Structure via PubChem · Public domain (PubChem)
iproniazid
Sign in to saveIproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until 2015.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 443877867
- Drug.IUPAC_name
- N-isopropylisonicotinohydrazide
- Drug.image
- Iproniazid.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150
- Drug.tradename
- Marsilid, others
- Drug.bioavailability
- 1
- Drug.CAS_number
- 54-92-2
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AF05
- Drug.PubChem
- 3748
- Drug.DrugBank
- DB04818
- Drug.ChemSpiderID
- 3617
- Drug.UNII
- D892HFI3XA
- Drug.KEGG
- D02579
- Drug.ChEMBL
- 92401
- Drug.C
- 9
via Wikipedia infobox
Chemical data
- Formula
- C9H13N3O
- Molecular weight
- 179.22 g/mol
- IUPAC name
- N'-propan-2-ylpyridine-4-carbohydrazide
- SMILES
- CC(C)NNC(=O)C1=CC=NC=C1
- InChIKey
- NYMGNSNKLVNMIA-UHFFFAOYSA-N
- XLogP
- 0.4
- Polar surface area
- 54 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
1,832 papers- [Iproniazid].Revista medica de Chile · 1959
- [Iproniazid].Revista clinica espanola · 1959
- Iproniazid jaundice.The American journal of gastroenterology · 1961
- IPRONIAZID phosphate.Journal of the American Medical Association · 1958
- The role of metabolism in the hepatotoxicity of isoniazid and iproniazid.Drug metabolism reviews · 1979
via PubMed
Wikidata facts
- Mass
- 179.105862
Show 4 more facts
- chemical formula
- C₉H₁₃N₃O
- World Health Organisation international non-proprietary name
- iproniazid
- canonical SMILES
- CC(C)NNC(=O)C1=CC=NC=C1
- Commons category
- Iproniazid
via Wikidata · CC0
~12 min read
Article
19 sectionsContents
- History
- Structure and reactivity
- Synthesis
- Reactions and mechanism of action
- Metabolism and toxicity
- Isopropyl radical
- Liver necrosis
- Metabolism to other forms
- Isonicotinic acid
- Other toxic effects
- Excretion
- Indication
- Efficacy and side effects
- Efficacy
- Adverse effects
- Effects on animals
- Lethality
- See also
- References
Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until 2015.
== History == Iproniazid was originally developed for the treatment of tuberculosis, but in 1952, the compounds's antidepressant properties were discovered when researchers noted that patients became inappropriately happy when given isoniazid, a related antibiotic. Subsequently, adding a isopropyl chain onto isoniazid led to development as an antidepressant and was approved for use in 1958. It was withdrawn in most of the world a few years later in 1961 due to a high incidence of hepatitis, and was replaced by less hepatotoxic drugs such as phenelzine and isocarboxazid. Canada surprisingly withdrew iproniazid in July 1964 due to interactions with food products containing tyramine. Nevertheless, iproniazid has historic value as it helped establish the relationship between psychiatric disorders and the metabolism of neurotransmitters.