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Ritonavir Impurity S

Ritonavir Impurity S is a structurally related synthetic byproduct arising from the amidation step in Ritonavir production. It retains the core dipeptide scaffold (pyrrolidin-2-one and 3-methylbutyric acid moieties) but features an additional N-terminal cyclohexylmethyl group and a truncated C-terminal sulfonamide linkage compared to the parent compound. The molecule exhibits two chiral centers, a disulfide bridge, and a hydrophobic alkyl chain that disrupts the pharmacophoric interactions of Ritonavir. This impurity is generated via premature termination of the peptide coupling reaction, resulting in a non-pharmacologically active analog. It functions as a critical HPLC reference standard for quantifying process-related impurities in Ritonavir drug substance.

On Request
Molecular Formula C52H61N7O8S2
Molecular Weight 976.2000
CAS Number 2084828-53-3 โœ“ Verified
PubChem CID 76962732 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Ritonavir
Lead Time On Request
IUPAC Name 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[[(2S)-1-[[(2S,4S,5S)-4-hydroxy-1,6-diphenyl-5-(1,3-thiazol-5-ylmethoxycarbonylamino)hexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoylamino]-1,6-diphenylhexan-2-yl]carbamate

๐Ÿ“ Synonyms

Ritonavir EP Impurity S 2084828-53-3 (3S,4S,6S,10S,13S,15S,16S)-bis(thiazol-5-ylmethyl)-4,15-dihydroxy-10-isopropyl-8,11-dioxo-3,6,13,16-tetrabenzyl-2,7,9,12,17-pentaazaoctadecanedioate I8743EEB07 RITONAVIR IMPURITY S [EP IMPURITY] Q27280562 2,7,9,12,17-Pentaazaoctadecanedioic acid, 4,15-dihydroxy-10-(1-methylethyl)-8,11-dioxo-3,6,13,16-tetrakis(phenylmethyl)-, 1,18-bis(5-thiazolylmethyl) ester, (3S,4S,6S,10S,13S,15S,16S) BIS(THIAZOL-5-YLMETHYL)-4,15-DIHYDROXY-10-ISOPROPYL-8,11-DIOXO-3,6,13,16-TETRABENZYL-2,7,9,12,17-PENTAAZAOCTADECANEDIOATE, (3S,4S,6S,10S,13S,15S,16S)- THIAZOL-5-YLMETHYL ((1S,2S,4S)-1-BENZYL-4-(((2S)-2-((((1S,3S,4S)-1-BENZYL-3-HYDROXY-5-PHENYL-4-(((THIAZOL-5-YLMETHOXY)CARBONYL)AMINO)PENTYL)CARBAMOYL)AMINO)-3-METHYLBUTANOYL)AMINO)-2-HYDROXY-5-PHENYLPENTYL)CARBAMATE thiazol-5-ylmethyl ((5S,6S,8S,11S,15S,17S,18S)-5,8,15-tribenzyl-6,17-dihydroxy-11-isopropyl-3,10,13-trioxo-19-phenyl-1-(thiazol-5-yl)-2-oxa-4,9,12,14-tetraazanonadecan-18-yl)carbamate

๐Ÿ”ฌ Chemical Identifiers

CC(C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C[C@@H]([C@H](CC2=CC=CC=C2)NC(=O)OCC3=CN=CS3)O)NC(=O)N[C@@H](CC4=CC=CC=C4)C[C@@H]([C@H](CC5=CC=CC=C5)NC(=O)OCC6=CN=CS6)O
InChI=1S/C52H61N7O8S2/c1-35(2)48(49(62)55-40(23-36-15-7-3-8-16-36)27-46(60)44(25-38-19-11-5-12-20-38)57-51(64)66-31-42-29-53-33-68-42)59-50(63)56-41(24-37-17-9-4-10-18-37)28-47(61)45(26-39-21-13-6-14-22-39)58-52(65)67-32-43-30-54-34-69-43/h3-22,29-30,33-35,40-41,44-48,60-61H,23-28,31-32H2,1-2H3,(H,55,62)(H,57,64)(H,58,65)(H2,56,59,63)/t40-,41-,44-,45-,46-,47-,48-/m0/s1
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