/Chemical-Structure.3164.html

http://chem.sis.nlm.nih.gov/

http://pubchem.ncbi.nlm.nih.gov/

http://www.google.com/

Ethambutol Specification

Ingestion:If Tibutol (74-55-5) is swallowed, wash out mouth with water provided person is conscious. Call a physician.
Inhalation:If inhaled, remove to fresh air. If not breathing give artificial respiration. If breathing is difficult, give oxygen.
Eyes:Assure adequate flushing of the eyes by separating the eyelids with fingers.
Handling and Storage Back to Contents
Storage:Keep tightly closed. Store Tibutol (74-55-5) at 2-8 °C.
Personal Protection:Wear appropriate government approved respirator, chemical-resistant gloves, safety goggles, other protective clothing. Faceshield (8-inch minimum).
Exposure Effects:Irritant. Causes severe irritation. Severe lachrymator.
Fire Fighting:Extinguish: using carbon dioxide, dry chemical powder, or appropriate foam. Water spray: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.
Small spills/leaks:Cover with dry lime or soda ash, pick up, keep in a closed container, and hold for waste disposal. Ventilate area and wash spill site after material pickup is complete.
Incompatibilities:Strong oxidizing agents, Strong bases, Strong reducing agents.
Decomposition:Carbon monoxide, Carbon dioxide.

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