Pantethine
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MedKoo CAT#: 598493

CAS#: 16816-67-4

Description: Pantethine is a derivative of vitamin B5.

Chemical Structure

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Pantethine
CAS# 16816-67-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 598493
Name: Pantethine
CAS#: 16816-67-4
Chemical Formula: C22H42N4O8S2
Exact Mass: 554.24
Molecular Weight: 554.718
Elemental Analysis: C, 47.64; H, 7.63; N, 10.10; O, 23.07; S, 11.56

Price and Availability

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1g USD 260
5g USD 550
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Synonym: Pantethine; LBF disulfide; Lipodel; Pantosin; D-Pantethine;

IUPAC/Chemical Name: (2R,2'R)-N,N'-(((disulfanediylbis(ethane-2,1-diyl))bis(azanediyl))bis(3-oxopropane-3,1-diyl))bis(2,4-dihydroxy-3,3-dimethylbutanamide)

InChi Key: DJWYOLJPSHDSAL-ROUUACIJSA-N

InChi Code: 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)/t17-,18-/m0/s1

SMILES Code: O=C(NCCSSCCNC(CCNC([C@H](O)C(C)(C)CO)=O)=O)CCNC([C@H](O)C(C)(C)CO)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Pantethine is a dimeric form of pantothenic acid, is an intermediate in the production of Coenzyme A, is available as a dietary supplement, and is used to treat acne and improve the blood-cholesterol profile.
In vitro activity: Here, this study explored the potential antiviral effects of pantethine in two in vitro experimental models of SARS-CoV-2 infection, in Vero E6 cells and in Calu-3a cells. Pantethine reduced the infection of cells by SARS-CoV-2 in both preinfection and postinfection treatment regimens. Accordingly, cellular expression of the viral spike and nucleocapsid proteins was substantially reduced, and we observed a significant reduction in viral copy numbers in the supernatant of cells treated with pantethine. In addition, pantethine inhibited the infection-induced increase in TMPRSS2 and HECT E3 ligase expression in infected cells as well as the increase in antiviral interferon-beta response and inflammatory gene expression in Calu-3a cells. Reference: Sci Rep. 2023 Feb 8;13(1):2237. https://pubmed.ncbi.nlm.nih.gov/36754974/
In vivo activity: These properties of pantethine prompted the study to investigate its potential benefits in vivo in the 5XFAD (Tg) mouse model of Alzheimer's disease (AD). This study observed that long-term pantethine treatment significantly reduced glial reactivity and Αβ deposition, and abrogated behavioral alteration in Tg mice. Moreover, the transcriptomic profiles revealed that after pantethine treatment, the expression of genes differentially expressed in Tg mice, and in particular those known to be related to AD, were significantly alleviated. Reference: Neurotherapeutics. 2019 Oct;16(4):1237-1254. https://pubmed.ncbi.nlm.nih.gov/31267473/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 180.27
Ethanol 100.0 180.27
Water 100.0 180.27

Preparing Stock Solutions

The following data is based on the product molecular weight 554.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Abou-Hamdan M, Saleh R, Mani S, Dournaud P, Metifiot M, Blondot ML, Andreola ML, Abdel-Sater F, De Reggi M, Gressens P, Laforge M. Potential antiviral effects of pantethine against SARS-CoV-2. Sci Rep. 2023 Feb 8;13(1):2237. doi: 10.1038/s41598-023-29245-0. PMID: 36754974; PMCID: PMC9906591. 2. van Gijsel-Bonnello M, Baranger K, Benech P, Rivera S, Khrestchatisky M, de Reggi M, Gharib B. Metabolic changes and inflammation in cultured astrocytes from the 5xFAD mouse model of Alzheimer's disease: Alleviation by pantethine. PLoS One. 2017 Apr 14;12(4):e0175369. doi: 10.1371/journal.pone.0175369. Erratum in: PLoS One. 2018 Mar 14;13(3):e0194586. PMID: 28410378; PMCID: PMC5391924. 3. Baranger K, van Gijsel-Bonnello M, Stephan D, Carpentier W, Rivera S, Khrestchatisky M, Gharib B, De Reggi M, Benech P. Long-Term Pantethine Treatment Counteracts Pathologic Gene Dysregulation and Decreases Alzheimer's Disease Pathogenesis in a Transgenic Mouse Model. Neurotherapeutics. 2019 Oct;16(4):1237-1254. doi: 10.1007/s13311-019-00754-z. PMID: 31267473; PMCID: PMC6985318. 4. Penet MF, Krishnamachary B, Wildes F, Mironchik Y, Mezzanzanica D, Podo F, de Reggi M, Gharib B, Bhujwalla ZM. Effect of Pantethine on Ovarian Tumor Progression and Choline Metabolism. Front Oncol. 2016 Nov 16;6:244. doi: 10.3389/fonc.2016.00244. PMID: 27900284; PMCID: PMC5110532.
In vitro protocol: 1. Abou-Hamdan M, Saleh R, Mani S, Dournaud P, Metifiot M, Blondot ML, Andreola ML, Abdel-Sater F, De Reggi M, Gressens P, Laforge M. Potential antiviral effects of pantethine against SARS-CoV-2. Sci Rep. 2023 Feb 8;13(1):2237. doi: 10.1038/s41598-023-29245-0. PMID: 36754974; PMCID: PMC9906591. 2. van Gijsel-Bonnello M, Baranger K, Benech P, Rivera S, Khrestchatisky M, de Reggi M, Gharib B. Metabolic changes and inflammation in cultured astrocytes from the 5xFAD mouse model of Alzheimer's disease: Alleviation by pantethine. PLoS One. 2017 Apr 14;12(4):e0175369. doi: 10.1371/journal.pone.0175369. Erratum in: PLoS One. 2018 Mar 14;13(3):e0194586. PMID: 28410378; PMCID: PMC5391924.
In vivo protocol: 1. Baranger K, van Gijsel-Bonnello M, Stephan D, Carpentier W, Rivera S, Khrestchatisky M, Gharib B, De Reggi M, Benech P. Long-Term Pantethine Treatment Counteracts Pathologic Gene Dysregulation and Decreases Alzheimer's Disease Pathogenesis in a Transgenic Mouse Model. Neurotherapeutics. 2019 Oct;16(4):1237-1254. doi: 10.1007/s13311-019-00754-z. PMID: 31267473; PMCID: PMC6985318. 2. Penet MF, Krishnamachary B, Wildes F, Mironchik Y, Mezzanzanica D, Podo F, de Reggi M, Gharib B, Bhujwalla ZM. Effect of Pantethine on Ovarian Tumor Progression and Choline Metabolism. Front Oncol. 2016 Nov 16;6:244. doi: 10.3389/fonc.2016.00244. PMID: 27900284; PMCID: PMC5110532.

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1: Kavian N, Marut W, Servettaz A, Nicco C, Chéreau C, Lemaréchal H, Guilpain P, Chimini G, Galland F, Weill B, Naquet P, Batteux F. Pantethine Prevents Murine Systemic Sclerosis Through the Inhibition of Microparticle Shedding. Arthritis Rheumatol. 2015 Jul;67(7):1881-90. doi: 10.1002/art.39121. PubMed PMID: 25776044.

2: Evans M, Rumberger JA, Azumano I, Napolitano JJ, Citrolo D, Kamiya T. 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. Vasc Health Risk Manag. 2014 Feb 27;10:89-100. doi: 10.2147/VHRM.S57116. eCollection 2014. PubMed PMID: 24600231; PubMed Central PMCID: PMC3942300.

3: Chen YQ, Zhao SP, Zhao YH. Efficacy and tolerability of coenzyme A vs pantethine for the treatment of patients with hyperlipidemia: A randomized, double-blind, multicenter study. J Clin Lipidol. 2015 Sep-Oct;9(5):692-7. doi: 10.1016/j.jacl.2015.07.003. Epub 2015 Jul 11. PubMed PMID: 26350816.

4: van Gijsel-Bonnello M, Acar N, Molino Y, Bretillon L, Khrestchatisky M, de Reggi M, Gharib B. Pantethine Alters Lipid Composition and Cholesterol Content of Membrane Rafts, With Down-Regulation of CXCL12-Induced T Cell Migration. J Cell Physiol. 2015 Oct;230(10):2415-25. doi: 10.1002/jcp.24971. PubMed PMID: 25728249.

5: Shibata K, Kaneko M, Fukuwatari T. D-pantethine has vitamin activity equivalent to d-pantothenic acids for recovering from a deficiency of D-pantothenic acid in rats. J Nutr Sci Vitaminol (Tokyo). 2013;59(2):93-9. PubMed PMID: 23727638.

6: Vécsei L, Horváth Z, Tuka B. OLD AND NEW NEUROENDOCRINE MOLECULES: SOMATOSTATIN, CYSTEAMINE, PANTETHINE AND KYNURENINE. Ideggyogy Sz. 2014 Mar 30;67(3-4):107-12. Review. PubMed PMID: 26118251.

7: Penet MF, Krishnamachary B, Wildes F, Mironchik Y, Mezzanzanica D, Podo F, de Reggi M, Gharib B, Bhujwalla ZM. Effect of Pantethine on Ovarian Tumor Progression and Choline Metabolism. Front Oncol. 2016 Nov 16;6:244. eCollection 2016. PubMed PMID: 27900284; PubMed Central PMCID: PMC5110532.

8: Panchuk RR, Skorokhyd NR, Kozak YS, Lehka LV, Chumak VV, Omelyanchik SN, Gurinovich VA, Moiseenok AG, Stoika RS. Antioxidants selenomethionine and D-pantethine decrease the negative side effects of doxorubicin in NL/Ly lymphoma-bearing mice. Croat Med J. 2016 Apr 23;57(2):180-92. PubMed PMID: 27106359; PubMed Central PMCID: PMC4856192.

9: Avetisov SÉ, Sheremet NL, Muranov KO, Polianskiĭ NB, Polunin GS, Ostrovskiĭ MA. [Deceleration of cataract development in rats under the action of N-acetylcarnosine and D-pantethine mixture]. Eksp Klin Farmakol. 2014;77(11):11-5. Russian. PubMed PMID: 25668941.

10: Brunetti D, Dusi S, Giordano C, Lamperti C, Morbin M, Fugnanesi V, Marchet S, Fagiolari G, Sibon O, Moggio M, d'Amati G, Tiranti V. Pantethine treatment is effective in recovering the disease phenotype induced by ketogenic diet in a pantothenate kinase-associated neurodegeneration mouse model. Brain. 2014 Jan;137(Pt 1):57-68. doi: 10.1093/brain/awt325. Epub 2013 Dec 6. PubMed PMID: 24316510; PubMed Central PMCID: PMC3891449.

11: Canavesi R, Aprile S, Varese E, Grosa G. Development and validation of a stability-indicating LC-UV method for the determination of pantethine and its degradation product based on a forced degradation study. J Pharm Biomed Anal. 2014 Aug;97:141-50. doi: 10.1016/j.jpba.2014.04.025. Epub 2014 May 2. PubMed PMID: 24863372.

12: Wu J, Sandberg M, Weber SG. Integrated electroosmotic perfusion of tissue with online microfluidic analysis to track the metabolism of cystamine, pantethine, and coenzyme A. Anal Chem. 2013 Dec 17;85(24):12020-7. doi: 10.1021/ac403005z. Epub 2013 Nov 22. PubMed PMID: 24215585; PubMed Central PMCID: PMC3899583.

13: Suzuki Y, Itoh H, Abe T, Nishimura F, Sato Y, Takeyama M. Comparison of the effects of pantethine and fursultiamine on plasma gastrointestinal peptide levels in healthy volunteers. Biol Pharm Bull. 2011;34(10):1640-3. PubMed PMID: 21963510.

14: Rumberger JA, Napolitano J, Azumano I, Kamiya T, Evans M. 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. Nutr Res. 2011 Aug;31(8):608-15. doi: 10.1016/j.nutres.2011.08.001. PubMed PMID: 21925346.

15: Rana A, Seinen E, Siudeja K, Muntendam R, Srinivasan B, van der Want JJ, Hayflick S, Reijngoud DJ, Kayser O, Sibon OC. Pantethine rescues a Drosophila model for pantothenate kinase-associated neurodegeneration. Proc Natl Acad Sci U S A. 2010 Apr 13;107(15):6988-93. doi: 10.1073/pnas.0912105107. Epub 2010 Mar 29. PubMed PMID: 20351285; PubMed Central PMCID: PMC2872433.

16: Wittwer CT, Gahl WA, Butler JD, Zatz M, Thoene JG. Metabolism of pantethine in cystinosis. J Clin Invest. 1985 Oct;76(4):1665-72. PubMed PMID: 4056044; PubMed Central PMCID: PMC424158.

17: Cornille E, Abou-Hamdan M, Khrestchatisky M, Nieoullon A, de Reggi M, Gharib B. Enhancement of L-3-hydroxybutyryl-CoA dehydrogenase activity and circulating ketone body levels by pantethine. Relevance to dopaminergic injury. BMC Neurosci. 2010 Apr 23;11:51. doi: 10.1186/1471-2202-11-51. PubMed PMID: 20416081; PubMed Central PMCID: PMC2880308.

18: Abucham J, Bollinger-Gruber J, Reichlin S. Pantethine, a somatostatin depleting agent, increases food intake in rats. Pharmacol Biochem Behav. 1989 Jul;33(3):585-9. PubMed PMID: 2587601.

19: Wittwer CT, Graves CP, Peterson MA, Jorgensen E, Wilson DE, Thoene JG, Wyse BW, Windham CT, Hansen RG. Pantethine lipomodulation: evidence for cysteamine mediation in vitro and in vivo. Atherosclerosis. 1987 Nov;68(1-2):41-9. PubMed PMID: 3689482.

20: Balibar CJ, Hollis-Symynkywicz MF, Tao J. Pantethine rescues phosphopantothenoylcysteine synthetase and phosphopantothenoylcysteine decarboxylase deficiency in Escherichia coli but not in Pseudomonas aeruginosa. J Bacteriol. 2011 Jul;193(13):3304-12. doi: 10.1128/JB.00334-11. Epub 2011 May 6. PubMed PMID: 21551303; PubMed Central PMCID: PMC3133259.