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
| Molecular Formula | C3H6N2 |
| Molecular Weight | 70.0931 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| High glucose increases lysyl oxidase expression and activity in retinal endothelial cells: mechanism for compromised extracellular matrix barrier function. | 2010-12 |
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| Lysyl oxidase silencing impairs keratinocyte differentiation in a reconstructed-epidermis model. | 2010-12 |
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| Prognostic implications of carboxyl-terminus of Hsc70 interacting protein and lysyl-oxidase expression in human breast cancer. | 2010-11-12 |
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| T3 affects expression of collagen I and collagen cross-linking in bone cell cultures. | 2010-11-12 |
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| Allosteric inhibition of lysyl oxidase-like-2 impedes the development of a pathologic microenvironment. | 2010-09 |
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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. | 2010-09 |
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| Pdcd4 repression of lysyl oxidase inhibits hypoxia-induced breast cancer cell invasion. | 2010-07-08 |
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| Modulation of lysyl oxidase-like 2 enzymatic activity by an allosteric antibody inhibitor. | 2010-07-02 |
|
| Intracellular lysyl oxidase: effect of a specific inhibitor on nuclear mass in proliferating cells. | 2010-06-11 |
|
| Id1, inhibitor of differentiation, is a key protein mediating anti-tumor responses of gamma-tocotrienol in breast cancer cells. | 2010-05-28 |
|
| Bleomycin induces upregulation of lysyl oxidase in cultured human fetal lung fibroblasts. | 2010-05 |
|
| Pharmacologically induced thoracic and abdominal aortic aneurysms in mice. | 2010-05 |
|
| The effect of lathyrism on dentin structure of the rat incisors: a morphometric and scanning electron microscopic investigation. | 2010-05 |
|
| Lysyl oxidase expression and inhibition in uveal melanoma. | 2010-04 |
|
| Differential effects of homocysteine and beta aminopropionitrile on preosteoblastic MC3T3-E1 cells. | 2010-03 |
|
| Circulating tumour cells demonstrate an altered response to hypoxia and an aggressive phenotype. | 2010-02-02 |
|
| Bioreductively activated lysyl oxidase inhibitors against hypoxic tumours. | 2009-10 |
|
| Comparison of the effects of semicarbazide and beta-aminopropionitrile on the arterial extracellular matrix in the Brown Norway rat. | 2009-09-15 |
|
| 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. | 2009-09 |
|
| Reduced collagen biosynthesis is the hallmark of cerebral aneurysm: contribution of interleukin-1beta and nuclear factor-kappaB. | 2009-07 |
|
| Sea urchin arylsulfatase, an extracellular matrix component, is involved in gastrulation during embryogenesis. | 2009-06 |
|
| Proteoglycan production is required in initial stages of new cartilage matrix formation but inhibits integrative cartilage repair. | 2009-02 |
|
| Wound-healing modulation in upper airway stenosis-Myths and facts. | 2009-01 |
|
| The lysyl oxidase inhibitor, beta-aminopropionitrile, diminishes the metastatic colonization potential of circulating breast cancer cells. | 2009 |
|
| 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. | 2008-11 |
|
| Ultrastructural and histomorphometric alterations of rat jaw bones after experimental induction of lathyrism. | 2008-10 |
|
| Lysyl oxidase oxidizes cell membrane proteins and enhances the chemotactic response of vascular smooth muscle cells. | 2008-08-29 |
|
| Collagen cross-linking influences osteoblastic differentiation. | 2008-05 |
|
| Contribution of collagen network features to functional properties of engineered cartilage. | 2008-03 |
|
| 50 years ago in CORR : skeletal lesions produced by aminonitriles by Ignacio V. Ponseti MD CORR 1957;9:131-144. | 2008-01 |
|
| Cartilage growth and remodeling: modulation of balance between proteoglycan and collagen network in vitro with beta-aminopropionitrile. | 2008-01 |
|
| Increased stiffness of the rat liver precedes matrix deposition: implications for fibrosis. | 2007-12 |
|
| Active lysyl oxidase (LOX) correlates with focal adhesion kinase (FAK)/paxillin activation and migration in invasive astrocytes. | 2007-12 |
|
| Unilateral pedicle screws asymmetric tethering: an innovative method to create idiopathic deformity. | 2007-10-31 |
|
| Covalent binding of rofecoxib, but not other cyclooxygenase-2 inhibitors, to allysine aldehyde in elastin of human aorta. | 2007-10 |
|
| Essential role of lysyl oxidases in notochord development. | 2007-07-15 |
|
| Regulation of elastin promoter by lysyl oxidase and growth factors: cross control of lysyl oxidase on TGF-beta1 effects. | 2007-07 |
|
| Distinct steps of cross-linking, self-association, and maturation of tropoelastin are necessary for elastic fiber formation. | 2007-06-08 |
|
| Effect of cellular aging on collagen biosynthesis: I. Methodological considerations and pharmacological applications. | 2007-05-12 |
|
| Mechanism for covalent binding of rofecoxib to elastin of rat aorta. | 2007-03 |
|
| The aminolysis of N-aroyl beta-lactams occurs by a concerted mechanism. | 2007-02-07 |
|
| Bonding of articular cartilage using a combination of biochemical degradation and surface cross-linking. | 2007 |
|
| Functional diversity of lysyl hydroxylase 2 in collagen synthesis of human dermal fibroblasts. | 2006-11-01 |
|
| Use of an in vitro model of tissue-engineered skin to investigate the mechanism of skin graft contraction. | 2006-11 |
|
| A novel type of lysine oxidase: L-lysine-epsilon-oxidase. | 2006-10 |
|
| Periodontal & systemic bone changes in rats with experimental lathyrism. | 2006-04 |
|
| The lysyl oxidase LOX is absent in basal and squamous cell carcinomas and its knockdown induces an invading phenotype in a skin equivalent model. | 2006-03-01 |
|
| Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. | 2006-03 |
|
| Synthesis and evaluation of long-acting D-penicillamine derivatives. | 2005 |
|
| The effect of beta-aminopropionitrile on elastin gene expression in smooth muscle cell cultures. | 1991-09-16 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:58:52 GMT 2025
by
admin
on
Mon Mar 31 17:58:52 GMT 2025
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| Record UNII |
38D5LJ4KH2
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| Record Status |
Validated (UNII)
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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 |
