Iproniazid
(Synonyms: 异丙烟肼) 目录号 : GC60939Iproniazid (Marsilid, Iprazid) is a non-selective, irreversible monoamine oxidase (MAO) inhibitor (MAOI) that is used as an antidepressive agent.
Cas No.:54-92-2
Sample solution is provided at 25 µL, 10mM.
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Iproniazid (Marsilid, Iprazid) is a non-selective, irreversible monoamine oxidase (MAO) inhibitor (MAOI) that is used as an antidepressive agent.
[1] Shen W, et al. Molecules. 2014, 19(11):18620-31.
Cas No. | 54-92-2 | SDF | |
别名 | 异丙烟肼 | ||
Canonical SMILES | O=C(C1=CC=NC=C1)NNC(C)C | ||
分子式 | C9H13N3O | 分子量 | 179.22 |
溶解度 | DMSO: 100 mg/mL (557.97 mM) | 储存条件 | -20°C, stored under nitrogen |
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1 mg | 5 mg | 10 mg | |
1 mM | 5.5797 mL | 27.8987 mL | 55.7973 mL |
5 mM | 1.1159 mL | 5.5797 mL | 11.1595 mL |
10 mM | 0.558 mL | 2.7899 mL | 5.5797 mL |
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Hepatotoxicity and metabolism of Iproniazid and isopropylhydrazine
J Pharmacol Exp Ther 1978 Sep;206(3):574-85.PMID:702322doi
Iproniazid (1-isonicotinoyl-2-isopropylhydrazine), an antidepressant drug removed from clinical use because of hepatic injury, and isopropylhydrazine, a metabolite of Iproniazid, were found to be potent hepatotoxins in rats. This animal model was used in studies in vivo and in vitro to define better the biochemical and chemical mechanism(s) by which Iproniazid and isopropylhydrazine mediate hepatotoxicity. Phenobarbital, an inducer of a class of hepatic microsomal cytochrome P-450 enzymes, greatly potentiated the necrosis, whereas inhibitors of these microsomal enzymes such as cobalt chloride, piperonyl butoxide and alpha-naphthylisothiocyanate, prevented the necrosis. Bis-para-nitrophenyl phosphate, an inhibitor of esterase and amidase enzymes, prevented the necrosis caused by Iproniazid but had no effect on the necrosis caused by isopropylhydrazine. Iproniazid and isopropylhydrazine labeled with tritium or carbon-14 in the isopropyl group were found to bind covalently to hepatic tissue macromolecules, and those pretreatments that increased hepatic necrosis significantly increased covalent binding, whereas those pretreatments which prevented necrosis significantly decreased covalent binding. Iproniazid labeled with tritium in the pyridine ring or carbon-14 in the carbonyl group did not bind significantly to hepatic tissue. Rats that were given Iproniazid or isopropylhydrazine, labeled specifically with tritium and carbon-14 on the c-2 methine position of the isopropyl group, expired acetone and carbon dioxide labeled with carbon-14. More importantly, propane was expired and contained a ratio of 3H/14C that was identical to that in the administered Iproniazid or isopropylhydrazine and also identical to the 3H/14C ratio of the metabolite that was covalently bound to hepatic tissue macromolecules. Experiments carried out with rat liver microsomes and isopropylhydrazine specifically labeled with deuterium, tritium and carbon-14 support the view that isopropylhydrazine is the metabolite of Iproniazid that is oxidized by a microsomal P-450 enzyme to a species that alkylates tissue macromolecules. Some of the urinary metabolites excreted by rats that were administered hepatotoxic doses of Iproniazid and isopropylhydrazine have been identified by cochromatography and isotope dilution with synthetic standards and by comparative mass spectra. Compounds excreted into the urine of rats dosed with Iproniazid include Iproniazid, iproniazid-1-oxide, isonicotinic acid, isonicotinoyl glycine, acetylisoniazid, isopropylhydrazine, 1-acetyl-2-isopropylhydrazine and acetone. Isopropylhydrazine, 1-acetyl-2-isopropylhydrazine, and acetone have been found in the urine of animals administered toxic doses of isopropylhydrazine.
Antiphlogistic activity of Iproniazid
Br J Pharmacol Chemother 1959 Dec;14(4):484-7.PMID:14445195DOI:10.1111/j.1476-5381.1959.tb00952.x.
Iproniazid was found to inhibit formalin-induced oedema of the foot, dextran-induced oedema and cotton-pellet-induced granulomatous tissue in the rat. The presence of the adrenals was essential for the antiphlogistic activity. The antiphlogistic action was not accompanied by any antipyretic effect. Inhibition of formalin-induced oedema was also observed with phenylbutazone and with salicylamide.
Clinical observations on Iproniazid in idiots with epilepsy
Calif Med 1960 Mar;92(3):207-9.PMID:14436745doi
In contradistinction to the observation made before that Iproniazid has a potentiating effect on certain amines in guinea pigs, human studies have shown that this effect has very little clinical importance, when both the amines and the amine oxidase inhibitor are given in the usual therapeutic doses. However, neither in man nor in the guinea pig pretreatment with Iproniazid showed a potentiating effect on amines which are not substrates of monoamine oxidase (ephedrine and amphetamine). Patients with epilepsy and allergic disease may receive Iproniazid.
Effect of 5-hydroxytryptamine and Iproniazid on pregnancy
Science 1960 Apr 15;131(3407):1101-2.PMID:14434518DOI:10.1126/science.131.3407.1101.
The effects of 5-hydroxytryptamine and Iproniazid on pregnancy in mice and rabbits were investigated. 5-Hydroxytryptamine can interrupt pregnancy at all stages in mice but is particularly effective early and late in pregnancy. Iproniazid exerts its action essentially in the first half of pregnancy. 5-Hydroxytryptamine produces striking hemorrhage in the placenta.
[Iproniazid-induced acute hepatitis]
Recenti Prog Med 1992 Jun;83(6):354-5.PMID:1496185doi
Many drugs can cause an acute liver damage. The patient history is the guideline for diagnosis. Iproniazid, a monoamine-oxidase inhibitor not for sale in Italy, can frequently cause severe acute hepatitis. A case of acute iproniazid-induced, hepatitis in which the course was favourable, is reported.