Synonym
Ropivacaine Hydrochloride Monohydrate; Naropin; Ropivacaine hydrochloride hydrate; Naropin hydrochloride monohydrate; ropivacaine monohydrochloride, (S)-isomer; AL 381; AL-381; LEA 103; LEA-103;
IUPAC/Chemical Name
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide;hydrate;hydrochloride
InChi Key
VSHFRHVKMYGBJL-CKUXDGONSA-N
InChi Code
InChI=1S/C17H26N2O.ClH.H2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3;;/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20);1H;1H2/t15-;;/m0../s1
SMILES Code
CCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.O.Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Ropivacain blocks impulse conduction via reversible inhibition of sodium ion influx in nerve fibrese. Ropivacaine is also an inhibitor of K2P TREK-1 with an IC50 of 402.7 μM in COS-7 cell's membrane.
In vitro activity:
Ropivacaine exerted an anti-tumor impact on glioblastoma via mediating the miR-21-5p/KANSL2 axis. Ropivacaine constrained glioblastoma cell proliferation, invasion, and migration but boosted apoptosis.
Reference: Bioengineered. 2022 Mar;13(3):5975-5986. https://pubmed.ncbi.nlm.nih.gov/35191804/
In vivo activity:
In this study’s animal model, ropivacaine prevented pressure-induced lung edema and associated hyperpermeability. Ropivacaine inhibited pressure-induced NO production. Ropivacaine has potential for use in preventing endothelial hyperpermeability when pulmonary pressure is acutely increased and inhibiting pressure-induced lung endothelial hyperpermeability.
Reference: Life Sci. 2019 Apr 1;222:22-28. https://pubmed.ncbi.nlm.nih.gov/30822427/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
304.06 |
| Water |
50.0 |
152.03 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
328.88
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Deng Z, Jian Y, Cai H. Ropivacaine represses the proliferation, invasion, and migration of glioblastoma via modulating the microRNA-21-5p/KAT8 regulatory NSL complex subunit 2 axis. Bioengineered. 2022 Mar;13(3):5975-5986. doi: 10.1080/21655979.2022.2037955. PMID: 35191804; PMCID: PMC8973733.
2. Zhao L, Han S, Hou J, Shi W, Zhao Y, Chen Y. The local anesthetic ropivacaine suppresses progression of breast cancer by regulating miR-27b-3p/YAP axis. Aging (Albany NY). 2021 Jun 14;13(12):16341-16352. doi: 10.18632/aging.203160. Epub 2021 Jun 14. PMID: 34126594; PMCID: PMC8266352.
3. Lv H, Cheng Q, Li Y, Zhang Y, Chen J, Chen W. The Protective Effects of Ropivacaine Against High Glucose-induced Brain Microvascular Endothelial Injury by Reducing MMPs and Alleviating Oxidative Stress. Neurotox Res. 2021 Jun;39(3):851-859. doi: 10.1007/s12640-020-00324-8. Epub 2021 Feb 4. PMID: 33538995.
4. Patel M, Chignalia AZ, Isbatan A, Bommakanti N, Dull RO. 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. Epub 2019 Feb 26. PMID: 30822427.
In vitro protocol:
1. Deng Z, Jian Y, Cai H. Ropivacaine represses the proliferation, invasion, and migration of glioblastoma via modulating the microRNA-21-5p/KAT8 regulatory NSL complex subunit 2 axis. Bioengineered. 2022 Mar;13(3):5975-5986. doi: 10.1080/21655979.2022.2037955. PMID: 35191804; PMCID: PMC8973733.
2. Zhao L, Han S, Hou J, Shi W, Zhao Y, Chen Y. The local anesthetic ropivacaine suppresses progression of breast cancer by regulating miR-27b-3p/YAP axis. Aging (Albany NY). 2021 Jun 14;13(12):16341-16352. doi: 10.18632/aging.203160. Epub 2021 Jun 14. PMID: 34126594; PMCID: PMC8266352.
In vivo protocol:
1. Lv H, Cheng Q, Li Y, Zhang Y, Chen J, Chen W. The Protective Effects of Ropivacaine Against High Glucose-induced Brain Microvascular Endothelial Injury by Reducing MMPs and Alleviating Oxidative Stress. Neurotox Res. 2021 Jun;39(3):851-859. doi: 10.1007/s12640-020-00324-8. Epub 2021 Feb 4. PMID: 33538995.
2. Patel M, Chignalia AZ, Isbatan A, Bommakanti N, Dull RO. 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. Epub 2019 Feb 26. PMID: 30822427.
1: Shen Y, Ji Y, Xu S, Chen da Q, Tu J. Multivesicular liposome formulations for
the sustained delivery of ropivacaine hydrochloride: preparation,
characterization, and pharmacokinetics. Drug Deliv. 2011 Jul;18(5):361-6. doi:
10.3109/10717544.2011.557788. Epub 2011 Mar 23. PubMed PMID: 21428705.
2: Robustelli della Cuna FS, Mella M, Magistrali G, Ricci M, Losurdo A, Goglio
AM. Stability and compatibility of methylprednisolone acetate and ropivacaine
hydrochloride in polypropylene syringes for epidural administration. Am J Health
Syst Pharm. 2001 Sep 15;58(18):1753-6. PubMed PMID: 11571819.
3: Porter J, Crowe B, Cahill M, Shorten G. The effects of ropivacaine
hydrochloride on platelet function: an assessment using the platelet function
analyser (PFA-100). Anaesthesia. 2001 Jan;56(1):15-8. PubMed PMID: 11167430.
4: Mizikov VM. [New long-acting local anesthetic: ropivacaine hydrochloride
(naropin)]. Anesteziol Reanimatol. 2000 Jul-Aug;(4):72-7. Review. Russian. PubMed
PMID: 11014004.
5: Plowman AN, Bolsin S, Mather LE. Central nervous system toxicity attributable
to epidural ropivacaine hydrochloride. Anaesth Intensive Care. 1998
Apr;26(2):204-6. PubMed PMID: 9564403.
6: Eremenko AA, Ziuliaeva TP, Shandruk ID, Kolpakov PE, Egorov VM, Iavorovskiĭ
AG. [Continuous epidural infusion of ropivacaine hydrochloride (naropin) during
postoperative analgesia in cardiosurgical patients]. Anesteziol Reanimatol. 2003
Sep-Oct;(5):63-7. Russian. PubMed PMID: 14671915.
7: Skarda RT, Muir WW 3rd. Analgesic, behavioral, and hemodynamic and respiratory
effects of midsacral subarachnoidally administered ropivacaine hydrochloride in
mares. Vet Anaesth Analg. 2003 Jan;30(1):37-50. PubMed PMID: 14498916.
8: Bátai I, Kerényi M, Falvai J, Szabó G. Bacterial growth in ropivacaine
hydrochloride. Anesth Analg. 2002 Mar;94(3):729-31; table of contents. PubMed
PMID: 11867406.
9: Porter JM, Kelleher N, Flynn R, Shorten GD. Epidural ropivacaine hydrochloride
during labour: protein binding, placental transfer and neonatal outcome.
Anaesthesia. 2001 May;56(5):418-23. PubMed PMID: 11350325.
10: Porter JM, McGinley J, O'Hare B, Shorten GD. The effects of ropivacaine
hydrochloride on coagulation and fibrinolysis. An assessment using
thromboelastography. Anaesthesia. 1999 Sep;54(9):902-6. PubMed PMID: 10460568.
11: Sänger-van de Griend CE, Wahlström H, Gröningsson K, Widahl-Näsman M. A
chiral capillary electrophoresis method for ropivacaine hydrochloride in
pharmaceutical formulations: validation and comparison with chiral liquid
chromatography. J Pharm Biomed Anal. 1997 May;15(8):1051-61. PubMed PMID:
9215957.
12: Fyhr P, Högström C. A preformulation study on the kinetics of the
racemization of ropivacaine hydrochloride. Acta Pharm Suec. 1988;25(3):121-32.
PubMed PMID: 3239398.
