CHEBI:4885 - ethionamide

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ChEBI Name ethionamide
ChEBI ID CHEBI:4885
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB7125746, ChemicalBook:CB2752440, eMolecules:494705, eMolecules:29781161, Selleckchem:Levonorgestrel(Levonelle), ZINC000003814395
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Levonorgestrel is a hormonal medication which is used in a number of birth control methods. It is combined with an estrogen to make combination birth control pills. As an emergency birth control, sold under the brand names Plan B One-Step and Julie, among others, it is useful within 72 hours of unprotected sex. The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (implantation) has occurred. Levonorgestrel works by preventing ovulation or fertilization from occurring. It decreases the chances of pregnancy by 57–93%. In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy. A levonorgestrel-releasing implant is also available in some countries. Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding. When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use harms the fetus. It is safe to use during breastfeeding. Birth control that contains levonorgestrel will not change the risk of sexually transmitted infections. It is a progestin and has effects similar to those of the hormone progesterone. It works primarily by preventing ovulation and closing off the cervix to prevent the passage of sperm. Levonorgestrel was patented in 1960 and introduced for medical use together with ethinylestradiol in 1970. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In the United States, levonorgestrel-containing emergency contraceptives are available over the counter (OTC) for all ages. In 2020, it was the 323rd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.
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Formula C8H10N2S
Net Charge 0
Average Mass 166.24448
Monoisotopic Mass 166.05647
InChI InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
InChIKey AEOCXXJPGCBFJA-UHFFFAOYSA-N
SMILES CCc1cc(ccn1)C(N)=S
Roles Classification
Biological Role(s): antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
fatty acid synthesis inhibitor
Any pathway inhibitor that inhibits the synthesis of fatty acids.
leprostatic drug
A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
Application(s): antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
leprostatic drug
A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ethionamide (CHEBI:4885) has role antilipemic drug (CHEBI:35679)
ethionamide (CHEBI:4885) has role antitubercular agent (CHEBI:33231)
ethionamide (CHEBI:4885) has role fatty acid synthesis inhibitor (CHEBI:50185)
ethionamide (CHEBI:4885) has role leprostatic drug (CHEBI:35816)
ethionamide (CHEBI:4885) has role prodrug (CHEBI:50266)
ethionamide (CHEBI:4885) is a pyridines (CHEBI:26421)
ethionamide (CHEBI:4885) is a thiocarboxamide (CHEBI:47956)
Incoming ethionamide S-oxide (CHEBI:87805) has functional parent ethionamide (CHEBI:4885)
IUPAC Name
2-ethylpyridine-4-carbothioamide
INNs Sources
ethionamidum ChemIDplus
etionamida ChemIDplus
Synonyms Sources
2-ethyl-4-thiopyridylamide ChEBI
ETH DrugBank
Ethinamide DrugBank
ethionamide UniProt
Ethionamide KEGG COMPOUND
Ethioniamide DrugBank
Ethylisothiamide DrugBank
Ethyonomide DrugBank
Etionamid DrugBank
Etionamide DrugBank
Etioniamid DrugBank
ETP DrugBank
Brand Name Source
Trecator ChemIDplus
Manual Xrefs Databases
1083 DrugCentral
C07665 KEGG COMPOUND
D00591 KEGG DRUG
DB00609 DrugBank
Ethionamide Wikipedia
GB800250 Patent
HMDB0014747 HMDB
LSM-5620 LINCS
View more database links
Registry Numbers Types Sources
116474 Reaxys Registry Number Reaxys
536-33-4 CAS Registry Number KEGG COMPOUND
536-33-4 CAS Registry Number NIST Chemistry WebBook
536-33-4 CAS Registry Number ChemIDplus
Citations Types Sources
14651620 PubMed citation Europe PMC
15673755 PubMed citation Europe PMC
15850780 PubMed citation Europe PMC
Last Modified
22 February 2017