Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H13N3O.H3O4P |
Molecular Weight | 277.2142 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.CC(C)NNC(=O)C1=CC=NC=C1
InChI
InChIKey=YPDVTKJXVHYWFY-UHFFFAOYSA-N
InChI=1S/C9H13N3O.H3O4P/c1-7(2)11-12-9(13)8-3-5-10-6-4-8;1-5(2,3)4/h3-7,11H,1-2H3,(H,12,13);(H3,1,2,3,4)
Iproniazid is a non-selective, irreversible monoamine oxidase inhibitor (MAO) of the hydrazine class. It was originally developed for the treatment of Tuberculosis, but in 1952, its antidepressant properties were discovered when researchers noted that patients given isoniazid became inappropriately happy. Iproniazid is no longer clinically prescribed and has been withdrawn due to incidences of hepatotoxicity.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P21397 Gene ID: 4128.0 Gene Symbol: MAOA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21200377 |
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Target ID: P27338 Gene ID: 4129.0 Gene Symbol: MAOB Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21200377 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Marsilid Approved UseDepression Launch Date1951 |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
50 patients with depression who had been considered suitable for E.C.T. were given iproniazid in doses up to 450 mg/day for periods varying from two to forty weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7340462
MItochondrial fractions were isolated from bovine tissue homogenates of bovine brain and suspended in 0.1 M phosphate buffer (pH 7.4). Mitochondrial fractions were pre-incubated with 5-HT (1 mM), 2-phenylethylamine
(0.8 mM), tyramine (3.2 mM), dopamine (3 mM) or Hi (10
mM) at 37 deg-C for 30 - 45 minutes. Bovine mitochondrial were further incubated with increasing concentrations of Iproniazid (0.001 to 0.1 mM) which caused gradual inhibition of the deamination of 5-HT, tyramine, and dopamine. At 1 mM of Iproniazid, there was a marked increase in HDA, which was quite small in the mitochondria not treated with Iproniazid. Treatment of bovine brain mitochondria with 1 mM Iproniazid did not induce the appearance of HDA if the catalytic sites of the MAO-A were blocked by clorgyline. A selective inhibitor of the MAO-B deprenyl did not prevent the appearance of HDA after treatment with Iproniazid.
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ACTIVE MOIETY
SUBSTANCE RECORD