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Chemistry

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Also known as: Chloroprocain, 2-chloroprocaine, 133-16-4, Chlorprocaine, Halestyn, 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate
Molecular Formula
C13H19ClN2O2
Molecular Weight
270.75  g/mol
InChI Key
VDANGULDQQJODZ-UHFFFAOYSA-N
FDA UNII
5YVB0POT2H

Chloroprocaine
Chloroprocaine hydrochloride is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine, like other local anesthetics, blocks 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.
Chloroprocaine is an Ester Local Anesthetic. The physiologic effect of chloroprocaine is by means of Local Anesthesia.
1 2D Structure

Chloroprocaine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(diethylamino)ethyl 4-amino-2-chlorobenzoate
2.1.2 InChI
InChI=1S/C13H19ClN2O2/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
2.1.3 InChI Key
VDANGULDQQJODZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)CCOC(=O)C1=C(C=C(C=C1)N)Cl
2.2 Other Identifiers
2.2.1 UNII
5YVB0POT2H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-chloroprocaine

2. Chlor-procaine

3. Chloroprocaine Hydrochloride

4. Nesacaine

5. Nesacaine Mpf

2.3.2 Depositor-Supplied Synonyms

1. Chloroprocain

2. 2-chloroprocaine

3. 133-16-4

4. Chlorprocaine

5. Halestyn

6. 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate

7. Piocaine

8. Chloroprocainum

9. Cloroprocaina

10. Chloroprocaine [inn]

11. Nesacaine

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

13. 2-diethylaminoethyl 4-amino-2-chloro-benzoate

14. Chloroprocaine (inn)

15. 5yvb0pot2h

16. Chlor-procaine

17. 4-amino-2-chlorobenzoic Acid 2-(diethylamino)ethyl Ester

18. Chebi:3636

19. Chlorprocainum

20. Chloroprocainum [inn-latin]

21. Cloroprocaina [inn-spanish]

22. Hsdb 3301

23. Unii-5yvb0pot2h

24. 2-(diethylaminoethyl)-4-amino-2-chlorobenzoate

25. Brn 2808071

26. Chloroprocaine [mi]

27. Schembl6676

28. Chloroprocaine [hsdb]

29. 4-14-00-01273 (beilstein Handbook Reference)

30. Chloroprocaine [vandf]

31. Gtpl7145

32. Chloroprocaine [who-dd]

33. Chembl1179047

34. Dtxsid8022799

35. Hy-b1604a

36. Zinc1530938

37. Akos010575135

38. Db01161

39. Ncgc00183273-04

40. Cs-0013537

41. Ft-0713386

42. C07877

43. D07678

44. Sr-01000944416

45. Q2964133

46. Sr-01000944416-1

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 270.75 g/mol
Molecular Formula C13H19ClN2O2
XLogP32.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass270.1135055 g/mol
Monoisotopic Mass270.1135055 g/mol
Topological Polar Surface Area55.6 Ų
Heavy Atom Count18
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 Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameChloroprocaine hydrochloride
PubMed HealthChloroprocaine (Injection)
Drug ClassesAnesthetic, Local
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 4  
Drug NameNesacaine
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
Strength1%; 2%
Market StatusPrescription
CompanyFresenius Kabi Usa

3 of 4  
Drug NameChloroprocaine hydrochloride
PubMed HealthChloroprocaine (Injection)
Drug ClassesAnesthetic, Local
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 of 4  
Drug NameNesacaine
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
Strength1%; 2%
Market StatusPrescription
CompanyFresenius Kabi Usa

4.2 Therapeutic Uses

Anesthetics, Local

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


A LOCAL ANESTHETIC AGENT SIMILAR IN CHEM STRUCTURE & PHARMACOLOGICAL ACTION TO PARENT COMPD, PROCAINE HCL. IT IS MORE RAPID IN ONSET OF ACTION & HAS ANESTHETIC POTENCY AT LEAST TWICE THAT OF PROCAINE. TOXICITY IS LOW & QUALITATIVELY SIMILAR TO PROCAINE. /CHLOROPROCAINE HCL/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 988


...USED TO PRODUCE ANESTHESIA BY TECHNIQUES OF INFILTRATION, FIELD BLOCK, & REGIONAL NERVE BLOCK, INCL CAUDAL & EPIDURAL BLOCK. /CHLOROPROCAINE HCL/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 988


... ACT ON ANY PART OF THE NERVOUS SYSTEM & ON EVERY TYPE OF NERVE FIBER. /LOCAL ANESTHETICS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 331


For more Therapeutic Uses (Complete) data for CHLOROPROCAINE (13 total), please visit the HSDB record page.


4.3 Drug Warning

A FEW CASES OF THROMBOPHLEBITIS HAVE BEEN REPORTED FOLLOWING IV REGIONAL ANESTHESIA. THIS REACTION MAY HAVE BEEN DUE TO ACIDITY OF SOLN. /CHLOROPROCAINE HCL/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 272


... NOT EFFECTIVE TOPICALLY & HAS NOT BEEN STUDIED SUFFICIENTLY TO BE USED FOR SPINAL ANESTHETIC. /CHLOROPROCAINE HCL/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 165


IN PRESENCE OF HEMORRHAGE, SYMPATHETIC BLOCK PRODUCED BY EPIDURAL ANESTHESIA BECOMES EXTREMELY SIGNIFICANT & MAY RESULT IN RAPID & DELETERIOUS CIRCULATORY CHANGES. /LOCAL ANESTHETICS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 399


ANIMALS WITH EXPTL PRODUCED HEPATIC DAMAGE ARE MUCH MORE SUSCEPTIBLE TO TOXIC ACTIONS OF LOCAL ANESTHETICS, SO THAT EXTENSIVE USE OF LOCAL ANESTHETIC IN PT WITH SEVERE HEPATIC DAMAGE SHOULD PERHAPS BE AVOIDED. /LOCAL ANESTHETICS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 386


For more Drug Warnings (Complete) data for CHLOROPROCAINE (19 total), please visit the HSDB record page.


4.4 Drug Indication

For the production of local anesthesia by infiltration and peripheral nerve block. They are not to be used for lumbar or caudal epidural anesthesia.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Chloroprocaine is an ester type anesthetic agent indicated for production of local or regional anesthesia, particularly for oral surgery. Chloroprocaine (like cocaine) has the advantage of constricting blood vessels which reduces bleeding, unlike other local anesthetics like lidocaine.


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
CHLOROPROCAINE
5.3.2 FDA UNII
5YVB0POT2H
5.3.3 Pharmacological Classes
Physiologic Effects [PE] - Local Anesthesia
5.4 ATC Code

N - Nervous system

N01 - Anesthetics

N01B - Anesthetics, local

N01BA - Esters of aminobenzoic acid

N01BA04 - Chloroprocaine


5.5 Absorption, Distribution and Excretion

Absorption

The rate of systemic absorption of local anesthetic drugs is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic injection.


Route of Elimination

Chloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase. Urinary excretion is affected by urinary perfusion and factors affecting urinary pH.


PROCAINE IS READILY ABSORBED FOLLOWING PARENTERAL ADMIN ... DOES NOT LONG REMAIN @ SITE OF INJECTION. ... FOLLOWING ABSORPTION, PROCAINE IS RAPIDLY HYDROLYZED ... /PROCAINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 388


... Binding of the anesthetic to proteins in the serum and to tissues reduces the concentration of free drug in the systemic circulation and, consequently, reduces toxicity. ... /Ester local anesthetics/ are hydrolyzed and inactivated primarily by a plasma esterase, probably plasma cholinesterase. The liver also participates in hydrolysis of local anesthetics. /Local anesthetics/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 338


THE SYSTEMIC TOXICITY OF CHLOROPROCAINE IS LESS THAN THAT OF ALL OTHER LOCAL ANESTHETICS BECAUSE OF ITS RAPID HYDROLYSIS BY PLASMA CHOLINESTERASE ... WHICH SHORTENS THE PLASMA HALF-LIFE.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 165


... ENZYMATIC HYDROLYSIS OF PROCAINE /GIVES/ ... PARA-AMINOBENZOIC ACID & DIETHYLAMINOETHANOL. FORMER IS EXCRETED IN URINE TO EXTENT OF ABOUT 80%, EITHER UNCHANGED OR IN CONJUGATED FORM. ONLY 30% OF DIETHYLAMINOETHANOL CAN BE RECOVERED IN URINE; REMAINDER UNDERGOES METABOLIC DEGRADATION ... /PROCAINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 388


For more Absorption, Distribution and Excretion (Complete) data for CHLOROPROCAINE (9 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Chloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase.


2-DIETHYLAMINOETHYL 4-AMINO-2-CHLOROBENZOATE YIELDS 4-AMINO-2-CHLOROBENZOIC ACID IN GUINEA PIGS. LIVETT, BH & RM LEE, BIOCHEM PHARMAC 17, 385 (1968). /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. D-27


HYDROLYZED /CHIEFLY/ BY PLASMA PSEUDOCHOLINESTERASES /& ALSO BY ESTERASES IN LIVER/ AS DIETHYLAMINOETHANOL & 2-CHLORO-4-AMINOBENZOIC ACID /HUMAN, PARENTERAL. ANIMAL STUDIES SUGGEST THAT SOME LOCAL ANESTHETICS MAY UNDERGO BILIARY RECYCLING/ /CHLOROPROCAINE HCL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1974


5.7 Biological Half-Life

21 +/- 2 seconds


... Plasma half-life /is/ approximately 25 seconds.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 339


5.8 Mechanism of Action

Chloroprocaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. It is hypothesized that Chloroprocaine binds or antagonizes the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.


Local anesthetics prevent the generation and the conduction of the nerve impulse. Their primary site of action is the cell membrane. ... Local anesthetics block conduction by decreasing or preventing the large transient increase in the permeability of excitable membranes to Na+ that normally is produced by a slight depolarization of the membrane. ... As the anesthetic action progressively develops in a nerve, the threshold for electrical excitability gradually increases, the rate of rise of the action potential declines, impulse conduction slows, and the safety factor for conduction decreases; these factors decrease the probability of propagation of the action potential, and nerve conduction fails. ... /Local anesthetics/ can block K+ channels. ... blockade of conduction is not accompanied by any large or consistent change in resting membrane potential due to block of K+ channels. /Local anesthetics/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 332


... SITE AT WHICH LOCAL ANESTHETICS ACT, AT LEAST IN ... CHARGED FORM, IS ACCESSIBLE ONLY FROM THE INNER SURFACE OF THE MEMBRANE. ... LOCAL ANESTHETICS APPLIED EXTERNALLY FIRST MUST CROSS THE MEMBRANE BEFORE THEY CAN EXERT A BLOCKING ACTION. /LOCAL ANESTHETICS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 332


... /TWO POSSIBILITIES:/ ACHIEVE BLOCK BY INCR SURFACE PRESSURE OF LIPID LAYER THAT CONSTITUTES NERVE MEMBRANE ... CLOSING PORES THROUGH WHICH IONS MOVE. ... /OR:/ AFFECT PERMEABILITY BY INCR DEGREE OF DISORDER OF MEMBRANE. /LOCAL ANESTHETICS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 382


... ACID SALT MUST BE NEUTRALIZED IN TISSUE & FREE AMINE LIBERATED BEFORE DRUG CAN PENETRATE TISSUES & PRODUCE ANESTHETIC ACTION. ... FORM OF MOLECULE ACTIVE IN NERVE FIBERS IS CATION. ... CATION ... COMBINES WITH SOME RECEPTOR IN MEMBRANE TO PREVENT GENERATION OF ACTION POTENTIAL. /LOCAL ANESTHETICS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 383


... /SUGGESTED/ THAT PROCAINE ... DIMINISHES RELEASE OF ACETYLCHOLINE BY MOTOR-NERVE ENDINGS. /PROCAINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 385


ABOUT THIS PAGE

Chloroprocaine Manufacturers

A Chloroprocaine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Chloroprocaine, including repackagers and relabelers. The FDA regulates Chloroprocaine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Chloroprocaine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Chloroprocaine Suppliers

A Chloroprocaine supplier is an individual or a company that provides Chloroprocaine active pharmaceutical ingredient (API) or Chloroprocaine finished formulations upon request. The Chloroprocaine suppliers may include Chloroprocaine API manufacturers, exporters, distributors and traders.

Chloroprocaine GMP

Chloroprocaine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Chloroprocaine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Chloroprocaine GMP manufacturer or Chloroprocaine GMP API supplier for your needs.

Chloroprocaine CoA

A Chloroprocaine CoA (Certificate of Analysis) is a formal document that attests to Chloroprocaine's compliance with Chloroprocaine specifications and serves as a tool for batch-level quality control.

Chloroprocaine CoA mostly includes findings from lab analyses of a specific batch. For each Chloroprocaine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Chloroprocaine may be tested according to a variety of international standards, such as European Pharmacopoeia (Chloroprocaine EP), Chloroprocaine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Chloroprocaine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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