Ethambutol

Modify Date: 2024-01-02 19:48:10

Ethambutol Structure
Ethambutol structure
Common Name Ethambutol
CAS Number 74-55-5 Molecular Weight 204.310
Density 1.0±0.1 g/cm3 Boiling Point 345.3±22.0 °C at 760 mmHg
Molecular Formula C10H24N2O2 Melting Point 199 - 204ºC
MSDS N/A Flash Point 113.7±12.9 °C

 Use of Ethambutol


Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.Target: AntibacterialEthambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. In M. smegmatis, Ethambutol inhibits synthesis of arabinan completely and inhibits AG synthesis most likely as a consequence of this; more than 50% of the cell arabinan is released from the bacteria following Ethambutol treatment, whereas no galactan is released. Ethambutol main targets against embB gene product in M. avium. Ethambutol induces 60% changes in the embB gene in M. tuberculosis resistant mutants [1]. Ethambutol is effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of the M. aviumcomplex (MAC) are sensitive to Ethambutol. [1] Ethambutol is potency against M. tuberculosis (H37Rv) with MIC of 0.5 μg/mL in vitro [2]. Ethambutol is efficient on treatment of mycobacterial-infected macrophages. When M. tuberculosis infected macrophages are treated with 6 μg/mL Ethambutol, the log CFUs following treatment for 3 days is 4.17, while value in control group is 4.8. The MICs for M. avium (MTCC 1723) and M. smegmatis (MTCC 6) are 15 μg/mL and 0.18 μg/mL, respectively. Ethambutol is efficient in animal model. 100 mg/kg Ethambutol given orally 15 days post i.v. infection 1 ×/week for 5 weeks, induces a lower log CFU compared with untreatment (4.59 vs 5.07) [3].

 Names

Name ethambutol
Synonym More Synonyms

 Ethambutol Biological Activity

Description Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.Target: AntibacterialEthambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. In M. smegmatis, Ethambutol inhibits synthesis of arabinan completely and inhibits AG synthesis most likely as a consequence of this; more than 50% of the cell arabinan is released from the bacteria following Ethambutol treatment, whereas no galactan is released. Ethambutol main targets against embB gene product in M. avium. Ethambutol induces 60% changes in the embB gene in M. tuberculosis resistant mutants [1]. Ethambutol is effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of the M. aviumcomplex (MAC) are sensitive to Ethambutol. [1] Ethambutol is potency against M. tuberculosis (H37Rv) with MIC of 0.5 μg/mL in vitro [2]. Ethambutol is efficient on treatment of mycobacterial-infected macrophages. When M. tuberculosis infected macrophages are treated with 6 μg/mL Ethambutol, the log CFUs following treatment for 3 days is 4.17, while value in control group is 4.8. The MICs for M. avium (MTCC 1723) and M. smegmatis (MTCC 6) are 15 μg/mL and 0.18 μg/mL, respectively. Ethambutol is efficient in animal model. 100 mg/kg Ethambutol given orally 15 days post i.v. infection 1 ×/week for 5 weeks, induces a lower log CFU compared with untreatment (4.59 vs 5.07) [3].
Related Catalog
References

[1]. Ethambutol. Tuberculosis (Edinb), 2008. 88(2): p. 102-5.

[2]. Rastogi, N., V. Labrousse, and K.S. Goh, In vitro activities of fourteen antimicrobial agents against drug susceptible and resistant clinical isolates of Mycobacterium tuberculosis and comparative intracellular activities against the virulent H37Rv strain

[3]. Kaur, D. and G.K. Khuller, In vitro, ex-vivo and in vivo activities of ethambutol and sparfloxacin alone and in combination against mycobacteria. Int J Antimicrob Agents, 2001. 17(1): p. 51-5.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 345.3±22.0 °C at 760 mmHg
Melting Point 199 - 204ºC
Molecular Formula C10H24N2O2
Molecular Weight 204.310
Flash Point 113.7±12.9 °C
Exact Mass 204.183777
PSA 64.52000
LogP -0.05
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.478
Storage condition 2-8℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EL3640000
CHEMICAL NAME :
1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (R)-
CAS REGISTRY NUMBER :
74-55-5
LAST UPDATED :
199706
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C10-H24-N2-O2
MOLECULAR WEIGHT :
204.36
WISWESSER LINE NOTATION :
Q1Y2&M2MY2&1Q -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
900 mg/kg/60D-I
TOXIC EFFECTS :
Liver - jaundice, cholestatic
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 292,866,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - structural change in nerve or sheath Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,1105,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1200 mg/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure) Immunological Including Allergic - anaphylaxis
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,1105,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
8700 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
DPHFAK Dissertationes Pharmaceuticae et Pharmacologicae. (Warsaw, Poland) V.18-24, 1966-72. For publisher information, see PJPPAA. Volume(issue)/page/year: 23,463,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1075 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
DPHFAK Dissertationes Pharmaceuticae et Pharmacologicae. (Warsaw, Poland) V.18-24, 1966-72. For publisher information, see PJPPAA. Volume(issue)/page/year: 23,463,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
DPHFAK Dissertationes Pharmaceuticae et Pharmacologicae. (Warsaw, Poland) V.18-24, 1966-72. For publisher information, see PJPPAA. Volume(issue)/page/year: 23,463,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
890 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 63(3),114S,1967
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
350 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 63(3),114S,1967

 Safety Information

HS Code 2922191000

 Synthetic Route

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Journal of the American Chemical Society, , vol. 122, # 25 p. 5968 - 5976

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Journal of the American Chemical Society, , vol. 122, # 25 p. 5968 - 5976

~78%

Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Kotkar, Shriram P.; Sudalai, Arumugam Tetrahedron Asymmetry, 2006 , vol. 17, # 11 p. 1738 - 1742

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Doklady Chemistry, , vol. 145, p. 597 - 600 Doklady Akademii Nauk SSSR, , vol. 145, p. 332 - 335

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Justus Liebigs Annalen der Chemie, , p. 1455 - 1464

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Justus Liebigs Annalen der Chemie, , p. 1455 - 1464

~%

Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Tetrahedron, , vol. 58, # 49 p. 9765 - 9767

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Journal of the American Chemical Society, , vol. 83, p. 2212 - 2213

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Ethambutol Structure

Ethambutol

CAS#:74-55-5

Literature: Journal of Medicinal and Pharmaceutical Chemistry, , vol. 5, p. 835 - 845

 Customs

HS Code 2922191000

 Synonyms

(S,S)-Et,Et-FerroTANE
(+)-1,1'-BIS[(2R,4R)-2,4-DIETHYLPHOSPHONATO]FERROCENE
R,R-Et-FerroTANE
(S,S)-2,2'-(ethylenediimino)di-1-butanol
(R,R)-ET-FERROTANE(TM)
(+)-1,1'-BIS((2R,4R)-2,4-DIETHYLPHOSPHOTANO)FERROCENE
(S,S)-1-[1-(DI-TERT-BUTYLPHOSPHINO)ETHYL]-2-(DIPHENYLPHOSPHINO)FERROCENE
Et-Ferrotane
1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-
Ethambutol
(S)-(+)-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE
2,2'-(1,2-Ethanediyldiimino)di(1-butanol)
JOSIPHOS SL-J002-2