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Sodium Pantothenate

Sodium Pantothenate

Synopsis, Chemistry

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Also known as: 867-81-2, Sodium d-pantothenate, Sodium (r)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate, D-pantothenic acid sodium, D-pantothenic acid sodium salt, Pantothenate sodium

Molecular Formula

C₉H₁₆NNaO₅

Molecular Weight

241.22 g/mol

InChI Key

GQTHJBOWLPZUOI-FJXQXJEOSA-M

FDA UNII

OES0R93F0C

1 2D Structure

Sodium Pantothenate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoate

2.1.2 InChI

InChI=1S/C9H17NO5.Na/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13;/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13);/q;+1/p-1/t7-;/m0./s1

2.1.3 InChI Key

GQTHJBOWLPZUOI-FJXQXJEOSA-M

2.1.4 Canonical SMILES

CC(C)(CO)C(C(=O)NCCC(=O)[O-])O.[Na+]

2.1.5 Isomeric SMILES

CC(C)(CO)[C@H](C(=O)NCCC(=O)[O-])O.[Na+]

2.2 Other Identifiers

2.2.1 UNII

OES0R93F0C

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 867-81-2

2. Sodium D-pantothenate

3. Sodium (r)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate

4. D-pantothenic Acid Sodium

5. D-pantothenic Acid Sodium Salt

6. Pantothenate Sodium

7. Sodium Pantothenic Acid

8. D-pantothenic Acid (sodium)

9. Pantothenic Acid, Monosodium Salt, D-

10. Oes0r93f0c

11. Sodium;3-[[(2r)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoate

12. D-pantothenate Sodium

13. Mfcd00002767

14. Unii-oes0r93f0c

15. Pantothenic Acid, Sodium Salt

16. Ccris 1905

17. Hsdb 760

18. Vitamin B5 Sodium

19. Einecs 212-768-6

20. Sodium Pantothenate,(s)

21. Pantothenic Acid Sodium Salt

22. Dsstox_cid_27173

23. Dsstox_rid_82171

24. Dsstox_gsid_47173

25. Panthothenic Acid Sodium Salt

26. Schembl124920

27. Dtxsid4047173

28. Hy-b0430a

29. Hms2093p20

30. Sodium Pantothenate [hsdb]

31. Sodium Pantothenate [inci]

32. Tox21_302487

33. Pantothenate Sodium [who-dd]

34. Sodium N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanine, (r)-

35. Ccg-213530

36. Cs-5150

37. Beta-alanine, N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, Monosodium Salt, (r)-

38. Ncgc00256852-01

39. Cas-867-81-2

40. Pantothenic Acid Sodium Salt [mi]

41. P0013

42. D11519

43. O12072

44. Q-201535

45. Q27285618

46. Beta-alanine, N-((2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, Monosodium Salt

47. Beta-alanine, N-((2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, Sodium Salt (1:1)

48. .beta.-alanine, N-((2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, Sodium Salt (1:1)

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₆NNaO₅
Molecular Weight	241.22 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	241.09261689 g/mol
Monoisotopic Mass	241.09261689 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	244
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

Topical application of pantothenate is widely used in clinical practice for wound healing.

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

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Distribution of pantothenate from plasma into liver was very rapid; during 10 min after iv admin about 80% of dose was cleared from plasma.

PMID:1265350 Taylor T et al; Res Vet Sci 20 (2): 151-4 (1976).

Total blood pantothenic acid levels were higher after oral admin of 21.6 uM/kg pantethine than after calcium pantothenate in rats but no difference in amount of bound pantothenic acid. Max concentrations were observed at 2-4.5 hr after ingestion of both groups.

Ono S et al; J Nutr Sci Vitaminol 20(3) 203 (1974)

Total pantothenic acid excretions after 24 hr oral admin to rats were 29% and 18% after administration of pantethine and calcium pantothenate, respectively. Pantethine was more readily absorbed from GI tract than calcium pantothenate.

Ono S et al; J Nutr Sci Vitaminol 20(3) 203 (1974)

5.2 Mechanism of Action

... 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