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Also known as: 84057-95-4, (s)-ropivacaine, Naropin, Ropivacaine [inn], Ropivacaine hydrochloride, Ropivacaina
Molecular Formula
C17H26N2O
Molecular Weight
274.4  g/mol
InChI Key
ZKMNUMMKYBVTFN-HNNXBMFYSA-N
FDA UNII
7IO5LYA57N

Ropivacaine Hydrochloride
An anilide used as a long-acting local anesthetic. It has a differential blocking effect on sensory and motor neurons.
Ropivacaine is an Amide Local Anesthetic. The physiologic effect of ropivacaine is by means of Local Anesthesia.
1 2D Structure

Ropivacaine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
2.1.2 InChI
InChI=1S/C17H26N2O/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)/t15-/m0/s1
2.1.3 InChI Key
ZKMNUMMKYBVTFN-HNNXBMFYSA-N
2.1.4 Canonical SMILES
CCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
2.1.5 Isomeric SMILES
CCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
2.2 Other Identifiers
2.2.1 UNII
7IO5LYA57N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1 Propyl 2',6' Pipecoloxylidide

2. 1-propyl-2',6'-pipecoloxylidide

3. Al 381

4. Al-381

5. Al381

6. Lea 103

7. Lea-103

8. Lea103

9. Naropeine

10. Naropin

11. Ropivacaine Hydrochloride

12. Ropivacaine Monohydrochloride

13. Ropivacaine Monohydrochloride, (s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 84057-95-4

2. (s)-ropivacaine

3. Naropin

4. Ropivacaine [inn]

5. Ropivacaine Hydrochloride

6. Ropivacaina

7. Ropivacainum

8. Ropivacaina [spanish]

9. (s)-n-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

10. Ropivacainum [inn-latin]

11. Ropivacaina [inn-spanish]

12. (2s)-n-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

13. Ropivicaine

14. 7io5lya57n

15. (-)-1-propyl-2',6'-pipecoloxylidide

16. Lea 103

17. Chebi:8890

18. Tlc590

19. (2s)-n-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide

20. (2s)-n-(2,6-dimethylphenyl)-1-propyl-piperidine-2-carboxamide

21. Tlc-590

22. Ropivacaine (inn)

23. L-n-n-propylpipecolic Acid-2,6-xylidide

24. Lea-103

25. 2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2s)-

26. S-ropivacaine

27. (s)-(-)-1-propyl-2',6'-pipecoloxylidide

28. 1-propyl-2',6'-pipecoloxylidide

29. Noropine

30. Narop

31. Lea-103 Hcl

32. Naropin (tn)

33. Ncgc00164597-01

34. Ropivacaine [inn:ban]

35. 98717-15-8

36. Unii-7io5lya57n

37. Ropivacaine Base

38. Mfcd00864425

39. Al-381

40. Ropivacaine [mi]

41. Ropivacaine [vandf]

42. Schembl33292

43. Ropivacaine [usp-rs]

44. Ropivacaine [who-dd]

45. Bidd:gt0203

46. Narop; Noropine; Lea-103

47. Gtpl7602

48. (-)-1-propyl-2',6'-dimethyl-2-piperidylcarboxyanilid

49. Chembl1077896

50. Dtxsid4040187

51. Zinc897002

52. Hy-b0563

53. Bbl102321

54. S5504

55. Stl556120

56. Akos017343283

57. Ccg-267197

58. Db00296

59. As-35173

60. Cs-0009514

61. R0251

62. C07532

63. D08490

64. Ab00698466-07

65. Ab00698466_10

66. 057r954

67. A840710

68. Q279504

69. (s)-(-)-1-propyl-2',6'-pipecoloxylidine

70. Q-201677

71. (-)-1-propyl-2',6'-dimethyl-2-piperidylcarboxyanilide

72. (s)-n-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide

73. (s)-(-)-1-propylpiperidine-2-carboxylic Acid (2,6-dimethylphenyl)amide

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 274.4 g/mol
Molecular Formula C17H26N2O
XLogP32.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass274.204513457 g/mol
Monoisotopic Mass274.204513457 g/mol
Topological Polar Surface Area32.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity308
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameNaropin
PubMed HealthRopivacaine (Injection)
Drug ClassesAnesthetic, Local
Drug LabelNaropin Injection contains ropivacaine HCl which is a member of the amino amide class of local anesthetics. Naropin Injection is a sterile, isotonic solution that contains the enantiomerically pure drug substance, sodium chloride for isotonicity an...
Active IngredientRopivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength2mg/ml; 10mg/ml; 5mg/ml; 7.5mg/ml
Market StatusPrescription
CompanyFresenius Kabi Usa

2 of 2  
Drug NameNaropin
PubMed HealthRopivacaine (Injection)
Drug ClassesAnesthetic, Local
Drug LabelNaropin Injection contains ropivacaine HCl which is a member of the amino amide class of local anesthetics. Naropin Injection is a sterile, isotonic solution that contains the enantiomerically pure drug substance, sodium chloride for isotonicity an...
Active IngredientRopivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength2mg/ml; 10mg/ml; 5mg/ml; 7.5mg/ml
Market StatusPrescription
CompanyFresenius Kabi Usa

4.2 Drug Indication

Used in obstetric anesthesia and regional anesthesia for surgery.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ropivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.


5.2 MeSH Pharmacological Classification

Anesthetics, Local

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ROPIVACAINE
5.3.2 FDA UNII
7IO5LYA57N
5.3.3 Pharmacological Classes
Amides [CS]; Local Anesthesia [PE]; Amide Local Anesthetic [EPC]
5.4 ATC Code

N01BB09

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N01 - Anesthetics

N01B - Anesthetics, local

N01BB - Amides

N01BB09 - Ropivacaine


5.5 Absorption, Distribution and Excretion

Absorption

Bioavailability is 87%98% following epidural administration.


Route of Elimination

Ropivacaine is extensively metabolized in the liver, predominantly by aromatic hydroxylation mediated by cytochrome P4501A to 3-hydroxy ropivacaine. After a single IV dose approximately 37% of the total dose is excreted in the urine as both free and conjugated 3-hydroxy ropivacaine. In total, 86% of the ropivacaine dose is excreted in the urine after intravenous administration of which only 1% relates to unchanged drug.


Clearance

387+/- 107 mL/min

unbound plasma clearance=7.2 +/- 1.6 L/min


5.6 Metabolism/Metabolites

Hepatic


Ropivacaine has known human metabolites that include 3-hydroxy-ropivacaine and PPX.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

Approximately 4.2 hours.


5.8 Mechanism of Action

Local anesthetics such as Ropivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Specifically, they block the sodium-channel and decrease chances of depolarization and consequent action potentials. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers.


API Reference Price

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05-Jan-2021
23-Oct-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - SOLUTION;INJECTION - 100MG/10ML (10M...DOSAGE - SOLUTION;INJECTION - 100MG/10ML (10MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 100MG/20ML (5MG...DOSAGE - SOLUTION;INJECTION - 100MG/20ML (5MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 150MG/30ML (5MG...DOSAGE - SOLUTION;INJECTION - 150MG/30ML (5MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 150MG/20ML (7.5...DOSAGE - SOLUTION;INJECTION - 150MG/20ML (7.5MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 1GM/200ML (5MG/...DOSAGE - SOLUTION;INJECTION - 1GM/200ML (5MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 200MG/20ML (10M...DOSAGE - SOLUTION;INJECTION - 200MG/20ML (10MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 200MG/100ML (2M...DOSAGE - SOLUTION;INJECTION - 200MG/100ML (2MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 20MG/10ML (2MG/...DOSAGE - SOLUTION;INJECTION - 20MG/10ML (2MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 400MG/200ML (2M...DOSAGE - SOLUTION;INJECTION - 400MG/200ML (2MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 40MG/20ML (2MG/...DOSAGE - SOLUTION;INJECTION - 40MG/20ML (2MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 500MG/100ML (5M...DOSAGE - SOLUTION;INJECTION - 500MG/100ML (5MG/ML)

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 50MG/10ML (5MG/...DOSAGE - SOLUTION;INJECTION - 50MG/10ML (5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20533

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DOSAGE - SOLUTION;INJECTION - 75MG/10ML (7.5M...DOSAGE - SOLUTION;INJECTION - 75MG/10ML (7.5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20533

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Global Sales Information

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Market Place

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Patents & EXCLUSIVITIES

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REF. STANDARDS & IMPURITIES

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