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Doripenem
Systematic (IUPAC) name
(4R,5S,6S)-6-(1-hydroxyethyl)-4-methyl-7-oxo-3-
[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]
sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Identifiers
CAS number 148016-81-3
ATC code J01DH04
PubChem 73303
Chemical data
Formula C 15H24N4O6S2  
Mol. mass 420.50426 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism Renal
Half life  ?
Excretion  ?
Therapeutic considerations
Licence data

US FDA:link

Pregnancy cat.  ?
Legal status -only (US)
Routes IM, IV

Doripenem (common name doripenem monohydrate) is an ultra-broad spectrum injectable antibiotic. It is a beta-lactam and belongs to the subgroup of carbapenems. It was launched by Shionogi Co. of Japan under the brand name Finibax in 2005, and is being marketed outside Japan by Johnson & Johnson. It is particularly active against Pseudomonas aeruginosa.

Doripenem can be used to for bacteria infections such as: complex abdominal infections, pneumonia within the setting of a hospital, complicated infections of the urinary tract including kidney infections progressed into the bloodstream. When Doripenem is absorbed into the body, the drug takes effect by eliminating the initial bacteria causing the infection. Primarily, Doripenem decreases the process of cell wall growth which eventually leads to elimination of the infectious cell bacteria altogether.

If allergic to Doripenem or allergic to any type of beta-lactam antibiotics such as Cephalosporin, or other Carbapenems it is recommended not to receive Doripenem.

Doripenem was approved by the United States Food and Drug Administration on October 12, 2007, to be sold under the tradename Doribax.[1]

Contents

Chemistry and Pharmacology

Doripenem is beta-lactam antibiotic agent belonging to the carbapenem group with a broad spectrum of functions. Although Doripenem may be quite similar to other related carbapenem agents, the antibiotic includes several divergent properties. For example, Doripenem includes a tranfiguration of hydroxyethyl group, and in position 1 there is a carbon atom. These differences makes the agent more stable against other pathogens. Doripenem has the ability to prevent renal dehydropeptidase-1 hydrolysis due to its structure containing a single side chain, 1-beta methyl. Additionally within the molecular structure a sulfamoylaminomethyl-pyrrolindinylthio group is attached to a side chain giving the molecule increased antibacterial movement against gram-negative antimicrobials. When induced into the body Doripenem has the efficiency to restrain the synthesis of cell walls by attaching itself onto penicillin binding proteins, also known as PBPs.

Physicochemical Properties

Doripenem appears as crystalline powder anywhere from a white to somewhat yellowish colour. In moderation Doripenem is soluble in water, slightly soluble in methanol and virtually insoluble in ethanol. Doripenem is also solution in N,N-dimethylformamide. Doripenem is composed of a 6 asymmetrical carbon molecule and is most commonly displayed by one pure isomer. In terms of Doripenem for injections, the crystallized powered drug can form a monohydrate when mixed with water. However Doripenem has not been proven to possess polymorphism.

Resistance

Potential influences for resistance mechanisms of Doripenem are the following: altered PBP’s (penicillin binding protein), activity in the permeability of the outer membrane is reduced especially when accepting foreign toxic substances within the cell, and hydrolyzing enzymes from the Carbapenem deactivate the drug from functioning. Beta-lactamases formed by gram-positive and gram-negative bacteria such as Penicillinases can stable Doripenem to hydrolysis. However, Carbapenem hydrolyzing beta-lactamases are an exception.

Pharmacokinetics

Distribution

On average, about 8.1% of plasma proteins attached to Doripenem, it is also separate from drug concentrations of plasma. Doripenem’s distribution volume is close to that of extracellular fluid volume in humans (18.2 L). When Doripenem is essentially stable the average volume of distribution is approximately 16.8 L. Within the few of the body’s fluids and tissues, Doripenem is able to be filtered successfully as well as reach concentration levels that are able to restrain from more vulnerable bacteria than what is required.

Metabolism

When metabolized, Doripenem breaks down by means of an enzyme called dehydropeptidase-I into an inactive ring-opened metabolite.

Excretion

In young and healthy adults, the elimination half-life of Doripenem considering the average plasma terminal is normally around 1 hour. The plasma clearance is about 15.9L/hour and the average renal clearance is 10.3 L/hour. Research has been found that Doripenem is filtered by the glomerulus capillary bed in the Bowman’s capsule and the tubular secretions in the nephron.

References

  1. ^ U.S. Food and Drug Administration (October 17, 2007). "FDA Approves New Drug to Treat Complicated Urinary Tract and Intra-Abdominal Infections". Press release. http://www.fda.gov/bbs/topics/NEWS/2007/NEW01728.html. Retrieved 2007-10-25.  

2. Janssen-Ortho Inc. (September 1, 2009) "Doribax". Retrieved November 22,2009. http://www.janssen-ortho.com/JOI/pdf_files/Doribax_E.pdf

3. Chemical Process Research and Development. American Chemical Society. (September 24, 2003) "Practical Large-Scale Synthesis of Doripenem: A Novel 1β-Methylcarbapenem Antibiotic". Retrieved November 22, 2009. http://pubs.acs.org/doi/abs/10.1021/op034088n

4. European Medicines Agency. (2008) "CHMP Assessment Report for Doribax". Retrieved November 22, 2009. http://www.emea.europa.eu/humandocs/PDFs/EPAR/doribax/H-891-en6.pdf

5. Formulary Journal Vol. 42 (December 2007)"Doripenem: A new extended-spectrum carbapenem antibiotic". Retrieved November 26, 2009. http://web.ebscohost.com/ehost/pdf?vid=8&hid=4&sid=8ccb7619-3d37-431f-bf13-d0ddc9ffc481%40sessionmgr114

6. Drugs R & D (2003) "Doripenem: S 4661". Retrieved November 23, 2009. http://web.ebscohost.com/ehost/pdf?vid=14&hid=106&sid=ee346c2a-d844-4d2b-a065-bdd8e7bf2348%40sessionmgr4

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