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Chloroprocaine Hydrochloride
Also known as: 3858-89-7, Chloroprocaine hcl, Chloroprocaine (hydrochloride), 2-chloroprocaine hydrochloride, Nesacaine, Chebi:3637
Molecular Formula
C13H20Cl2N2O2
Molecular Weight
307.21  g/mol
InChI Key
SZKQYDBPUCZLRX-UHFFFAOYSA-N
FDA UNII
LT7Z1YW11H

Chloroprocaine Hydrochloride is a synthetic, aminoester, local, anesthetic agent. At the injection site, chloroprocaine hydrochloride acts by inhibiting sodium influx through binding to specific membrane sodium ion channels in the neuronal cell membranes, restricting sodium permeability, and blocking nerve impulse conduction. This leads to a loss of sensation. Chloroprocaine hydrochloride is short-acting due to rapid hydrolysis by pseudocholinesterase into para-aminobenzoic acid in plasma.
1 2D Structure

Chloroprocaine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(diethylamino)ethyl 4-amino-2-chlorobenzoate;hydrochloride
2.1.2 InChI
InChI=1S/C13H19ClN2O2.ClH/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14;/h5-6,9H,3-4,7-8,15H2,1-2H3;1H
2.1.3 InChI Key
SZKQYDBPUCZLRX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)CCOC(=O)C1=C(C=C(C=C1)N)Cl.Cl
2.2 Other Identifiers
2.2.1 UNII
LT7Z1YW11H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-chloroprocaine

2. Chlor-procaine

3. Chloroprocaine

4. Nesacaine

5. Nesacaine Mpf

2.3.2 Depositor-Supplied Synonyms

1. 3858-89-7

2. Chloroprocaine Hcl

3. Chloroprocaine (hydrochloride)

4. 2-chloroprocaine Hydrochloride

5. Nesacaine

6. Chebi:3637

7. 2-chloroprocaine;halestyn; Piocaine

8. 2-diethylaminoethyl 4-amino-2-chlorobenzoate Hydrochloride

9. 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate;hydrochloride

10. 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate Monohydrochloride

11. 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate Hydrochloride

12. Lt7z1yw11h

13. Chloroprocaine Hydrochloride (usp)

14. 4-amino-2-chlorobenzoic Acid 2-(diethylamino)ethyl Ester Hydrochloride

15. Benzoic Acid, 4-amino-2-chloro-, 2-(diethylamino)ethyl Ester, Monohydrochloride

16. Ncgc00183273-01

17. Clorotekal (tn)

18. Nesacaine (tn)

19. Clorotekal

20. Chloroprocainhydrochlorid

21. Chloroprocainehydrochloride

22. Chembl944

23. Chlorprocaine Chloride

24. Dsstox_cid_28521

25. Dsstox_rid_82793

26. Dsstox_gsid_48595

27. Schembl24096

28. Dtxsid6048595

29. Hy-b1604

30. Tox21_112925

31. S4284

32. Ccg-267543

33. Chloroprocaine Hydrochloride [mi]

34. Cas-3858-89-7

35. Chloroprocaine Hydrochloride [mart.]

36. Chloroprocaine Hydrochloride [vandf]

37. Chloroprocaine Hydrochloride [usp-rs]

38. Chloroprocaine Hydrochloride [who-dd]

39. Cs-0013536

40. Sw220257-1

41. A14260

42. D00732

43. 858c897

44. A912305

45. Chloroprocaine Hydrochloride [orange Book]

46. Chloroprocaine Hydrochloride [usp Monograph]

47. W-106476

48. Q27068150

49. Chloroprocaine Hydrochloride 1000 Microg/ml In Methanol

50. 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate Hcl

51. Benzoic Acid,4-amino-2-chloro-,2-(diethylamino)ethyl Ester

52. [2-(4-amino-2-chloro-benzoyloxy)-ethyl]-diethyl-ammonium; Chloride

53. 4-amino-2-chlorobenzoicacid2-(diethylamino)ethylesterhydrochloride

54. Benzoic Acid,4-amino-2-chloro-, 2-(diethylamino)ethyl Ester

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 307.21 g/mol
Molecular Formula C13H20Cl2N2O2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass306.0901833 g/mol
Monoisotopic Mass306.0901833 g/mol
Topological Polar Surface Area55.6 Ų
Heavy Atom Count19
Formal Charge0
Complexity259
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameChloroprocaine hydrochloride
Drug LabelNesacaine and Nesacaine-MPF Injections are sterile non pyrogenic local anesthetics. The active ingredient in Nesacaine and Nesacaine-MPF Injections is chloroprocaine HCL (benzoic acid, 4-amino-2-chloro-2-(diethylamino) ethyl ester, monohydrochloride)...
Active IngredientChloroprocaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength2%; 3%
Market StatusPrescription
CompanyHospira; Eurohlth Intl

2 of 2  
Drug NameChloroprocaine hydrochloride
Drug LabelNesacaine and Nesacaine-MPF Injections are sterile non pyrogenic local anesthetics. The active ingredient in Nesacaine and Nesacaine-MPF Injections is chloroprocaine HCL (benzoic acid, 4-amino-2-chloro-2-(diethylamino) ethyl ester, monohydrochloride)...
Active IngredientChloroprocaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength2%; 3%
Market StatusPrescription
CompanyHospira; Eurohlth Intl

4.2 Drug Indication

Intrathecal anaesthesia


Ocular surface anaesthesia


Epidural anaesthesia


Peripheral nerve block (local anaesthesia by perineural injection)


Intrathecal anaesthesia


Ocular surface anaesthesia


5 Pharmacology and Biochemistry
5.1 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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Esters [CS]; Local Anesthesia [PE]; Ester Local Anesthetic [EPC]
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  • SOLUTION;INTRATHECAL - 50MG/5ML (10MG/ML)
  • INJECTABLE;INJECTION - 1%
  • INJECTABLE;INJECTION - 2%
  • INJECTABLE;INJECTION - 3%
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