Imipenem
Synonym(s):(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 monohydrate;Imipenem monohydrate;Primaxin monohydrate;Tienam monohydrate
- CAS NO.:74431-23-5
- Empirical Formula: C12H19N3O5S
- Molecular Weight: 317.36
- MDL number: MFCD00864955
- EINECS: 680-398-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-07 08:52:35
What is Imipenem?
Chemical properties
Off-White Solid
The Uses of Imipenem
Imipenem has a broad spectrum of antimicrobial action, which includes most clinically
significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is
resistant with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. It is used for bacterial infections of the lower respiratory tract, infections of the urinary
and sexual tracts, infections of bones, joints, skin, soft tissues, intraabdominal and gynecological infections, bacterial septicemia, and endocarditis.
Imipenem undergoes enzymatic inactivation in the kidneys. In order to avoid this problem,
it is used in a 1:1 ratio in combination with cilastatin—the sodium salt of [R-[R,S-(Z)]]-7-[(2-
amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)aminocarbonyl-2-heptenoic acid
(32.1.3.6), which inhibits metabolisms of imipenem in the kidneys. This combination of two
compounds is also used in medicine under the name primaxin.
The Uses of Imipenem
An extremely broad-spectrum semi-synthetic antibiotic
The Uses of Imipenem
antiulcer
The Uses of Imipenem
antidiabetic
Definition
ChEBI: Imipenem hydrate is a member of carbapenems. It contains an imipenem.
General Description
Chemical structure: ?-lactam
Biochem/physiol Actions
Imipenem is found effective against gram positive and negative aerobes and anaerobes. Imipenem is often combined with cilastatin, to inhibit its metabolism in kidney.
Synthesis
Imipenem, [5R-[5|á,6|á(R)]]-6-(1-hydroxyethyl)-3-[[2-[(iminomethyl)amino] ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-2-carboxylic acid (32.1.3.1), is the only carbapenem presently used in clinics. It is synthesized from thienamycin isolated from Streptomyces cattleya by reacting it with the methyl formimidate.
Unlike penicillins and cephalosporins, which have a side aminoacyl group joined to the betalactam ring, imipenem has a |á-hydroxyethyl side chain. Significant resistance to hydrolysis by beta-lactamases is observed in this compound, evidently thanks to the trans-configuration of the side chain, while the side chain of penicillins and cephalosporins have a cis configuration.
Properties of Imipenem
Melting point: | 193-198°C |
Boiling point: | 567℃ |
RTECS | CL5446516 |
Flash point: | >110°(230°F) |
storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
solubility | H2O: >5mg/mL |
form | powder |
pka | pKa 3.2/9.9(H2O,t = 25) (Uncertain) |
color | white to beige |
Water Solubility | Soluble in water at 5mg/ml |
CAS DataBase Reference | 74431-23-5(CAS DataBase Reference) |
Safety information for Imipenem
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for Imipenem
New Products
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