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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H17N3O4S
Molecular Weight 299.346
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMIPENEM ANHYDROUS

SMILES

[H][C@]12CC(SCCNC=N)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

InChI

InChIKey=ZSKVGTPCRGIANV-ZXFLCMHBSA-N
InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1

HIDE SMILES / InChI

Description

Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem has a broad spectrum of activity against aerobic and anaerobic Gram positive as well as Gram negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. Imipenem is rapidly degraded by the renal enzyme dehydropeptidase when administered alone, and is always co-administered with cilastatin to prevent this inactivation. The bactericidal activity of imipenem results from the inhibition of cell wall synthesis. Its greatest affinity is for penicillin binding proteins (PBPs) 1A, 1B, 2, 4, 5 and 6 of Escherichia coli, and 1A, 1B, 2, 4 and 5 of Pseudomonas aeruginosa. The lethal effect is related to binding to PBP 2 and PBP 1B. Imipenem is marketed under the brand name Primaxin. PRIMAXIN I.M. (Imipenem and Cilastatin for Injectable Suspension) is a formulation of imipenem (a thienamycin antibiotic) and cilastatin sodium (the inhibitor of the renal dipeptidase, dehydropeptidase I). PRIMAXIN I.M. is a potent broad spectrum antibacterial agent for intramuscular administration.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PRIMAXIN
Curative
PRIMAXIN
Curative
PRIMAXIN
Curative
PRIMAXIN
Curative
PRIMAXIN
Curative
PRIMAXIN

Cmax

ValueDoseCo-administeredAnalytePopulation
15.86 mg/L
0.5 g 4 times / day multiple, oral
IMIPENEM blood
Homo sapiens
48.43 mg/L
0.5 g 4 times / day multiple, oral
IMIPENEM blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
28.17 mg × h/L
0.5 g 4 times / day multiple, oral
IMIPENEM blood
Homo sapiens
18.7 mg × h/L
250 mg 1 times / week other, intravenous
IMIPENEM plasma
Homo sapiens
36.5 mg × h/L
500 mg 1 times / week other, intravenous
IMIPENEM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.28 h
0.5 g 4 times / day multiple, oral
IMIPENEM blood
Homo sapiens
1 h
250 mg 1 times / week other, intravenous
IMIPENEM plasma
Homo sapiens
1 h
500 mg 1 times / week other, intravenous
IMIPENEM plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
PRIMAXIN I.M. (Imipenem and Cilastatin for Injection) is for intramuscular use only. Patients with lower respiratory tract infections, skin and skin structure infections, and gynecologic infections of mild to moderate severity may be treated with 500 mg or 750 mg administered every 12 hours depending on the severity of the infection. Intra-abdominal infection may be treated with 750 mg every 12 hours. Total daily IM dosages greater than 1500 mg per day are not recommended.
Route of Administration: Intramuscular
In Vitro Use Guide
The concentration of Imipenem that inhibited binding of radiolabeled [3H]penicillin to PBP 2a by 50% was 68 ug/ml