Discuss This Drug

Metronidazole

CHEBI:CHEBI_6909

Definition

A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.

Chemical Information

Molecular Formula
C6H9N3O3
Molecular Mass
171.15400
Charge
0
SMILES
Cc1ncc(n1CCO)[N+]([O-])=O
InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
InChIKey
VAOCPAMSLUNLGC-UHFFFAOYSA-N

Alternative Names

  • 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole
  • 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole
  • 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole
  • 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole
  • 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole
  • 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
  • 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole
  • 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole
  • 2-methyl-5-nitroimidazole-1-ethanol
  • metronidazol
  • metronidazole
  • metronidazolum

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
6922
oboInOwl#hasDbXref
Wikipedia:Metronidazole
core#notation
CHEBI:6909

Additional References

Wikipedia:Metronidazole

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

labeler_name
Redpharm Drug, inc.
application_number
ANDA216692
product_ndc
72162-2159
dosage_form
SUSPENSION
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
marketing_start_date
19950920
package_ndc
0904-7156-61
route
VAGINAL
spl_id
a23b7362-0d16-4e23-b4db-ce8d8c6c856d
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
6922
oboInOwl#hasDbXref
Wikipedia:Metronidazole
oboInOwl#hasAlternativeId
CHEBI:63636
oboInOwl#id
CHEBI:6909
generic_name
Metronidazole Benzoate Micronized
brand_name
Metronidazole500 mg 500 mg
brand_name_base
Metronidazole500 mg
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_50266
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
chebi#is_conjugate_base_of
http://purl.obolibrary.org/obo/CHEBI_64682
package_marketing_start_date
19950920
package_description
6 TABLET in 1 BOTTLE (68071-2809-6)
active_ingredient_strength
65 mg/5g
active_ingredient_name
METRONIDAZOLE BENZOATE
spl_set_id
a56c2842-8ad4-4396-8eb6-cbcd1629fcb1
listing_expiration_date
20241231
core#notation
CHEBI:6909
nui
M0014907
pharm_class_epc
Nitroimidazole Antimicrobial [EPC]
pharm_class
Nitroimidazoles [CS]
pharm_class_cs
Nitroimidazoles [CS]
upc
0370882131148
brand_name_suffix
500 mg
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
rxcui
1604336
unii
140QMO216E
manufacturer_name
AvPAK
has_treatment
http://purl.obolibrary.org/obo/DOID_3767
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect31217
chebi#is_conjugate_acid_of
http://purl.obolibrary.org/obo/CHEBI_64682
owl#someValuesFrom
t3009527
owl#annotatedSource
t276775