ABC00085ED

Tigecycline Epimer (Crude)

Tigecycline Epimer (Crude) is a stereoisomeric impurity arising from stereochemical inversion at a chiral center within the glycylcycline scaffold of the parent drug, Tigecycline. This epimer retains the core tetracycline backbone with a glycylamido substituent at position 9 but exhibits altered configuration at a critical chiral carbon, disrupting the parent compound's pharmacophoric alignment. The molecule contains multiple hydroxyl, amino, and amide functional groups, with the epimeric modification influencing its solubility and chromatographic behavior. Synthetically, it emerges as a byproduct during asymmetric synthesis steps, necessitating its quantification in API purity profiling. This crude form serves as an HPLC reference standard for detecting epimeric impurities in Tigecycline drug substance batches.

On Request
Molecular Formula C29H39N5O8
Molecular Weight 585.6000
CAS Number 1422262-97-2 โœ“ Verified
PubChem CID 58747637 โ†—
Purity 95%
Product Type API Impurity
Parent Drug Tigecycline
Lead Time 14 Days
IUPAC Name (4R,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

๐Ÿ“ Synonyms

Tigecycline, (4R)- 1422262-97-2 Tigecycline Epimer U98SS1SU9R (4R,4aS,5aR,12aS)-9-(2-(tert-Butylamino)acetamido)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (4R,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((2-((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4R,4aS,5aR,12aS)- UNII-U98SS1SU9R (4R)-tigecycline SCHEMBL12593995

๐Ÿ”ฌ Chemical Identifiers

C(C)(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@H](C(=C(C([C@]4(C(=C3C(C2=C1O)=O)O)O)=O)C(=O)N)O)N(C)C)N(C)C
InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21+,29-/m0/s1
FPZLLRFZJZRHSY-RXEYFDPISA-N

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