Imipenem | CAS#64221-86-9 | antibacterial

MedKoo Cat#: 584478 | Name: Imipenem

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Imipenem is a broad-spectrum, β-lactam antibiotic of the carbapenem class, primarily used against Gram-positive and Gram-negative bacteria, including many multidrug-resistant strains. It exerts its bactericidal effect by inhibiting penicillin-binding proteins (PBPs), thereby blocking bacterial cell wall synthesis. Imipenem is notably effective against Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, and Bacteroides fragilis. In vitro, its minimum inhibitory concentration (MIC) values typically range from 0.06–4 µg/mL for susceptible strains. For example, the MIC₉₀ for E. coli and K. pneumoniae is commonly reported at ≤1 µg/mL, while for P. aeruginosa it is around 2–4 µg/mL. Due to rapid degradation by renal dehydropeptidase I, it is co-administered with cilastatin to inhibit enzymatic hydrolysis and prolong its plasma half-life.

Chemical Structure

Imipenem

CAS#64221-86-9 (anhydrous)

Theoretical Analysis

MedKoo Cat#: 584478

Name: Imipenem

CAS#: 64221-86-9 (anhydrous)

Chemical Formula: C12H17N3O5S

Exact Mass: 315.0889

Molecular Weight: 315.34

Elemental Analysis: C, 45.71; H, 5.43; N, 13.33; O, 25.37; S, 10.17

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Related CAS #

74431-23-5 (hydrate) 64221-86-9 (anhydrous)

Synonym

Primaxin, MK-0787; MK 0787; MK0787; MK-787; MK787; MK 787; N-Formimidoylthienamycin; Tienamycin; Imipemide; Imipenem hydrate; Recarbrio；

IUPAC/Chemical Name

(5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure hydrate

InChi Key

VBTPAOZKIGVELK-ZXFLCMHBSA-N

InChi Code

InChI=1S/C12H17N3O5S/c1-6(16)9-7-4-8(21-3-2-14-5-13)11(20-12(18)19)15(7)10(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1

SMILES Code

O=C(O)OC(N12)=C(SCCNC=N)C[C@]2([H])[C@@H]([C@H](O)C)C1=O

Appearance

Solid powder

Purity

>90% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Imipenem (MK0787), a stable crystalline derivative of thienamycin, is an antibiotic and has the excellent activity against a broad range of gram-positive and gram-negative aerobic and anaerobic bacteria. Imipenem can be used for the research of carbapenem-nonsusceptible and P. aeruginosa biofilm infections.

In vitro activity:

Imipenem, a β-lactam antibiotic, binds to penicillin binding protein 2 with the highest affinity and produces rounded cells. The binding of imipenem causes cells to lyse quickly and thereby to release less free endotoxin. Reference: Antimicrob Agents Chemother. 2014 Jun;58(6):3276-84. https://pubmed.ncbi.nlm.nih.gov/24687492/

In vivo activity:

Using a rabbit ear model, this study also demonstrated that imipenem was highly effective against preformed K. pneumoniae biofilms in wounds. Reference: Antimicrob Agents Chemother. 2014;58(2):1208-13. https://pubmed.ncbi.nlm.nih.gov/24247132/

Preparing Stock Solutions

The following data is based on the product molecular weight 315.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Heine HS, Louie A, Adamovicz JJ, Amemiya K, Fast RL, Miller L, Opal SM, Palardy J, Parejo NA, Sörgel F, Kinzig-Schippers M, Drusano GL. Evaluation of imipenem for prophylaxis and therapy of Yersinia pestis delivered by aerosol in a mouse model of pneumonic plague. Antimicrob Agents Chemother. 2014 Jun;58(6):3276-84. doi: 10.1128/AAC.02420-14. Epub 2014 Mar 31. PMID: 24687492; PMCID: PMC4068467. 2. Chakraborty S, Asgeirsson B, Minda R, Salaye L, Frère JM, Rao BJ. Inhibition of a cold-active alkaline phosphatase by imipenem revealed by in silico modeling of metallo-β-lactamase active sites. FEBS Lett. 2012 Oct 19;586(20):3710-5. doi: 10.1016/j.febslet.2012.08.030. Epub 2012 Sep 11. PMID: 22982109. 3. Chen P, Seth AK, Abercrombie JJ, Mustoe TA, Leung KP. Activity of imipenem against Klebsiella pneumoniae biofilms in vitro and in vivo. Antimicrob Agents Chemother. 2014;58(2):1208-13. doi: 10.1128/AAC.01353-13. Epub 2013 Nov 18. PMID: 24247132; PMCID: PMC3910830. 4. Dupuis A, Couet W, Paquereau J, Debarre S, Portron A, Jamois C, Bouquet S. Pharmacokinetic-pharmacodynamic modeling of the electroencephalogram effect of imipenem in healthy rats. Antimicrob Agents Chemother. 2001 Jun;45(6):1682-7. doi: 10.1128/AAC.45.6.1682-1687.2001. PMID: 11353611; PMCID: PMC90531.

In vitro protocol:

In vivo protocol:

1. Chen P, Seth AK, Abercrombie JJ, Mustoe TA, Leung KP. Activity of imipenem against Klebsiella pneumoniae biofilms in vitro and in vivo. Antimicrob Agents Chemother. 2014;58(2):1208-13. doi: 10.1128/AAC.01353-13. Epub 2013 Nov 18. PMID: 24247132; PMCID: PMC3910830. 2. Dupuis A, Couet W, Paquereau J, Debarre S, Portron A, Jamois C, Bouquet S. Pharmacokinetic-pharmacodynamic modeling of the electroencephalogram effect of imipenem in healthy rats. Antimicrob Agents Chemother. 2001 Jun;45(6):1682-7. doi: 10.1128/AAC.45.6.1682-1687.2001. PMID: 11353611; PMCID: PMC90531.

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