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
C[C@H]1C(=O)O[C@@H]2CCN3CC=C(COC(=O)[C@](C)(O)[C@]1(C)O)[C@H]23
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 |
|---|---|---|
| Chronic sildenafil treatment inhibits monocrotaline-induced pulmonary hypertension in rats. | 2004-01-01 |
|
| Beneficial effects of GH/IGF-1 on skeletal muscle atrophy and function in experimental heart failure. | 2004-01 |
|
| Activation of the right ventricular endothelin (ET) system in the monocrotaline model of pulmonary hypertension: response to chronic ETA receptor blockade. | 2003-12 |
|
| Experience influences gustatory responsiveness to pyrrolizidine alkaloids in the polyphagous caterpillar, Estigmene acrea. | 2003-11 |
|
| Rhythmical contractions in pulmonary arteries of monocrotaline-induced pulmonary hypertensive rats. | 2003-11 |
|
| Augmented pulmonary vascular and venous constrictions to N(G)-nitro-L-arginine methyl ester in rats with monocrotaline-induced pulmonary hypertension. | 2003-11 |
|
| Basement membrane and matrix metalloproteinases in monocrotaline-induced liver injury. | 2003-11 |
|
| Decreased hepatic nitric oxide production contributes to the development of rat sinusoidal obstruction syndrome. | 2003-10 |
|
| Simvastatin rescues rats from fatal pulmonary hypertension by inducing apoptosis of neointimal smooth muscle cells. | 2003-09-30 |
|
| The activation pattern of the antioxidant enzymes in the right ventricle of rat in response to pressure overload is of heart failure type. | 2003-09-25 |
|
| Identification of DNA adducts derived from riddelliine, a carcinogenic pyrrolizidine alkaloid. | 2003-09 |
|
| Sinusoidal obstruction syndrome (veno-occlusive disease) in the rat is prevented by matrix metalloproteinase inhibition. | 2003-09 |
|
| Liver inflammation during monocrotaline hepatotoxicity. | 2003-08-28 |
|
| Hybrid cell-gene therapy for pulmonary hypertension based on phagocytosing action of endothelial progenitor cells. | 2003-08-19 |
|
| Mechanical load-dependent regulation of gene expression in monocrotaline-induced right ventricular hypertrophy in the rat. | 2003-08-08 |
|
| DA-8159, a potent cGMP phosphodiesterase inhibitor, attenuates monocrotaline-induced pulmonary hypertension in rats. | 2003-08 |
|
| The coagulation system contributes to synergistic liver injury from exposure to monocrotaline and bacterial lipopolysaccharide. | 2003-08 |
|
| Comparative scoring of micronucleated reticulocytes in rat peripheral blood by flow cytometry and microscopy. | 2003-08 |
|
| Taste receptors for pyrrolizidine alkaloids in a monophagous caterpillar. | 2003-07 |
|
| Endothelial cell injury and coagulation system activation during synergistic hepatotoxicity from monocrotaline and bacterial lipopolysaccharide coexposure. | 2003-07 |
|
| Inhibition of matrix metalloproteinases by lung TIMP-1 gene transfer limits monocrotaline-induced pulmonary vascular remodeling in rats. | 2003-06-10 |
|
| Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae. | 2003-06 |
|
| Embolization by sinusoidal lining cells obstructs the microcirculation in rat sinusoidal obstruction syndrome. | 2003-06 |
|
| Protective role of angiopoietin-1 in experimental pulmonary hypertension. | 2003-05-16 |
|
| Granulocyte colony-stimulating factor enhances alpha-naphthylthiourea-induced pulmonary hypertension. | 2003-05 |
|
| Effect of a surgical aortocaval fistula on monocrotaline-induced pulmonary hypertension. | 2003-04 |
|
| Tachykinin dysfunction attenuates monocrotaline-induced pulmonary hypertension. | 2003-03-15 |
|
| Effects of monocrotaline pyrrole and thrombin on pulmonary endothelial cell junction and matrix adhesion proteins. | 2003-03-03 |
|
| Final height outcome and value of height prediction in boys with constitutional delay in growth and adolescence treated with intramuscular testosterone 125 mg per month for 3 months. | 2003-03 |
|
| Skeletal muscle abnormalities in rats with experimentally induced heart hypertrophy and failure. | 2003-03 |
|
| Cardiac beta-adrenoceptor changes in monocrotaline-treated rats: differences between membrane preparations from whole ventricles and isolated ventricular cardiomyocytes. | 2003-03 |
|
| Role of neutrophils in the synergistic liver injury from monocrotaline and bacterial lipopolysaccharide exposure. | 2003-03 |
|
| The role of Kupffer cells and TNF-alpha in monocrotaline and bacterial lipopolysaccharide-induced liver injury. | 2003-01 |
|
| 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 |
|
| Pyrrolizidine alkaloid clivorine inhibits human normal liver L-02 cells growth and activates p38 mitogen-activated protein kinase in L-02 cells. | 2002-12 |
|
| Pulmonary effects of ultrafine and fine ammonium salts aerosols in healthy and monocrotaline-treated rats following short-term exposure. | 2002-12 |
|
| Ventricular hypertrophy plus neurohumoral activation is necessary to alter the cardiac beta-adrenoceptor system in experimental heart failure. | 2002-11-29 |
|
| Simvastatin attenuates smooth muscle neointimal proliferation and pulmonary hypertension in rats. | 2002-11-15 |
|
| Acute and chronic effects of T-1032, a novel selective phosphodiesterase type 5 inhibitor, on monocrotaline-induced pulmonary hypertension in rats. | 2002-11 |
|
| Anti-monocyte chemoattractant protein-1 gene therapy attenuates pulmonary hypertension in rats. | 2002-11 |
|
| Dexfenfluramine protects against pulmonary hypertension in rats. | 2002-11 |
|
| Cardiac and thermoregulatory effects of instilled particulate matter-associated transition metals in healthy and cardiopulmonary-compromised rats. | 2002-10-25 |
|
| Calibrated histochemistry applied to oxygen supply and demand in hypertrophied rat myocardium. | 2002-09-01 |
|
| Pyrrolizidine alkaloids from Senecio jacobaea affect fungal growth. | 2002-09 |
|
| [The effect and mechanism of felodipine on monocrotaline induced pulmonary hypertension in rats]. | 2002-08 |
|
| Reduction of monocrotaline-induced hepatic injury by deleted variant of hepatocyte growth factor (dHGF) in rats. | 2002-08 |
|
| Heme oxygenase-1 reduces murine monocrotaline-induced pulmonary inflammatory responses and resultant right ventricular overload. | 2002-08 |
|
| Myocardial force development and structural changes associated with monocrotaline induced cardiac hypertrophy and heart failure. | 2002 |
|
| Molecular mechanisms of cardiac hypertrophy induced by toxicants. | 2001 |
Patents
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
73077K8HYV
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