Details of the Drug

General Information of Drug (ID: DMQ5S6C)

Drug Name
Tebipenem pivoxil
Synonyms
161715-24-8; Orapenem; TBPM-PI; L-084; ME1211; UNII-95AK1A52I8; LJC 11,084; 95AK1A52I8; LJC-11084; ME-1211; 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; Tebipenempivoxil; Tebipenem [INN]; (4R,5S,6S)-(Pivaloyloxy)methyl 3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (4R,5S,6S)-; Tebipenem pivoxil (L-084); Tebipenem pivoxil(L-084); Orapenem (TN); (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester; MLS006011128; SCHEMBL305541; Tebipenem pivoxil [USAN:INN]; CHEMBL2107486; GTPL10864; DTXSID00167228; CHEBI:135799; EX-A1256; HY-B0396; WHO 7924; ZINC4217736; Tebipenem pivoxil (JAN/USAN/INN); 2748AH; CT0255; LJC 11084; MFCD17215369; s2159; AKOS015899532; CCG-269673; LJC-11,084; NCGC00346570-01; NCGC00346570-04; (pivaloyloxy)methyl (4R,5S,6S)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; [(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate; AC-22712; AS-75334; L-084;ME1211; SMR004702908; L 084; D09598; AB01566835_01; Q1623593; (4R,5R,6S)-3-((1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy) methyl ester; 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Indication
Disease Entry ICD 11 Status REF
Respiratory tract infection CA45 Approved [1]
ATC Code
J01DH06: Tebipenem pivoxil
J01DH: Carbapenems
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 497.6
Logarithm of the Partition Coefficient (xlogp) 2.3
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C22H31N3O6S2
IUPAC Name
2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Canonical SMILES
C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)OCOC(=O)C(C)(C)C)[C@@H](C)O
InChI
InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1
InChIKey
SNUDIPVBUUXCDG-QHSBEEBCSA-N
Cross-matching ID
PubChem CID
9892071
ChEBI ID
CHEBI:135799
CAS Number
161715-24-8
UNII
95AK1A52I8
DrugBank ID
DB16840
TTD ID
D4LOR2

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Pharmacodynamics of Tebipenem: New Options for Oral Treatment of Multidrug-Resistant Gram-Negative Infections. Antimicrob Agents Chemother. 2019 Jul 25;63(8):e00603-19.
2 In Vitro Activity of Tebipenem (SPR859) against Penicillin-Binding Proteins of Gram-Negative and Gram-Positive Bacteria. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02181-18.