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1. B 5, Vitamin
2. B5, Vitamin
3. Calcium Pantothenate
4. Dexol
5. Pantothenate, Calcium
6. Pantothenate, Zinc
7. Vitamin B 5
8. Vitamin B5
9. Zinc Pantothenate
1. D-pantothenic Acid
2. Vitamin B5
3. 79-83-4
4. Pantothenate
5. Chick Antidermatitis Factor
6. (r)-pantothenate
7. (+)-pantothenic Acid
8. (r)-pantothenic Acid
9. Pantothenoic Acid
10. (d)-(+)-pantothenic Acid
11. Kyselina Pantothenova [czech]
12. Hsdb 1020
13. Pantothenic Acid [ban]
14. D(+)-n-(2,4-dihydroxy-3,3-dimethylbutyryl)-beta-alanine
15. Vitamin B-5
16. Brn 1727064
17. Pantothenic Acid (d)
18. 3-[[(2r)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoic Acid
19. Beta-alanine, N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, (r)-
20. N-[(2r)-2,4-dihydroxy-3,3-dimethylbutanoyl]-beta-alanine
21. (d,+)-n(alpha-gamma-dihydroxy-beta,beta-dimethylbutyryl)-beta-alanine
22. N-(2,4-dihydroxy-3,3-dimethylbutyryl)-beta-alanine
23. Chebi:46905
24. 19f5hk2737
25. (r)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic Acid
26. Pantothenic Acid (ban)
27. (+)-pantothenate
28. Pantothenic Acid, D-
29. (r)-n-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanine
30. D-pantothenate
31. Pau
32. Kyselina Pantothenova
33. Einecs 201-229-0
34. Pantothenic-acid
35. Unii-19f5hk2737
36. Delta-pantothenate
37. Delta-pantothenic Acid
38. D-(+)-pantothenic Acid
39. (d)-(+)-pantothenate
40. Bmse000287
41. Schembl5436
42. Chembl1594
43. Pantothen Pharmaselect (tn)
44. Vitamin B5 [vandf]
45. 4-04-00-02569 (beilstein Handbook Reference)
46. Pantothenic Acid [mi]
47. Pantothenic Acid, D- (8ci)
48. Gtpl4668
49. Pantothenic Acid [hsdb]
50. Pantothenic Acid [inci]
51. Dtxsid9023417
52. Pantothenic Acid [vandf]
53. Pantothenic Acid [mart.]
54. Vitamin B5 [green Book]
55. Pantothenic Acid [who-dd]
56. Hms2090p08
57. Hms3656k08
58. Hy-b0430
59. N-[(2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl]-beta-alanine
60. Zinc5356910
61. .beta.-alanine, N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, (r)-
62. Pantothenic Acid [orange Book]
63. Db01783
64. Ncgc00346610-01
65. As-75446
66. Sbi-0206933.p001
67. Sw220291-1
68. C00864
69. D07413
70. E83797
71. Q63390527
72. D(+)-n-(2,4-dihydroxy-3,3-dimethylbutyryl)-b-alanine
73. 3-[(2r)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic Acid
74. 450b5472-a689-4bca-9bc1-58691b72d00f
75. N-[(2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl]-ss-alanine
76. 3-((r)-2,4-dihydroxy-3,3-dimethyl-butyrylamino)-propionic Acid
77. 3-[[(2r)-2,4-dihydroxy-3,3-dimethyl-butanoyl]amino]propionic Acid
78. Beta-alanine, N-[(2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl]-
79. 3-[[(2r)-3,3-dimethyl-2,4-bis(oxidanyl)butanoyl]amino]propanoic Acid
80. B-alanine, N-[(2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl]- (9ci)
81. Beta-alanine, N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-, (r)- (9ci)
82. N-((2r)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-.beta.-alanine
| Molecular Weight | 219.23 g/mol |
|---|---|
| Molecular Formula | C9H17NO5 |
| XLogP3 | -1.1 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Exact Mass | 219.11067264 g/mol |
| Monoisotopic Mass | 219.11067264 g/mol |
| Topological Polar Surface Area | 107 Ų |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Complexity | 239 |
| 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 | 1 |
A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
Pantothenic acid is not generally accepted as having any therapeutic use, but it has been prescribed for streptomycin neurotoxicity, salicylate toxicity, gray hair, alopecia, catarrhal respiratory disorders, osteoarthritis, diabetic neuropathy, psychiatric states, and to ameliorate untoward symptoms during thyroid therapy in patients with congenital hypothyroidism (cretinism).
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
Pantothenic acid has been used for a wide range of disorders such as acne, alopecia, allergies, burning feet, asthma, grey hair, dandruff, cholesterol lowering, improving exercise performance, depression, osteoarthritis, rheumatoid arthritis, multiple sclerosis, stress, shingles, ageing and Parkinson's disease. It has been investigated in clinical trials for arthritis, cholesterol lowering and exercise performance.[Mason P; Dietary Supplements,
online] London: Pharmaceutical Press. Available form, as of January 19, 2010: https://www.medicinescomplete.com/
Pantothenic acid deficiency has rarely been identified in humans except in conjunction with deficiency of other B complex vitamins. Diagnosis of pantothenic acid deficiency is aided by a serum pantothenate concentration of less than 50 mcg/mL. Whenever possible, poor dietary habits should be corrected, and some clinicians recommend administration of multivitamin preparations containing pantothenic acid in patients with vitamin deficiencies since poor dietary habits may result in concurrent deficiencies.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
For more Therapeutic Uses (Complete) data for D-Pantothenic Acid (10 total), please visit the HSDB record page.
...This vitamin should not be used alone ... /and/ since no data are available on the effects of topical preparations, these should not be used.
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 192
A 76-year-old white woman was admitted to the hospital because of chest pain and dyspnea related to pleurisy and a pericardial tamponade. This patient had no history of allergy and had been taking vitamins B5 and H for two months. ... After withdrawal of the vitamins, the patient recovered and the eosinophilia disappeared. ... This case suggests that vitamins B5 and H may cause symptomatic, life-threatening, eosinophilic pleuropericarditis. Physicians prescribing these commonly used vitamins should be aware of this potential adverse reaction.
PMID:11302404 Debourdeau PM et al; Ann Pharmacother 35 (4): 424-6 (2001).
A report of life-threatening eosinophilic pleuropericarditis associated with the use of biotin and panthothenic acid. Symptoms resolved on stopping the vitamins.
Sweetman SC (ed), Martindale: The Complete Drug Reference. London: Pharmaceutical Press (2009), p.1959.
... Three patients (two are brothers) with confirmed Barth syndrome /were/ treated with pantothenic acid. This treatment is still controversial and only one study has reported positive results to date. In /the three/ patients, long-term treatment has failed to reduce the number of infectious episodes and prevent dilated cardiomyopathy...
Rugolotto S et al; Mol Gen Metab 80 (4): 408-11 (2003). Available from, as of March 16, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=14654353
Studied for the treatment of many uses such as treatment of testicular torsion, diabetic ulceration, wound healing, acne, obesity, diabetic peripheral polyneuropathy. It has also been investigated for its hypolipidemic effects and as cholesterol lowering agent.
Pantothenic acid is used in the synthesis of coenzyme A (CoA). CoA is thought to act as a carrier molecule, allowing the entry of acyl groups into cells. This is of critical importance as these acyl groups are used as substrates in the tricarboxylic acid cycle to generate energy and in the synthesis of fatty acids, cholesterol, and acetylcholine. Additionally, CoA is part of acyl carrier protein (ACP), which is required in the synthesis of fatty acids in addition to CoAs use as a substrate. Pantothenic acid in the form of CoA is also required for acylation and acetylation, which, for example, are involved in signal transduction and enzyme activation and deactivation, respectively. Since pantothenic acid participates in a wide array of key biological roles, it may have numerous wide-ranging effects.
Vitamin B Complex
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)
Absorption
Dietary pantothenic acid is primarily in the form of CoA or ACP and must be converted into free pantothenic acid for absorption. CoA and ACP are hydrolyzed into 4'-phosphopantetheine which is then dephosphorylated into pantetheine and subsequently hydrolyzed again to free pantothenic acid by Pantetheinase in the intestinal lumen. Free pantothenic acid is absorbed into intestinal cells via a saturable, sodium-dependent active transport system with passive diffusion acting as a secondary pathway. As intake increases up to 10-fold absorption rate can decrease to as low as 10% due to transporter saturation.
Pantothenic acid is absorbed in the small intestine by active transport at low concentrations of the vitamin and by passive transport at higher concentrations. Because the active transport system is saturable, absorption is less efficient at higher concentrations of intake. However, the exact intake levels at which absorption decreases in humans are not known. Pantothenic acid is excreted in the urine in amounts that are proportional with dietary intake over a wide range of intake values.
Otten JJ, Hellwig JP, Meyers LD, eds; Dietary Reference Intakes: The Essential Guide to Nutrient Requirements, Washington, DC: The National Academies Press, 2006, p.271
Pantothenic acid is readily absorbed from the GI tract. It is present in all tissues, in concentrations ranging from 2-45 ug/g. Pantothenic acid apparently is not destroyed in human body since intake and excretion ... are approximately equal. About 70% of unchanged pantothenic acid is excreted in urine and about 30% in feces.
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1564
Pantothenic acid is readily absorbed from the GI tract following oral administration. Normal serum pantothenate concentrations are 100 ug/mL or greater. /Pantothenic acid/ 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.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2000.Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2000 (Plus Supplements)., p. 3317
... /N/ewborn pantothenic acid levels are significantly greater than maternal levels. At term, mean pantothenate levels in 174 mothers were 430 ng/mL (range 250-710) and in their newborns 780 ng/mL (range 400-1480). Placental transfer of pantothenate to the fetus is by active transport, but it is slower than transfer of other B complex vitamins. In one report, low-birth-weight infants had significantly lower levels of pantothenic acid than did normal weight infants.
Briggs, G.G, R.K. Freeman, S.J. Yaffe. A Reference Guide to Fetal and Neonatal Risk. Drugs in Pregnancy and Lactation. 4th ed. Baltimore, MD: Williams & Wilkins 1994., p. 656
For more Absorption, Distribution and Excretion (Complete) data for D-Pantothenic Acid (20 total), please visit the HSDB record page.
The synthesis of Coenzyme A (CoA) from pantothenate is regulated primarily by pantothenate kinase, an enzyme that is inhibited by the pathway end products, CoA and acyl CoA.
NAS, Food and Nutrition Board, Institute of Medicine; Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C., pg. 358, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html
/P/antothenic acid is required for intermediary metabolism of carbohydrates, proteins, and lipids. Pantothenic acid is a precursor of coenzyme A which is required for acetylation (acyl group activation) reactions in gluconeogenesis, in the release of energy from carbohydrates, the synthesis and degradation of fatty acids, and the synthesis of sterols and steroid hormones, porphyrins, acetylcholine, and other compounds.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2000.Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2000 (Plus Supplements)., p. 3316
Absorption Coenzyme A (CoA). CoA in the diet is hydrolyzed in the intestinal lumen to dephospho CoA, phosphopantetheine, and pantetheine, with the pantetheine subsequently hydrolyzed to pantothenic acid. Pantothenic acid was the only one of these pantothenate-containing compounds absorbed by rats in studies on absorption of the various forms. Absorption is by active transport at low concentrations of the vitamin and by passive transport at higher concentrations in animal models. Because the active transport system is saturable, absorption will be less efficient at higher concentrations of intake, but the intake levels at which absorptive efficiency decreases in humans are not known.
NAS, Food and Nutrition Board, Institute of Medicine; Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C., pg. 358, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html
Intestinal microflora have been observed to synthesize pantothenic acid in mice, but the contribution of bacterial synthesis to body pantothenic acid levels or fecal losses in humans has not been quantified. If microbial synthesis is substantial, balance studies in humans may have underestimated pantothenic acid absorption and requirements.
NAS, Food and Nutrition Board, Institute of Medicine; Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C., pg. 358, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html
Coenzyme A (CoA) is hydrolyzed to pantothenate in a multiple-step reaction. The pantothenic acid is excreted intact in urine, ... . The amount excreted varies proportionally with dietary intake over a discrete yet wide range of intake values.
NAS, Food and Nutrition Board, Institute of Medicine; Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C., pg. 358, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html
Pantothenic acid is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.
... 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
Coenzyme A (CoA) is the major acyl group carrier in intermediary metabolism. Hopantenate (HoPan), a competitive inhibitor of the pantothenate kinases, was used to chemically antagonize CoA biosynthesis. HoPan dramatically reduced liver CoA and mice developed severe hypoglycemia. Insulin was reduced, glucagon and corticosterone were elevated, and fasting accelerated hypoglycemia. Metabolic profiling revealed a large increase in acylcarnitines, illustrating the role of carnitine in buffering acyl groups to maintain the nonesterified CoASH level. HoPan triggered significant changes in hepatic gene expression that substantially increased the thioesterases, which liberate CoASH from acyl-CoA, and increased pyruvate dehydrogenase kinase 1, which prevents the conversion of CoASH to acetyl-CoA. These results identify the metabolic rearrangements that maintain the CoASH pool which is critical to mitochondrial functions, including gluconeogenesis, fatty acid oxidation, and the tricarboxylic acid and urea cycles.
Zhang Y-M et al; Chem Biol 14 (3): 291-302 (2007). Available from, as of March 16, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=17379144
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