Ethionamid

Ethionamide Struktur
536-33-4
CAS-Nr.
536-33-4
Bezeichnung:
Ethionamid
Englisch Name:
Ethionamide
Synonyma:
Thioamide;Trecator;Amidazine;Atina;1314th;Aetina;Aetiva;Ethina;Etimid;th1314
CBNumber:
CB1292374
Summenformel:
C8H10N2S
Molgewicht:
166.24
MOL-Datei:
536-33-4.mol

Ethionamid Eigenschaften

Schmelzpunkt:
164 °C
Siedepunkt:
167 °C / 1mmHg
Dichte
1.1332 (rough estimate)
Brechungsindex
1.5500 (estimate)
Flammpunkt:
>110°(230°F)
storage temp. 
2-8°C
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
pKa 4.37(H2O t=25.0 I=0.025) (Uncertain)
Farbe
Yellow
Wasserlöslichkeit
Soluble in DMSO. Sparingly soluble in water
Merck 
14,3737
BCS Class
3/1
InChIKey
AEOCXXJPGCBFJA-UHFFFAOYSA-N
CAS Datenbank
536-33-4(CAS DataBase Reference)
IARC
3 (Vol. 13, Sup 7) 1987
NIST chemische Informationen
Ethionamide(536-33-4)
EPA chemische Informationen
Ethionamide (536-33-4)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn
R-Sätze: 22-63
S-Sätze: 36/37
WGK Germany  3
RTECS-Nr. NS0350000
HS Code  29333990
Giftige Stoffe Daten 536-33-4(Hazardous Substances Data)
Toxizität LD50 oral in rat: 1320mg/kg
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

Ethionamid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R63:Kann das Kind im Mutterleib möglicherweise schädigen.

S-Sätze Betriebsanweisung:

S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.

Beschreibung

Ethionamide is an antimycobacterial compound that is active against M. tuberculosis (MICs = 0.3-1.25 μg/ml). It is activated via oxidation by flavin monooxygenase and inhibits the InhA enzyme involved in mycolic acid biosynthesis. Formulations containing ethionamide have been used in the second-line treatment of multi-drug resistant tuberculosis.

Chemische Eigenschaften

Yellow Solid

Verwenden

Ethionamide is used in antimicrobials and in potency assay of test compounds on M. tuberculosis.

Definition

ChEBI: A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding S-oxide.

Indications

Ethionamide (Trecator) is a derivative of isonicotinic acid and is chemically related to isoniazid. It is a secondary agent used in combination when primary agents are ineffective or contraindicated; it is a bacteriostatic antituberculosis agent. Its exact mechanism of action is unknown but is believed to involve inhibition of oxygen-dependent mycolic acid synthesis. It is thought that mutations in the region of the (inhA) gene that are involved in mycolic acid synthesis can cause both isoniazid and ethionamide resistance.

Allgemeine Beschreibung

Yellow crystals or canary yellow powder with a faint to moderate sulfide odor.

Air & Water Reaktionen

Insoluble in water.

Reaktivität anzeigen

A thiocarbamate/amine. Thiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.

Brandgefahr

Flash point data for Ethinamide are not available. Ethinamide is probably combustible.

Mechanism of action

Evidence has been presented suggesting that the mechanism of action of ethionamide is similar to that of INH. Similar to INH, ethionamide is considered to be a pro-drug, which is converted via oxidation by catalase-peroxidase to an active acylating agent, ethionamide sulfoxide, which in turn inactivates the inhA enoyl reductase enzyme. In the case of ethionamide, it has been proposed that the ethionamide sulfoxide acylates Cys-243 in inhA protein.

Pharmakologie

Ethionamide is well absorbed following oral administration. It is rapidly and widely distributed to all body tissues and fluids, including the cerebrospinal fluid. Metabolism of ethionamide is extensive, and several dihydropyridine metabolites are produced. Less than 1% of the drug is eliminated in the urine unchanged. GI disturbances, including nausea, vomiting, and intense gastric irritation, are frequent. In addition, ethionamide may cause a wide range of neurological side effects, such as confusion, peripheral neuropathy, psychosis, and seizures. Neurological effects can be minimized by pyridoxine supplementation. Other rare side effects include gynecomastia, impotence, postural hypotension, and menorrhagia.

Clinical Use

2-Ethylthioisonicotinamide (Trecator SC) occurs as a yellowcrystalline material that is sparingly soluble in water. Thisnicotinamide has weak bacteriostatic activity in vitro but, becauseof its lipid solubility, is effective in vivo. In contrast tothe isoniazid series, 2-substitution enhances activity in thethioisonicotinamide series.
Ethionamide is rapidly and completely absorbed followingoral administration. It is widely distributed throughoutthe body and extensively metabolized to predominantly inactiveforms that are excreted in the urine. Less than 1% ofthe parent drug appears in the urine.Ethionamide is considered a secondary drug for the treatmentof tuberculosis. It is used in the treatment of isoniazidresistanttuberculosis or when the patient is intolerant toisoniazid and other drugs. Because of its low potency, thehighest tolerated dose of ethionamide is usually recommended.Gastrointestinal intolerance is the most commonside effect associated with its use. Visual disturbances andhepatotoxicity have also been reported.

Stoffwechsel

Ethionamide is orally active but is not well tolerated in a single large dose (>500 mg). The GI irritation can be reduced by administration with meals. Additional side effects may include central nervous system (CNS) effects, hepatitis, and hypersensitivities. Less than 1% of the drug is excreted in the free form, with the remainder of the drug appearing as one of six metabolites. Among the metabolites are ethionamide sulfoxide, 2-ethylisonicotinamide, and the N-methylated- 6-oxodihydropyridines.

läuterung methode

It crystallises from EtOH as lemon yellow needles. The hydrochloride crystallises from EtOH (+ few drops of HCl) as orange yellow needles with m 212-214o. [Kutscherowa et al. J Gen Chem USSR (English transl) 29 915 1959, Beilstein 22 III/IV 737.] It causes peripheral and occular neuropathy and is carcinogenic and teratogenic.

Ethionamid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Ethionamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 287)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806
sales@capot.com China 29791 60
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
sales01@cooperate-pharm.com CHINA 1803 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21639 55
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29886 58
Hebei Weibang Biotechnology Co., Ltd
+8615531157085
abby@weibangbio.com China 8816 58
Xiamen AmoyChem Co., Ltd
+86-86-5926051114 +8618959220845
sales@amoychem.com China 6383 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58
Wuhan Chemwish Technology Co., Ltd
027-67849912
sales@chemwish.com CHINA 10821 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427
sales@conier.com China 49374 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12829 58

536-33-4(Ethionamid)Verwandte Suche:


  • 1314 TH
  • 1314 TN
  • 1314th
  • 2-Ethyl-4-thioamidylpyridine
  • 2-Ethyl-4-thiocarbamoylpyridine
  • 2-Ethylisonicotinic acid thioamide
  • 2-Ethylisonicotinic thioamide
  • 2-ethylisonicotinicacidthioamide
  • 2-ethylisonicotinicthioamide
  • 2-Ethylisonicotinothiamide
  • 2-Ethylisonicotinothioamide
  • 2-Ethylisonicotinthioamide
  • 2-Ethylisothionicotinamide
  • 2-ethylthio-isonicotinamid
  • 4-Pyridinecarbothioamide, 2-ethyl-
  • Aetina
  • Aetiva
  • alpha-Ethylisonicotinic acid thioamide
  • alpha-ethylisonicotinicacidthioamide
  • alpha-Ethylisonicotinoylthioamide
  • alpha-Ethylisothionicotinamide
  • alpha-Ethylthioisonicotinamide
  • Atina
  • Bayer 5312
  • bayer5312
  • Ethimide
  • Ethina
  • Ethinamide
  • Ethionamid prothionamid
  • Ethioniamide
  • Ethylisothiamide
  • Ethyonomide
  • Trecator-SC
  • Trekator
  • Trescatyl
  • Trescazide
  • Tubenamide
  • Tubermin
  • Tuberoid
  • Tuberoson
  • 2-ethylisonicotinethioamide
  • ETHIONAMIDE
  • LABOTEST-BB LT00771973
  • AMIDAZIN
  • 2-ETHYLPYRIDINE-4-CARBOTHIOAMIDE
  • 2-ETHYLTHIOISONICOTINAMIDE
  • 2-ETHYL-4-AMINOTHIOCARBONYLPYRIDINE
  • 2-ETHYL-4-PYRIDINECARBOTHIOAMIDE
  • 2-ETHYLTHIO-4-ISONICOTINAMIDE
  • Thiodine
  • Athehina
  • 2-Ethylpyridine-4-carbothioamide 2-Ethylthioisonicotinamide
  • Ethionamidel
  • Ethionamide,2-Ethyl-4-pyridinecarbothioamide
  • TRECATOR (ethionaMide)
  • Ethionamide (200 mg)
  • ethionnaMide
  • Ethionamide for system suitability
Copyright 2019 © ChemicalBook. All rights reserved