iproniazide

Iproniazid
Systematic (IUPAC) name
	N'-isopropylisonicotinohydrazide
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?;
Legal status	?;
Routes	?
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half-life	?
Excretion	?
Identifiers
CAS number	54-92-2
ATC code	N06AF05
PubChem	CID 3748
DrugBank	DB04818
ChemSpider	3617
UNII	D892HFI3XA
KEGG	D02579
ChEMBL	CHEMBL92401
Chemical data
Formula	C9H13N3O
Mol. mass	179.219
	SMILES O=C(NNC(C)C)c1ccncc1;
	InChI InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13) ; Key:NYMGNSNKLVNMIA-UHFFFAOYSA-N ;
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関: iproniazid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/11 07:46:15」(JST)

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Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class.^[1]^[2] It was discontinued in most of the world in the 1960s, but remained in use in France up until fairly recently.^[3]

Iproniazid was the first antidepressant ever marketed. It was originally developed for the treatment of tuberculosis,^[1] but in 1952, its antidepressant properties were discovered when researchers noted that patients given isoniazid became "inappropriately happy".^[1] Subsequently N-isopropyl addition lead to development as an antidepressant and was approved for use in 1958.^[1] It was withdrawn a few years later in 1961 due to a high incidence of hepatitis, and was replaced by less hepatotoxic drugs such as phenelzine and isocarboxazid.^[1]

References

^ ^a ^b ^c ^d ^e Robert A. Maxwell, Shohreh B. Eckhardt (1990). Drug discovery. Humana Press. pp. 143–154. ISBN 0-89603-180-2. ISBN 9780896031807.
^ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical pharmacology 35 (8): 1381–7. doi:10.1016/0006-2952(86)90285-6. PMID 2870717.
^ Maille F, Duvoux C, Cherqui D, Radier C, Zafrani ES, Dhumeaux D (October 1999). "[Auxiliary hepatic transplantation in iproniazid-induced subfulminant hepatitis. Should iproniazid still be sold in France?]". Gastroenterol. Clin. Biol. (in French) 23 (10): 1083–5. PMID 10592880.

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English Journal

Hydroxycoumarins as selective MAO-B inhibitors.

Serra S, Ferino G, Matos MJ, Vázquez-Rodríguez S, Delogu G, Viña D, Cadoni E, Santana L, Uriarte E.SourceDipartimento Farmaco Chimico Tecnologico, Università degli Studi di Cagliari, Via Ospedale 72, 09124 Cagliari, Italy. silvserra@tiscali.it
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2012 Jan 1;22(1):258-61. doi: 10.1016/j.bmcl.2011.11.020. Epub 2011 Nov 11.
A series of 3-aryl-4-hydroxycoumarin derivatives was synthesized with the aim to find out the structural features for the MAO inhibitory activity and selectivity. Methoxy and/or chloro substituents were introduced in the 3-phenyl ring, whereas the position 6 in the coumarin moiety was not substitute
PMID 22137786

MAO inhibitory activity modulation: 3-Phenylcoumarins versus 3-benzoylcoumarins.

Matos MJ, Vazquez-Rodriguez S, Uriarte E, Santana L, Viña D.SourceDepartamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2011 Jul 15;21(14):4224-7. doi: 10.1016/j.bmcl.2011.05.074. Epub 2011 May 30.
With the aim of finding the structural features for the human MAO inhibitory activity and selectivity, in the present communication we report the synthesis, pharmacological evaluation and a comparative study of a new series of 3-phenylcoumarins (compounds 1-4) and 3-benzoylcoumarins (compounds 5-8).
PMID 21684743

New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors.

Matos MJ, Viña D, Janeiro P, Borges F, Santana L, Uriarte E.SourceDepartamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, Santiago de Compostela, Spain. mariacmatos@gmail.com
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2010 Sep 1;20(17):5157-60. doi: 10.1016/j.bmcl.2010.07.013. Epub 2010 Jul 8.
With the aim to find out the structural features for the MAO inhibitory activity and selectivity, in the present communication we report the synthesis and pharmacological evaluation of a new series of bromo-6-methyl-3-phenylcoumarin derivatives (with bromo atom in both different benzene rings of the
PMID 20659799

Japanese Journal

Amines and the rat exocrine pancreas. 2. Effects of receptor blockers on turnover of L-5HTP.

Mori Jo [他],HASHIMOTO Masaharu,MUKUMOTO Sueo,HONDA Fumio
The Japanese Journal of Pharmacology 29(6), 913-921, 1979
… α-blockers (phenoxybenzamine and phentolamine) and monoamine oxidase (MAO) inhibitor (iproniazide) produced an increased accumulation of 5-HT fluorescence in the apical regions of acinar cells where the zymogen granules are stored. …
NAID 130000839833

The Regulatory Mechanism of Serotonin Level in Rat Brain and Intestine

湊川洋介,野口知雄,城戸亮
Proceedings of the Symposium on Chemical Physiology and Pathology 13(0), 2-4, 1974
… and iproniazide as a monoamine oxidase inhibitor. …
NAID 130003355233

Related Pictures

[bookDrug_discovery-1] Robert A. Maxwell, Shohreh B. Eckhardt (1990). Drug discovery. Humana Press. pp. 143–154. ISBN 0-89603-180-2. ISBN 9780896031807.

[pmid2870717-2] Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical pharmacology 35 (8): 1381–7. doi:10.1016/0006-2952(86)90285-6. PMID 2870717.

[pmid10592880-3] Maille F, Duvoux C, Cherqui D, Radier C, Zafrani ES, Dhumeaux D (October 1999). "[Auxiliary hepatic transplantation in iproniazid-induced subfulminant hepatitis. Should iproniazid still be sold in France?]". Gastroenterol. Clin. Biol. (in French) 23 (10): 1083–5. PMID 10592880.

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