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Also known as: 637-58-1, Pramoxine hcl, Pramocaine hydrochloride, Prax lotion, Tronothane, Pramocaine (hydrochloride)
Molecular Formula
C17H28ClNO3
Molecular Weight
329.9  g/mol
InChI Key
SYCBXBCPLUFJID-UHFFFAOYSA-N
FDA UNII
88AYB867L5

Pramoxine Hydrochloride
Pramocaine Hydrochloride is the hydrochloride salt form of pramoxine, a morpholine derivative with local anesthetic property. Pramocaine hydrochloride decreases the permeability of the neuronal membrane to sodium ions by reversibly binding to and inhibiting voltage-gated sodium channels. This results in stabilization of the membrane and, thereby inhibiting the ionic fluxes required for membrane depolarization, hence resulting in the failure to initiate a propagated action potential and subsequent conduction blockade.
1 2D Structure

Pramoxine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[3-(4-butoxyphenoxy)propyl]morpholine;hydrochloride
2.1.2 InChI
InChI=1S/C17H27NO3.ClH/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18;/h5-8H,2-4,9-15H2,1H3;1H
2.1.3 InChI Key
SYCBXBCPLUFJID-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCOC1=CC=C(C=C1)OCCCN2CCOCC2.Cl
2.2 Other Identifiers
2.2.1 UNII
88AYB867L5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-(3-(4-butoxyphenoxy)propyl)morpholine

2. 4-(3-(p-butoxyphenoxy)propyl)morpholine

3. Balsabit

4. Fleet Pain Relief

5. Itch-x

6. Pramegel

7. Pramocaine

8. Pramocaine Hydrochloride

9. Pramox

10. Pramoxine

11. Prax

12. Proctofoam

13. Tronolane

14. Tronothane

2.3.2 Depositor-Supplied Synonyms

1. 637-58-1

2. Pramoxine Hcl

3. Pramocaine Hydrochloride

4. Prax Lotion

5. Tronothane

6. Pramocaine (hydrochloride)

7. Morpholine, 4-[3-(4-butoxyphenoxy)propyl]-, Hydrochloride

8. 4-[3-(4-butoxyphenoxy)propyl]morpholine Hydrochloride

9. Nsc-25573

10. 4-(3-(4-butoxyphenoxy)propyl)morpholine Hydrochloride

11. Pramoxine Hydrochloride [usp]

12. Mls000028604

13. Tronolane

14. 88ayb867l5

15. 4-(3-(p-butoxyphenoxy)propyl)morpholine Hydrochloride

16. 4-[3-(4-butoxyphenoxy)propyl]morpholine;hydrochloride

17. 637-58-1 (hcl)

18. Morpholine, 4-(3-(4-butoxyphenoxy)propyl)-, Hydrochloride

19. Smr000058670

20. Dsstox_cid_27757

21. Dsstox_rid_82534

22. Dsstox_gsid_47777

23. Pramoxine Hydrochloride (usp)

24. Tronothane Hydrochloride

25. Proctofoam-ns

26. Hsdb 7220

27. Ncgc00016529-01

28. Cas-637-58-1

29. Einecs 211-293-1

30. Nsc 25573

31. 4-[3-(p-butoxyphenoxy)propyl]morpholine Hydrochloride

32. Unii-88ayb867l5

33. Sr-01000000243

34. Pramoxine, Hcl

35. Tronothane (tn)

36. Prestwick_1044

37. P-butoxyphenyl Gamma-morpholinopropyl Ether Hydrochloride

38. Gamma-morpholinopropyl 4-n-butoxyphenyl Ether Hydrochloride

39. Opera_id_1593

40. Pramoxine Hcl [inci]

41. Mls002222295

42. Schembl180542

43. Spectrum1501139

44. Amy585

45. Chebi:8358

46. Chembl1201171

47. Dtxsid2047777

48. Morpholine, 4-(3-(p-butoxyphenoxy)propyl)-, Hydrochloride

49. Hms1570o13

50. Hms1921j07

51. Pharmakon1600-01501139

52. Hy-b1319

53. Nsc25573

54. Pramoxine Hydrochloride [mi]

55. Tox21_110477

56. Mfcd00054323

57. Nsc757847

58. S4092

59. Pramoxine Hydrochloride [hsdb]

60. Akos015895041

61. Tox21_110477_1

62. Ac-2094

63. Ccg-212937

64. Cs-4643

65. Nsc-757847

66. Pramoxine Hydrochloride [vandf]

67. Wln: T6n Dotj A3or Do4 &gh

68. Pramocaine Hydrochloride [mart.]

69. Pramoxine Hydrochloride [usp-rs]

70. Ncgc00016529-07

71. Ncgc00094907-01

72. Ncgc00094907-02

73. Ncgc00094907-03

74. Pramocaine Hydrochloride [who-dd]

75. As-12691

76. Db-054541

77. Ft-0603501

78. Pramoxine Hydrochloride [orange Book]

79. Sw197114-3

80. Vu0239834-5

81. D00739

82. D97624

83. Epifoam Component Pramoxine Hydrochloride

84. Pramoxine Hydrochloride [usp Monograph]

85. A834509

86. Pramosone Component Pramoxine Hydrochloride

87. Pramoxine Hydrochloride Component Of Epifoam

88. Pramoxine Hydrochloride, Analytical Standard, >=98%

89. Q-100732

90. Sr-01000000243-3

91. Pramoxine Hydrochloride Component Of Pramosone

92. Proctofoam Hc Component Pramoxine Hydrochloride

93. Q27269918

94. 4-[3-(4-butoxyphenoxy)propyl]morpholin-4-ium;chloride

95. Pramoxine Hydrochloride Component Of Proctofoam Hc

96. P-butoxyphenyl .gamma.-morpholinopropyl Ether Hydrochloride

97. .gamma.-morpholinopropyl 4-n-butoxyphenyl Ether Hydrochloride

98. 4-[3-(4-butoxyphenoxy)propyl]morpholine Hydrochloride (1:1)

99. Morpholine, 4-[3-(p-n-butoxyphenoxy )propyl]-, Hydrochloride

100. 4-n-butoxyphenyl.gamma.-morpholinopropyl Ether Hydrochloride

101. Morpholine, 4-[3-(4-butoxyphenoxy)propyl]-, Hydrochloride (1:1)

102. 4-[3-(4-butoxyphenoxy)propyl]morpholine Chloride;pramocaine Hydrochloride

103. Pramoxine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

104. Pramoxine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 329.9 g/mol
Molecular Formula C17H28ClNO3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass329.1757714 g/mol
Monoisotopic Mass329.1757714 g/mol
Topological Polar Surface Area30.9 Ų
Heavy Atom Count22
Formal Charge0
Complexity248
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 Therapeutic Uses

Anesthetic (local)

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1376


Indicated for the symptomatic relief of: hemorrhoids, anorectal inflammation and anorectal pain. (these medications /including pramoxine/ are effective when applied to the anal, periana, or anorectal areas. However, they are not likely to relieve symptoms associated with conditions confined to the rectum, which lacks sensory nerve fibers.) /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 153


Pramoxine preparations are used topically for the temporary relief of pain and itching associated with dermatoses; rashes due to poison ivy, poison oak, poison sumac, insect bites; minor burns; anogenital pruritus or irritation; and fissures; or hemorrhoids. The drug should not be used for bronchoscopy or gastroscopy since it is not sufficiently potent to abolish the gag reflex.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414


4.2 Drug Warning

Local effects, such as burning or stinging, may occur following topical application of pramoxine. The drug has a low index of sensitization, and cross-sensitization with other local anesthetics is unlikely.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414


Topical pramoxine preparations should not be used in or near the eyes or nose.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414


The preparations should not be applied to extensive areas of skin and are not for prolonged use. The aerosol foam for rectal administration should not be used longer than 4 consecutive weeks.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414


If pramoxine preparations are used for self-medication and the condition worsens or symptoms persist for prolonged periods (e.g., for more than 7 days) or clear and occur again within a few days, the drug should be discontinued and a physician consulted.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414


If rectal bleeding occurs during use of pramoxine for pain and itching of hemorrhoids or if erythema, irritation, swelling, or pain occurs during use of pramoxine preparations, the drug should be discontinued and a physician consulted.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414


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 Absorption, Distribution and Excretion

... These agents are readily absorbed through mucous membranes into the systemic circulation. The rate of absorption is influenced by the vascularity or rate of blood flow at the site of application, the total dosage (concentration and volume) administered, and the duration of exposure. ... /Local anesthetics/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 154


5.3 Mechanism of Action

Local anesthetics block both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade. /Local anesthetics/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 154


API Reference Price

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23-Mar-2022
22-Jun-2024
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