Identification

Name
Meropenem
Accession Number
DB00760  (APRD01097, EXPT02153)
Type
Small Molecule
Groups
Approved, Investigational
Description

Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.

In August 2017, a combination antibacterial therapy under the market name vabomere was approved for treatment of adult patients with complicated urinary tract infections (cUTI). Vabomere consists of meropenem and Vaborbactam and is intravenously admininstered. The treatment aims to resolve infection-related symptoms and achieve negative urine culture, where the infections are proven or strongly suspected to be caused by susceptible bacteria.

Structure
Thumb
Synonyms
  • (1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid
  • (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • Antibiotic sm 7338
  • Meropenem
  • Meropenem anhydrous
  • Meropenem Hydrate
  • Meropenem trihydrate
  • Meropenemum
  • Meropenemum trihydricum
External IDs
ICI 194660 / SM 7338
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Meropenem for InjectionPowder, for solution500 mgIntravenousSandoz Canada Incorporated2012-01-26Not applicableCanada
Meropenem for InjectionPowder, for solution1 gIntravenousFresenius Kabi2014-06-05Not applicableCanada
Meropenem for InjectionPowder, for solution1 gIntravenousAuro Pharma Inc2017-10-20Not applicableCanada
Meropenem for InjectionPowder, for solution1 gIntravenousSandoz Canada Incorporated2012-01-26Not applicableCanada
Meropenem for InjectionPowder, for solution500 mgIntravenousFresenius Kabi2014-10-20Not applicableCanada
Meropenem for InjectionPowder, for solution500 mgIntravenousAuro Pharma Inc2017-10-20Not applicableCanada
Meropenem for Injection SdzPowder, for solution1 gIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Meropenem for Injection SdzPowder, for solution500 mgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Meropenem for Injection USPPowder, for solution500 mgIntravenousPfizer2015-03-17Not applicableCanada
Meropenem for Injection USPPowder, for solution1 gIntravenousSterimax Inc2015-06-11Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MeropenemInjection, powder, for solution500 mg/20mLIntravenousPar Pharmaceutical2016-08-01Not applicableUs
MeropenemInjection1 g/30mLIntravenousGland Pharma Limited2016-07-25Not applicableUs
MeropenemInjection500 mg/20mLIntravenousSandoz2016-08-29Not applicableUs
MeropenemInjection, powder, for solution1 g/30mLIntravenousBlue Point Laboratories2017-04-30Not applicableUs
MeropenemInjection, powder, for solution500 mg/20mLIntravenousDaewoong Pharmaceutical Co., Ltd.2015-12-182017-01-14Us
MeropenemInjection, powder, for solution500 mg/1IntravenousAuro Medics Pharma Llc2017-03-27Not applicableUs
MeropenemInjection, powder, for solution1 g/20mLIntravenousCardinal Health2010-06-23Not applicableUs
MeropenemInjection500 mg/20mLIntravenousSavior Lifetec Corporation2016-04-19Not applicableUs
MeropenemInjection, powder, for solution1 g/1IntravenousSagent Pharmaceuticals2017-01-15Not applicableUs
MeropenemInjection, powder, for solution1 g/30mLIntravenousAmneal Biosciences Llc2016-05-09Not applicableUs
International/Other Brands
Aronem (ACI) / Aropen (Aristopharma) / Carbanem (Sanofi-Aventis) / Erope (Lincoln) / Fulspec (Acme) / I-penam (Incepta) / Merenz (Admac) / Merofit (FHC) / Meronem (AstraZeneca) / Meronis (Neiss) / Meropen (Swiss Parenterals) / Merotec (Zuventus) / Merrem (AstraZeneca) / Merrem I.V. (AstraZeneca) / Monan (AstraZeneca) / Ropenem (Drug International) / Zeropenem (Sanofi-Aventis)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Meropenem and Sodium ChlorideMeropenem (1 g/50mL) + Sodium Chloride (0.9 g/50mL)Injection, solutionIntravenousB. Braun Medical Inc.2015-04-30Not applicableUs
Meropenem and Sodium ChlorideMeropenem (500 mg/50mL) + Sodium Chloride (.9 g/50mL)Injection, solutionIntravenousB. Braun Medical Inc.2015-04-30Not applicableUs
VabomereMeropenem (1 g/2g) + Vaborbactam (1 g/2g)Injection, powder, for solutionIntravenousThe Medicines Company2017-10-02Not applicableUs
Categories
UNII
YOP6PX0BAO
CAS number
119478-56-7
Weight
Average: 383.463
Monoisotopic: 383.151491615
Chemical Formula
C17H25N3O5S
InChI Key
DMJNNHOOLUXYBV-PQTSNVLCSA-N
InChI
InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
IUPAC Name
(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
SMILES
[H][[email protected]]1([[email protected]@H](C)O)C(=O)N2C(C(O)=O)=C(S[[email protected]@H]3CN[[email protected]@H](C3)C(=O)N(C)C)[[email protected]](C)[[email protected]]12[H]

Pharmacology

Indication

For use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: complicated skin and skin structure infections due to Staphylococcus aureus (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (excluding vancomycin-resistant isolates), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis and Peptostreptococcus species; complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. Also for use in the treatment of bacterial meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and Neisseria meningitidis.

Structured Indications
Pharmacodynamics

Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.

Mechanism of action

The bactericidal activity of meropenem results from the inhibition of cell wall synthesis. Meropenem readily penetrates the cell wall of most Gram-positive and Gram-negative bacteria to reach penicillin-binding- protein (PBP) targets. Its strongest affinities are toward PBPs 2, 3 and 4 of Escherichia coli and Pseudomonas aeruginosa; and PBPs 1, 2 and 4 of Staphylococcus aureus.

TargetActionsOrganism
AD-alanyl-D-alanine carboxypeptidase DacB
inhibitor
Escherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

Approximately 2%.

Metabolism

Primarily excreted unchanged. There is one metabolite which is microbiologically inactive.

Route of elimination

Approximately 70% of the intravenously administered dose is recovered as unchanged meropenem in the urine over 12 hours, after which little further urinary excretion is detectable.

Half life

Approximately 1 hour in adults and children 2 years of age and older with normal renal function. Approximately 1.5 hours in children 3 months to 2 years of age.

Clearance
Not Available
Toxicity

In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Meropenem.Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Meropenem.Approved
ProbenecidThe serum concentration of Meropenem can be increased when it is combined with Probenecid.Approved
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Meropenem.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Yoon Seok Song, Sung Woo Park, Yeon Jung Yoon, Hee Kyoon Yoon, Seong Cheol Moon, Byung Goo Lee, Soo Jin Choi, Sun Ah Jun, "METHOD FOR PREPARING MEROPENEM USING ZINC POWDER." U.S. Patent US20120065392, issued March 15, 2012.

US20120065392
General References
Not Available
External Links
Human Metabolome Database
HMDB14898
KEGG Drug
D02222
PubChem Compound
441130
PubChem Substance
46504928
ChemSpider
389924
ChEBI
43968
ChEMBL
CHEMBL127
Therapeutic Targets Database
DAP000441
PharmGKB
PA164764445
HET
MEM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Meropenem
ATC Codes
J01DH02 — Meropenem
AHFS Codes
  • 08:12.07.08 — Carbapenems
PDB Entries
4euz
FDA label
Download (276 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBMI >30 kg/m2 / Bone destruction / Diabetes Mellitus (DM) / Inflammatory Reaction1
0RecruitingTreatmentOsteomyelitis1
1CompletedTreatmentGram-Negative Bacterial Infections1
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentBacterial Infections1
1RecruitingTreatmentUrinary Tract Infections (UTIs)1
1, 2CompletedTreatmentAcute Pancreatitis (AP)1
1, 2CompletedTreatmentIntra-Abdominal Infections / Necrotizing Enterocolitis1
1, 2CompletedTreatmentMeningitis1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2CompletedTreatmentComplicated Intra-Abdominal Infections / Complicated Intra-Abdominal Infections (cIAIs)1
2CompletedTreatmentTuberculosis, Pulmonary1
2Not Yet RecruitingTreatmentComplicated Intra-Abdominal Infections1
2Not Yet RecruitingTreatmentComplicated Urinary Tract Infections / Pyelonephritis1
2RecruitingTreatmentOsteomyelitis1
2RecruitingTreatmentTuberculosis, Pulmonary1
2TerminatedTreatmentInfections, Intestinal1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
2TerminatedTreatmentPneumonia, Bacterial1
2, 3TerminatedTreatmentAscites / Liver Cirrhosis / Nosocomial Spontaneous Bacterial Peritonitis1
3Active Not RecruitingTreatmentComplicated Appendicitis / Complicated Intra-Abdominal Infections1
3CompletedTreatmentAbscesses / Cellulitis / Skin-structure infections1
3CompletedTreatmentAcute Pyelonephritis (AP) Due to CRE / Bloodstream Infections (BSI) Due to CRE / Complicated Urinary Tract Infection (cUTI) Due to CRE / Hospital-Acquired Bacterial Pneumonia (HABP) Due to CRE / Ventilator-Associated Bacterial Pneumonia (VABP) Due to CRE1
3CompletedTreatmentAcute Pyelonephritis / Bacteremia / Hospital Acquired Bacterial Pneumonia / Urinary Tract Infection Complicated / Ventilator-associated Bacterial Pneumonia1
3CompletedTreatmentAcute Pyelonephritis / Complicated Urinary Tract Infections1
3CompletedTreatmentAcute Pyelonephritis / Urinary Tract Infection Complicated1
3CompletedTreatmentComplicated Intra-Abdominal Infections4
3CompletedTreatmentSepsis1
3CompletedTreatmentSevere Sepsis / Shock, Septic1
3CompletedTreatmentHospital-acquired bacterial pneumonia / Ventilator-Associated Pneumonia (VAP)1
3CompletedTreatmentVentilator-associated Bacterial Pneumonia1
3Not Yet RecruitingTreatmentShock, Septic1
3RecruitingTreatmentBlood Stream Infections / Pneumonia1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentHealthcare-associated Pneumonia (HCAP) / Hospital-acquired bacterial pneumonia / Ventilator-associated Bacterial Pneumonia1
3RecruitingTreatmentInfection Due to ESBL Escherichia Coli / Infection Due to Multidrug-resistant Escherichia Coli1
3RecruitingTreatmentHospital-acquired bacterial pneumonia1
3TerminatedTreatmentAbdominal Abscess / Abdominal Pain (AP) / Abscess, Intra-Abdominal / Acute Abdomen / Appendicitis / Ileus / Infection NOS / Intestinal Perforations / Peritonitis / Rupture1
3TerminatedTreatmentBacterial Infections1
3TerminatedTreatmentUrinary Tract Infections (UTIs)1
4CompletedNot AvailableInitial Phase of Severe Sepsis and Septic Shock1
4CompletedNot AvailableVentilator-Associated Pneumonia (VAP)1
4CompletedPreventionPancreatitis,Acute Necrotizing1
4CompletedTreatmentBacterial Infections1
4CompletedTreatmentCentral Nervous System Infections1
4CompletedTreatmentCystic Fibrosis (CF) / Pneumonia / Pseudomonas Aeruginosa Infection1
4CompletedTreatmentGram-Negative Bacterial Infections1
4CompletedTreatmentPancreatitis1
4CompletedTreatmentSepsis1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingTreatmentBloodstream Infections1
4RecruitingTreatmentBronchiectasis1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentBloodstream Infections1
4Unknown StatusTreatmentCystic Fibrosis (CF)1
4Unknown StatusTreatmentDrug Safety1
4Unknown StatusTreatmentPancreatitis,Acute Necrotizing1
Not AvailableCompletedNot AvailableAllogenic Blood Stem Cell Transplantation / Neutropenia, Febrile1
Not AvailableCompletedTreatmentAppendicitis / Children1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableCompletedTreatmentSepsis1
Not AvailableEnrolling by InvitationNot AvailableCritical Illness1
Not AvailableEnrolling by InvitationBasic ScienceCystic Fibrosis (CF)1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableNot Yet RecruitingNot AvailableAntibiotic Selection Pressure1
Not AvailableNot Yet RecruitingTreatmentSepsis1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cyanide Poisoning / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / GYNAECOLOGICAL INFECTION / Headaches / Herpes Simplex Virus / High Blood Cholesterol Level / High Blood Pressure (Hypertension) / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombosis / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableChildren; Infection / Newborn; Infection1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingNot AvailableGeneral Surgery1
Not AvailableRecruitingBasic ScienceAlcoholic Hepatitis (AH)1
Not AvailableRecruitingTreatmentCarbapenem / Clinical Outcome / Critical Illness / Morality / Organ Failure, Multiple / Pharmacodynamics / Pharmacokinetics / Sepsis / Shock, Septic1
Not AvailableUnknown StatusTreatmentBurkholderia pseudomallei infection1

Pharmacoeconomics

Manufacturers
  • Hospira inc
  • Astrazeneca uk ltd
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous1 g/20mL
Injection, powder, for solutionIntravenous1 g/30mL
Injection, powder, for solutionIntravenous500 mg/1
Injection, powder, for solutionIntravenous500 mg/10mL
Injection, powder, for solutionIntravenous500 mg/20mL
Injection, solutionIntravenous
Powder, for solutionIntravenous1 g
Powder, for solutionIntravenous500 mg
InjectionIntravenous1 g/30mL
InjectionIntravenous500 mg/20mL
Injection, powder, for solutionIntravenous
Prices
Unit descriptionCostUnit
Merrem 1 gm Solution Vial81.32USD vial
Merrem iv 1 gm vial78.19USD vial
Merrem 500 mg Solution Vial48.79USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4943569No1993-06-212010-06-21Us
CA1322371No1993-09-212010-09-21Canada
US9694025No2011-08-082031-08-08Us
US8680136No2011-08-172031-08-17Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySparinglyNot Available
logP-0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.63 mg/mLALOGPS
logP-0.69ALOGPS
logP-4.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.18 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.89 m3·mol-1ChemAxon
Polarizability39.29 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7086
Blood Brain Barrier-0.9901
Caco-2 permeable-0.6556
P-glycoprotein substrateSubstrate0.8057
P-glycoprotein inhibitor INon-inhibitor0.6779
P-glycoprotein inhibitor IINon-inhibitor0.952
Renal organic cation transporterNon-inhibitor0.9053
CYP450 2C9 substrateNon-substrate0.8286
CYP450 2D6 substrateNon-substrate0.8136
CYP450 3A4 substrateSubstrate0.6007
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9798
Ames testNon AMES toxic0.68
CarcinogenicityNon-carcinogens0.8623
BiodegradationNot ready biodegradable0.8801
Rat acute toxicity1.9158 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9969
hERG inhibition (predictor II)Non-inhibitor0.8683
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Thienamycins
Alternative Parents
Proline and derivatives / Alpha amino acid amides / Pyrroline carboxylic acids / Pyrrolidinecarboxamides / Azepines / Vinylogous thioesters / Tertiary carboxylic acid amides / Thioenol ethers / Secondary alcohols / Amino acids
show 10 more
Substituents
Thienamycin / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Pyrroline carboxylic acid / Pyrroline carboxylic acid or derivatives / Azepine / Vinylogous thioester
show 28 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
pyrrolidinecarboxamide, alpha,beta-unsaturated monocarboxylic acid, carbapenemcarboxylic acid (CHEBI:43968)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name
dacB
Uniprot ID
P24228
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacB
Molecular Weight
51797.85 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Kanazawa K, Nouda H, Sunagawa M: Structure-activity relationships of carbapenem compounds to anti-Haemophilus influenzae activity and affinity for penicillin-binding proteins. Effect of 1 beta-methyl group and C-2 side chain. J Antibiot (Tokyo). 1997 Feb;50(2):162-8. [PubMed:9099227]
  4. Ubukata K, Shibasaki Y, Yamamoto K, Chiba N, Hasegawa K, Takeuchi Y, Sunakawa K, Inoue M, Konno M: Association of amino acid substitutions in penicillin-binding protein 3 with beta-lactam resistance in beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2001 Jun;45(6):1693-9. [PubMed:11353613]

Enzymes

Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Unknown
Actions
Substrate
General Function
Penicillin binding
Specific Function
Hydrolyzes both carbenicillin and oxacillin.
Gene Name
bla
Uniprot ID
P14489
Uniprot Name
Beta-lactamase OXA-10
Molecular Weight
29506.575 Da
References
  1. Pryka RD, Haig GM: Meropenem: a new carbapenem antimicrobial. Ann Pharmacother. 1994 Sep;28(9):1045-54. [PubMed:7803882]
  2. Bonfiglio G, Russo G, Nicoletti G: Recent developments in carbapenems. Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. [PubMed:11922861]

Drug created on June 13, 2005 07:24 / Updated on January 14, 2018 10:04