Details of the Drug

General Information of Drug (ID: DMDU0BV)

Drug Name

Pivmecillinam

Synonyms

Coactabs; PMPC; Pivamdinocillin; Pivmecilinamo; Pivmecillinamum; Selexid; Amdinocillin Pivoxil; Amdinocillin pivoxil [USAN]; Mecillinam Pivaloyl Ester; Amdinocillin pivoxil (USAN); Amdinocillin, pivaloyloxymethyl ester; Coactabs (TN); Penomax (TN); Pivmecilinamo [INN-Spanish]; Pivmecillinam (INN); Pivmecillinamum [INN-Latin]; Ro 10-9071; Selexid (TN); [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylate; [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; [(2,2-dimethylpropanoyl)oxy]methyl(2s,5r,6r)-6-{[(e)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; Hydroxymethyl (2S,5R,6R)-6-(((hexahydro-1H-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate pivalate (ester); 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 2,2-dimethylpropanoyloxymethyl (5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Indication

Disease Entry	ICD 11	Status	REF
Urinary tract infection	GC08	Approved	[1], [2]

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

439.6

Topological Polar Surface Area (xlogp)

3.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is well absorbed after oral administration [3]

Chemical Identifiers

Formula: C21H33N3O5S
IUPAC Name: 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C
InChI: InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChIKey: NPGNOVNWUSPMDP-HLLBOEOZSA-N

Cross-matching ID

PubChem CID: 115163
ChEBI ID: CHEBI:51210
CAS Number: 32886-97-8
DrugBank ID: DB01605
TTD ID: D08HDY

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	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drug information of Pivmecillinam, 2008. eduDrugs.
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4	Association between antimicrobial consumption and resistance in Escherichia coli. Antimicrob Agents Chemother. 2009 Mar;53(3):912-7.
5	Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80.
6	Bacteriological characteristics of Staphylococcus aureus isolates from humans and bulk milk. J Dairy Sci. 2008 Feb;91(2):564-9.
7	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8	Activities of antibiotics against methicillin-resistant Staphylococcus aureus with particular reference to synergetic effect between ticarcillin and fosfomycin on penicillinase non-producing methicillin-resistant S. aureus. Jpn J Antibiot. 1993 Jun;46(6):421-7.
9	Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
10	Penicillin-binding protein sensitive to cephalexin in sporulation of Bacillus cereus. Microbiol Res. 1997 Sep;152(3):227-32.
11	Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30.
12	Relationship between penicillin-binding protein patterns and beta-lactamases in clinical isolates of Bacteroides fragilis with different susceptibility to beta-lactam antibiotics. J Med Microbiol. 2004 Mar;53(Pt 3):213-21.
13	Resistance of Pseudomonas aeruginosa to cefsulodin: modification of penicillin-binding protein 3 and mapping of its chromosomal gene. J Antimicrob Chemother. 1990 Apr;25(4):513-23.