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 |
|---|---|---|
| The effect of beta-aminopropionitrile on elastin gene expression in smooth muscle cell cultures. | 1991 Sep 16 |
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| Synthesis and evaluation of long-acting D-penicillamine derivatives. | 2005 |
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| Periodontal & systemic bone changes in rats with experimental lathyrism. | 2006 Apr |
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| Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. | 2006 Mar |
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| The lysyl oxidase LOX is absent in basal and squamous cell carcinomas and its knockdown induces an invading phenotype in a skin equivalent model. | 2006 Mar 1 |
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| Use of an in vitro model of tissue-engineered skin to investigate the mechanism of skin graft contraction. | 2006 Nov |
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| Functional diversity of lysyl hydroxylase 2 in collagen synthesis of human dermal fibroblasts. | 2006 Nov 1 |
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| A novel type of lysine oxidase: L-lysine-epsilon-oxidase. | 2006 Oct |
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| Bonding of articular cartilage using a combination of biochemical degradation and surface cross-linking. | 2007 |
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| Increased stiffness of the rat liver precedes matrix deposition: implications for fibrosis. | 2007 Dec |
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| Active lysyl oxidase (LOX) correlates with focal adhesion kinase (FAK)/paxillin activation and migration in invasive astrocytes. | 2007 Dec |
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| The aminolysis of N-aroyl beta-lactams occurs by a concerted mechanism. | 2007 Feb 7 |
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| Regulation of elastin promoter by lysyl oxidase and growth factors: cross control of lysyl oxidase on TGF-beta1 effects. | 2007 Jul |
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| Essential role of lysyl oxidases in notochord development. | 2007 Jul 15 |
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| Distinct steps of cross-linking, self-association, and maturation of tropoelastin are necessary for elastic fiber formation. | 2007 Jun 8 |
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| Mechanism for covalent binding of rofecoxib to elastin of rat aorta. | 2007 Mar |
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| Covalent binding of rofecoxib, but not other cyclooxygenase-2 inhibitors, to allysine aldehyde in elastin of human aorta. | 2007 Oct |
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| Unilateral pedicle screws asymmetric tethering: an innovative method to create idiopathic deformity. | 2007 Oct 31 |
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| Lysyl oxidase oxidizes cell membrane proteins and enhances the chemotactic response of vascular smooth muscle cells. | 2008 Aug 29 |
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| 50 years ago in CORR : skeletal lesions produced by aminonitriles by Ignacio V. Ponseti MD CORR 1957;9:131-144. | 2008 Jan |
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| Cartilage growth and remodeling: modulation of balance between proteoglycan and collagen network in vitro with beta-aminopropionitrile. | 2008 Jan |
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| 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 |
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| Effect of cellular aging on collagen biosynthesis: I. Methodological considerations and pharmacological applications. | 2008 Nov-Dec |
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| Ultrastructural and histomorphometric alterations of rat jaw bones after experimental induction of lathyrism. | 2008 Oct |
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| The lysyl oxidase inhibitor, beta-aminopropionitrile, diminishes the metastatic colonization potential of circulating breast cancer cells. | 2009 |
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| Proteoglycan production is required in initial stages of new cartilage matrix formation but inhibits integrative cartilage repair. | 2009 Feb |
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| Wound-healing modulation in upper airway stenosis-Myths and facts. | 2009 Jan |
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| Reduced collagen biosynthesis is the hallmark of cerebral aneurysm: contribution of interleukin-1beta and nuclear factor-kappaB. | 2009 Jul |
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| Sea urchin arylsulfatase, an extracellular matrix component, is involved in gastrulation during embryogenesis. | 2009 Jun |
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| Bioreductively activated lysyl oxidase inhibitors against hypoxic tumours. | 2009 Oct |
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| Functional consequences of mitochondrial DNA deletions in human skin fibroblasts: increased contractile strength in collagen lattices is due to oxidative stress-induced lysyl oxidase activity. | 2009 Sep |
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| Comparison of the effects of semicarbazide and beta-aminopropionitrile on the arterial extracellular matrix in the Brown Norway rat. | 2009 Sep 15 |
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| Lysyl oxidase expression and inhibition in uveal melanoma. | 2010 Apr |
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| High glucose increases lysyl oxidase expression and activity in retinal endothelial cells: mechanism for compromised extracellular matrix barrier function. | 2010 Dec |
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| Lysyl oxidase silencing impairs keratinocyte differentiation in a reconstructed-epidermis model. | 2010 Dec |
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| Circulating tumour cells demonstrate an altered response to hypoxia and an aggressive phenotype. | 2010 Feb 2 |
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| 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 |
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| Differential effects of homocysteine and beta aminopropionitrile on preosteoblastic MC3T3-E1 cells. | 2010 Mar |
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| Bleomycin induces upregulation of lysyl oxidase in cultured human fetal lung fibroblasts. | 2010 May |
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| Pharmacologically induced thoracic and abdominal aortic aneurysms in mice. | 2010 May |
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| The effect of lathyrism on dentin structure of the rat incisors: a morphometric and scanning electron microscopic investigation. | 2010 May |
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| Id1, inhibitor of differentiation, is a key protein mediating anti-tumor responses of gamma-tocotrienol in breast cancer cells. | 2010 May 28 |
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| Prognostic implications of carboxyl-terminus of Hsc70 interacting protein and lysyl-oxidase expression in human breast cancer. | 2010 Nov 12 |
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| T3 affects expression of collagen I and collagen cross-linking in bone cell cultures. | 2010 Nov 12 |
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| Allosteric inhibition of lysyl oxidase-like-2 impedes the development of a pathologic microenvironment. | 2010 Sep |
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| In search of a new therapeutic target for the treatment of genetically triggered thoracic aortic aneurysms and cardiovascular conditions: insights from human and animal lathyrism. | 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
