MEROPENEM

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J01DH02
UNII: FV9J3JU8B1

Structure
InChI Key DMJNNHOOLUXYBV-PQTSNVLCSA-N
Smile C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H25N3O5S
Molecular Weight 383.47
AlogP -0.31
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 110.18
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial penicillin-binding protein inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - 0.3463 -
Enzyme Kinase
127 - - - -
Enzyme Transferase
- 53-130 - - -4.064-10.85
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -20.08--6.58

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Urinary Tract Infections 4 D014552 ClinicalTrials
Bacteremia 4 D016470 ClinicalTrials
Meningitis 4 D008581 ClinicalTrials
Enterobacteriaceae Infections 3 D004756 ClinicalTrials
Mental Disorders 3 D001523 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Shock, Septic 3 D012772 ClinicalTrials
Pneumonia, Bacterial 3 D018410 ClinicalTrials
Neonatal Sepsis 3 D000071074 ClinicalTrials
Sepsis 3 D018805 ClinicalTrials
Pyelonephritis 3 D011704 ClinicalTrials
Pneumonia, Ventilator-Associated 3 D053717 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Lung Diseases 3 D008171 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Tuberculosis, Pulmonary 2 D014397 ClinicalTrials
Appendicitis 2 D001064 ClinicalTrials
Communicable Diseases 2 D003141 ClinicalTrials
Pancreatitis 1 D010195 ClinicalTrials
Osteomyelitis 1 D010019 ClinicalTrials
Gram-Negative Bacterial Infections 1 D016905 ClinicalTrials
Respiratory Insufficiency 1 D012131 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 7.8
Gastrointestinal disorders Nausea 7.8
Gastrointestinal disorders Constipation 7.0
Gastrointestinal disorders Diarrhoea 7.0
Blood and lymphatic system disorders Anaemia 5.5
General disorders and administration site conditions Pain 5.1
Gastrointestinal disorders Diarrhoea 5.0
Gastrointestinal disorders Diarrhoea 4.8
Gastrointestinal disorders Vomiting 3.6
Gastrointestinal disorders Diarrhoea 2.5
Nervous system disorders Headache 2.3
Skin and subcutaneous tissue disorders Dermatitis 1.9
Skin and subcutaneous tissue disorders Rash 1.9
Infections and infestations Sepsis 1.6
Gastrointestinal disorders Constipation 1.4
Respiratory, thoracic and mediastinal disorders Apnoea 1.3
Skin and subcutaneous tissue disorders Pruritus 1.2
Vascular disorders Shock 1.2
Gastrointestinal disorders Vomiting 1.2
Skin and subcutaneous tissue disorders Dermatitis 1.1
Skin and subcutaneous tissue disorders Rash 1.1
Infections and infestations Vulvovaginal candidiasis 0.7
Infections and infestations Vulvovaginal mycotic infection 0.7
Skin and subcutaneous tissue disorders Pruritus 0.6
Gastrointestinal disorders Gastrointestinal haemorrhage 0.5
Nervous system disorders Headache 0.5
Infections and infestations Candida infection 0.3
Gastrointestinal disorders Melaena 0.3
Gastrointestinal disorders Oral candidiasis 0.3
Immune system disorders Urticaria 0.3
Infections and infestations Vaginal infection 0.3
Vaginal inflammation 0.3
Investigations Body temperature increased 0.2
Respiratory, thoracic and mediastinal disorders Epistaxis 0.2
Peritoneal haemorrhage 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
14.66
Infections and infestations
9.18
Skin and subcutaneous tissue disorders
7.83
Investigations
7.4
Nervous system disorders
7.04
Blood and lymphatic system disorders
6.64
Injury, poisoning and procedural complications
6.47
Gastrointestinal disorders
5.72
Respiratory, thoracic and mediastinal disorders
5.58
Vascular disorders
5.32
Immune system disorders
5.07
Cardiac disorders
3.84
Metabolism and nutrition disorders
3.7
Renal and urinary disorders
3.2
Hepatobiliary disorders
2.92

Cross References

Resources Reference
CAS NUMBER 96036-03-2
ChEBI 43968
ChEMBL CHEMBL127
DrugBank DB00760
DrugCentral 1709
EPA CompTox DTXSID7045526
FDA SRS FV9J3JU8B1
Human Metabolome Database HMDB14898
Guide to Pharmacology 10829
PDB MEM
PubChem 441130
SureChEMBL SCHEMBL34442
ZINC ZINC000003808779
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