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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.