Skip to content
iproniazid

Structure via PubChem · Public domain (PubChem)

EntityQ421368· pop 20· linked from 500 articles

iproniazid

Sign in to save

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 However, it was withdrawn from the market because of its hepatotoxicity.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.

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

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
Sources (3)

via Wikidata · CC0

~12 min read

Article

19 sections
Contents
  • 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 However, it was withdrawn from the market because of its hepatotoxicity.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.

Gallery (3)

Connections

Categories