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Chemistry

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Also known as: D-panthenol, 81-13-0, Pantothenol, Ilopan, D-pantothenyl alcohol, Bepanthen
Molecular Formula
C9H19NO4
Molecular Weight
205.25  g/mol
InChI Key
SNPLKNRPJHDVJA-ZETCQYMHSA-N
FDA UNII
1O6C93RI7Z

D-Panthenol
Dexpanthenol is a metabolite found in the aging mouse brain.
1 2D Structure

D-Panthenol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R)-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)/t7-/m0/s1
2.1.3 InChI Key
SNPLKNRPJHDVJA-ZETCQYMHSA-N
2.1.4 Canonical SMILES
CC(C)(CO)C(C(=O)NCCCO)O
2.1.5 Isomeric SMILES
CC(C)(CO)[C@H](C(=O)NCCCO)O
2.2 Other Identifiers
2.2.1 UNII
1O6C93RI7Z
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 Heumann

8. Dl-panthenol

9. Ilopan

10. Marolderm

11. Nasenspray Ratiopharm Panthenol

12. Nasicur

13. Otriven Dexpanthenol

14. Pan Rhinol

15. Pan-ophtal

16. Panthenol

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. D-panthenol

2. 81-13-0

3. Pantothenol

4. Ilopan

5. D-pantothenyl Alcohol

6. Bepanthen

7. Pantol

8. Bepanthene

9. Bepantol

10. (+)-panthenol

11. Provitamin B

12. Motilyn

13. Panadon

14. Panthoderm

15. Thenalton

16. Zentinic

17. D-pantothenol

18. Pantothenyl Alcohol

19. Cozyme

20. D-p-a Injection

21. D(+)-panthenol

22. Pantenyl

23. Synapan

24. Urupan

25. D(+)-pantothenyl Alcohol

26. Intrapan

27. D Panthenol

28. D-panthenol 50

29. Provitamin B5

30. Pantothenylol

31. (2r)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutanamide

32. Dexpantenol

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

34. Dextro Pantothenyl Alcohol

35. Propanolamine, N-pantoyl-

36. Dexpanthenolum

37. Alcopan-250

38. Penthenol

39. Varitan

40. N-pantoyl-propanolamine

41. Panthenol (d)

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

43. Panthenol (jan)

44. Prestwick_529

45. Dexpanthenol (1.20 G/ml)

46. Ilopan (tn)

47. D-(+)-panthenol

48. Panthenol, (+)-

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

50. N-pantoyl-3-propanolamine

51. Nsc 302962

52. D-(+)-pantothenyl Alcohol

53. 1o6c93ri7z

54. Chebi:27373

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

56. Pro-itamin B5

57. Butyramide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, D-(+)-

58. Component Of Pantho-f

59. Ncgc00142622-03

60. Panthenol [jan]

61. 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutanamide, (r)-

62. 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutyramide, D-(+)-

63. Dsstox_cid_2906

64. Dsstox_rid_76783

65. Dsstox_gsid_22906

66. Panthenolum

67. Pantenol

68. Pantenolo

69. Sinecort

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

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

72. Component Of Zentinic

73. Pantothenol, D-

74. Alcool Dl-pantotenilico

75. (+-)-pantothenyl Alcohol

76. Dexpanthenol [usan]

77. Dexpantenol [inn-spanish]

78. Dexpanthenolum [inn-latin]

79. Unii-1o6c93ri7z

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

81. Dexpanthenol;

82. Ccris 3947

83. Hsdb 296

84. Nsc302962

85. Fancol Dl

86. Nsc-302962

87. Cas-81-13-0

88. Ncgc00186658-01

89. Dexpanthenol [usan:usp:inn:ban]

90. Einecs 201-327-3

91. Dexpanthenol (usp)

92. Mfcd00065006

93. Cornergel

94. Dolobene

95. Bay 81-2996

96. Brn 1724947

97. Panthenol, (+ )-

98. Panthenol 50w

99. Prestwick0_000022

100. Prestwick1_000022

101. Prestwick2_000022

102. Prestwick3_000022

103. Dexpanthenol (usp/inn)

104. Dexpanthenol [mi]

105. D-panthenol Usp/bp/ip

106. Compnent Of Ilopan-choline

107. Dexpanthenol [fcc]

108. Dexpanthenol [inn]

109. Bmse000445

110. Panthenol, (r)-

111. Dexpanthenol [hsdb]

112. Ec 201-327-3

113. Alcopan 250

114. D-panthenol [vandf]

115. Dexpanthenol [vandf]

116. Schembl15861

117. Bspbio_000083

118. Dexpanthenol [mart.]

119. 4-04-00-01652 (beilstein Handbook Reference)

120. Dexpanthenol [usp-rs]

121. Dexpanthenol [who-dd]

122. Spbio_002004

123. Bpbio1_000093

124. Chembl1200979

125. Dexpanthenol - Usp/fcc Kosher

126. Dtxsid3022906

127. Schembl20553090

128. Dexpanthenol [orange Book]

129. Hms1568e05

130. Hms2094e09

131. Hms2095e05

132. Hms3712e05

133. Dexpanthenol [ep Monograph]

134. (r)-2,4-dihydroxy-n-(3-hydroxy-propyl)-3,3-dimethylbutanamide

135. Hy-b1391

136. Zinc1530303

137. D-panthenol, >=98.0% (nt)

138. Dexpanthenol [usp Monograph]

139. Tox21_111563

140. Lmfa08020198

141. S4695

142. Akos015841507

143. Akos015901947

144. Calcium D-pantothenate Usp/bp/ep/ip

145. D(+)-alpha,gamma-dihydroxy-n-(3-hydroxypropyl)-beta,beta-dimethylbutyramide

146. Tox21_111563_1

147. Ccg-213429

148. Cs-8175

149. Db09357

150. Alpha,gamma-dihydroxy-n-(3-hydroxypropyl)-beta,beta-dimethylbutyramide, D-(+)-

151. Ncgc00142622-01

152. Ncgc00142622-04

153. As-14732

154. D-panthenol 10 Microg/ml In Acetonitrile

155. Dexpanthenol, Tested According To Ph.eur.

156. Sbi-0206936.p001

157. D-panthenol, Vetec(tm) Reagent Grade, 98%

158. P0692

159. C05944

160. D00193

161. D70909

162. Q-201048

163. Q47495755

164. A6cf1a81-5b98-4c28-a379-ea28fa9dd210

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

166. Dexpanthenol, European Pharmacopoeia (ep) Reference Standard

167. (2r)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-butanamide

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

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

170. (r)-2,4-dihydroxy-3,3-dimethyl-n-(3-hydroxypropyl)-butanamide

171. (r)-2,4-dihydroxy-n-(3-hydroxy-propyl)-3,3-dimethyl-butyramide

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

173. D-panthenol, >=98% (perchloric Acid Titration), >=98% (tlc)

174. Dexpanthenol, United States Pharmacopeia (usp) Reference Standard

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

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

177. D(+)-.alpha.,.gamma.-dihydroxy-n-(3-hydroxypropyl)-.beta.,.beta.-dimethylbutyramide

178. Dexpanthenol, Pharmaceutical Secondary Standard; Certified Reference Material

179. 1113-70-8

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 205.25 g/mol
Molecular Formula C9H19NO4
XLogP3-0.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass205.13140809 g/mol
Monoisotopic Mass205.13140809 g/mol
Topological Polar Surface Area89.8 Ų
Heavy Atom Count14
Formal Charge0
Complexity182
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Dexpanthenol (topical) relieves itching and aids healing of skin in mild eczemas and dermatoses; itching skin, minor wounds, stings, bites, poison ivy, poison oak (dry sage) and minor skin irritations. Also, used in infants and children for diaper rash, chafing and mild skin irritations.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 2636


Prophylactic use immediately after major abdominal surgery to minimize the possibility of paralytic ileus. Intestinal atony causing abdominal distention; postoperative or post partum retention of flatus, or post operative delay in resumption of intestinal motility; paralytic ileus.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 1767


Vet: ... Dexpanthenol ... /is/ often used as source of B5. Only the D-isomers are active biologically, but dl-isomers are often used ... Equivalents: 1 g D-pantothenic acid = 936 mg D-dexpanthenol.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 645


/Exptl Use (Vet)/: The effect of B-complex vitamin on experimental liver damage in rats was studied. Ip injection of panthenol inhibited initial deposit of lipids after having removed 2/3 of the regenerating fatty liver in rats.

PMID:4235781 Petzold H, Weigel K; Int Z Vitaminforsch 38 (1): 97 (1968)


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


4.2 Drug Warning

Administration of dexpanthenol injection directly into the vein is not advised.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 1767


One case of heartburn and a few cases of GI cramps have been reported after dexpanthenol administration. Allergic reactions to dexpanthenol have been reported occasionally; however, these reactions have not been directly attributed to the drug. Although isolated reports of itching, tingling, difficulty in breathing, erythema, generalized dermatitis, urticaria, temporary respiratory difficulty (when dexpanthenol injection was administered 5 minutes after succinylcholine had been discontinued), hypotension, persistent (up to 10 days) diarrhea, and agitation have been associated with use of dexpanthenol injection, a causal relationship to the drug has not been established.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


It is not known whether dexpanthenol can cause fetal harm when administered to pregnant women. Dexpanthenol injection should be used during pregnancy only when clearly needed.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Dexpanthenol injection should not be used for the management of mechanical obstruction; in these patients, therapy should be directed mainly at correcting the obstruction. The manufacturer of dexpanthenol injection cautions that the management of adynamic ileus includes correction of fluid and electrolyte abnormalities (especially hypokalemia), anemia, and hypoproteinemia; treatment of infection; avoidance of drugs that decrease GI motility; and decompression of the GI tract using nasogastric suction or a long intestinal tube when there is considerable distention.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


For more Drug Warnings (Complete) data for Dexpanthenol (9 total), please visit the HSDB record page.


4.3 Drug Indication

Injection: Prophylactic use immediately after major abdominal surgery to minimize the possibility of paralytic ileus. Intestinal atony causing abdominal distention; postoperative or postpartum retention of flatus, or postoperative delay in resumption of intestinal motility; paralytic ileus. Topical: This medication is used as a moisturizer to treat or prevent dry, rough, scaly, itchy skin and minor skin irritations (e.g., diaper rash, skin burns from radiation therapy).


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

A - Alimentary tract and metabolism

A11 - Vitamins

A11H - Other plain vitamin preparations

A11HA - Other plain vitamin preparations

A11HA30 - Dexpanthenol


D - Dermatologicals

D03 - Preparations for treatment of wounds and ulcers

D03A - Cicatrizants

D03AX - Other cicatrizants

D03AX03 - Dexpanthenol


S - Sensory organs

S01 - Ophthalmologicals

S01X - Other ophthalmologicals

S01XA - Other ophthalmologicals

S01XA12 - Dexpanthenol


5.3 Absorption, Distribution and Excretion

Absorption

Dexpanthenol is soluble in water and alcohol, although insoluble in fats and oil based substances. With the appropriate vehicle, Dexpanthenol is easily penetrated into the skin. Rate of penetration and absorption is reduced when Dexpanthenol is administered as an oil/water formula.


Route of Elimination

Milk of nursing mothers receiving a normal diet contains about 2 ug of pantothenic acid per mL. About 70% of an oral dose of pantothenic acid is excreted unchanged in urine and about 30% in feces.


Volume of Distribution

Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A. Highest concentrations are found in the liver, adrenal glands, heart, and kidneys.


Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A. Highest concentrations are found in the liver, adrenal glands, heart, and kidneys. Milk of nursing mothers receiving a normal diet contains about 2 ug of pantothenic acid per mL. About 70% of an oral dose of pantothenic acid is excreted unchanged in urine and about 30% in feces.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


5.4 Metabolism/Metabolites

Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A.


Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Dexpanthenol is converted to pantothenic acid ... which then produces acetylcholine.

Evaluations of Drug Interactions. 1st ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1973, 1974., p. 396


5.5 Biological Half-Life

Half life have not been reported


5.6 Mechanism of Action

Dexpanthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Dexpanthenol is enzymatically cleaved to form pantothenic acid, which is an essential component of Coenzyme A, which 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.


This alcohol ... is said to increase the amount of coenzyme A available for the synthesis of acetylcholine. Increased formation of acetylcholine is thought to increase peristalsis and intestinal tone.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 752


... To test the functional effect of pantothenate on dermal fibroblasts, cells were cultured and in vitro proliferation tests were performed using a standardized scratch test procedure. For all three donors analyzed, a strong stimulatory effect of pantothenate at a concentration of 20 ug/mL on the proliferation of cultivated dermal fibroblasts was observed. To study the molecular mechanisms resulting in the proliferative effect of pantothenate, gene expression was analyzed in dermal fibroblasts cultivated with 20 ug/mL of pantothenate compared with untreated cells using the GeneChip Human Exon 1.0 ST Array. A number of significantly regulated genes were identified including genes coding for interleukin (IL)-6, IL-8, Id1, HMOX-1, HspB7, CYP1B1 and MARCH-II. Regulation of these genes was subsequently verified by quantitative real-time polymerase chain reaction analysis. Induction of HMOX-1 expression by pantothenol and pantothenic acid in dermal cells was confirmed on the protein level using immunoblots. Functional studies revealed the enhanced suppression of free radical formation in skin fibroblasts cultured with panthenol. In conclusion, these studies provided new insight in the molecular mechanisms linked to the stimulatory effect of pantothenate and panthenol on the proliferation of dermal fibroblasts. /Calcium pantotenate/

Wiederholt T et al; Exper Dermatol 18 (11): 969-78 (2009). Available from, as of March 16, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=19397697


... Pantothenic acid, pantothenol and other derivatives ... are precursors of CoA /that/ protect cells and whole organs against peroxidative damage by increasing the content of cell glutathione...

Slyshenkov V et al; FEBS Lett 569 (1-3): 169-72 (2004). Available from, as of March 16, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15225628


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02-Jan-2021
21-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL...DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL;0.02MG/VIAL;0.001MG/VIAL;5MG/VIAL;0.01MG/VIAL;0.14MG/VIAL;17MG/VIAL;0.2MG/VIAL;1MG/VIAL;1.4MG/VIAL;EQ 1.2MG BASE/VIAL;0.7MG/VIAL;7MG/VIAL

USFDA APPLICATION NUMBER - 18920

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DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/...DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/ML;12MCG/ML;40 IU/ML;1MCG/ML;3MG/ML;120MCG/ML;8MG/ML;1.2MG/ML;0.72MG/ML;1.2MG/ML;660 IU/ML;0.03MG/ML

USFDA APPLICATION NUMBER - 21163

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DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/...DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/ML;12MCG/ML;40 IU/ML;1MCG/ML;3MG/ML;120MCG/ML;8MG/ML;1.2MG/ML;0.72MG/ML;1.2MG/ML;660 IU/ML;30MCG/ML

USFDA APPLICATION NUMBER - 21163

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DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;...DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;0.06MG/VIAL;0.005MG/VIAL;15MG/VIAL;0.005MG/VIAL;0.6MG/VIAL;40MG/VIAL;6MG/VIAL;3.6MG/VIAL;6MG/VIAL;1MG/VIAL;10MG/VIAL;0.15MG/VIAL

USFDA APPLICATION NUMBER - 21625

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DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006...DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006MG/ML;0.05MCG/ML;1.5MG/ML;0.0005MG/ML;0.06MG/ML;4MG/ML;0.6MG/ML;0.36MG/ML;0.6MG/ML;0.1MG/ML;1MG/ML

USFDA APPLICATION NUMBER - 8809

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