Sitagliptin N-sulfate | CAS# 2470126-25-9 (N-sulfate) | Metabolite

Sitagliptin N-sulfate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574283

CAS#: 2470126-25-9 (N-sulfate)

Description: Sitagliptin N-sulfate is a phase II metabolite of the dipeptidyl peptidase 4 (DPP-4) inhibitor (–)-sitagliptin. Sitagliptin N-sulfate is formed via sulfation.

Chemical Structure

Sitagliptin N-sulfate

CAS# 2470126-25-9 (N-sulfate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574283
Name: Sitagliptin N-sulfate
CAS#: 2470126-25-9 (N-sulfate)
Chemical Formula: C16H14F6N5NaO4S
Exact Mass: 0.00
Molecular Weight: 509.360
Elemental Analysis: C, 37.73; H, 2.77; F, 22.38; N, 13.75; Na, 4.51; O, 12.56; S, 6.29

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 600	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Sitagliptin N-sulfate

IUPAC/Chemical Name: (R)-(4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)sulfamate, monosodium salt

InChi Key: FYMJQXVEWOAVBS-SBSPUUFOSA-M

InChi Code: InChI=1S/C16H15F6N5O4S.Na/c17-10-6-12(19)11(18)4-8(10)3-9(25-32(29,30)31)5-14(28)26-1-2-27-13(7-26)23-24-15(27)16(20,21)22;/h4,6,9,25H,1-3,5,7H2,(H,29,30,31);/q;+1/p-1/t9-;/m1./s1

SMILES Code: FC1=CC(C[C@@H](NS([O-])(=O)=O)CC(N2CC3=NN=C(C(F)(F)F)N3CC2)=O)=C(F)C=C1F.[Na+]

Appearance: Solid powder

Purity: >95% (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: To be determined

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: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Sitagliptin is a potent and orally active inhibitor of DPP4 with an IC50 of 19 nM in Caco-2 cell extracts.
In vitro activity:	Sitagliptin induces differentiation of tolerogenic dendritic cells, and the effect is important when considering sitagliptin for treating autoimmune diseases and allotransplant rejection. Sitagliptin impaired differentiation and maturation of human dendritic cells generated from monocytes (MoDCs), while the expression of CD26, tolerogenic DC markers, and production of immunoregulatory cytokines increased. Sitagliptin inhibited p65 expression of NF-kB and p38MAPK during the maturation of MoDCs. Reference: Int J Mol Sci. 2023 Nov 27;24(23):16829. https://pubmed.ncbi.nlm.nih.gov/38069152/
In vivo activity:	Sitagliptin showed significant antinociceptive and anti-inflammatory effects. In the carrageenan test, sitagliptin significantly reduced paw thickness in male Wistar rats. Pretreatment with yohimbine, prazosin, propranolol, naloxone, and cyproheptadine could not reverse the antinociceptive effect of sitagliptin, which indicates that adrenergic, opioid, and serotonin receptors are not involved in the antinociceptive effects. L-NAME, methylene blue, glibenclamide, ondansetron, and sulpiride were able to reverse this effect. Reference: Korean J Pain. 2023 Dec 21. https://pubmed.ncbi.nlm.nih.gov/38123184/

Preparing Stock Solutions

The following data is based on the product molecular weight 509.36 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.

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. Drakul M, Tomić S, Bekić M, Mihajlović D, Vasiljević M, Rakočević S, Đokić J, Popović N, Bokonjić D, Čolić M. Sitagliptin Induces Tolerogenic Human Dendritic Cells. Int J Mol Sci. 2023 Nov 27;24(23):16829. doi: 10.3390/ijms242316829. PMID: 38069152; PMCID: PMC10706581. 2. Kosowska A, Garczorz W, Kłych-Ratuszny A, Aghdam MRF, Kimsa-Furdzik M, Simka-Lampa K, Francuz T. Sitagliptin Modulates the Response of Ovarian Cancer Cells to Chemotherapeutic Agents. Int J Mol Sci. 2020 Nov 26;21(23):8976. doi: 10.3390/ijms21238976. PMID: 33256016; PMCID: PMC7731375. 3. Hajhashemi V, Sadeghi H, Karimi Madab F. Anti-inflammatory and antinociceptive effects of sitagliptin in animal models and possible mechanisms involved in the antinociceptive activity. Korean J Pain. 2023 Dec 21. doi: 10.3344/kjp.23262. Epub ahead of print. PMID: 38123184. 4. Zong Y, Wang X, Zhang Y, Tan N, Zhang Y, Li L, Liu L. Sitagliptin Ameliorates Creb5/lncRNA ENSMUST00000213271-Mediated Vascular Endothelial Dysfunction in Obese Mice. Cardiovasc Drugs Ther. 2023 Feb 4. doi: 10.1007/s10557-023-07436-1. Epub ahead of print. PMID: 36738369.
In vitro protocol:	1. Drakul M, Tomić S, Bekić M, Mihajlović D, Vasiljević M, Rakočević S, Đokić J, Popović N, Bokonjić D, Čolić M. Sitagliptin Induces Tolerogenic Human Dendritic Cells. Int J Mol Sci. 2023 Nov 27;24(23):16829. doi: 10.3390/ijms242316829. PMID: 38069152; PMCID: PMC10706581. 2. Kosowska A, Garczorz W, Kłych-Ratuszny A, Aghdam MRF, Kimsa-Furdzik M, Simka-Lampa K, Francuz T. Sitagliptin Modulates the Response of Ovarian Cancer Cells to Chemotherapeutic Agents. Int J Mol Sci. 2020 Nov 26;21(23):8976. doi: 10.3390/ijms21238976. PMID: 33256016; PMCID: PMC7731375.
In vivo protocol:	1. Hajhashemi V, Sadeghi H, Karimi Madab F. Anti-inflammatory and antinociceptive effects of sitagliptin in animal models and possible mechanisms involved in the antinociceptive activity. Korean J Pain. 2023 Dec 21. doi: 10.3344/kjp.23262. Epub ahead of print. PMID: 38123184. 2. Zong Y, Wang X, Zhang Y, Tan N, Zhang Y, Li L, Liu L. Sitagliptin Ameliorates Creb5/lncRNA ENSMUST00000213271-Mediated Vascular Endothelial Dysfunction in Obese Mice. Cardiovasc Drugs Ther. 2023 Feb 4. doi: 10.1007/s10557-023-07436-1. Epub ahead of print. PMID: 36738369.

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1. Beconi, M.G., Reed, J.R., Teffera, Y., et al. Disposition of the dipeptidyl peptidase 4 inhibitor sitagliptin in rats and dogs. Drug Metab. Dispos. 35(4), 525-532 (2007).

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