Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C3H6N2 |
| Molecular Weight | 70.0931 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCC#N
InChI
InChIKey=AGSPXMVUFBBBMO-UHFFFAOYSA-N
InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2
3-Aminopropionitrile (beta-aminopropionitrile, BAPN) is a poisonous substance found in Lathyrus spp. (wild peas), for example, Lathyrus hirsutus (wild winter pea), sometimes sown with grasses to provide early-spring grazing. BAPN is a specific and irreversible inhibitor of LOX activity. It has been shown to reduce body weight gain and improve the metabolic profile in diet-induced obesity in rats. The administration of beta-aminopropionitrile has been proposed for pharmacological control of unwanted scar tissue in human beings. BAPN has been shown to have preventive effect in the development of fibrosis by decreasing tissue damage in an experimental model of corrosive esophagitis in rats. BAPN is FDA approved for the treatment of tendinitis of the superficial digital flexor tendon (SDFT) in horses where there is sonographic evidence of fiber tearing.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Amine oxidase-like activity of polyphenols. Mechanism and properties. | 2001 Apr |
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| Characterization of a model compound for the lysine tyrosylquinone cofactor of lysyl oxidase. | 2001 Feb 16 |
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| Beta-aminopropionitrile treatment can accelerate recovery of mice after spinal cord injury. | 2001 Oct 26 |
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| Force deficits after stretches of activated rat muscle-tendon complex with reduced collagen cross-linking. | 2001 Sep |
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| A molecular role for lysyl oxidase in breast cancer invasion. | 2002 Aug 1 |
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| Biochemical and toxicological evaluation of agent-cofactor reactivity as a mechanism of action for osteolathyrism. | 2002 Aug 15 |
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| An angiotensin-converting enzyme inhibitor, not an angiotensin II type-1 receptor blocker, prevents beta-aminopropionitrile monofumarate-induced aortic dissection in rats. | 2002 Oct |
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| Treatment of acute schistosomiasis mansoni with praziquantel and an antifibrotic agent in mice. Maintenance of resistance to infection. | 2003 |
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| Collagen crosslinking and cell density have distinct effects on fibroblast-mediated contraction of collagen gels. | 2003 Aug |
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| Elastic fiber production in cardiovascular tissue-equivalents. | 2003 Jun |
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| Tropoelastin inhibits vascular calcification via 67-kDa elastin binding protein in cultured bovine aortic smooth muscle cells. | 2004 |
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| A role for lysyl oxidase regulation in the control of normal collagen deposition in differentiating osteoblast cultures. | 2004 Jul |
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| The effects of beta-aminopropionitrile on colonic anastomosis in rats. | 2004 Jul-Aug |
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| The role of ascorbic acid on collagen structure and levels of serum interleukin-6 and tumour necrosis factor-alpha in experimental lathyrism. | 2004 Mar |
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| The propeptide domain of lysyl oxidase induces phenotypic reversion of ras-transformed cells. | 2004 Sep 24 |
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| Collagen and elastin cross-linking: a mechanism of constrictive remodeling after arterial injury. | 2005 Nov |
|
| Examination of the stress-induced expression of the collagen binding heat shock protein, hsp47, in Xenopus laevis cultured cells and embryos. | 2006 Jan |
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| A novel type of lysine oxidase: L-lysine-epsilon-oxidase. | 2006 Oct |
|
| The aminolysis of N-aroyl beta-lactams occurs by a concerted mechanism. | 2007 Feb 7 |
|
| Mechanism for covalent binding of rofecoxib to elastin of rat aorta. | 2007 Mar |
|
| Covalent binding of rofecoxib, but not other cyclooxygenase-2 inhibitors, to allysine aldehyde in elastin of human aorta. | 2007 Oct |
|
| Contribution of collagen network features to functional properties of engineered cartilage. | 2008 Mar |
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| Collagen cross-linking influences osteoblastic differentiation. | 2008 May |
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| Osteitis fibrosa is mediated by Platelet-Derived Growth Factor-A via a phosphoinositide 3-kinase-dependent signaling pathway in a rat model for chronic hyperparathyroidism. | 2008 Nov |
|
| The lysyl oxidase inhibitor, beta-aminopropionitrile, diminishes the metastatic colonization potential of circulating breast cancer cells. | 2009 |
|
| Proteoglycan production is required in initial stages of new cartilage matrix formation but inhibits integrative cartilage repair. | 2009 Feb |
|
| Wound-healing modulation in upper airway stenosis-Myths and facts. | 2009 Jan |
|
| Reduced collagen biosynthesis is the hallmark of cerebral aneurysm: contribution of interleukin-1beta and nuclear factor-kappaB. | 2009 Jul |
|
| Sea urchin arylsulfatase, an extracellular matrix component, is involved in gastrulation during embryogenesis. | 2009 Jun |
|
| High glucose increases lysyl oxidase expression and activity in retinal endothelial cells: mechanism for compromised extracellular matrix barrier function. | 2010 Dec |
|
| Circulating tumour cells demonstrate an altered response to hypoxia and an aggressive phenotype. | 2010 Feb 2 |
|
| Modulation of lysyl oxidase-like 2 enzymatic activity by an allosteric antibody inhibitor. | 2010 Jul 2 |
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| Pdcd4 repression of lysyl oxidase inhibits hypoxia-induced breast cancer cell invasion. | 2010 Jul 8 |
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| Intracellular lysyl oxidase: effect of a specific inhibitor on nuclear mass in proliferating cells. | 2010 Jun 11 |
|
| Bleomycin induces upregulation of lysyl oxidase in cultured human fetal lung fibroblasts. | 2010 May |
|
| The effect of lathyrism on dentin structure of the rat incisors: a morphometric and scanning electron microscopic investigation. | 2010 May |
|
| Prognostic implications of carboxyl-terminus of Hsc70 interacting protein and lysyl-oxidase expression in human breast cancer. | 2010 Nov 12 |
|
| Allosteric inhibition of lysyl oxidase-like-2 impedes the development of a pathologic microenvironment. | 2010 Sep |
Sample Use Guides
For treatment of tendinitis of the superficial digital flexor tendon (SDFT) in horses where there is sonographic evidence of fiber tearing. Administer 7 mg by intralesional injection every other day for five treatments beginning about 30 days after initial injury.
Route of Administration:
Other
The initial interaction of BAPN with aortic lysyl oxidase is competitive with elastin or alkyl amine substrates. Irreversible inhibition develops in a time- and temperature-dependent fashion upon incubation of enzyme with BAPN in the absence of substrate with a limiting inactivation rate constant of 0.16 min-1 and a KI of 6 uM at 37 degrees C.
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NCI_THESAURUS |
C471
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WHO-VATC |
QM01AX91
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2897
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27413
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151-18-8
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40641
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Aminopropionitrile
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DTXSID6048418
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C83513
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1647
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m1735
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38D5LJ4KH2
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205-786-0
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SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
