Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H23NO6 |
| Molecular Weight | 325.3569 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12[C@H]3CCN1CC=C2COC(=O)[C@](C)(O)[C@](C)(O)[C@@H](C)C(=O)O3
InChI
InChIKey=QVCMHGGNRFRMAD-XFGHUUIASA-N
InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1
| Molecular Formula | C16H23NO6 |
| Molecular Weight | 325.3569 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid derived from the seeds of the Crotalaria spectabilis plant. Monocrotaline is activated to the reactive pyrrole metabolite dehydromonocrotaline in the liver, a reaction that is highly dependent on cytochrome P-450 (CYP3A4). Monocrotaline induces a syndrome characterized, among other manifestations, by pulmonary hypertension, pulmonary mononuclear vasculitis (acute necrotizing pulmonary arteritis in about one-third of the animals), and right ventricular hypertrophy. Monocrotaline is widely used to model pulmonary arterial hypertension in rodents. Monocrotaline aggregates on and activates the extracellular calcium-sensing receptor (CaSR) of pulmonary artery endothelial cells to trigger endothelial damage and, ultimately, induces pulmonary hypertension.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular mechanisms of cardiac hypertrophy induced by toxicants. | 2001 |
|
| Attenuation of compensatory right ventricular hypertrophy and heart failure following monocrotaline-induced pulmonary vascular injury by the Na+-H+ exchange inhibitor cariporide. | 2001 Aug |
|
| Development of a (32)P-postlabeling/HPLC method for detection of dehydroretronecine-derived DNA adducts in vivo and in vitro. | 2001 Jan |
|
| Contribution of chloride channel activation to the elevated muscular tone of the pulmonary artery in monocrotaline-induced pulmonary hypertensive rats. | 2001 Jul |
|
| 5-HT1B receptor augmented 5-HT vasoconstrictor response of pulmonary artery in monocrotaline-induced pulmonary hypertensive rats. | 2001 Mar |
|
| Reactive oxygen species and substance P in monocrotaline-induced pulmonary hypertension. | 2001 Mar 15 |
|
| Microarray analysis of hepatotoxins in vitro reveals a correlation between gene expression profiles and mechanisms of toxicity. | 2001 Mar 31 |
|
| Beneficial effects on skeletal muscle of the angiotensin II type 1 receptor blocker irbesartan in experimental heart failure. | 2001 May 1 |
|
| Attenuation of inhibitory effect of CNP on the secretion of ANP from hypertrophied atria. | 2001 Nov |
|
| Cell-based gene transfer of vascular endothelial growth factor attenuates monocrotaline-induced pulmonary hypertension. | 2001 Oct 30 |
|
| Decrease in the Ca2+-activated K+ current of pulmonary arterial smooth muscle in pulmonary hypertension rats. | 2001 Sep |
|
| Pulmonary effects of ultrafine and fine ammonium salts aerosols in healthy and monocrotaline-treated rats following short-term exposure. | 2002 Dec |
|
| Defective intracellular calcium handling in monocrotaline-induced right ventricular hypertrophy: protective effect of long-term endothelin-A receptor blockade with 2-benzo[1,3]dioxol-5-yl-3-benzyl-4-(4-methoxy-phenyl-)- 4-oxobut-2-enoate-sodium (PD 155080). | 2002 Feb |
|
| Changes of sequestered leukocytes and platelets by inhalation prostaglandin E(1) in the pulmonary microvasculature of rats with monocrotaline-induced pulmonary hypertension. | 2002 Jan-Feb |
|
| Effects of diesel exhaust enriched concentrated PM2.5 in ozone preexposed or monocrotaline-treated rats. | 2002 Jul |
|
| Dexfenfluramine protects against pulmonary hypertension in rats. | 2002 Nov |
|
| L-Carnitine: a potential treatment for blocking apoptosis and preventing skeletal muscle myopathy in heart failure. | 2002 Sep |
|
| Gender differences in pulmonary arterial reactivity to dilatory agonists in pulmonary hypertension. | 2003 |
|
| Cytostatic properties of some angiotensin I converting enzyme inhibitors and of angiotensin II type I receptor antagonists. | 2003 |
|
| The role of Kupffer cells and TNF-alpha in monocrotaline and bacterial lipopolysaccharide-induced liver injury. | 2003 Jan |
|
| Skeletal muscle abnormalities in rats with experimentally induced heart hypertrophy and failure. | 2003 Mar |
|
| Role of neutrophils in the synergistic liver injury from monocrotaline and bacterial lipopolysaccharide exposure. | 2003 Mar |
|
| Experience influences gustatory responsiveness to pyrrolizidine alkaloids in the polyphagous caterpillar, Estigmene acrea. | 2003 Nov |
|
| Rhythmical contractions in pulmonary arteries of monocrotaline-induced pulmonary hypertensive rats. | 2003 Nov |
|
| Decreased hepatic nitric oxide production contributes to the development of rat sinusoidal obstruction syndrome. | 2003 Oct |
|
| Beneficial effects of GH/IGF-1 on skeletal muscle atrophy and function in experimental heart failure. | 2004 Jan |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:13:27 GMT 2023
by
admin
on
Fri Dec 15 19:13:27 GMT 2023
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| Record UNII |
73077K8HYV
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Validated (UNII)
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