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[ CAS No. 18614-51-2 ] {[proInfo.proName]}

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Chemical Structure| 18614-51-2
Chemical Structure| 18614-51-2
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William T. McClintic ; Zachary D. Chandler ; Lalitha M. Karchalla , et al. DOI:

Abstract: Botulinum neurotoxin (BoNT) is a potent protein toxin that causes muscle paralysis and death by asphyxiation. Treatments for symptomatic botulism are intubation and supportive care until respiratory function recovers. Aminopyridines have recently emerged as potential treatments for botulism. The clinically approved drug (3,4-DAP) rapidly reverses toxic signs of botulism and has antidotal effects when continuously administered in rodent models of lethal botulism. Although the therapeutic effects of likely result from the reversal of diaphragm paralysis, the corresponding effects on respiratory physiology are not understood. Here, we combined unrestrained whole-body plethysmography (UWBP) with arterial blood gas measurements to study the effects of , and other aminopyridines, on ventilation and respiration at terminal stages of botulism in mice. Treatment with clinically relevant doses of restored ventilation in a dose-dependent manner, producing significant improvements in ventilatory parameters within 10 minutes. Concomitant with improved ventilation, treatment reversed botulism-induced respiratory acidosis, restoring blood levels of CO2, pH, and lactate to normal physiologic levels. Having established that 3,4-DAP–mediated improvements in ventilation were directly correlated with improved respiration, we used UWBP to quantitatively evaluate nine additional aminopyridines in BoNT/A-intoxicated mice. Multiple aminopyridines were identified with comparable or enhanced therapeutic efficacies compared with , including aminopyridines that selectively improved tidal volume versus respiratory rate and vice versa. In addition to contributing to a growing body of evidence supporting the use of aminopyridines to treat clinical botulism, these data lay the groundwork for the development of aminopyridine derivatives with improved pharmacological properties.

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Product Details of [ 18614-51-2 ]

CAS No. :18614-51-2 MDL No. :MFCD03095284
Formula : C5H5FN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :JSAKBYXSHKYFQU-UHFFFAOYSA-N
M.W : 112.11 Pubchem ID :2762830
Synonyms :

Calculated chemistry of [ 18614-51-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 28.6
TPSA : 38.91 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 0.6
Log Po/w (WLOGP) : 1.23
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 0.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.47
Solubility : 3.82 mg/ml ; 0.034 mol/l
Class : Very soluble
Log S (Ali) : -0.99
Solubility : 11.4 mg/ml ; 0.102 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 1.46 mg/ml ; 0.013 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 18614-51-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:
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