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Ropivacaine mesylate

Product NameRopivacaine mesylate
CAS854056-07-8
MFC18H30N2O4S
MW370.51
EINECS264-407-7
MOL File854056-07-8.mol

Chemical Properties

storage temp.	Store at -20°C
form	Solid
color	White to off-white
Water Solubility	Water: 250 mg/mL (674.75 mM)
InChI	InChI=1/C17H26N2O.CH4O3S/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3;1-5(2,3)4/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20);1H3,(H,2,3,4)/t15-;/s3
InChIKey	YPTSIOMXZOPKAF-AVAJOTNLNA-N
SMILES	S(O)(=O)(=O)C.C([C@@H]1CCCCN1CCC)(=O)NC1C(=CC=CC=1C)C \|&1:6,r\|

Usage And Synthesis

Uses

Ropivacaine mesylate is a long-acting amide local anaesthetic agent for a spinal block and effectively blocks neuropathic pain. Ropivacaine blocks impulse conduction via reversible inhibition ofsodium ion influxin nerve fibressup>[1][2]. Ropivacaine is also an inhibitor of K2P (two-pore domain potassium channel)TREK-1with an IC50of 402.7 μM in COS-7 cell's membrane[3].

in vivo

Epidural administration of Ropivacaine mesylate effectively blocks neuropathic pain (both mechanical allodynia and heat hyperalgesia) without induction of analgesic tolerance and significantly delays the development of neuropathic pain produced by peripheral nerve injury^[1].
Ropivacaine mesylate inhibits pressure-induced increases in filtration coefficient (Kf) without affecting pulmonary artery pressure (Ppa), pulmonary capillary pressures (Ppc), and zonal characteristics (ZC)^[2].
Ropivacaine mesylate prevents pressure-induced lung edema and associated hyperpermeability as evidence by maintaining PaO2, lung wet-to-dry ratio and plasma volume in levels similar to sham rats^[2].
Ropivacaine mesylate inhibits pressure-induced NO production as evidenced by decreased lung nitro-tyrosine content when compared to hypertensive lungs^[2].

Animal Model:	Adult Sprague-Dawley rats (300-400g)^[2]
Dosage:	1 μM
Administration:	Infusion (added to the perfusate reservoir)
Result:	Attenuated pressure-dependent increases in filtration coefficient (K_f).

References

[1] Li TF, et al. Epidural sustained release ropivacaine prolongs anti-allodynia and anti-hyperalgesia in developing and established neuropathic pain. PLoS One. 2015 Jan 24;10(1):e0117321. DOI:10.1371/journal.pone.0117321
[2] Milan Patel, et al. Ropivacaine Inhibits Pressure-Induced Lung Endothelial Hyperpermeability in Models of Acute Hypertension. Life Sci. 2019 Apr 1;222:22-28. DOI:10.1016/j.lfs.2019.02.053
[3] Dene Simpson, et al. Ropivacaine: a review of its use in regional anaesthesia and acute pain management. Drugs. 2005;65(18):2675-717. DOI:10.2165/00003495-200565180-00013
[4] Hye Won Shin, et al. The inhibitory effects of bupivacaine, levobupivacaine, and ropivacaine on K2P (two-pore domain potassium) channel TREK-1. J Anesth. 2014 Feb;28(1):81-6. DOI:10.1007/s00540-013-1661-1

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