74431-23-5 Usage
Description
Imipenem, also known as N-formimidoylthienamycin monohydrate, is a crystalline derivative of thienamycin, which is produced by Streptomyces cattleya. It is an off-white, non-hygroscopic crystalline compound with a molecular weight of 317.37. Imipenem is an extremely broad-spectrum semi-synthetic antibiotic with a chemical structure of β-lactam.
Uses
1. Used in Pharmaceutical Industry:
Imipenem is used as an extremely broad-spectrum semi-synthetic antibiotic for treating various bacterial infections. It has a broad spectrum of antimicrobial action, which includes most clinically significant microorganisms such as Gram-positive, Gram-negative, aerobic, and anaerobic bacteria. It is resistant to most beta-lactamases of Gram-positive and Gram-negative bacteria.
2. Used in Treatment of Lower Respiratory Tract Infections:
Imipenem is used as an antibiotic for bacterial infections of the lower respiratory tract, providing effective treatment against a wide range of bacteria causing such infections.
3. Used in Treatment of Urinary and Sexual Tract Infections:
Imipenem is used as an antibiotic for infections of the urinary and sexual tracts, offering a broad spectrum of activity against the bacteria responsible for these infections.
4. Used in Treatment of Bone, Joint, Skin, and Soft Tissue Infections:
Imipenem is used as an antibiotic for infections of bones, joints, skin, and soft tissues, effectively targeting the bacteria causing these types of infections.
5. Used in Treatment of Intra-abdominal and Gynecological Infections:
Imipenem is used as an antibiotic for intra-abdominal and gynecological infections, providing a broad spectrum of activity against the bacteria involved in these conditions.
6. Used in Treatment of Bacterial Septicemia and Endocarditis:
Imipenem is used as an antibiotic for bacterial septicemia and endocarditis, offering effective treatment against the bacteria causing these severe infections.
7. Used in Combination with Cilastatin (Primaxin):
Imipenem undergoes enzymatic inactivation in the kidneys. 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, providing a more effective treatment option for various bacterial infections.
Discovery
Imipenem is an intravenous β-lactam antibiotic discovered by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s. Imipenem was patented in 1975 and approved for medical use in 1985.
Imipenem has a broad spectrum of activity against aerobic and anaerobic, Gram-positive and Gram-negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. It is not active against MRSA, however.
Broad-spectrum antibiotic
Imipenem is a 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 many beta-lactamases. Similar compounds include meropenem, known for having greater activity against Gram negative bacteria, and the newer ertapenem which exhibits a longer half-life due to increased binding to plasma proteins.
Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria.This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to penicillin-binding proteins (PBPs).
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-[5α,6α(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 α-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.
Check Digit Verification of cas no
The CAS Registry Mumber 74431-23-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,4,3 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 74431-23:
(7*7)+(6*4)+(5*4)+(4*3)+(3*1)+(2*2)+(1*3)=115
115 % 10 = 5
So 74431-23-5 is a valid CAS Registry Number.
InChI:InChI=1/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
