Ertapenem - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (8)

Targets (8)Biointeractions (7)

Identification

Name

Ertapenem

Accession Number

DB00303 (APRD00952)

Type

Small Molecule

Groups

Approved, Investigational

Description

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz®. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group. [Wikipedia]

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(1R,5S,6S,8R,2'S,4's)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid

(4R,5S,6S)-3-((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

ERTAPENEM

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Ertapenem sodium	2T90KE67L0	153773-82-1	Not applicable	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Invanz	Injection, powder, lyophilized, for solution	1 g/1	Intramuscular; Intravenous	Merck Sharp & Dohme Limited	2001-11-21	Not applicable	US
Invanz	Injection, powder, for solution	1 g	Intravenous	Merck Sharp & Dohme Limited	2002-04-18	Not applicable	EU
Invanz	Injection, powder, lyophilized, for solution	1 g/1	Intravenous	Merck Sharp & Dohme Limited	2001-11-21	Not applicable	US
Invanz	Injection, powder, for solution	1 g	Intravenous	Merck Sharp & Dohme Limited	2002-04-18	Not applicable	EU
Invanz	Powder, for solution	1 g	Intramuscular; Intravenous	Merck Ltd.	2003-08-27	Not applicable	Canada

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

G32F6EID2H

CAS number

153832-46-3

Weight

Average: 475.515
Monoisotopic: 475.141320859

Chemical Formula

C₂₂H₂₅N₃O₇S

InChI Key

JUZNIMUFDBIJCM-ANEDZVCMSA-N

InChI

InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1

IUPAC Name

(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]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][C@]12[C@@H](C)C(S[C@]3([H])CN[C@@]([H])(C3)C(=O)NC3=CC=CC(=C3)C(O)=O)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

Pharmacology

Indication

For the treatment the following moderate to severe infections caused by susceptible isolates of the designated microorganisms: (1) complicated intra-abdominal infections due to Escherichia coli, Clostridium clostridioforme, Eubacterium lentum, Peptostreptococcus species, Bacteroides fragilis, Bacteroides distasonis, Bacteroides ovatus, Bacteroides thetaiotaomicron, or Bacteroides uniformis, (2) complicated skin and skin structure infections, including diabetic foot infections without osteomyelitis due to Staphylococcus aureus (methicillin susceptible isolates only), Streptococcus agalactiae, Streptococcus pyogenes, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Bacteroides fragilis, Peptostreptococcus species, Porphyromonas asaccharolytica, or Prevotella bivia, (3) community acquired pneumonia due to Streptococcus pneumoniae (penicillin susceptible isolates only) including cases with concurrent bacteremia, Haemophilus influenzae (beta-lactamase negative isolates only), or Moraxella catarrhalis, (4) complicated urinary tract infections including pyelonephritis due to Escherichia coli, including cases with concurrent bacteremia, or Klebsiella pneumoniae, (5) acute pelvic infections including postpartum endomyometritis, septic abortion and post surgical gynecologic infections due to Streptococcus agalactiae, Escherichia coli, Bacteroides fragilis, Porphyromonas asaccharolytica, Peptostreptococcus species, or Prevotella bivia.

Structured Indications

Pharmacodynamics

Ertapenem has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria.

Mechanism of action

The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Ertapenem is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ertapenem is hydrolyzed by metallo-beta-lactamases.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Penicillin-binding protein 2	Protein	yes	inhibitor	Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)	P44469	details
Penicillin-binding protein 2	Protein	yes	inhibitor	Escherichia coli (strain K12)	P0AD65	details
Peptidoglycan synthase FtsI	Protein	yes	inhibitor	Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)	P45059	details
Peptidoglycan synthase FtsI	Protein	yes	inhibitor	Escherichia coli (strain K12)	P0AD68	details
D-alanyl-D-alanine carboxypeptidase DacB	Protein	yes	inhibitor	Escherichia coli (strain K12)	P24228	details
Penicillin-binding protein 1A	Protein	yes	inhibitor	Escherichia coli (strain K12)	P02918	details
Penicillin-binding protein 1B	Protein	yes	inhibitor	Escherichia coli (strain K12)	P02919	details
D-alanyl-D-alanine carboxypeptidase DacC	Protein	yes	inhibitor	Escherichia coli (strain K12)	P08506	details

Absorption

Ertapenem is almost completely absorbed following intramuscular administration. The bioavailability of a 1 g intramuscular dose approximated 92% in 26 healthy subjects [77% male; median (range) age, 29 (22–41) years]. Plasma concentrations of total ertapenem were similar whether given intramuscularly or intravenously.

Volume of distribution

0.12 liter/kg [adults]
0.2 liter/kg [pediatric, 3 months to 12 years]
0.16 liter/kg [pediatric patients 13 to 17 years]

Protein binding

Ertapenem is highly bound to human plasma proteins, primarily albumin, in a concentration-dependent manner. The protein binding of ertapenem decreases as plasma concentrations increase. At a plasma concentration of <100 µg/mL, approximately 95% of ertapenem is protein bound. Protein binding of ertapenem decreases to approximately 85% at an approximate plasma concentration of 300 µg/mL.

Metabolism

The major metabolite is the inactive ring-opened derivative formed by hydrolysis of the β-lactam ring. Ertapenem did not inhibit metabolism mediated by cytochrome P450 (CYP) isoforms 1A2, 2C9, 2C19, 2D6, 2E1, or 3A4 when evaluated by in vitro studies in human liver microsomes. Ertapenem is neither a substrate nor an inhibitor of P-glycoprotein or cytochrome P450 enzymes; significant drug interactions between ertapenem and drugs handled by these systems are not expected [PMID: 15150180]

Route of elimination

Of the 80% recovered in urine, approximately 38% is excreted as unchanged drug and approximately 37% as the ring-opened metabolite.

Half life

The mean plasma half-life is approximately 4 hours.

Clearance

1.8 L/h

Toxicity

Not Available

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
BCG vaccine	The therapeutic efficacy of Bcg can be decreased when used in combination with Ertapenem.	Investigational
Picosulfuric acid	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ertapenem.	Approved
Probenecid	The serum concentration of Ertapenem can be increased when it is combined with Probenecid.	Approved
Tacrolimus	The serum concentration of Tacrolimus can be increased when it is combined with Ertapenem.	Approved, Investigational
Valproic Acid	The serum concentration of Valproic Acid can be decreased when it is combined with Ertapenem.	Approved, Investigational

Food Interactions

Not Available

References

Synthesis Reference

Ying Shi, Kun Li, Zan Xie, Xuebin Zhao, Jian Lv, Xiuqin Yu, "INTERMEDIATE OF ERTAPENEM, A COMPOSITION COMPRISING THE SAME AND PREPARATION METHODS THEREOF." U.S. Patent US20120095209, issued April 19, 2012.

US20120095209

General References

Nix DE, Majumdar AK, DiNubile MJ: Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians. J Antimicrob Chemother. 2004 Jun;53 Suppl 2:ii23-8. [PubMed:15150180 ]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB14448
KEGG Drug	D07908
PubChem Compound	150610
PubChem Substance	46506508
ChemSpider	132758
ChEBI	404903
ChEMBL	CHEMBL1359
Therapeutic Targets Database	DAP000431
PharmGKB	PA164777032
Drug Product Database	13153
RxList	http://www.rxlist.com/cgi/generic3/invanz.htm
Drugs.com	http://www.drugs.com/cdi/ertapenem.html
Wikipedia	Ertapenem

ATC Codes

J01DH03 — Ertapenem

AHFS Codes

08:12.07.08

PDB Entries

Not Available

FDA label

Download (140 KB)

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Health Services Research	Healthy Volunteers	1
1	Terminated	Treatment	Endometritis	1
2	Completed	Other	End Stage Renal Disease (ESRD)	1
2	Completed	Treatment	Community Acquired Pneumonia (CAP)	1
2	Completed	Treatment	Complicated Intra-Abdominal Infections	1
2	Not Yet Recruiting	Treatment	Acute Appendicitis	1
2	Recruiting	Not Available	PK of Ertapenem in TB Patients	1
2	Recruiting	Treatment	Acute Pyelonephritis / Infection Due to Escherichia Coli	1
2, 3	Completed	Prevention	Surgical Site Infections	1
2, 3	Recruiting	Treatment	Anti-Infective Agents, Urinary / Escherichia Coli Infections / Klebsiella Infections / Transplantation, Kidney / Urinary Tract Infections (UTIs)	1
3	Completed	Prevention	Infection NOS / Surgical Site Infections	1
3	Completed	Treatment	Complicated Intra-Abdominal Infections	1
3	Completed	Treatment	Diabetic Foot / Infections, Bacterial / Osteomyelitis	1
3	Completed	Treatment	Infection NOS	1
3	Completed	Treatment	Infection; Diabetic Foot	1
3	Completed	Treatment	Intraabdominal Infections	1
3	Completed	Treatment	Urinary Tract Infections (UTIs)	2
3	Recruiting	Treatment	Complicated Urinary Tract Infections	1
3	Recruiting	Treatment	Enterobacteriaceae Infections	1
3	Terminated	Treatment	Urinary Tract Infections (UTIs)	1
3	Unknown Status	Treatment	Community Acquired Pneumonia (CAP)	1
4	Completed	Not Available	Acute Renal Failure (ARF)	1
4	Completed	Not Available	Continuous ambulatory peritoneal dialysis therapy / End Stage Renal Disease (ESRD)	1
4	Completed	Not Available	Healthy Volunteers	1
4	Completed	Not Available	Infection NOS	1
4	Completed	Prevention	Benign Prostatic Hyperplasia (BPH) Requiring Surgical Resection	1
4	Completed	Treatment	Burn Patients	1
4	Completed	Treatment	Colonic Neoplasms / Diverticulosis, Colonic / Rectal Neoplasms	1
4	Completed	Treatment	Intra-Abdominal Infections	1
4	Terminated	Treatment	To Assess the Tissular and Plasma Kinetics of Ertapenem	1
4	Unknown Status	Not Available	Allergies / IgE-Mediated Hypersensitivity	1
4	Unknown Status	Educational/Counseling/Training	Acute Disease / Diverticulitis, Colonic	1
4	Unknown Status	Treatment	Acute Appendicitis Without Peritonitis	1
4	Unknown Status	Treatment	Drug Safety	1
Not Available	Active Not Recruiting	Treatment	Acute Appendicitis	1
Not Available	Completed	Treatment	Perforated Appendicitis	1
Not Available	Recruiting	Treatment	Liver Abscess, Pyogenic	1
Not Available	Unknown Status	Not Available	Urinary Tract Infections (UTIs)	1
Not Available	Withdrawn	Treatment	Amputations	1

Pharmacoeconomics

Manufacturers

Merck and co inc

Packagers

Merck & Co.

Dosage forms

Form	Route	Strength
Injection, powder, for solution	Intravenous	1 g
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous	1 g/1
Injection, powder, lyophilized, for solution	Intravenous	1 g/1
Powder, for solution	Intramuscular; Intravenous	1 g

Prices

Unit description	Cost	Unit
Invanz 1 gm add-vantage vial	72.85USD	vial
Invanz 1 gm vial	69.4USD	vial

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
CA2106370	No	2003-11-25	2013-02-02	Canada
US5478820	Yes	1996-05-21	2016-05-21	US
US5652233	No	1993-02-02	2013-02-02	US
US5952323	Yes	1997-11-15	2017-11-15	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Soluble as sodium salt	Not Available
logP	0.3	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.286 mg/mL	ALOGPS
logP	-0.2	ALOGPS
logP	-3.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.27 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.8 m³·mol^-1	ChemAxon
Polarizability	48.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.5982
Blood Brain Barrier	-	0.9811
Caco-2 permeable	-	0.7052
P-glycoprotein substrate	Substrate	0.7716
P-glycoprotein inhibitor I	Non-inhibitor	0.917
P-glycoprotein inhibitor II	Non-inhibitor	0.9955
Renal organic cation transporter	Non-inhibitor	0.9253
CYP450 2C9 substrate	Non-substrate	0.7891
CYP450 2D6 substrate	Non-substrate	0.8229
CYP450 3A4 substrate	Non-substrate	0.5
CYP450 1A2 substrate	Non-inhibitor	0.8677
CYP450 2C9 inhibitor	Non-inhibitor	0.867
CYP450 2D6 inhibitor	Non-inhibitor	0.8964
CYP450 2C19 inhibitor	Non-inhibitor	0.8511
CYP450 3A4 inhibitor	Non-inhibitor	0.9658
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9695
Ames test	Non AMES toxic	0.6766
Carcinogenicity	Non-carcinogens	0.8052
Biodegradation	Not ready biodegradable	0.9821
Rat acute toxicity	2.0803 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9947
hERG inhibition (predictor II)	Non-inhibitor	0.8848

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Lactams

Direct Parent

Thienamycins

Alternative Parents

Acylaminobenzoic acid and derivatives / Proline and derivatives / Alpha amino acid amides / Anilides / Benzoic acids / Pyrroline carboxylic acids / Pyrrolidinecarboxamides / Benzoyl derivatives / N-arylamides / Azepines

Substituents

Thienamycin / Acylaminobenzoic acid or derivatives / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Benzoic acid or derivatives / Benzoic acid / Anilide / Benzoyl / Pyrrolidine carboxylic acid or derivatives

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrrolidinecarboxamide, carbapenemcarboxylic acid (CHEBI:404903 )

Targets

Details

1. Penicillin-binding protein 2

Kind: Protein
Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action: yes
Actions: inhibitor

General Function:: Penicillin binding
Specific Function:: Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. Its synthesize cross-linked peptidoglycan from the lipid intermediates (By similarity).
Gene Name:: mrdA
Uniprot ID:: P44469
Uniprot Name:: Penicillin-binding protein 2
Molecular Weight:: 73812.47 Da

References

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 ]
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 ]
Odenholt I: Ertapenem: a new carbapenem. Expert Opin Investig Drugs. 2001 Jun;10(6):1157-66. [PubMed:11772242 ]
Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

2. Penicillin-binding protein 2

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: yes
Actions: inhibitor

General Function:: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:: Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
Gene Name:: mrdA
Uniprot ID:: P0AD65
Uniprot Name:: Penicillin-binding protein 2
Molecular Weight:: 70856.1 Da

References

Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

3. Peptidoglycan synthase FtsI

Kind: Protein
Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action: yes
Actions: inhibitor

General Function:: Peptidoglycan glycosyltransferase activity
Specific Function:: Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum. Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors.
Gene Name:: ftsI
Uniprot ID:: P45059
Uniprot Name:: Peptidoglycan synthase FtsI
Molecular Weight:: 67165.845 Da

References

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 ]
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 ]
Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

4. Peptidoglycan synthase FtsI

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: yes
Actions: inhibitor

General Function:: Peptidoglycan glycosyltransferase activity
Specific Function:: Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:: ftsI
Uniprot ID:: P0AD68
Uniprot Name:: Peptidoglycan synthase FtsI
Molecular Weight:: 63876.925 Da

References

Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

5. D-alanyl-D-alanine carboxypeptidase DacB

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

Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

6. Penicillin-binding protein 1A

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: yes
Actions: inhibitor

General Function:: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:: Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:: mrcA
Uniprot ID:: P02918
Uniprot Name:: Penicillin-binding protein 1A
Molecular Weight:: 93635.545 Da

References

Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

7. Penicillin-binding protein 1B

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: yes
Actions: inhibitor

General Function:: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:: Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:: mrcB
Uniprot ID:: P02919
Uniprot Name:: Penicillin-binding protein 1B
Molecular Weight:: 94291.875 Da

References

Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Details

8. D-alanyl-D-alanine carboxypeptidase DacC

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: yes
Actions: inhibitor

General Function:: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:: Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name:: dacC
Uniprot ID:: P08506
Uniprot Name:: D-alanyl-D-alanine carboxypeptidase DacC
Molecular Weight:: 43608.595 Da

References

Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [PubMed:10223931 ]

Drug created on June 13, 2005 07:24 / Updated on July 27, 2017 15:59

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Structure for DB00303 (Ertapenem)

Targets

References

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