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Chemistry

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Also known as: Dl-panthenol, 16485-10-2, Dl-pantothenol, Dl-pantothenyl alcohol, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutanamide, Butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-

Molecular Formula

C₉H₁₉NO₄

Molecular Weight

205.25 g/mol

InChI Key

SNPLKNRPJHDVJA-UHFFFAOYSA-N

FDA UNII

WV9CM0O67Z

Panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Panthenol exists as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol). While pantothenic acid is optically active, only the dextrorotatory form ([DB09357]) is biologically active. Dexpanthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium. Due to its good penetration and high local concentrations, dexpanthanol is used in many topical products, such as ointments and lotions for treatment of dermatological conditions to relieve itching or promote healing. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties.

1 2D Structure

Panthenolum

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide

2.1.2 InChI

InChI=1S/C9H19NO4/c1-9(2,6-12)7(13)8(14)10-4-3-5-11/h7,11-13H,3-6H2,1-2H3,(H,10,14)

2.1.3 InChI Key

SNPLKNRPJHDVJA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(CO)C(C(=O)NCCCO)O

2.2 Other Identifiers

2.2.1 UNII

WV9CM0O67Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide

2. 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutanamide

3. Bepanthen

4. Butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (+--)-

5. Corneregel

6. D-panthenol

7. Dexpanthenol

8. Dexpanthenol Heumann

9. Dl-panthenol

10. Ilopan

11. Marolderm

12. Nasenspray Ratiopharm Panthenol

13. Nasicur

14. Otriven Dexpanthenol

15. Pan Rhinol

16. Pan-ophtal

17. Panthenol Braun

18. Panthenol Jenapharm

19. Panthenol Law

20. Panthenol Lichtenstein

21. Panthenol Von Ct

22. Panthenol-ratiopharm

23. Panthoderm

24. Panthogenat

25. Pantothenol

26. Repa-ophtal

27. Rhinoclir

28. Siozwo Sana

29. Ucee D

30. Urupan

31. Wund- Und Heilsalbe Law

2.3.2 Depositor-Supplied Synonyms

1. Dl-panthenol

2. 16485-10-2

3. Dl-pantothenol

4. Dl-pantothenyl Alcohol

5. 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutanamide

6. Butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-

7. Panthenol, Racemic

8. Panthenolum

9. 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide

10. 62507-76-0

11. Nsc-759899

12. Wv9cm0o67z

13. Pantenol

14. Pantenolo

15. (+-)-pantothenyl Alcohol

16. Dl-pantothenol;dl-pantothenyl Alcohol

17. Alcool Dl-pantotenilico

18. Panthenol , Dl-form

19. Butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (+)- (9ci)

20. Pantenolo [dcit]

21. Pantenol [inn-spanish]

22. Panthenolum [inn-latin]

23. Component Of Zentinic

24. Dexpanthenol [usan)

25. Smr000857333

26. Alcool Dl-pantotenilico [italian]

27. Sr-05000001760

28. Einecs 240-540-6

29. Mfcd00002944

30. Unii-wv9cm0o67z

31. Nsc302962

32. D,l- Panthenol

33. Nsc-302962

34. Ncgc00186658-01

35. Pantothenylol Alcohol

36. Panthenol [usan:usp:inn:ban:jan]

37. 2,3-dimethylbutyramide

38. Dl-panthenol, 99%

39. Panthenol (usp/inn)

40. Panthenol [inn]

41. Panthenol, Dl-

42. Panthenol [inci]

43. Panthenol [usan]

44. (+-)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide

45. Panthenol [vandf]

46. Panthenol [mart.]

47. Ec 240-540-6

48. Dl-panthenol [fcc]

49. Panthenol [who-dd]

50. Dsstox_cid_24598

51. Dsstox_rid_80341

52. Dsstox_gsid_44598

53. Schembl15567

54. Dl-panthenol [vandf]

55. (r)-2,4-dihydroxy-3,3-dimethylbutyric 3-hydroxypropylamide

56. Mls001336015

57. Mls001336016

58. Chembl1371937

59. D-(+)-2,3-dimethylbutyramide

60. Dtxsid3044598

61. Panthenol [usp Monograph]

62. Dexpanthenol (pantothenyl Alcohol)

63. Hms2093b14

64. Hms2234m16

65. Hms3371m11

66. Pharmakon1600-01505420

67. Pharmakon1600-01505656

68. (+/-)-pantothenyl Alcohol

69. Hy-b1024

70. Panthenol, Racemic [usp-rs]

71. Tox21_302660

72. Butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (+-)-

73. Butyramide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, Dl-

74. Nsc759127

75. Nsc759899

76. S4566

77. Stl453540

78. Akos015841508

79. Butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (+/-)-

80. Ccg-213502

81. Cs-4541

82. Nsc 759899

83. Nsc-759127

84. Sb44496

85. Ncgc00256864-01

86. As-56363

87. Da-09547

88. Sbi-0206818.p001

89. Cas-16485-10-2

90. Db-056494

91. Ft-0625499

92. Ft-0625596

93. Ft-0693817

94. P1318

95. A19436

96. D03726

97. H11256

98. Ab00918367_05

99. A810597

100. Butyramide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3

101. Q196473

102. Q-201031

103. Sr-05000001760-1

104. Sr-05000001760-3

105. 3-(2,4-dihydroxy-3,3-dimethylbutyramido)-1-propanol

106. Brd-a59413292-001-04-1

107. Butanamide,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-

108. (+/-)-2,4-dihydroxy-3,3-dimethylbutyric 3-hydroxypropylamide

109. 3,3-dimethyl-2,4-bis(oxidanyl)-n-(3-oxidanylpropyl)butanamide

110. D-2,4-dihydroxy-3,3-dimethyl-n-(3-hydroxypropyl)butyramide

111. Dl-2 4-dihydroxy-n-(3-hydroxypropyl)-3 3-dimethylbutyramide

112. (+/-)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide

113. (r)-(+)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide

114. Butanamide,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (r)-

115. Butyramide,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)-

116. Panthenol, Racemic, United States Pharmacopeia (usp) Reference Standard

117. (+/-)-alpha,gamma-dihydroxy-n-(3-hydroxypropyl)-beta,beta-dimethylbutyramide

118. Butyramide, .alpha.,.gamma.-dihydroxy-n-(3-hydroxypropyl)-.beta.,.beta.-dimethyl-

119. Butyramide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (+/-)-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₉NO₄
Molecular Weight	205.25 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	205.13140809 g/mol
Monoisotopic Mass	205.13140809 g/mol
Topological Polar Surface Area	89.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	182
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Panthenol (containing a racemic mixture of dexpanthenol and levopanthenol) is not currently available in any FDA-approved products and therefore does not have an indication. Please see [DB09357] for FDA-approved uses of the dextrorotatory form of Panthenol.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pantothenic acid is a precursor of coenzyme A, which serves as a cofactor for a variety of enzyme-catalyzed reactions involving transfer of acetyl groups. The final step in the synthesis of acetylcholine consists of the choline acetylase transfer of acetyl group from acetylcoenzyme A to choline. Acetylcholine is the neurohumoral transmitter in the parasympathetic system and as such maintains the normal functions of the intestine. Decrease in acetylcholine content would result in decreased peristalsis and in extreme cases adynamic ileus.

5.2 ATC Code

D03AX03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

5.3 Mechanism of Action

Panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Dexpanthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties.

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