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Home> Encyclopedia >Antibiotic and antimicrobial agents>Agrochemical Intermediates>Pharmaceutical Intermediates
Imipenem structure
Imipenem structure


Iupac Name:(5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CAS No.: 64221-86-9
Molecular Weight:299.35
Modify Date.: 2022-12-11 12:28
Introduction: Imipenem is a chemically stable thienamycin derivative with an antibacterialactivity that is broader in spectrum and of greater potency than most of the thirdgeneration cephalosporins. Combination with cilastatin, an inhibitor of renalbrush-border dehydropeptidase-I, increases both urinary and plasma levels ofimipenem. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(5r-(5-alpha,6-alpha(r*)))-nomethyl)amino)ethyl)thio)-7-oxo (5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure (5R,6S)-6-(1-hydroxyethyl)-3-({2-[(iminiomethyl)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid [5R-[5alpha, 6alpha(R*)]]-6-(1-Hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylicacid,6-(1-hydroxyethyl)-3-((2-((imi 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5R,6S)- 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5R,6S)- 2-[1,3-dioxo-1-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)amino]butan-2-yl]azobenzene-1,4-dicarboxylic acid dimethyl ester EINECS 264-734-5 imipemide imipenam Imipenem (JP14) Imipenem (MK-0787) Imipenen LMipeneM MFCD00864955 mk-787 N-Formimidoylthiena N-Formimidoylthienamycin Tienamycin

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1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C12H17N3O4S (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
1.62±0.1 g/cm3(Predicted)
2.1 Melting point
106-111 C
2.1 Boiling point
530.2±60.0 °C(Predicted)
2.1 Refractive index
2.1 Flash Point
296.9 °C
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Appearance
white crystalline powder
2.2 Chemical Properties
White Crystals
2.3 pKa
2.4 Water Solubility
Sparingly soluble in water, slightly soluble in methanol.
2.5 StorageTemp
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
3. Use and Manufacturing
3.1 Usage
Carbapenem antibacterial.
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Safety
Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-27-36/37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27:Take off immediately all contaminated clothing
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
HS Code:29419000
4.2 Specification

The 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-,(5R,6S)-, with the?CAS registry number 64221-86-9, has the IUPAC name of (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid. Its product categories are including Active Pharmaceutical Ingredients.

The physical properties of this chemical are as follows: (1)ACD/LogP: -2.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.74; (4)ACD/LogD (pH 7.4): -4.79; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 96.74; (13)Index of Refraction: 1.721; (14)Molar Refractivity: 72.7 cm3; (15)Molar Volume: 183.8 cm3; (16)Polarizability: 28.82 ×10-24 cm3; (17)Surface Tension: 71 dyne/cm; (18)Density: 1.62 g/cm3; (19)Flash Point: 296.9 °C; (20)Enthalpy of Vaporization: 97.84 kJ/mol; (21)Boiling Point: 567.3 °C at 760 mmHg; (22)Vapour Pressure: 3.11E-15 mmHg at 25°C; (23)Exact Mass: 299.093977; (24)MonoIsotopic Mass: 299.093977; (25)Topological Polar Surface Area: 142; (26)Heavy Atom Count: 20; (27)Complexity: 491.

When you are dealing with this chemical, you should be much more cautious. For being among the? irritant chemicals, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And take off immediately all contaminated clothing after contacting.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
(2)Isomeric SMILES: C[C@@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
(3)InChI: 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+/m0/s1

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 664ug/kg (0.664mg/kg) ? Journal of Antibiotics. Vol. 48, Pg. 408, 1995.
mouse LD50 oral > 5gm/kg (5000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 33(Suppl,
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

Chemotherapy Vol. 33(Suppl,
rat LD50 intravenous 1972mg/kg (1972mg/kg) ? Chemotherapy Vol. 33(Suppl,
rat LD50 oral > 5gm/kg (5000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 33(Suppl,

Chemotherapy Vol. 33(Suppl,

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4.3 Toxicity
Organic Compound; Amine; Ether; Amide; Ester; Drug; Anti-Bacterial Agent; Synthetic Compound

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)

no data available


no data available


no data available


no data available

2.3 Other hazards which do not result in classification

no data available

7. Precursor and Product
8. Other Information
8.0 Description
Imipenem is a chemically stable thienamycin derivative with an antibacterial activity that is broader in spectrum and of greater potency than most of the third generation cephalosporins. Combination with cilastatin, an inhibitor of renal brush-border dehydropeptidase-I, increases both urinary and plasma levels of imipenem.
8.1 Chemical Properties
White Crystals
8.2 Originator
Merck (USA)
8.3 Uses
Carbapenem antibacterial.
8.4 Manufacturing Process
Preparation of N-formimidoyl thienamycin:
Thienamycin (517 mg) is dissolved in pH 7 0.1 N phosphate buffer (25 ml) and cooled in an ice bath with magnetic stirring. The solution is adjusted to pH 8.5 using 2.5 N sodium hydroxide solution dispensed from an automatic burette. While maintaining a pH of 8.5, methyl formimidate hydrochloride (711 mg) is added portionwise over 2-3 minutes. After an additional 10 min, the pH of the solution is brought to 7.0 using 2.5 N hydrochloric acid. The solution is chromatographed on a column of XAD-2 resin (150 ml) which is eluted with water. The N-formimidoyl thienamycin derivative (imipenem) elutes in 1.5-2.0 column volumes (200-300 ml) and is lyophilized to a white solid (217 mg). UV (pH 7 0.1 N phosphate buffer); λmax297 nm (8,590); ir (Nujol mull) 1767 Cm-1(β-lactam).
Another method preparation of imipenem:
6-(1)-Hydroxyethyl-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate is converted to the diphenoxyphosphate enol ester and this in turn reacted with N,S-bistrimethylsilyl-N-formimidoylcysteamine (use of the bistrimethylsilylated reagent is necessary in order to avoid side reactions caused by cyclization reactions). As a result the (PhO)2OPO-groups are converted to Me3SiN = CHNH-groups. Removal of the protecting groups complete the synthesis of 1- azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-3-((2- ((iminomethyl)amino)ethyl)thio)-7-oxo-, (5R-(5-alpha,6-alpha(R*)))-.
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8.5 Brand name
8.6 Therapeutic Function
8.7 Antimicrobial activity
Imipenem shows potent activity against a wide range of Grampositive and Gram-negative aerobes and anaerobes, including many resistant to other agents.Concentrations (mg/L) inhibiting 50% of strains of other organisms are: Listeria monocytogenes, 0.03; Legionella pneumophila, 0.03; Enterococcus faecium, 4; Yersinia spp., 0.06. Mycobacterium fortuitum is inhibited by 6.25 mg/L. Imipenem is active against many Pseudomonas species, but not Sten. maltophilia. It is active against most anaerobes, with the exception of Cl. perfringens, which is only moderately susceptible. It is bactericidal at 2–4 times the MIC for most species, but some strains of Staph. aureus exhibit ‘tolerance’ . Bactericidal synergy with aminoglycosides, glycopeptides, fosfomycin and rifampicin (rifampin) has been observed against many strains of Staph. aureus and enterococci.
Antibacterial activity is unaffected by the presence of cilastatin, which is itself devoid of antimicrobial activity.
Imipenem is stable to hydrolysis by most serine β-lactamases, with the exception of the group 2f carbapenem-hydrolyzingenzymes hydrolyzingenzymes . Strains of B. fragilis, Aeromonas spp. and Sten. maltophilia can produce metallo-β-lactamases that hydrolyze the drug rapidly. These strains, in addition to occasional strains of enterobacteria, Acinetobacter baumannii and Ps. aeruginosa, show variable resistance to imipenem depending upon the level of carbapenem-hydrolyzing enzymes and the presence or absence of imipenem-specific porins. Efflux pumps also exist that may extrude imipenem from Gramnegative bacteria.
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8.8 Acquired resistance
Some strains of Citrobacter, Enterobacter, Proteus vulgaris, Providencia, Ps. aeruginosa and Serratia spp. may be resistant to imipenem and other β-lactam agents, often because of the selection of stably derepressed mutants expressing high levels of group 1 β-lactamases coupled with decreased intracellular drug levels due to porin mutations or increased efflux.
Induction of class 1 β-lactamases by imipenem in strains of Aeromonas, Pseudomonas and Serratia spp. is responsible for antagonism of β-lactamase-labile β-lactam agents in vitro. Imipenem resistance in Ps. aeruginosa can occur following selection of mutants that hyperproduce the group 1 cephalosporinase and which are also deficient in an outer membrane protein (OprD or D2) which specifically transports imipenem, but not cephalosporins or monobactams.
8.9 Clinical Use
Lower respiratory tract infections
Urinary tract infections (complicated and uncomplicated)
Intra-abdominal infections
Gynecological infections
Bacterial septicemia
Bone and joint infections
Skin and skin structure infections
Polymicrobial infections
8.10 Side effects
CNS effects such as confusional states and seizures have been reported, especially when recommended doses were exceeded, and in patients with renal failure or creatinine clearances of ≤20 mL/min/1.73 m2.
Other reactions include phlebitis/thrombophlebitis (3.1%), nausea (2.0%), diarrhea (1.8%) and vomiting (1.5%).
Increased hepatic enzymes may be seen in adults and children. Superinfection with Aspergillus, Candida and resistant Pseudomonas spp. have been described and pseudomembranous colitis has been reported.
Patients with a history of hypersensitivity reactions to penicillins, cephalosporins or other β-lactam antibiotics should be treated cautiously with carbapenems.
9. Computational chemical data
  • Molecular Weight: 299.35g/mol
  • Molecular Formula: C12H17N3O4S
  • Compound Is Canonicalized: True
  • XLogP3-AA: -0.7
  • Exact Mass: 299.09397721
  • Monoisotopic Mass: 299.09397721
  • Complexity: 491
  • Rotatable Bond Count: 6
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Topological Polar Surface Area: 142
  • Heavy Atom Count: 20
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
10. Question & Answer
  • Imipenem itself has outstanding antibacterial effects against both Gram-positive and Gram-negative bacteria. However, many people are not particularly familiar with the difference between Imipenem cru..
  • What are imipenem? Apr 04 2022
    Imipenem is an intravenous β-lactam antibiotic discovered by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s.
  • What is Imipenem? May 15 2020
    Imipenem (N-formimidoylthienamycin monohydrate) is a crystalline derivative of thienamycin, which is produced by Streptomyces cattleya. Its chemical name is (5 R,6S)-3-[[2-(formimidoylamino)ethyl]thio..
  • Imipenem (Imipenem) is a N-formimidoyl derivative of the natural antibiotic thienamycin. It is the first carbapenem antibiotic available for clinical use, combining the superior pharmacological effect..
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