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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Pentoxyverine, 77-23-6, Pentoxyverin, Pentoxiverin, Atussil, U.c.b. 2543

Molecular Formula

C₂₀H₃₁NO₃

Molecular Weight

333.5 g/mol

InChI Key

CFJMRBQWBDQYMK-UHFFFAOYSA-N

FDA UNII

32C726X12W

Pentoxyverine, also referred to as carbetapentane, is a non-opioid central acting antitussive with antimuscarinic, anticonvulsant, and local anesthetic properties. It is an active ingredient in over-the-counter cough suppressants in combination with guaifenesin and H1-receptor antagonists. Pentoxyverine acts on sigma-1 receptors, as well as kappa and mu-opioid receptors.

1 2D Structure

Carbetapentane

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentane-1-carboxylate

2.1.2 InChI

InChI=1S/C20H31NO3/c1-3-21(4-2)14-15-23-16-17-24-19(22)20(12-8-9-13-20)18-10-6-5-7-11-18/h5-7,10-11H,3-4,8-9,12-17H2,1-2H3

2.1.3 InChI Key

CFJMRBQWBDQYMK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CC)CCOCCOC(=O)C1(CCCC1)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

32C726X12W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(2-diethylaminoethoxy)ethyl 1-phenylcyclopentyl-1-carboxylate

2. Carbetapentane 1,5-napthalenedisulfonate (2:1)

3. Carbetapentane 2,6-napthalenedisulfonate (2:1)

4. Carbetapentane Citrate

5. Carbetapentane Tannate

6. Pentoxyverine

2.3.2 Depositor-Supplied Synonyms

1. Pentoxyverine

2. 77-23-6

3. Pentoxyverin

4. Pentoxiverin

5. Atussil

6. U.c.b. 2543

7. Chembl73234

8. 2-(2-diethylaminoethoxy)ethyl 1-phenylcyclopentanecarboxylate

9. 2-(diethylaminoethoxy)ethyl 1-phenyl-1-cyclopentanecarboxylate

10. 2-(diethylaminoethoxy)ethyl 1-phenylcyclopentyl-1-carboxylate

11. 2-(2-(diethylamino)ethoxy)ethyl 1-phenylcyclopentanecarboxylate

12. 1-phenylcyclopentane-1-carboxylic Acid Diethylaminoethoxyethyl Ester

13. 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentane-1-carboxylate

14. 1-phenylcyclopentanecarboxylic Acid,2-(2-(diethylamino)ethoxy)ethyl Ester

15. Cyclopentanecarboxylic Acid, 1-phenyl-, 2-(2-(diethylamino)ethoxy)ethyl Ester

16. Ethanol, 2-(2-(diethylamino)ethoxy)-, 1-phenylcyclopentanecarboxylate (ester)

17. Pentoxyverine (inn)

18. 32c726x12w

19. Ncgc00024595-03

20. Pentoxiverinum

21. Sedotussin (tn)

22. 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentanecarboxylate

23. Dsstox_cid_2734

24. Cyclopentanecarboxylic Acid, 1-phenyl-, 2-[2-(diethylamino)ethoxy]ethyl Ester

25. Pentoxyverine [inn]

26. Dsstox_rid_76706

27. Dsstox_gsid_22734

28. Pentoxiverina

29. Pentoxiverine

30. Pentoxyverinum

31. Pentoxyverine [inn:ban]

32. Cas-77-23-6

33. Pentoxyverinum [inn-latin]

34. Pentoxiverina [inn-spanish]

35. Hsdb 3299

36. 1-phenyl-1-cyclopentanecarboxylate

37. Ucb 2543

38. Einecs 201-014-1

39. Brn 2299701

40. Pentoxyverine (base)

41. Sedotussin

42. Unii-32c726x12w

43. Ethanol, 2-[2-(diethylamino)ethoxy]-, 1-phenylcyclopentanecarboxylate (ester)

44. Carbapentane

45. Toclase (salt/mix)

46. Tuclase (salt/mix)

47. Spectrum_001366

48. Spectrum_001952

49. Tocris-0454

50. Sedotussin (salt/mix)

51. Prestwick0_000387

52. Prestwick1_000387

53. Prestwick2_000387

54. Prestwick3_000387

55. Spectrum2_001412

56. Spectrum3_000922

57. Spectrum4_001021

58. 1-phenylcyclopentanecarboxylic Acid 2-(2-diethylaminoethoxy)ethyl Ester

59. Carbetapentane [mi]

60. Cyclopentanecarboxylic Acid, 1-phenyl-, 2-(2-(diethylamino)ethoxy)ethylester

61. Pentoxyverine [hsdb]

62. Lopac0_000313

63. Schembl67879

64. Bspbio_000573

65. Kbiogr_001541

66. Kbioss_001846

67. Kbioss_002506

68. Cid_90010

69. Carbetapentane [vandf]

70. Divk1c_000356

71. Pentoxyverine [mart.]

72. Spbio_001484

73. Spbio_002494

74. Pentoxyverine [who-dd]

75. Bpbio1_000631

76. Dtxsid9022734

77. Bdbm94507

78. Chebi:94484

79. Kbio1_000356

80. Kbio2_001846

81. Kbio2_002498

82. Kbio2_004414

83. Kbio2_005066

84. Kbio2_006982

85. Kbio2_007634

86. Kbio3_001924

87. Ninds_000356

88. Zinc3830375

89. Tox21_110909

90. 2,2-dimethyl-7-octenoicacid

91. Pdsp1_001673

92. Pdsp2_001656

93. 1-phenylcyclopentanecarboxylic Acid 2-[2-(diethylamino)ethoxy]ethyl Ester

94. Akos015918339

95. Tox21_110909_1

96. Ccg-204408

97. Db11186

98. Sdccgsbi-0050301.p004

99. Idi1_000356

100. Ncgc00024595-01

101. Ncgc00024595-02

102. Ncgc00024595-04

103. Ncgc00024595-05

104. Ncgc00024595-06

105. Ncgc00024595-08

106. Ncgc00024595-15

107. Sbi-0050301.p003

108. Db-056191

109. Hy-134004

110. Ab00053602

111. Cs-0136428

112. Ft-0603066

113. S0869

114. D08334

115. Ab00053602_09

116. Q174786

117. W-104325

118. Brd-k06181161-048-04-5

119. Brd-k06181161-048-07-8

120. 1-cyclopentanecarboxylate, 2-(diethylaminoethoxy)ethyl-1-phenyl-

121. 2-[2-(diemthylamino)ethoxy]ethyl 1-phenylcyclopentanecarboxylate

122. 2-{[2-(diethylamino)ethyl]oxy}ethyl 1-phenylcyclopentanecarboxylate

123. 1-phenyl-1-cyclopentanecarboxylic Acid 2-[2-(diethylamino)ethoxy]ethyl Ester

124. Citric Acid;1-phenylcyclopentanecarboxylic Acid 2-[2-(diethylamino)ethoxy]ethyl Ester

125. 2-(2-diethylaminoethoxy)ethyl 1-phenylcyclopentane-1-carboxylate; 2-hydroxypropane-1,2,3-tricarboxylic Acid

126. 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentane-1-carboxylate;2-oxidanylpropane-1,2,3-tricarboxylic Acid

127. 2-hydroxypropane-1,2,3-tricarboxylic Acid;1-phenyl-1-cyclopentanecarboxylic Acid 2-[2-(diethylamino)ethoxy]ethyl Ester

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₁NO₃
Molecular Weight	333.5 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	11
Exact Mass	333.23039385 g/mol
Monoisotopic Mass	333.23039385 g/mol
Topological Polar Surface Area	38.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	356
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	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Antitussive Agents

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

...DRUGS THAT HAVE BEEN USED AS CENTRALLY ACTING ANTITUSSIVES INCL...CARBETAPENTANE...

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 530

4.2 Drug Warning

OTHER DRUGS THAT HAVE BEEN USED AS...ANTITUSSIVES INCL...CARBETAPENTANE, CARAMIPHEN, & OXOLAMINE. ...IN GENERAL THEIR TOXICITY IS LOW, BUT CONTROLLED CLINICAL STUDIES ARE STILL INSUFFICIENT TO DETERMINE WHETHER THEY MERIT CONSIDERATION AS ALTERNATIVES TO MORE THOROUGHLY STUDIED AGENTS.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 530

GENERALLY, ANY CENTRALLY ACTING ANTITUSSIVE SHOULD BE GIVEN CAUTIOUSLY WITH OTHER CENTRALLY ACTING AGENTS. /ANTITUSSIVES/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 976

4.3 Drug Indication

Indicated as a cough suppressant to relieve cough caused by the common cold, flu, bronchitis, and sinusitis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pentoxyverine induces an antitussive action. In animal studies, intraperitoneal administration of pentoxyverine inhibited citric-acid-induced cough in guinea-pigs _in vivo_. Some mice and rat studies suggest that pentoxyverine may also exert anticonvulsant activities without inducing a protective effect from NMDA-induced lethality. Protective effects against maximal electroshock-induced seizures in a dose-related fashion was also observed following either intraperitoneal or oral administration. In hERG-transfected cells, pentoxyverine inhibited the outward current of the hERG ion channel with half-maximal inhibition concentrations (IC50) of 3.0 M. In rats receiving intrathecal administration, pentoxyverine exhibited dose-dependent spinal blockade with a more sensory-selective action over motor blockade. It induced a spinal blockade with a more sensory/nociceptive-selective action over motor blockade compared to lidocaine.

5.2 MeSH Pharmacological Classification

Antitussive Agents

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

5.3 ATC Code

R - Respiratory system

R05 - Cough and cold preparations

R05D - Cough suppressants, excl. combinations with expectorants

R05DB - Other cough suppressants

R05DB05 - Pentoxyverine

5.4 Absorption, Distribution and Excretion

Absorption

In humans, maximum plasma concentrations are achieved 1.2 hours after oral dosing.

Route of Elimination

No pharmacokinetic data available.

Volume of Distribution

No pharmacokinetic data available.

Clearance

No pharmacokinetic data available.

5.5 Metabolism/Metabolites

No pharmacokinetic data available.

5.6 Biological Half-Life

The half-life is 2.3 hours following oral dosing.

5.7 Mechanism of Action

While the mechanism of antitussive action of pentoxyverine is not fully understood, it is thought to be mediated via sigma-1 receptors expressed in the central nervous system. Pentoxyverine acts as an agonist at sigma receptors with the Ki of 7528 nM, as demonstrated in a competitive binding assay. The function of sigma receptors on cough suppressant activities is unclear, however these receptors are highly expressed in the nucleus tractus solitarius (NTS) of the brainstem where the afferent fibres first synapse. NTS is located very close to the cough centre in the brainstem thus may function as a gate' for the cough reflex and allow sigma-1 receptor agonists to modulate afferent activity prior to reaching the cough center. It is suggested that highly lipophilic sigma-1 agonists may penetrate the CNS following systemic administration. When administered as aerosols, sigma-1 receptor agonists may temporarily act in the periphery to modulate cough by acting activate sigma receptors expressed in the lungs. However there is limited evidence of peripheral localization of the sigma agonists following aerosol administration and the ruling out of systemic exposure. The local anesthesia action of pentoxyverine may occur through inhibition of voltage-gated Na(+) currents.

NUMBER OF DRUGS ARE KNOWN TO REDUCE COUGH AS RESULT OF THEIR CENTRAL ACTIONS, ALTHOUGH EXACT MECHANISMS ARE STILL NOT ENTIRELY CLEAR. /NONOPIOID ANTITUSSIVES/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 530

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