Doripenem

CAS# 148016-81-3

Doripenem

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Chemical structure

Doripenem

3D structure

Chemical Properties of Doripenem

Cas No. 148016-81-3 SDF Download SDF
PubChem ID 73303 Appearance Powder
Formula C15H24N4O6S2 M.Wt 420.5
Type of Compound N/A Storage Desiccate at -20°C
Synonyms S 4661
Solubility Soluble in DMSO
Chemical Name (4R,5S,6S)-6-[(1R)-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
SMILES C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(=C(N2C1=O)C(O)=O)S[C@@H]3CN[C@H](CN[S](N)(=O)=O)C3
Standard InChIKey AVAACINZEOAHHE-VFZPANTDSA-N
Standard InChI InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Doripenem

DescriptionDoripenem is a new member of the carbapenem class of beta-lactam antibiotics with broad-spectrum coverage of Gram-positive, Gram-negative and anaerobic pathogens. Target: Antibacterial Doripenem 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. It is recommended that those allergic to doripenem or to any type of beta-lactam antibiotics such as cephalosporin or other Carbapenems not receive doripenem. Doripenem appears as crystalline powder anywhere from a white to somewhat yellowish colour.Doripenem is moderately soluble in water, slightly soluble in methanol, and virtually insoluble in ethanol. Doripenem is also solution in N,N-dimethylformamide. Doripenem's chemical configuration has 6 asymmetrical carbon atoms (6 stereocentres) and is most commonly supplied as one pure isomer. In terms of doripenem for injection, the crystallized powered drug can form a monohydrate when mixed with water. However, Doripenem has not been proven to possess polymorphism.

References:
[1]. Anderson DL. Doripenem. Drugs Today (Barc). 2006 Jun;42(6):399-404. [2]. Jones RN, et al. Doripenem (S-4661), a novel carbapenem: comparative activity against contemporary pathogens including bactericidal action and preliminary in vitro methods evaluations. J Antimicrob Chemother. 2004 Jul;54(1):144-54. Epub 2004 Jun 9.

Doripenem Dilution Calculator

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Doripenem Molarity Calculator

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Preparing Stock Solutions of Doripenem

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3781 mL 11.8906 mL 23.7812 mL 47.5624 mL 59.453 mL
5 mM 0.4756 mL 2.3781 mL 4.7562 mL 9.5125 mL 11.8906 mL
10 mM 0.2378 mL 1.1891 mL 2.3781 mL 4.7562 mL 5.9453 mL
50 mM 0.0476 mL 0.2378 mL 0.4756 mL 0.9512 mL 1.1891 mL
100 mM 0.0238 mL 0.1189 mL 0.2378 mL 0.4756 mL 0.5945 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Doripenem

Doripenem is a new member of the carbapenem class of beta-lactam antibiotics with broad-spectrum coverage of Gram-positive, Gram-negative and anaerobic pathogens.

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References on Doripenem

Untargeted metabolomics analysis reveals key pathways responsible for the synergistic killing of colistin and doripenem combination against Acinetobacter baumannii.[Pubmed:28358014]

Sci Rep. 2017 Mar 30;7:45527.

Combination therapy is deployed for the treatment of multidrug-resistant Acinetobacter baumannii, as it can rapidly develop resistance to current antibiotics. This is the first study to investigate the synergistic effect of colistin/Doripenem combination on the metabolome of A. baumannii. The metabolite levels were measured using LC-MS following treatment with colistin (2 mg/L) or Doripenem (25 mg/L) alone, and their combination at 15 min, 1 hr and 4 hr (n = 4). Colistin caused early (15 min and 1 hr) disruption of the bacterial outer membrane and cell wall, as demonstrated by perturbation of glycerophospholipids and fatty acids. Concentrations of peptidoglycan biosynthesis metabolites decreased at 4 hr by Doripenem alone, reflecting its mechanism of action. The combination induced significant changes to more key metabolic pathways relative to either monotherapy. Down-regulation of cell wall biosynthesis (via D-sedoheptulose 7-phosphate) and nucleotide metabolism (via D-ribose 5-phosphate) was associated with perturbations in the pentose phosphate pathway induced initially by colistin (15 min and 1 hr) and later by Doripenem (4 hr). We discovered that the combination synergistically killed A. baumannii via time-dependent inhibition of different key metabolic pathways. Our study highlights the significant potential of systems pharmacology in elucidating the mechanism of synergy and optimizing antibiotic pharmacokinetics/pharmacodynamics.

Population Pharmacokinetics and Pharmacodynamics of Doripenem in Obese, Hospitalized Patients.[Pubmed:28168884]

Ann Pharmacother. 2017 Mar;51(3):209-218.

BACKGROUND: Doripenem population pharmacokinetics and dosing recommendations are limited in obesity. OBJECTIVE: To evaluate the population pharmacokinetics and pharmacodynamics of Doripenem in obese patients. METHODS: Hospitalized adults with a body mass index (BMI) >/= 40 kg/m(2) or total body weight (TBW) >/=45.5 kg over their ideal body weight received Doripenem 500 mg every 8 hours, infused over 1 hour. Population pharmacokinetic analyses were performed using NONMEM, and Monte Carlo simulations were performed for 5 intermittent and prolonged infusion dosing regimens to calculate probability of target attainment (PTA) at 40% and 100% fT>MIC (free drug concentrations above the minimum inhibitory concentration). RESULTS: A total of 20 patients were studied: 10 in an intensive care unit (ICU) and 10 in a non-ICU. A 2-compartment model with first-order elimination best described the serum concentration-time data. Doripenem clearance (CL) was significantly associated with creatinine CL (CRCL), volume of the central compartment with TBW and ICU residence, and volume of the peripheral compartment with TBW ( P < 0.05). Using 40% fT>MIC, PTA was >90% for all simulated dosing regimens at MICs MIC, prolonged infusions of 1 g every 6 hours and 2 g every 8 hours achieved >90% PTA at MICs Doripenem pharmacokinetics. Currently approved dosing regimens provide adequate pharmacodynamic exposures at 40% fT>MIC for susceptible bacteria in obese patients. However, prolonged infusions of larger doses are needed if a higher pharmacodynamic target is desired.

Therapeutic Drug Monitoring of Continuous Infusion Doripenem in a Pediatric Patient on Continuous Renal Replacement Therapy.[Pubmed:28337084]

J Pediatr Pharmacol Ther. 2017 Jan-Feb;22(1):69-73.

An 11-year-old African American male with severe combined immunodeficiency variant, non-cystic fibrosis bronchiectasis, pancreatic insufficiency, chronic mycobacterium avium-intracellulare infection, chronic sinusitis, and malnutrition presented with a 1-week history of fevers. He subsequently developed respiratory decompensation and cefepime was discontinued and Doripenem was initiated. Doripenem was the carbapenem used due to a national shortage of meropenem. By day 7 the patient (24.7 kg) had a positive fluid balance of 6925 mL (28% FO), and on days 7 into 8 developed acute kidney injury evidenced by an elevated serum creatinine of 0.68 mg/dL, an increase from the baseline of 0.28 mg/dL. On day 9, the patient was initiated on continuous renal replacement therapy (CRRT) and the Doripenem dosing was changed to a continuous infusion of 2.5 mg/kg/hr (60 mg/kg/day). Approximately 12.5 hours after the start of the Doripenem a serum concentration was obtained, which was 4.01 mg/L corresponding to a clearance of 10.5 mL/min/kg. The pediatric dosing and pharmacokinetic data available for Doripenem suggest a clearance estimate of 4.4 to 4.8 mL/min/kg, and the adult clearance estimate is 2.4 to 3.78 mL/min/kg. The calculated clearance in our patient of 10.5 mL/min/kg is over double the highest clearance estimate in the pediatric literature. This case demonstrates that Doripenem clearance is significantly increased with CRRT in comparison with the published pediatric and adult data. An appropriate pharmacodynamic outcome (time that free drug concentration > minimum inhibitory concentration) can be achieved by continuous infusion Doripenem with concurrent therapeutic drug monitoring.

Population Pharmacokinetic Analysis of Doripenem after Intravenous Infusion in Korean Patients with Acute Infections.[Pubmed:28223378]

Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: AAC.02185-16.

We investigated the population pharmacokinetics (PK) of Doripenem in Korean patients with acute infections and determined an appropriate dosing regimen using a Monte Carlo simulation for predicting pharmacodynamics (PD). Patients (n = 37) with a creatinine clearance (CLCR) of 20 to 50 ml/min or >50 ml/min who received a 250-mg or 500-mg dose of Doripenem over the course of 1 h every 8 h, respectively, were included in this study. Blood samples were taken predosing and 0 h, 0.5 h, and 4 to 6 h after the fourth infusion. A nonlinear mixed-effect modeling tool was used for the PK analysis and pharmacodynamic simulation; Doripenem PK were well described by a one-compartment model. The population mean values of the body weight (WT)-normalized clearance (CL/WT) and the body weight-normalized volume of distribution (V/WT) were 0.109 liter/h/kg of body weight (relative standard error, 9.197%) and 0.280 liter/kg (relative standard error, 9.56%), respectively. Doripenem CL was significantly influenced by CLCR The proposed equation to estimate Doripenem CL in Korean patients was CL/WT = 0.109 x WT x (CLCR/57)(0.688), where CL/WT is in liters per hour per kilogram. CL in Korean patients was expected to be lower than that in Caucasian patients, regardless of renal function. The Monte Carlo simulation showed that 90% attainment of target PK/PD magnitudes could be achieved with the usual dosing regimens when the MIC was Doripenem dosing regimen for patients with various renal functions and for patients infected with bacteria with decreased susceptibility.

Description

Doripenem is a new member of the carbapenem class of beta-lactam antibiotics with broad-spectrum coverage of Gram-positive, Gram-negative and anaerobic pathogens.

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