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Substance Name: Imipenem
RN: 64221-86-9
UNII: Q20IM7HE75
InChIKey: ZSKVGTPCRGIANV-ZXFLCMHBSA-N

Note

  • Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.

Molecular Formula

  • C12-H17-N3-O4-S

Molecular Weight

  • 299.3493
 

Classification Code

  • Drug / Therapeutic Agent
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Names and Synonyms

Results Name

  • Imipenem

Name of Substance

  • Imipenem
  • Imipenem anhydrous
  • Imipenem [INN]

MeSH Heading

  • Imipenem

Synonyms

  • (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
  • EINECS 264-734-5
  • Imipemide
  • Imipenem
  • Imipenemum
  • Imipenemum [Latin]
  • Imipenen
  • MK 0787
  • MK-787
  • N-Formimidoylthienamycin
  • Tienamycin
  • UNII-Q20IM7HE75

Systematic Names

  • 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*)))-
  • Imipenem

Registry Numbers

CAS Registry Number

  • 64221-86-9

FDA UNII

  • Q20IM7HE75

Other Registry Numbers

  • 127644-14-8
  • 345631-68-7
  • 75902-88-4

Related Registry Numbers

  • 64221-86-9 (anhydrous)
  • 64221-86-9 (Parent)

System Generated Number

  • 0064221869

Structure Descriptors

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

InChIKey

ZSKVGTPCRGIANV-ZXFLCMHBSA-N

Smiles

N12[C@@H]([C@H](C2=O)[C@@H](C)O)CC(=C1C(=O)O)SCCNC=N

Toxicity

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) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

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,
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 33(Suppl,