Imipenem hydrate | CAS#74431-23-5 | antibiotics

MedKoo Cat#: 318055 | Name: Imipenem hydrate

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 hydrate

CAS#74431-23-5 (hydrate)

Theoretical Analysis

MedKoo Cat#: 318055

Name: Imipenem hydrate

CAS#: 74431-23-5 (hydrate)

Chemical Formula: C12H19N3O5S

Exact Mass: 0.0000

Molecular Weight: 317.36

Elemental Analysis: C, 45.42; H, 6.03; N, 13.24; O, 25.21; S, 10.10

Price and Availability

Size	Price	Availability
500mg	USD 350.00	2 Weeks
1g	USD 550.00	2 Weeks
5g	USD 750.00	2 Weeks
10g	USD 1,250.00	2 Weeks

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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)-3-((2-((E)-(aminomethylene)amino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate

InChi Key

GSOSVVULSKVSLQ-JJVRHELESA-N

InChi Code

InChI=1S/C12H17N3O4S.H2O/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);1H2/t6-,7-,9-;/m1./s1

SMILES Code

O=C(C(N12)=C(SCC/N=C/N)C[C@]2([H])[C@@H]([C@H](O)C)C1=O)O.[H]O[H]

Appearance

Solid powder

Purity

>98% (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, not in water

Shelf Life

>2 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 monohydrate, 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 monohydrate 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/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	3.15
	PBS (pH 7.2)\	2.0	6.30
	Water	35.1	110.51

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 317.36 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.

1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548708/ PubMed PMID: 31644018. 2: Yang J, Wang Q, Wang S, Zhang Y, Wang Z. Unusual Drug Fever Caused by Imipenem/Cilastatin and a Review of Literature. Heart Surg Forum. 2019 Mar 8;22(2):E119-E123. doi: 10.1532/hsf.2141. Review. PubMed PMID: 31013221. 3: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500987/ PubMed PMID: 30000046. 4: Zhanel GG, Lawrence CK, Adam H, Schweizer F, Zelenitsky S, Zhanel M, Lagacé-Wiens PRS, Walkty A, Denisuik A, Golden A, Gin AS, Hoban DJ, Lynch JP 3rd, Karlowsky JA. Imipenem-Relebactam and Meropenem-Vaborbactam: Two Novel Carbapenem-β-Lactamase Inhibitor Combinations. Drugs. 2018 Jan;78(1):65-98. doi: 10.1007/s40265-017-0851-9. Review. Erratum in: Drugs. 2018 May 10;:. PubMed PMID: 29230684. 5: Sedighi M, Salehi-Abargouei A, Oryan G, Faghri J. Epidemiology of VIM-1-imipenem resistant Pseudomonas aeruginosa in Iran: A systematic review and meta-analysis. J Res Med Sci. 2014 Sep;19(9):899-903. Review. PubMed PMID: 25535506; PubMed Central PMCID: PMC4268200. 6: Sidorenko SV, Partina IV, Ageevets VA. [Imipenem: 30-year experience in therapy]. Antibiot Khimioter. 2013;58(5-6):55-61. Review. Russian. PubMed PMID: 24757826. 7: Zilberberg MD, Chen J, Mody SH, Ramsey AM, Shorr AF. Imipenem resistance of Pseudomonas in pneumonia: a systematic literature review. BMC Pulm Med. 2010 Aug 26;10:45. doi: 10.1186/1471-2466-10-45. Review. PubMed PMID: 20796312; PubMed Central PMCID: PMC2939581. 8: Hoffman J, Trimble J, Brophy GM. Safety of imipenem/cilastatin in neurocritical care patients. Neurocrit Care. 2009;10(3):403-7. doi: 10.1007/s12028-008-9170-z. Epub 2008 Dec 31. Review. PubMed PMID: 19116700. 9: Rodloff AC, Goldstein EJ, Torres A. Two decades of imipenem therapy. J Antimicrob Chemother. 2006 Nov;58(5):916-29. Epub 2006 Sep 22. Review. PubMed PMID: 16997845. 10: Edwards SJ, Emmas CE, Campbell HE. Systematic review comparing meropenem with imipenem plus cilastatin in the treatment of severe infections. Curr Med Res Opin. 2005 May;21(5):785-94. Review. PubMed PMID: 15969878. 11: Dailly E, Kergueris MF, Pannier M, Jolliet P, Bourin M. Population pharmacokinetics of imipenem in burn patients. Fundam Clin Pharmacol. 2003 Dec;17(6):645-50. Review. PubMed PMID: 15015709. 12: Klastersky JA. Use of imipenem as empirical treatment of febrile neutropenia. Int J Antimicrob Agents. 2003 May;21(5):393-402. Review. PubMed PMID: 12727070. 13: Salaria M. Imipenem. Indian Pediatr. 2001 Dec;38(12):1370-3. Review. PubMed PMID: 11752734. 14: Yew WW, Wong PC, Lee J, Fung SL, Wong CF, Chan CY. Report of eight cases of pulmonary actinomycosis and their treatment with imipenem-cilastatin. Monaldi Arch Chest Dis. 1999 Apr;54(2):126-9. Review. PubMed PMID: 10394825. 15: Hellinger WC, Brewer NS. Carbapenems and monobactams: imipenem, meropenem, and aztreonam. Mayo Clin Proc. 1999 Apr;74(4):420-34. Review. PubMed PMID: 10221472. 16: Boyer-Mariotte S. [Enzymatic resistance to imipenem in gram-negative bacilli: NMC-A, an original carbapenemase]. Ann Pharm Fr. 1998;56(6):244-9. Review. French. PubMed PMID: 9872010. 17: Balfour JA, Bryson HM, Brogden RN. Imipenem/cilastatin: an update of its antibacterial activity, pharmacokinetics and therapeutic efficacy in the treatment of serious infections. Drugs. 1996 Jan;51(1):99-136. Review. PubMed PMID: 8741235. 18: Tallarigo C, Comunale L, Baldassarre R, Poletti G. [Multicenter comparative study of meropenem vs. imipenem in the intramuscular treatment of hospital infections of the urinary tract]. Minerva Urol Nefrol. 1995 Sep;47(3):147-56. Review. Italian. PubMed PMID: 8815553. 19: Ennis DM, Cobbs CG. The newer cephalosporins. Aztreonam and imipenem. Infect Dis Clin North Am. 1995 Sep;9(3):687-713. Review. PubMed PMID: 7490439. 20: Edwards JR, Turner PJ. Laboratory data which differentiate meropenem and imipenem. Scand J Infect Dis Suppl. 1995;96:5-10. Review. PubMed PMID: 7652504.