Pantethine

Not to be confused with pantetheine.

Pantethine
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
CAS number	16816-67-4 Y
PubChem	4677
ChemSpider	4515 Y
UNII	7K81IL792L Y
Jmol-3D images	Image 1
SMILES O=C(NCCSSCCNC(=O)CCNC(=O)C(O)C(C)(C)CO)CCNC(=O)C(O)C(C)(C)CO
InChI 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) Y Key: DJWYOLJPSHDSAL-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C22H42N4O8S2
Molar mass	554.723 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pantethine (bis-pantethine or co-enzyme pantethine) is a dimeric form of pantothenic acid (vitamin B₅). It is composed of two molecules of pantothenic acid linked by cysteamine bridging groups. The monomer of this compound is known as pantetheine and is an intermediate in the production of Coenzyme A by the body. Pantethine is considered the more biologically active form of vitamin B₅, but it is less stable, decomposing over time if it is not kept refrigerated. Most vitamin B₅ supplements are therefore in the form of calcium pantothenate, a salt of pantothenic acid.

Dietary supplementation

Pantethine is available as a dietary supplement because of evidence of its health benefits. In multiple clinical trials of patients with elevated cholesterol and triglycerides, total and LDL cholesterol were decreased by 12%, triglycerides decreased by 18%, and HDL cholesterol was increased by 9%.^[1][2] These clinical trials were conducted with daily intakes ranging from 600 to 1200 mg/day. Within this dose range there is no evidence of a dose-effect relationship, i.e. changes in lipid concentrations overlapped across the range of doses. Direct dose-response evidence is not available because no trial tested more than one dose. A few trials tested 300 mg/day with more modest but still statistically significant results.^[3]

Physiological effects

Although pantethine can serve as a precursor for generation of vitamin B₅, this is not thought to be the mechanism of action. Vitamin B₅ requirements are on the order of 5 mg/day.

Two mechanisms of action are proposed for pantethine.^{[4][unreliable source?]} In the first, pantethine serves as the precursor for synthesis of coenzyme A. In the second, 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.

References

1. ^ Binaghi, P; Cellina, G; Lo Cicero, G; Bruschi, F; Porcaro, E; Penotti, M (1990). "Evaluation of the cholesterol-lowering effectiveness of pantethine in women in perimenopausal age". Minerva medica 81 (6): 475–9. PMID 2359503. 
2. ^ Arsenio, L; Bodria, P; Magnati, G; Strata, A; Trovato, R (1986). "Effectiveness of long-term treatment with pantethine in patients with dyslipidemia". Clinical therapeutics 8 (5): 537–45. PMID 3094958. 
3. ^ Gaddi, A; Descovich, GC; Noseda, G; Fragiacomo, C; Colombo, L; Craveri, A; Montanari, G; Sirtori, CR (1984). "Controlled evaluation of pantethine, a natural hypolipidemic compound, in patients with different forms of hyperlipoproteinemia". Atherosclerosis 50 (1): 73–83. doi:10.1016/0021-9150(84)90009-1. PMID 6365107. 
4. ^ 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.