74-55-5

74-55-5 structure

Name: Ethambutol
Chemical Name: ethambutol
CAS Number: 74-55-5
Molecular Formula: C₁₀H₂₄N₂O₂
Molecular Weight: 204.310
Catalog: API Synthetic anti-infective drugs Anti-tuberculosis leprosy
Create Date: 2018-07-05 13:14:30
Modify Date: 2024-01-02 19:48:10
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].

Name	ethambutol
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

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	Signaling Pathways >> Anti-infection >> Bacterial Research Areas >> Infection
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.

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℃

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