Ropivacaine

Names

[ Name ]:
Ropivacaine

[Synonym ]:
(S)-ROPIVACAINE HCL
(2S)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide
(S)-ROPIVACAINE HYDROCHLORIDE
(S)ROPIVACAINE HYDROCHLORIDE
(S)-ROPIVACAINEHYDROCHLORIDE
UNII-V910P86109
(S)-(-)-ropivacaine
(-)-1-propyl-2',6'-dimethyl-2-piperidylcarboxyanilide
Ropivacaine
Ropivacaine hydrochloride Monohydrate
(S)ROPIVACAINE HY DROCHLORIDE
2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2S)-, hydrochloride, hydrate (1:1:1)
S-ROPIVACAINE HCL
Ropivacaine (hydrochloride Monohydrate)
(2S)-N-(2,6-Dimethylphenyl)-1-propyl-2-piperidinecarboxamide
Ropivacaine API
(+-)-ropivacaine hydrochloride
(S)-ROPIVACAINEHCL
(S)-(-)-1-propyl-2',6'-pipecoloxylidide
S-ROPIVACAINEHCL
ROPACARAINEHCL
MFCD00864425
2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2S)-
RopivacaineHcl/MesylateBase
Ropivacainehydrochloride
Naropin
Ropivacaine hydrochloride
(S)-(-)-1-propyl-2',6'-pipecoloxylidine hydrochloride monohydrate
l-N-n-Propylpipecolic acid-2,6-xylidide
ROPIVACAINE MESYLATER
(-)-1-Propyl-2',6'-pipecoloxylidide
UNII-7IO5LYA57N
(S)-ropivacaine hydrochloride hydrate
(S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide
Naropine
(S)-N-propylpiperidine-2-carboxylic acid 2,6-dimethylphenyl amide
ropivacaine hydrochloride hydrate
Ropivacaine HCl.H2O
Ropivacaine HCl
S-ROPIVACAINE HYDROCHLORIDE
(2S)-N-(2,6-Dimethylphenyl)-1-propyl-2-piperidinecarboxamide hydrochloride hydrate
(2S)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride hydrate

Biological Activity

[Description]:

Ropivacain is a potent sodium channel blocker and acts as a local anesthetic agent. Ropivacain blocks impulse conduction via reversible inhibition of sodium ion influx in nerve fibrese[1][2]. Ropivacaine is also an inhibitor of K2P (two-pore domain potassium channel) TREK-1 with an IC50 of 402.7 μM in COS-7 cell's membrane[3]. Ropivacaine is used for the research of regional anesthesia and neuropathic pain management[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Cardiovascular Disease

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[Target]

IC50: sodium ion influx[1] IC50: 402.7 μM (TREK-1 in COS-7 cell's membrane)[2]

[In Vivo]

Epidural administration of Ropivacaine 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 inhibits pressure-induced increases in filtration coefficient (Kf) without affecting pulmonary artery pressure (Ppa), pulmonary capillary pressures (Ppc), and zonal characteristics (ZC)[2]. Ropivacaine 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 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)[1] Dosage: 1 μM Administration: Infusion (added to the perfusate reservoir) Result: Attenuated pressure-dependent increases in filtration coefficient (Kf).

[References]

[1]. Dene Simpson, et al. Ropivacaine: a review of its use in regional anaesthesia and acute pain management. Drugs. 2005;65(18):2675-717.

[2]. 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.

[3]. Hye Won Shin, et al. The inhibitory effects of bupivacaine, levobupivacaine, and ropivacaine on K2P (two-pore domain potassium) channel TREK-1. J Anesth

[4]. Milan Patel, et al. Ropivacaine Inhibits Pressure-Induced Lung Endothelial Hyperpermeability in Models of Acute Hypertension. Life Sci. 2019 Apr 1;222:22-28.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
410.2±45.0 °C at 760 mmHg

[ Melting Point ]:
144 - 146ºC

[ Molecular Formula ]:
C₁₇H₂₆N₂O

[ Molecular Weight ]:
274.401

[ Flash Point ]:
201.9±28.7 °C

[ Exact Mass ]:
274.204498

[ PSA ]:
32.34000

[ LogP ]:
3.11

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Storage condition ]:
-20℃

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
36/37/39-26

[ WGK Germany ]:
3

[ RTECS ]:
LK8650000

[ HS Code ]:
2933399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%