Pantoprazole EP Impurity D
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624742-53-6Pantoprazole EP Impurity D

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Catalogue No.:VE009260
CAS No.:624742-53-6
Mol. Formula:C17H17F2N3O4S
Mol. Weight:397.40 g/mol

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Additional information on CAS 624742-53-6

Parent drug

Pantoprazole

IUPAC Name

(R)-5-(difluoromethoxy)-2-(((3,4-dimethoxypyridin-2-yl)methyl)sulfinyl)-1-methyl-1H-benzo[d]imidazole

Smiles

CN1C([S@@](CC2=NC=CC(OC)=C2OC)=O)=NC3=CC(OC(F)F)=CC=C13

Pharmacopeial Synonyms

Pantoprazole BP Impurity D; Pantoprazole Related Compopund D

Synonyms

1H-Benzimidazole, 5-(difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-1-methyl; N1-Methyl pantoprazole

InChI

InChI=1S/C17H17F2N3O4S/c1-22-13-5-4-10(26-16(18)19)8-11(13)21-17(22)27(23)9-12-15(25-3)14(24-2)6-7-20-12/h4-8,16H,9H2,1-3H3/t27-/m1/s1

Pharmacopoeial Synonyms

Pantoprazole BP Impurity D; Pantoprazole Related Compopund D

Other Synonyms

1H-Benzimidazole, 5-(difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-1-methyl; N1-Methyl pantoprazole

InChl

InChI=1S/C17H17F2N3O4S/c1-22-13-5-4-10(26-16(18)19)8-11(13)21-17(22)27(23)9-12-15(25-3)14(24-2)6-7-20-12/h4-8,16H,9H2,1-3H3

Description

Pantoprazole EP Impurity D, also listed as Pantoprazole BP Impurity D and Pantoprazole Related Compound D, CAS 624742-53-6, is the N1-methyl analog of pantoprazole and an oxidized benzimidazole sulfoxide impurity with molecular formula C17H17F2N3O4S and molecular weight 397.40 g/mol. Its presence is typically associated with methylation-related process impurities or incomplete control of sulfoxide chemistry during synthesis of the proton pump inhibitor. Because structurally related heteroaromatic impurities can influence impurity profiles at low levels, characterization generally requires LC-MS/MS, LC-HRMS, and orthogonal HPLC methods, with MS fragmentation used to confirm substitution on the benzimidazole and pyridine moieties.

References

Bernshteyn, Michelle A., and Umair Masood. “Pantoprazole.” Nih.gov, StatPearls Publishing, 15 Jan. 2022, www.ncbi.nlm.nih.gov/books/NBK499945/. ‌

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