Ethionamide

Modify Date: 2024-01-02 09:58:51

Ethionamide Structure
Ethionamide structure
 Common Name Ethionamide
CAS Number 536-33-4 Molecular Weight 166.24300
Density 1.17 g/cm3 Boiling Point 167 °C / 1mmHg
Molecular Formula C8H10N2S Melting Point 164 °C
MSDS USA Flash Point 133.2ºC
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Warning

 Use of Ethionamide


Ethionamide(2-ethylthioisonicotinamide) is an antibiotic used in the treatment of tuberculosis.Target: AntibacterialEthionamide is a second-line antitubercular agent that inhibits mycolic acid synthesis. It also may be used for treatment of leprosy. Ethionamide is a prodrug. It is activated by the enzyme EthA, a mono-oxygenase in Mycobacterium tuberculosis, and binds NAD+ to form an adduct which inhibits InhA in the same way as isoniazid. Expression of the ethA gene is controlled by EthR, a transcriptional repressor. It is understood that improving ethA expression will increase the efficacy of ethionamide and so EthR inhibitors are of great interest to co-drug developers. The action may be through disruption of mycolic acid [1, 2].

 Names

Name ethionamide
Synonym More Synonyms

 Ethionamide Biological Activity

Description Ethionamide(2-ethylthioisonicotinamide) is an antibiotic used in the treatment of tuberculosis.Target: AntibacterialEthionamide is a second-line antitubercular agent that inhibits mycolic acid synthesis. It also may be used for treatment of leprosy. Ethionamide is a prodrug. It is activated by the enzyme EthA, a mono-oxygenase in Mycobacterium tuberculosis, and binds NAD+ to form an adduct which inhibits InhA in the same way as isoniazid. Expression of the ethA gene is controlled by EthR, a transcriptional repressor. It is understood that improving ethA expression will increase the efficacy of ethionamide and so EthR inhibitors are of great interest to co-drug developers. The action may be through disruption of mycolic acid [1, 2].
Related Catalog
References

[1]. Vannelli, T.A., A. Dykman, and P.R. Ortiz de Montellano, The antituberculosis drug ethionamide is activated by a flavoprotein monooxygenase. J Biol Chem, 2002. 277(15): p. 12824-9.

[2]. Quemard, A., G. Laneelle, and C. Lacave, Mycolic acid synthesis: a target for ethionamide in mycobacteria? Antimicrob Agents Chemother, 1992. 36(6): p. 1316-21.

 Chemical & Physical Properties

Density 1.17 g/cm3
Boiling Point 167 °C / 1mmHg
Melting Point 164 °C
Molecular Formula C8H10N2S
Molecular Weight 166.24300
Flash Point 133.2ºC
Exact Mass 166.05600
PSA 71.00000
LogP 1.97850
Index of Refraction 1.599
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NS0350000
CHEMICAL NAME :
Isonicotinamide, 2-ethylthio-
CAS REGISTRY NUMBER :
536-33-4
BEILSTEIN REFERENCE NO. :
0116474
LAST UPDATED :
199612
DATA ITEMS CITED :
30
MOLECULAR FORMULA :
C8-H10-N2-S
MOLECULAR WEIGHT :
166.26
WISWESSER LINE NOTATION :
T6NJ B2 DYZUS

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
856 mg/kg
TOXIC EFFECTS :
Liver - jaundice, other or unclassified Liver - change in gall bladder structure or function
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
482 mg/kg/5W
TOXIC EFFECTS :
Liver - jaundice, other or unclassified Liver - change in gall bladder structure or function
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1320 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
490 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1580 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
550 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
24 gm/kg/50W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Endocrine - thyroid tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
600 mg/kg
SEX/DURATION :
female 36-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
5400 mg/kg
SEX/DURATION :
female 12 week(s) pre-mating female 1-38 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral Reproductive - Effects on Newborn - other postnatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1800 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - body wall
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
900 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1800 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
486 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2430 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
450 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
108 mg/kg
SEX/DURATION :
female 7-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
216 mg/kg
SEX/DURATION :
female 7-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
900 mg/kg
SEX/DURATION :
female 8-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
450 mg/kg
SEX/DURATION :
female 8-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
540 mg/L
REFERENCE :
GMCRDC Gann Monograph on Cancer Research. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No. 11- 1971- Volume(issue)/page/year: 27,95,1981 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,83,1977 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,83,1977 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5544 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 307 (estimated) No. of Female Employees: 251 (estimated)

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H302-H361
Precautionary Statements P281
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn:Harmful;
Risk Phrases R22;R63
Safety Phrases S36/37
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS NS0350000
HS Code 2933990090

 Synthetic Route

2-Ethylisonicotinamid structure

2-Ethylisonicot...

CAS#:3376-95-2

~80%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Bergman, Jan; Pettersson, Birgitta; Hasimbegovic, Vedran; Svensson, Per H. Journal of Organic Chemistry, 2011 , vol. 76, # 6 p. 1546 - 1553
2-ethylisonicotinonitrile structure

2-ethylisonicot...

CAS#:1531-18-6

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Bulletin de la Societe Chimique de France, , p. 687,691
Methyl 2-ethylisonicotinate structure

Methyl 2-ethyli...

CAS#:1531-16-4

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Bulletin de la Societe Chimique de France, , p. 687,691
2-ethyl-6-chloro-isonicotinic acid methyl ester structure

2-ethyl-6-chlor...

CAS#:4104-77-2

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Bulletin de la Societe Chimique de France, , p. 687,691
4-Bromo-2-ethylpyridine structure

4-Bromo-2-ethyl...

CAS#:156761-88-5

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Zhurnal Obshchei Khimii, , vol. 29, p. 915,918; engl. Ausg. S. 898
2-Ethylpyridine 1-oxide structure

2-Ethylpyridine...

CAS#:4833-24-3

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Zhurnal Obshchei Khimii, , vol. 29, p. 915,918; engl. Ausg. S. 898
2-ethyl-4-nitropyridine N-oxide structure

2-ethyl-4-nitro...

CAS#:38594-62-6

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Zhurnal Obshchei Khimii, , vol. 29, p. 915,918; engl. Ausg. S. 898
2-ethylpyridin-4-amine structure

2-ethylpyridin-...

CAS#:50826-64-7

~%

Ethionamide Structure

Ethionamide

CAS#:536-33-4

Literature: Zhurnal Obshchei Khimii, , vol. 29, p. 915,918; engl. Ausg. S. 898

 Customs

HS Code 2933399090
Summary 2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

2-ethyl-4-thiopyridylamide
2-ethyl-4-thiocarbamoylpyridine
EINECS 208-628-9
Ethionamide
2-Ethyl-4-pyridinecarbothioamide
Etionamid
2-Ethyl-4-pyridinecarbothioamide,Ethionamide
Etioniamid
Trecator
Ethyonomide
Thioamide
Ethioniamide
Ethinamide
Ethylisothiamide
2-Ethylpyridine-4-carbothioamide
2-ethyl-4-thiocarbamoyl-4-pyridine
MFCD00057361
Trecator-SC
2-Ethylthioisonicotinamide
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