Details of the Drug

General Information of Drug (ID: DM9UCJK)

Drug Name

Doripenem

Synonyms

Doribax; S 4661; S-4661; Doripenem (USAN/INN); (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Urinary tract infection	GC08	Approved	[1], [2]
Gram-positive bacterial infection	1B74-1G40	Phase 3	[3]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

420.5

Topological Polar Surface Area (xlogp)

-3.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The clearance of drug is 10.3 L/h [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 1 hour [5]
Metabolism: The drug is metabolized via the dehydropeptidase-I into a microbiologically inactive ring-opened metabolite doripenem-M1 [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.92% [5]
Vd: The volume of distribution (Vd) of drug is 16.8 L [4]

Chemical Identifiers

Formula: C15H24N4O6S2
IUPAC Name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Canonical SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O
InChI: InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1
InChIKey: AVAACINZEOAHHE-VFZPANTDSA-N

Cross-matching ID

PubChem CID: 73303
ChEBI ID: CHEBI:135928
CAS Number: 148016-81-3
DrugBank ID: DB06211
TTD ID: D03QWT
INTEDE ID: DR0534

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Dihydropteroate synthetase (Bact folP)	TT4ILYC	DHPS_ECOLI	Inhibitor	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dehydropeptidase-I (DPEP1)	DEAMVR3	DPEP1_HUMAN	Substrate	[7]
Beta-lactamase (blaB)	DEC3G7M	A0A1S7IV31_ENTAS	Substrate	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	2007 FDA drug approvals: a year of flux. Nat Rev Drug Discov. 2008 Feb;7(2):107-9.
2	2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
3	Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
4	An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	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.
7	Disposition, metabolism, and excretion of [14C]doripenem after a single 500-milligram intravenous infusion in healthy men. Antimicrob Agents Chemother. 2008 Oct;52(10):3478-83.
8	FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.
9	In vitro activities of novel antifolate drug combinations against Plasmodium falciparum and human granulocyte CFUs. Antimicrob Agents Chemother. 1995 Apr;39(4):948-52.
10	Sulfadiazine/hydroxypropyl-beta-cyclodextrin host-guest system: Characterization, phase-solubility and molecular modeling. Bioorg Med Chem. 2008 May 15;16(10):5788-94.
11	Polymyxin B sulfate and colistin: old antibiotics for emerging multiresistant gram-negative bacteria. Ann Pharmacother. 1999 Sep;33(9):960-7.
12	The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
13	Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63.
14	A confirmatory method for the simultaneous extraction, separation, identification and quantification of Tetracycline, Sulphonamide, Trimethoprim an... J Chromatogr A. 2009 Nov 13;1216(46):8110-6.
15	Structures of gramicidins A, B, and C incorporated into sodium dodecyl sulfate micelles. Biochemistry. 2001 Oct 2;40(39):11676-86.
16	Structural transitions as determinants of the action of the calcium-dependent antibiotic daptomycin. Chem Biol. 2004 Jul;11(7):949-57.