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 |
|---|---|---|
| Genomic approaches to research in pulmonary hypertension. | 2001 |
|
| Role of endothelin-1 in lung disease. | 2001 |
|
| [Monocrotaline induce pulmonary hypertension in animal models]. | 2001 Apr-Jun |
|
| Clustering of hepatotoxins based on mechanism of toxicity using gene expression profiles. | 2001 Aug 15 |
|
| 40-O-(2-hydroxyethyl)-rapamycin attenuates pulmonary arterial hypertension and neointimal formation in rats. | 2001 Feb |
|
| Development of a (32)P-postlabeling/HPLC method for detection of dehydroretronecine-derived DNA adducts in vivo and in vitro. | 2001 Jan |
|
| Micronucleus formation in human lymphocytes and in the metabolically competent human hepatoma cell line Hep-G2: results with 15 naturally occurring substances. | 2001 Jan-Feb |
|
| All-trans retinoic acid in pulmonary vascular structural remodeling in rats with pulmonary hypertension induced by monocrotaline. | 2001 May |
|
| Stage-dependent activation of cell cycle and apoptosis mechanisms in the right ventricle by pressure overload. | 2002 Apr 24 |
|
| Pyrrolizidine alkaloid clivorine inhibits human normal liver L-02 cells growth and activates p38 mitogen-activated protein kinase in L-02 cells. | 2002 Dec |
|
| Effects of diesel exhaust enriched concentrated PM2.5 in ozone preexposed or monocrotaline-treated rats. | 2002 Jul |
|
| The temporal relationship between bacterial lipopolysaccharide and monocrotaline exposures influences toxicity: shift in response from hepatotoxicity to nitric oxide-dependent lethality. | 2002 Jul 26 |
|
| Dietary fish oil protects against lung and liver inflammation and fibrosis in monocrotaline treated rats. | 2002 Jun 14 |
|
| 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 |
|
| DA-8159, a potent cGMP phosphodiesterase inhibitor, attenuates monocrotaline-induced pulmonary hypertension in rats. | 2003 Aug |
|
| Liver inflammation during monocrotaline hepatotoxicity. | 2003 Aug 28 |
|
| Taste receptors for pyrrolizidine alkaloids in a monophagous caterpillar. | 2003 Jul |
|
| Effects of monocrotaline pyrrole and thrombin on pulmonary endothelial cell junction and matrix adhesion proteins. | 2003 Mar 3 |
|
| Granulocyte colony-stimulating factor enhances alpha-naphthylthiourea-induced pulmonary hypertension. | 2003 May |
|
| Rhythmical contractions in pulmonary arteries of monocrotaline-induced pulmonary hypertensive rats. | 2003 Nov |
|
| Basement membrane and matrix metalloproteinases in monocrotaline-induced liver injury. | 2003 Nov |
|
| Identification of DNA adducts derived from riddelliine, a carcinogenic pyrrolizidine alkaloid. | 2003 Sep |
|
| Sinusoidal obstruction syndrome (veno-occlusive disease) in the rat is prevented by matrix metalloproteinase inhibition. | 2003 Sep |
|
| Simvastatin rescues rats from fatal pulmonary hypertension by inducing apoptosis of neointimal smooth muscle cells. | 2003 Sep 30 |
|
| Beneficial effects of GH/IGF-1 on skeletal muscle atrophy and function in experimental heart failure. | 2004 Jan |
|
| Chronic sildenafil treatment inhibits monocrotaline-induced pulmonary hypertension in rats. | 2004 Jan 1 |
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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| Record Status |
Validated (UNII)
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