meropenem Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
analogues of penicillanic acid antibiotics modified in the five-membered ring 1709 96036-03-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • meropenem hydrate
  • meropenem
  • merrem
  • meropenem trihydrate
an antibacterial drug readily penetrates the cell wall of most Gram-positive and Gram-negative bacteria to reach penicillin-binding-protein (PBP) targets, the bactericidal activity of meropenem results from the inhibition of cell wall synthesis
  • Molecular weight: 383.46
  • Formula: C17H25N3O5S
  • CLOGP: -3.28
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 3
  • TPSA: 110.18
  • ALOGS: -1.83
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 70 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 111.76 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.87 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 21, 1996 FDA ASTRAZENECA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 371.49 60.66 90 1619 5428 2350948
Drug ineffective 338.67 60.66 174 1535 101450 2254926
Drug resistance 283.78 60.66 63 1646 2561 2353815
Multiple organ dysfunction syndrome 243.91 60.66 69 1640 7572 2348804
Acute kidney injury 202.73 60.66 83 1626 28039 2328337
Thrombocytopenia 196.31 60.66 73 1636 19058 2337318
Pyrexia 185.76 60.66 95 1614 53613 2302763
Pathogen resistance 182.54 60.66 36 1673 807 2355569
Septic shock 177.47 60.66 53 1656 7001 2349375
Toxic epidermal necrolysis 174.33 60.66 44 1665 3100 2353276
Pancytopenia 163.90 60.66 56 1653 11396 2344980
Clostridium difficile colitis 160.57 60.66 38 1671 2041 2354335
Drug interaction 150.37 60.66 68 1641 29095 2327281
Haemophagocytic lymphohistiocytosis 148.15 60.66 33 1676 1350 2355026
Rash 127.59 60.66 77 1632 59481 2296895
Neutropenia 126.20 60.66 55 1654 21493 2334883
Sepsis 114.13 60.66 49 1660 18439 2337937
Respiratory failure 107.63 60.66 43 1666 13485 2342891
C-reactive protein increased 98.83 60.66 33 1676 6222 2350154
Klebsiella infection 95.76 60.66 21 1688 796 2355580
Systemic candida 95.30 60.66 18 1691 317 2356059
Drug level decreased 92.15 60.66 21 1688 950 2355426
Febrile neutropenia 91.44 60.66 36 1673 10846 2345530
Clostridium difficile infection 78.12 60.66 23 1686 2867 2353509
Haemodynamic instability 77.80 60.66 19 1690 1160 2355216
Systemic inflammatory response syndrome 74.68 60.66 17 1692 764 2355612
Agranulocytosis 73.90 60.66 23 1686 3459 2352917
Meningitis candida 72.98 60.66 9 1700 1 2356375
Anaemia 71.64 60.66 44 1665 34748 2321628
Condition aggravated 69.83 60.66 42 1667 31937 2324439
Renal impairment 69.65 60.66 29 1680 10063 2346313
Multiple-drug resistance 68.86 60.66 13 1696 228 2356148
Pneumonia 66.75 60.66 48 1661 49248 2307128
Stenotrophomonas infection 66.71 60.66 12 1697 159 2356217
Seizure 66.32 60.66 37 1672 24429 2331947
Rash maculo-papular 65.39 60.66 22 1687 4230 2352146
Dyspnoea 62.46 60.66 56 1653 78677 2277699

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 742.22 57.54 321 1805 63480 1681175
Drug resistance 399.45 57.54 99 2027 3131 1741524
Septic shock 389.57 57.54 118 2008 7991 1736664
Pathogen resistance 333.56 57.54 70 2056 1019 1743636
Multiple organ dysfunction syndrome 308.60 57.54 102 2024 9140 1735515
Pyrexia 266.38 57.54 146 1980 46254 1698401
Sepsis 231.48 57.54 101 2025 19337 1725318
Toxic epidermal necrolysis 196.66 57.54 53 2073 2318 1742337
Drug reaction with eosinophilia and systemic symptoms 185.06 57.54 60 2066 5010 1739645
Hepatic function abnormal 169.23 57.54 61 2065 7013 1737642
Respiratory failure 167.85 57.54 74 2052 14431 1730224
Eosinophilia 167.25 57.54 51 2075 3476 1741179
Clostridium difficile infection 157.97 57.54 42 2084 1739 1742916
Klebsiella infection 152.43 57.54 35 2091 780 1743875
Thrombocytopenia 138.08 57.54 73 2053 21176 1723479
Rash 135.47 57.54 89 2037 38604 1706051
Enterococcal infection 123.02 57.54 30 2096 871 1743784
Pancytopenia 118.60 57.54 54 2072 11303 1733352
Herpes simplex oesophagitis 116.65 57.54 17 2109 15 1744640
Renal failure 116.61 57.54 64 2062 19953 1724702
Renal impairment 108.29 57.54 52 2074 12262 1732393
Rash maculo-papular 107.78 57.54 37 2089 3666 1740989
Pneumonia 107.76 57.54 83 2043 46099 1698556
C-reactive protein increased 101.51 57.54 40 2086 5845 1738810
Clostridium difficile colitis 101.35 57.54 29 2097 1575 1743080
Blister 92.88 57.54 34 2092 4058 1740597
Drug eruption 92.04 57.54 31 2095 2895 1741760
Drug interaction 91.97 57.54 62 2064 27896 1716759
Candida infection 91.37 57.54 28 2098 1930 1742725
Neutropenia 89.00 57.54 52 2074 18208 1726447
Tubulointerstitial nephritis 87.78 57.54 30 2096 2928 1741727
Multiple-drug resistance 83.73 57.54 18 2108 292 1744363
Condition aggravated 81.94 57.54 52 2074 21098 1723557
Anaemia 79.76 57.54 58 2068 29399 1715256
Pseudomembranous colitis 79.58 57.54 19 2107 502 1744153
Acute kidney injury 79.54 57.54 62 2064 34882 1709773
Agranulocytosis 78.50 57.54 29 2097 3547 1741108
Bronchopulmonary aspergillosis 75.63 57.54 23 2103 1543 1743112
Product use in unapproved indication 74.38 57.54 37 2089 9385 1735270
Acute generalised exanthematous pustulosis 74.07 57.54 21 2105 1101 1743554
Seizure 73.57 57.54 48 2078 20393 1724262
Bone marrow failure 71.31 57.54 30 2096 5170 1739485
Pseudomonas infection 70.95 57.54 21 2105 1283 1743372
Dysbiosis 69.84 57.54 12 2114 52 1744603
Dyspnoea 69.23 57.54 68 2058 51991 1692664
Enterococcus test positive 66.54 57.54 13 2113 127 1744528
Stevens-Johnson syndrome 65.58 57.54 25 2101 3332 1741323
Erythema 65.36 57.54 39 2087 14149 1730506
White blood cell count increased 64.53 57.54 31 2095 7281 1737374
Systemic candida 64.44 57.54 15 2111 354 1744301
Eosinophilic pneumonia 57.57 57.54 15 2111 570 1744085

Pharmacologic Action:

SourceCodeDescription
ATC J01DH02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Carbapenems
ATC J01DH52 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Carbapenems
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:36047 antibacterial drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Streptococcal meningitis indication 4510004 DOID:11574
Infection due to Pseudomonas aeruginosa indication 11218009
Peritonitis indication 48661000
Pneumococcal meningitis indication 51169003
Abdominal abscess indication 75100008
Bacterial meningitis indication 95883001 DOID:9470
Infectious disease of abdomen indication 128070006
Meningococcal meningitis indication 192644005
Complicated appendicitis indication 418171008
Peptostreptococcus Complicated Appendicitis indication
Pseudomonas Aeruginosa Complicated Appendicitis indication
E. Coli Complicated Appendicitis indication
Streptococcal Peritonitis indication
Bacteroides Peritonitis indication
Streptococcus Complicated Appendicitis indication
Klebsiella Pneumoniae Peritonitis indication
Complicated Skin and Skin Structure Infection indication
E. Coli Peritonitis indication
Peptostreptococcus Peritonitis indication
H. Influenzae Meningitis indication
Klebsiella Complicated Appendicitis indication
Bacteroides Complicated Appendicitis indication
Pyrexia of unknown origin off-label use 7520000
Bacterial septicemia off-label use 10001005 DOID:0040085
Inhalational anthrax off-label use 11389007
Nocardiosis off-label use 29227009 DOID:2312
Bacterial pneumonia off-label use 53084003 DOID:874
Cholangitis off-label use 82403002 DOID:9446
Gastrointestinal anthrax off-label use 111798006 DOID:13386
Infection by Campylobacter fetus off-label use 111835002
Sepsis of the newborn off-label use 206376005
Sepsis syndrome off-label use 238150007
Diverticulitis of gastrointestinal tract off-label use 271366000
Neonatal meningitis off-label use 276674008
Anthrax off-label use 409498004 DOID:7427
Nosocomial pneumonia off-label use 425464007
Melioidosis off-label use 428111003 DOID:5052
Pneumonia due to Gram negative bacteria off-label use 430395005
Clostridium Perfringens Empyema off-label use
Pseudomonas Respiratory Tract Infection in Cystic Fibrosis off-label use
Diabetic Foot Infection off-label use
Complicated Urinary Tract Infections off-label use
Kidney disease contraindication 90708001 DOID:557
Seizure disorder contraindication 128613002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.79 acidic
pKa2 8.04 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1GM/VIAL VABOMERE REMPEX PHARMS N209776 Aug. 29, 2017 RX POWDER INTRAVENOUS 10183034 Aug. 8, 2031 TREATMENT OF COMPLICATED URINARY TRACT INFECTION (CUTI) INCLUDING PYELONEPHRITIS CAUSED BY THE FOLLOWING SUSCEPTIBLE MICROORGANISMS: ESCHERICHIA COLI, KLEBSIELLA PNEUMONIA, AND ENTEROBACTER CLOACAE SPECIES COMPLEX
1GM/VIAL VABOMERE REMPEX PHARMS N209776 Aug. 29, 2017 RX POWDER INTRAVENOUS 10561675 Aug. 8, 2031 TREATMENT OF COMPLICATED URINARY TRACT INFECTION (CUTI) INCLUDING PYELONEPHRITIS CAUSED BY THE FOLLOWING SUSCEPTIBLE MICROORGANISMS: ESCHERICHIA COLI, KLEBSIELLA PNEUMONIA, AND ENTEROBACTER CLOACAE SPECIES COMPLEX
1GM/VIAL VABOMERE REMPEX PHARMS N209776 Aug. 29, 2017 RX POWDER INTRAVENOUS 9694025 Aug. 8, 2031 TREATMENT OF PATIENTS 18 YEARS OF AGE AND OLDER WITH COMPLICATED URINARY TRACT INFECTIONS CAUSED BY SUSCEPTIBLE MICROORGANISMS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D-alanyl-D-alanine carboxypeptidase DacB Enzyme INHIBITOR DRUGBANK CHEMBL
Penicillin-binding protein 4 Enzyme WOMBAT-PK
D-ala-D-ala-carboxypeptidase; D-alanyl-D-alanine carboxypeptidase; D-alanyl-D-alanine carboxypeptidase family protein; Penicillin-binding protein 5 Enzyme WOMBAT-PK
Penicillin-binding protein 1 Enzyme WOMBAT-PK
D-alanyl-D-alanine carboxypeptidase; D-alanyl-D-alanine carboxypeptidase penicillin-binding protein 6 Enzyme WOMBAT-PK
Streptokinase A Enzyme EC50 6.90 WOMBAT-PK
Penicillin-binding protein 2 Enzyme WOMBAT-PK
Beta-lactamase class B VIM-2 Unclassified Kd 4.92 CHEMBL

External reference:

IDSource
D000077731 MESH_DESCRIPTOR_UI
4021008 VUID
N0000148477 NUI
C0066005 UMLSCUI
D02222 KEGG_DRUG
96062004 SNOMEDCT_US
d04027 MMSL
5055 MMSL
29561 RXNORM
387540000 SNOMEDCT_US
4021008 VANDF
173661 MMSL
005166 NDDF
CHEMBL127 ChEMBL_ID
DB00760 DRUGBANK_ID
FV9J3JU8B1 UNII
119478-56-7 SECONDARY_CAS_RN
0RV PDB_CHEM_ID
8YL PDB_CHEM_ID
MER PDB_CHEM_ID
CHEBI:43968 CHEBI
441130 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MERREM HUMAN PRESCRIPTION DRUG LABEL 1 0069-0313 INJECTION 500 mg INTRAVENOUS NDA 19 sections
MERREM HUMAN PRESCRIPTION DRUG LABEL 1 0069-0314 INJECTION 1 g INTRAVENOUS NDA 19 sections
Meropenem and Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0264-3183 INJECTION, SOLUTION 500 mg INTRAVENOUS NDA 18 sections
Meropenem and Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0264-3185 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 0409-1390 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 0409-1391 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections
MEROPENEM HUMAN PRESCRIPTION DRUG LABEL 1 0781-3000 INJECTION 500 mg INTRAVENOUS ANDA 19 sections
MEROPENEM HUMAN PRESCRIPTION DRUG LABEL 1 0781-3098 INJECTION 1 g INTRAVENOUS ANDA 19 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 0781-3265 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 0781-3267 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 25021-155 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 17 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 25021-156 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 44567-400 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 44567-401 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections
MEROPENEM HUMAN PRESCRIPTION DRUG LABEL 1 44647-032 INJECTION 500 mg INTRAVENOUS ANDA 18 sections
MEROPENEM HUMAN PRESCRIPTION DRUG LABEL 1 44647-033 INJECTION 1 g INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 55150-207 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 17 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 55150-208 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 63323-507 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 63323-508 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 68001-323 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 68001-324 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 68083-146 INJECTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 68083-147 INJECTION 1 g INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 70121-1453 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 70121-1454 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 70278-103 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 17 sections
Meropenem HUMAN PRESCRIPTION DRUG LABEL 1 70278-104 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
VABOMERE HUMAN PRESCRIPTION DRUG LABEL 2 70842-120 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS NDA 18 sections