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Chloroprocaine HCl

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7 API Suppliers, 6 USDMF, 1 JDMF, 2 NDC API, 1 Listed Suppliers

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12 FDF Dossiers, 12 FDA Orange Book

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SOLUTION;INTRATHECAL - 50MG/5ML (10MG/ML), INJECTABLE;INJECTION - 1%, INJECTABLE;INJECTION - 2%, INJECTABLE;INJECTION - 3%

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SOLUTION;INTRATHECAL - 50MG/5ML (10MG/ML)
INJECTABLE;INJECTION - 1%
INJECTABLE;INJECTION - 2%
INJECTABLE;INJECTION - 3%

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Chemistry

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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 HCl

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 Formula	C₁₃H₂₀Cl₂N₂O₂
Molecular Weight	307.21 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	306.0901833 g/mol
Monoisotopic Mass	306.0901833 g/mol
Topological Polar Surface Area	55.6 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	259
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Chloroprocaine hydrochloride
Drug Label	Nesacaine 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 Ingredient	Chloroprocaine hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	2%; 3%
Market Status	Prescription
Company	Hospira; Eurohlth Intl

2 of 2
Drug Name	Chloroprocaine hydrochloride
Drug Label	Nesacaine 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 Ingredient	Chloroprocaine hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	2%; 3%
Market Status	Prescription
Company	Hospira; 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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