Imipenem

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Imipenem are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Imipenem?

The molecule Imipenem presents a molecular formula of C12H17N3O4S and its IUPAC name is (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Imipenem is a potent broad-spectrum antibiotic that is used to treat a variety of bacterial infections. It is a carbapenem, a class of antibiotics that are known for their effectiveness against gram-negative bacteria, including those that are resistant to other antibiotics..

The imipenem molecule is composed of a beta-lactam ring, which is the active site that inhibits the synthesis of the bacterial cell wall, and a side chain that is responsible for its antimicrobial activity. The beta-lactam ring is common to all penicillins and cephalosporins, and is responsible for the ability of these drugs to inhibit the production of peptidoglycan, a key component of the bacterial cell wall..

Imipenem is typically used to treat infections that are resistant to other antibiotics, such as those caused by Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa. It is often used in combination with other antibiotics, such as cilastatin, to increase its effectiveness and reduce the risk of resistance..

One of the key advantages of imipenem is its ability to penetrate the bacterial cell wall, which allows it to reach the site of infection and effectively kill the bacteria. It is also effective against a wide range of bacteria, including those that are resistant to other antibiotics..

However, like all antibiotics, imipenem can have side effects, including nausea, diarrhea, and allergic reactions. It should be used with caution in patients with a history of allergies or kidney problems, as it can be toxic to the kidneys at high doses..

Summary

From all the above, imipenem is a powerful antibiotic that is effective against a wide range of bacterial infections, including those that are resistant to other antibiotics. While it can have side effects, it is an important tool in the fight against bacterial infections and is often used in combination with other antibiotics to increase its effectiveness..

3D structure

Cartesian coordinates

Geometry of Imipenem in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Imipenem ZSKVGTPCRGIANV-ZXFLCMHBSA-N chemical compound 2D structure molecule svg
Imipenem

 

Molecule descriptors

 
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
InChI codeInChI=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
InChI KeyZSKVGTPCRGIANV-ZXFLCMHBSA-N
SMILESC[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(SCCNC=N)C[C@H]12

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (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)-3-((2-formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5R,6S)-3-(2-formimidamidoethylthio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-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-[(1R)-1-hydroxyethyl]-3-(2-methanimidamidoethylsulfanyl)-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,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • 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*)))-
  • 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)-
  • 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*)))-
  • 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)-
  • 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)-
  • 103730-39-8
  • 3-[(2-Aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methylester monohydrochloride compd. with 1-methyl-2-pyrrolidinone (1:1)
  • 64221-86-9
  • 74431-23-5
  • 847I667
  • AB01563339_01
  • AS-75130
  • Anhydrous Imipenem
  • BCP13012
  • BDBM50049708
  • BDBM50213266
  • BIDD:GT0686
  • BPBio1_000525
  • BSPBio_000477
  • C06665
  • CCG-220519
  • CCG-221583
  • CS-0077844
  • D04515
  • D96091
  • DB01598
  • DSSTox_CID_3143
  • DSSTox_GSID_23143
  • DSSTox_RID_76888
  • Epitope ID:120384
  • GTPL10821
  • HMS1569H19
  • HMS2090A15
  • HMS2096H19
  • HMS3260H20
  • HMS3713H19
  • HY-B1369A
  • IMIPENEM ANHYDRATE
  • Imipemide
  • Imipenem
  • Imipenem (INN)
  • Imipenem anhydrous
  • Imipenem hydrate
  • Imipenem, Anhydrous
  • Imipenem, N-Formimidoyl thienamycin
  • Imipenemum
  • Imipenen
  • LP00279
  • MK 0787
  • MK-0787
  • MK-787
  • MK0787
  • N-Formimidoylthienamycin
  • N-formimidoyl thienamycin
  • NCGC00016928-01
  • NCGC00167958-01
  • NCGC00167958-02
  • NCGC00167958-03
  • NCGC00167958-05
  • NCGC00167958-09
  • NCGC00260964-01
  • NSC-717864
  • NSC717864
  • NSC759901
  • Pharmakon1600-01506001
  • Prestwick0_000519
  • Prestwick1_000519
  • Prestwick2_000519
  • Prestwick3_000519
  • Prestwick_844
  • Primaxin (imipenem + cilastatin)
  • Q20IM7HE75
  • Q425152
  • Recarbrio (imipenem + cilastatin + relebactam).
  • SDCCGSBI-0633697.P001
  • SR-05000000294
  • SR-05000000294-2
  • SR-05000000294-5
  • Tienamycin
  • [5R-[5.alpha.,6.alpha.(R*)]]-6-(1-Hydroxyethyl)-3-[[2- [(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2- ene-2-carboxylic acid monohydrate
  • imipen
  • imipenem

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4097225
  • CAS-64221-86-9
  • UNII-Q20IM7HE75
  • AKOS016010844
  • DTXSID2023143
  • CHEMBL148
  • CHEBI:471744
  • Tox21_110689
  • Tox21_500279
  • Tox21_110689_1
  • EINECS 264-734-5
  • SPBio_002398
  • SCHEMBL1649260
  • SCHEMBL8781920

Physico-Chemical properties

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
Molecular formulaC12H17N3O4S
Molecular weight299.346
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity79.02
LogP0.3
Topological polar surface area139.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.