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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24N4O6S2
Molecular Weight 420.504
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DORIPENEM

SMILES

[H][C@]12[C@@H](C)C(S[C@@H]3CN[C@H](CNS(N)(=O)=O)C3)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

InChI

InChIKey=AVAACINZEOAHHE-VFZPANTDSA-N
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

HIDE SMILES / InChI

Description

Doripenem is a synthetic carbapenem that has broad antibacterial potency against aerobic and anaerobic gram-positive and gram-negative bacteria. Doripenem is structurally related to beta-lactam antibiotics and shares the bactericidal mode of action of other β-lactam antibiotics by targeting penicillin-binding proteins (PBPs) to inhibit the biosynthesis of the bacterial cell wall. Doripenem is resistant to hydrolysis by most β-lactamases and is resistant to inactivation by renal dehydropeptidases. Doripenem has many similarities to the other carbapenems, as well as some important differences, such as greater potency against Pseudomonas aeruginosa. It was found to be similar to comparator agents. The most common adverse effects related to doripenem therapy were headache, nausea, diarrhea, rash, and phlebitis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
47.6 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DORIBAX
Curative
DORIBAX
Curative
DORIBAX

Cmax

ValueDoseCo-administeredAnalytePopulation
16.87 μg/mL
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
12.94 μg/mL
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
10.2 mg/L
250 mg single, intravenous
DORIPENEM plasma
Homo sapiens
23 μg/mL
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
52.98 μg × h/mL
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
70.64 μg × h/mL
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
13.8 mg × h/L
250 mg single, intravenous
DORIPENEM plasma
Homo sapiens
36.3 μg × h/mL
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
47.1 mg*h/L
500 mg 1 times / 8 hour multiple, intravenous
DORIPENEM serum
Homo sapiens
66.4 mg*h/L
1000 mg 1 times / 8 hour multiple, intravenous
DORIPENEM serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.93 h
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
4.04 h
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
0.91 h
250 mg single, intravenous
DORIPENEM plasma
Homo sapiens
1 h
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens
2.2 h
500 mg 1 times / 8 hour multiple, intravenous
DORIPENEM serum
Homo sapiens
2.4 h
1000 mg 1 times / 8 hour multiple, intravenous
DORIPENEM serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
91.9%
500 mg single, intravenous
DORIPENEM plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
500 mg administered every 8 hours by intravenous infusion over one hour in patients ≥18 years of age; for complicated intra-abdominal infection 5–14 days, for complicated UTI, including pyelonephritis 10 days.
Route of Administration: Intravenous
In Vitro Use Guide
HardyDisk™ Doripenem Antimicrobial Susceptibility Test Disks are used for semi-quantitative in vitro susceptibility testing by the agar diffusion test procedure (Kirby-Bauer) of rapidly growing and certain fastidious bacterial pathogens. The concentration of doripenem 10ug has been shown to be active against most isolates of the following microorganisms both in vitro and in clinical infections: Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Streptococcus constellatus, Streptococcus intermedius