Pantethine

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
CAS Number	16816-67-4 Y
ChEMBL	ChEMBL2104786 N
ChemSpider	4515 Y
Jmol 3D model	Interactive image
PubChem	4677
UNII	7K81IL792L Y
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
SMILES O=C(NCCSSCCNC(=O)CCNC(=O)C(O)C(C)(C)CO)CCNC(=O)C(O)C(C)(C)CO
Properties
Chemical formula	C22H42N4O8S2
Molar mass	554.723 g/mol
Pharmacology
ATC code	A11HA32
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 is composed of two molecules of pantetheine linked by a bridging disulfide. 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 supplementation

Pantethine is available in the United States as a dietary supplement because of evidence of its health benefits for lowering elevated LDL-cholesterol and triglycerides, and raising HDL-cholesterol (the 'good' 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%. 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 conducted in Japan tested 300 mg/day and reported decreases in total cholesterol of about 4%, increases in HDL-cholesterol of 5% and inconsistent results for triglycerides. Most of the literature on pantethine and lipids is 20–30 years old, but recent carefully controlled trials of 600 and 900 mg/d doses have shown similar statistically significant lowering of LDL cholesterol in individuals with greatly or moderately elevated levels of blood lipids.

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. 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.