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Pantethine

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Not to be confused with pantetheine.
Pantethine
Names
IUPAC name
N-[2-[2-[2-[3-(2,4-Dihydroxy-3,3-dimethyl-butanoyl)aminopropanoylamino ]ethyldisulfanyl]ethylcarbamoyl]ethyl]-2,4-dihydroxy-3,3-dimethyl-butanamide
Other names
Bis-pantethine
Co-enzyme pantethine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.037.114 Edit this at Wikidata
UNII
  • InChI=1S/C22H42N4O8S2/c1-21(2,13-27)17(31)19(33)25-7-5-15(29)23-9-11-35-36-12-10-24-16(30)6-8-26-20(34)18(32)22(3,4)14-28/h17-18,27-28,31-32H,5-14H2,1-4H3,(H,23,29)(H,24,30)(H,25,33)(H,26,34) checkY
    Key: DJWYOLJPSHDSAL-UHFFFAOYSA-N checkY
  • InChI=1/C22H42N4O8S2/c1-21(2,13-27)17(31)19(33)25-7-5-15(29)23-9-11-35-36-12-10-24-16(30)6-8-26-20(34)18(32)22(3,4)14-28/h17-18,27-28,31-32H,5-14H2,1-4H3,(H,23,29)(H,24,30)(H,25,33)(H,26,34)
    Key: DJWYOLJPSHDSAL-UHFFFAOYAZ
  • O=C(NCCSSCCNC(=O)CCNC(=O)C(O)C(C)(C)CO)CCNC(=O)C(O)C(C)(C)CO
Properties
C22H42N4O8S2
Molar mass 554.72 g·mol−1
Pharmacology
A11HA32 (WHO)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Pantethine (bis-pantethine or co-enzyme pantethine) is a dimeric form of pantetheine, which is produced from pantothenic acid (vitamin B5) by the addition of cysteamine. Pantethine was discovered by Gene Brown, a PhD student at the time. Pantethine is two molecules of pantetheine linked by a disulfide bridge. Pantetheine is an intermediate in the production of coenzyme A by the body. Most vitamin B5 supplements are in the form of calcium pantothenate, a salt of pantothenic acid, with doses in the range of 5 to 10 mg/day. In contrast, pantethine is sold as a dietary supplement for lowering blood cholesterol and triglycerides at doses of 500 to 1200 mg/day.

Dietary supplement

Pantethine is available in the United States as a dietary supplement because of evidence for lowering elevated LDL-cholesterol and triglycerides and raising HDL-cholesterol. In multiple clinical trials of patients with elevated cholesterol and triglycerides, total and LDL cholesterol were decreased by an average of 12%, triglycerides decreased by 19%, and HDL cholesterol was increased by 9% in clinical trials with daily intakes ranging from 600 to 1200 mg/day.[1][2][3][4][5]

Physiological effects

Although pantethine can serve as a precursor for generation of vitamin B5 and consumption of therapeutic amounts of pantethine results in higher circulating concentrations of vitamin B5, this is not thought to be the mechanism of action. Vitamin B5 requirements are on the order of 5 mg/day. High doses of vitamin B5 do not result in the lipid changes seen with pantethine.Two mechanisms of action are proposed for pantethine.[6] In the first, pantethine serves as the precursor for synthesis of coenzyme A. CoA is involved in the transfer of acetyl groups, in some instances to attach to proteins closely associated with activating and deactivating genes. By this theory, either the genes responsible for cholesterol and triglyceride synthesis are suppressed or the genes governing the catabolism of compounds are turned on. In the second theory, pantethine is converted to two pantetheine molecules which are in turn metabolized to form two pantethenic acid and two cysteamine molecules. Cysteamine is theorized to bind to and thus inactivate sulfur-containing amino acids in liver enzymes involved in the production of cholesterol and triglycerides. What is known is that high doses of the related vitamin - pantothenic acid - has no effect on lipids.[2]

References

  1. ^ Chen YQ, Zhao SP, Zhao YH (2015). "Efficacy and tolerability of coenzyme A vs pantethine for the treatment of patients with hyperlipidemia: A randomized, double-blind, multicenter study". Journal of Clinical Lipidology. 9 (5): 692–7. doi:10.1016/j.jacl.2015.07.003. PMID 26350816.
  2. ^ a b "Pantethine. Monograph". Altern Med Rev. 15 (3): 279–82. September 2010. PMID 21155629.
  3. ^ McRae MP (April 2005). "Treatment of hyperlipoproteinemia with pantethine: a review and analysis of efficacy and tolerability". Nutrition Research. 25 (4): 319–33.
  4. ^ Rumberger JA, Napolitano J, Azumano I, Kamiya T, Evans M (August 2011). "Pantethine, a derivative of vitamin B(5) used as a nutritional supplement, favorably alters low-density lipoprotein cholesterol metabolism in low- to moderate-cardiovascular risk North American subjects: a triple-blinded placebo and diet-controlled investigation". Nutrition Research. 31 (8): 608–15. doi:10.1016/j.nutres.2011.08.001. PMID 21925346.
  5. ^ Evans M, Rumberger JA, Azumano I, Napolitano JJ, Citrolo D, Kamiya T (2014). "Pantethine, a derivative of vitamin B5, favorably alters total, LDL and non-HDL cholesterol in low to moderate cardiovascular risk subjects eligible for statin therapy: a triple-blinded placebo and diet-controlled investigation". Vascular Health and Risk Management. 10: 89–100. doi:10.2147/VHRM.S57116. PMC 3942300. PMID 24600231.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  6. ^ McCarty MF (2001). "Inhibition of acetyl-CoA carboxylase by cystamine may mediate the hypotriglyceridemic activity of pantethine". Medical Hypotheses. 56 (3): 314–317. doi:10.1054/mehy.2000.1155.
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