Identification

Name
Metronidazole
Accession Number
DB00916  (APRD00631)
Type
Small Molecule
Groups
Approved
Description

A nitroimidazole used to treat amebiasis; vaginitis; trichomonas infections; giardiasis; anaerobic bacteria; and treponemal infections. It has also been proposed as a radiation sensitizer for hypoxic cells. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985, p133), this substance may reasonably be anticipated to be a carcinogen (Merck, 11th ed).

Structure
Thumb
Synonyms
  • 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
  • 1-(β-ethylol)-2-methyl-5-nitro-3-azapyrrole
  • 1-(β-hydroxyethyl)-2-methyl-5-nitroimidazole
  • 1-(β-oxyethyl)-2-methyl-5-nitroimidazole
  • 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole
  • 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole
  • 2-methyl-5-nitroimidazole-1-ethanol
  • Metronidazol
  • Metronidazolum
External IDs
Bayer 5360 / BAYER-5360 / NSC-50364 / NSC-69587 / RP 8823 / RP-8823
Product Ingredients
IngredientUNIICASInChI Key
Metronidazole hydrochloride76JC1633UF69198-10-3FPTPAIQTXYFGJC-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FlagylTablet, film coated500 mg/1OralG.D. Searle LLC Division of Pfizer Inc1963-07-18Not applicableUs
FlagylCream10 %VaginalSanofi Aventis1970-12-31Not applicableCanada
FlagylCapsule375 mg/1OralG.D. Searle LLC Division of Pfizer Inc1995-05-03Not applicableUs
FlagylCapsule375 mg/1OralPhysicians Total Care, Inc.1995-05-032000-09-19Us
FlagylCapsule500 mgOralOdan Laboratories Ltd1979-12-31Not applicableCanada
FlagylTablet, film coated250 mg/1OralG.D. Searle LLC Division of Pfizer Inc1963-07-18Not applicableUs
Flagyl 500 500mgSuppository500 mgVaginalAventis Pharma Ltd.1960-12-312003-07-22Canada
Flagyl ERTablet, film coated, extended release750 mg/1OralG.D. Searle LLC Division of Pfizer Inc1997-11-262014-10-31Us
Florazole ERTablet, extended release750 mgOralFerring Pharmaceuticals2002-10-102012-09-30Canada
MetroCreamCream7.5 mg/1gTopicalPhysicians Total Care, Inc.1995-09-202010-06-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-metronidazoleCapsule500 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-metronidazoleCapsule500 mgOralApotex Corporation2003-11-27Not applicableCanada
Apo-metronidazoleTablet250 mgOralApotex CorporationNot applicableNot applicableCanada
Auro-metronidazoleCapsule500 mgOralAuro Pharma Inc2018-04-03Not applicableCanada
MetronidazoleTablet, film coated500 mg/1OralDenton Pharma, Inc. Dba Northwind Pharmaceuticals2018-05-17Not applicableUs
MetronidazoleTablet, film coated500 mg/1OralClinical Solutions Wholsesale2014-06-01Not applicableUs
MetronidazoleTablet250 mg/1OralAlembic Pharmaceuticals Limited2016-12-01Not applicableUs
MetronidazoleTablet500 mg/1Oralbryant ranch prepack1990-09-30Not applicableUs63629 138620180907 15195 1nkvmjp
MetronidazoleTablet, film coated500 mg/1OralSt. Marys Medical Park Pharmacy2017-12-15Not applicableUs
MetronidazoleTablet500 mg/1OralDirectrx2015-01-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FlagystatinMetronidazole (500 mg) + Nystatin (100000 unit)SuppositoryVaginalAventis Pharma Ltd.1972-12-312004-07-30Canada
Flagystatin CreamMetronidazole (500 mg) + Nystatin (100000 unit)CreamVaginalSanofi Aventis1976-12-31Not applicableCanada
Flagystatin Vaginal OvuleMetronidazole (500 mg) + Nystatin (100000 unit)SuppositoryVaginalSanofi Aventis1979-12-31Not applicableCanada
HELIDAC TherapyMetronidazole (250 mg/1) + Bismuth Subsalicylate (262.4 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralPrometheus Laboratories1996-08-152014-02-01Us
PyleraMetronidazole (125 mg) + Bismuth subcitrate potassium monohydrate (40 mg) + Tetracycline hydrochloride (125 mg)CapsuleOralAptalis Pharma Inc.Not applicableNot applicableCanada
PyleraMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralAxcan Pharma US, Inc.2007-05-012011-06-14Us
PyleraMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralPhysicians Total Care, Inc.2010-08-18Not applicableUs
PyleraMetronidazole (125 mg/1) + Bismuth subcitrate potassium monohydrate (140 mg/1) + Tetracycline hydrochloride (125 mg/1)CapsuleOralAllergan2013-08-01Not applicableUs
RosasolMetronidazole (1.0 %) + Avobenzone (2.0 %) + Octinoxate (7.5 %)CreamTopicalGlaxosmithkline Inc2001-03-282014-03-03Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MetronidazoleMetronidazole (500 mg/1)TabletOralNorth Star Rx Llc2016-12-01Not applicableUs
MetronidazoleMetronidazole (250 mg/1)TabletOralNorth Star Rx Llc2016-12-01Not applicableUs
Rosaclear SystemMetronidazole (7.5 mg/1g)KitOMP, INC.2012-12-29Not applicableUs
International/Other Brands
Acromona / Anabact (Cambridge Healthcare Supplies) / Arilin / Clont / Deflamon / Efloran / Elyzol / Entizol / Fossyol / Klion / Klont / Metrolyl / Metrotop / Nalox / Nidagel / Novonidazol / Orvagil / Protostat / Takimetol / Trichazole / Trichex / Trichopol / Tricowas B / Trikacide / Trikozol / Vagilen / Vagimid / Vertisal / Zadstat
Categories
UNII
140QMO216E
CAS number
443-48-1
Weight
Average: 171.154
Monoisotopic: 171.064391169
Chemical Formula
C6H9N3O3
InChI Key
VAOCPAMSLUNLGC-UHFFFAOYSA-N
InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
IUPAC Name
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
SMILES
CC1=NC=C(N1CCO)[N+]([O-])=O

Pharmacology

Indication

For the treatment of anaerobic infections and mixed infections, surgical prophylaxis requiring anaerobic coverage, Clostridium difficile-associated diarrhea and colitis, Helicobacter pylori infection and duodenal ulcer disease, bacterial vaginosis, Giardia lamblia gastro-enteritis, amebiasis caused by Entamoeba histolytica, acne rosacea (topical treatment), and Trichomonas infections.

Associated Conditions
Pharmacodynamics

Metronidazole, a synthetic antibacterial and antiprotozoal agent of the nitroimidazole class, is used against protozoa such as Trichomonas vaginalis, amebiasis, and giardiasis. Metronidazole is extremely effective against anaerobic bacterial infections and is also used to treat Crohn's disease, antibiotic-associated diarrhea, and rosacea.

Mechanism of action

Metronidazole is a prodrug. Unionized metronidazole is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. This reduced metronidazole then covalently binds to DNA, disrupt its helical structure, inhibiting bacterial nucleic acid synthesis and resulting in bacterial cell death.

TargetActionsOrganism
ADNA
binder
Human
AOxygen-insensitive NADPH nitroreductase
potentiator
Helicobacter pylori (strain ATCC 700392 / 26695)
UIron hydrogenase 1
inhibitor
Clostridium pasteurianum
ULanosterol 14-alpha demethylaseNot AvailableHuman
Absorption

Well absorbed (at least 80%) with peak plasma concentrations achieved in 1-3 hours following oral administration of therapeutic doses of immediate release formulation.

Volume of distribution
Not Available
Protein binding

Less than 20% bound to plasma proteins.

Metabolism

Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.

Route of elimination
Not Available
Half life

6-8 hours

Clearance
Not Available
Toxicity

LD50=500 mg/kg/day (orally in rat). Adverse effects include reversible peripheral neuropathy with prolonged therapy, CNS toxicity, disulfiram effect with alcohol, dark red-brown urine, metallic taste, nausea, epigastric distress, dizziness, vertigo and paresthesias associated with high doses, and neutropenia (reversible and mild).

Affected organisms
  • Bacteria and protozoa
  • Helicobacter pylori
  • Peptoclostridium difficile
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Metronidazole is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Metronidazole is combined with (S)-Warfarin.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Metronidazole.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Metronidazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Metronidazole.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Metronidazole.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Metronidazole.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Metronidazole.
AbexinostatThe risk or severity of QTc prolongation can be increased when Metronidazole is combined with Abexinostat.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Metronidazole.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

References

Synthesis Reference
US2944061
General References
  1. Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. [PubMed:16398774]
  2. Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [PubMed:15715599]
  3. Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [PubMed:10676835]
  4. Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. [PubMed:12022894]
External Links
Human Metabolome Database
HMDB0015052
KEGG Drug
D00409
KEGG Compound
C07203
PubChem Compound
4173
PubChem Substance
46508911
ChemSpider
4029
BindingDB
50375309
ChEBI
6909
ChEMBL
CHEMBL137
Therapeutic Targets Database
DAP000534
PharmGKB
PA450484
HET
2MN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Metronidazole
ATC Codes
G01AF01 — MetronidazoleA02BD08 — Bismuth subcitrate, tetracycline and metronidazoleP01AB01 — MetronidazoleA02BD01 — Omeprazole, amoxicillin and metronidazoleD06BX01 — MetronidazoleA02BD03 — Lansoprazole, amoxicillin and metronidazoleA01AB17 — MetronidazoleG01AF20 — Combinations of imidazole derivativesA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazoleP01AB51 — Metronidazole, combinationsA02BD02 — Lansoprazole, tetracycline and metronidazoleJ01XD01 — MetronidazoleJ01RA03 — Cefuroxime and metronidazoleJ01RA04 — Spiramycin and metronidazoleJ01RA10 — Ciprofloxacin and metronidazole
AHFS Codes
  • 84:04.04 — Antibiotics
  • 08:30.92 — Miscellaneous Antiprotozoals
  • 84:04.92 — Miscellaneous Local Anti-infectives
PDB Entries
1w3r
FDA label
Download (115 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentVaginal Inflammation1
0CompletedTreatmentAcute, uncomplicated Appendicitis1
0Enrolling by InvitationBasic ScienceDietary Modifications / Nutrition1
0Not Yet RecruitingBasic ScienceBioequivalence1
0RecruitingSupportive CareDiverticulitis / Inflammatory Bowel Diseases (IBD) / Neoplasms, Colorectal / Surgical Site Infections1
0RecruitingTreatmentOsteomyelitis1
0SuspendedTreatmentBacterial Vaginosis (BV)1
0Unknown StatusDiagnosticBacterial Vaginosis (BV)1
1Active Not RecruitingBasic ScienceBacterial Infections1
1CompletedNot AvailableBacterial Infections / Brain Injury1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableInfection NOS1
1CompletedNot AvailableTo Determine the Bioequivalence Study Under Fasting1
1CompletedNot AvailableTo Determine the Bioequivalence Study Under Fed1
1CompletedBasic ScienceBacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic SciencePerianal Crohns'1
1CompletedTreatmentBacterial Infections1
1CompletedTreatmentInfection NOS1
1CompletedTreatmentNecrotizing Enterocolitis / Serious Systemic Infections1
1CompletedTreatmentPrimary Sclerosing Cholangitis (PSC)1
1CompletedTreatmentRosaceas1
1Enrolling by InvitationTreatmentBioequivalence1
1RecruitingTreatmentSurgical Site Infection Rate / Surgical Site Infection Rate in Obese Women Who Have Labored Undergoing Cesarean Section / Surgical Site Infections1
1, 2CompletedNot AvailableBacterial Vaginosis (BV)1
1, 2CompletedTreatmentCentral Serous Chorioretinopathy (CSC)1
1, 2TerminatedTreatmentBacterial Vaginosis (BV)1
2Active Not RecruitingPreventionBacterial Vaginosis (BV)1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2Active Not RecruitingTreatmentMalnutrition1
2CompletedTreatmentAppendicitis1
2CompletedTreatmentBacterial Vaginosis (BV) / Vaginal Infections1
2CompletedTreatmentClostridium Difficile1
2CompletedTreatmentClostridium Difficile Associated Diarrhea1
2CompletedTreatmentComplicated Intra-Abdominal Infections2
2CompletedTreatmentComplicated Intra-Abdominal Infections (cIAIs) / Complicated Intra-Abdominal Infections, cIAIs1
2CompletedTreatmentComplicated Intra-Abdominal Infections / Complicated Intra-Abdominal Infections (cIAIs)1
2CompletedTreatmentMalignant Lymphomas2
2CompletedTreatmentMulti-Drug Resistant Tuberculosis / Tuberculosis1
2CompletedTreatmentPelvic Inflammatory Disease (PID)1
2CompletedTreatmentPeriodontal Diseases / Periodontitis2
2CompletedTreatmentPeriodontitis, Chronic1
2CompletedTreatmentRosacea Subtype 1 (Erythematotelangiectatic)1
2CompletedTreatmentTrichomonas Vaginitis1
2Not Yet RecruitingPreventionLeak, Anastomotic / Rectal Carcinoma1
2Not Yet RecruitingTreatmentAppendicitis Acute1
2RecruitingTreatmentClostridium Difficile1
2RecruitingTreatmentComplicated Intra-Abdominal Infections1
2RecruitingTreatmentGastric Diffuse Large B-cell Lymphoma1
2RecruitingTreatmentInfected Immature Permanent Teeth1
2RecruitingTreatmentUlcerative Colitis (UC)1
2TerminatedTreatmentCrohn's Disease (CD)1
2TerminatedTreatmentOsteomyelitis1
2Unknown StatusTreatmentHepatic Encephalopathy1
2, 3Active Not RecruitingTreatmentClostridium Difficile Infection (CDI)1
2, 3CompletedTreatmentAggressive Periodontitis, Generalized1
2, 3CompletedTreatmentBacterial Vaginosis (BV)1
2, 3CompletedTreatmentChronic Functional Diarrhea1
2, 3CompletedTreatmentComplicated Intra Abdominal Infections1
2, 3CompletedTreatmentHemorrhoidectomy1
2, 3CompletedTreatmentPeriodontitis, Aggressive1
2, 3Not Yet RecruitingPreventionSurgical Site Infections / Venous Thromboembolism (VTE)1
2, 3Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)1
2, 3RecruitingPreventionPeriodontitis, Chronic / Type 2 Diabetes Mellitus1
2, 3RecruitingTreatmentClostridium Difficile1
2, 3RecruitingTreatmentCrohn's Disease (CD)1
2, 3Unknown StatusTreatmentBacterial Vaginosis (BV)1
2, 3Unknown StatusTreatmentBacterial Vaginosis (BV) / Diarrhea / Human Immunodeficiency Virus (HIV) Infections1
2, 3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer (GU) / Gastritis / Helicobacter Infections1
3CompletedPreventionAppendicitis Acute / Perforated Gastroduodenal Ulcer / Small intestinal obstruction1
3CompletedPreventionBacterial Vaginosis (BV)2
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionInfection NOS / Surgical Site Infections1
3CompletedPreventionNeoplasms, Colorectal1
3CompletedSupportive CareNeoplasms / Wounds and Injuries1
3CompletedTreatmentAnal Incontinence1
3CompletedTreatmentAntibiotic-Associated Diarrhea / Clostridium Enterocolitis / Pseudomembranous Colitis / Pseudomembranous Enteritis / Pseudomembranous Enterocolitis1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3CompletedTreatmentBacterial Vaginosis (BV)1
3CompletedTreatmentBacterial Vaginosis (BV) / Trichomonas Vaginitis / Urogenital Diseases1
3CompletedTreatmentComplicated Intra-Abdominal Infections4
3CompletedTreatmentComplicated Intra-Abdominal Infections / Complicated Urinary Tract Infections1
3CompletedTreatmentComplicated Intra-Abdominal Infections / Intra-Abdominal Infections1
3CompletedTreatmentCrohn's Disease (CD)1
3CompletedTreatmentHelicobacter Infections1
3CompletedTreatmentHemorrhoids1
3CompletedTreatmentIntra-Abdominal Infections2
3CompletedTreatmentPapulopustular Rosacea (PPR)1
3CompletedTreatmentPapulopustular Rosacea (PPR) / Rosacea Subtype 1 (Erythematotelangiectatic)1
3CompletedTreatmentPelvic Inflammatory Disease (PID)1
3CompletedTreatmentVaginal Infections2
3Not Yet RecruitingTreatmentAntibiotic Resistance / Antibiotic Toxicity / Severe Malnutrition1
3RecruitingOtherRenal Stones1
3RecruitingPreventionRecurrent Bacterial Vaginosis1
3RecruitingTreatmentAntibiotic Resistant Infection / Complicated skin infection bacterial / Intra Abdominal Infections1
3RecruitingTreatmentDuodenal Ulcer1
3RecruitingTreatmentGingival Inflammation1
3RecruitingTreatmentHelicobacter-associated Gastritis1
3Unknown StatusTreatmentBacterial Vaginosis (BV) / Fungal Vaginal Infections1
3Unknown StatusTreatmentMalignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
3Unknown StatusTreatmentPost Gastrectomy State1
3WithdrawnTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3WithdrawnTreatmentSexual Active Women / Vaginal Discharge1
4Active Not RecruitingTreatmentBlastocystis Hominis Infections1
4CompletedNot AvailablePerforated Appendicitis1
4CompletedPreventionInfection Prophylaxis in Colo Rectal Surgery1
4CompletedSupportive CareGeneralized Aggressive Periodontitis / Periodontitis, Aggressive1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)7
4CompletedTreatmentBacterial Vaginosis (BV)4
4CompletedTreatmentComplicated Appendicitis1
4CompletedTreatmentComplicated Intra-Abdominal Infections1
4CompletedTreatmentCrohn's Disease (CD)1
4CompletedTreatmentCure Rate of Helicobacter Pylori Infection1
4CompletedTreatmentDientamoebiasis1
4CompletedTreatmentFunctional Dyspepsia / Scarred Peptic Ulcer1
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Infections2
4CompletedTreatmentHelicobacter Pylori Treatment Failure1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Trichomonas Infections1
4CompletedTreatmentIndigestion / Peptic Ulcers1
4CompletedTreatmentIrritable Bowel Syndrome (IBS)1
4CompletedTreatmentPapulopustular Rosacea (PPR)1
4CompletedTreatmentPelvic Inflammatory Disease (PID)1
4CompletedTreatmentPeptic Ulcers1
4CompletedTreatmentPeri-Implantitis and Peri-implant Mucositis1
4CompletedTreatmentPeriodontal Pocket1
4CompletedTreatmentPeriodontitis1
4CompletedTreatmentPeriodontitis, Chronic / Smoking1
4CompletedTreatmentRosaceas2
4CompletedTreatmentSkin Manifestations2
4CompletedTreatmentTrigger Finger Disorder1
4Enrolling by InvitationTreatmentSmall Intestinal Bacterial Overgrowth1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4Not Yet RecruitingTreatmentElective Colon Surgery1
4Not Yet RecruitingTreatmentHemorrhoids / Postoperative pain1
4RecruitingBasic ScienceRabies Human1
4RecruitingPreventionInfection, Postoperative Wound1
4RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)5
4RecruitingTreatmentBacterial Vaginosis (BV)2
4RecruitingTreatmentBacterial Vaginosis (BV) / Recurrences1
4RecruitingTreatmentGiardiasis1
4RecruitingTreatmentGingival Inflammation1
4RecruitingTreatmentPeri-Implantitis1
4RecruitingTreatmentSclerosis, Progressive Systemic / Small Intestinal Bacterial Overgrowth1
4RecruitingTreatmentUlcerative Colitis (UC)1
4TerminatedPreventionClostridium Difficile Diarrhea1
4TerminatedTreatmentAppendicitis1
4TerminatedTreatmentBacterial Vaginosis (BV)1
4TerminatedTreatmentSeptic Abortion1
4Unknown StatusTreatmentAdverse Effects / Digestive System Disorders1
4Unknown StatusTreatmentAmputation Wound / Wound Infections1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4Unknown StatusTreatmentBacterial Vaginosis (BV)1
4Unknown StatusTreatmentCommunity Acquired Pneumonia (CAP)1
4Unknown StatusTreatmentEradication Rate for Helicobacter1
4Unknown StatusTreatmentEradication Rates of the Two Regimens1
4Unknown StatusTreatmentGastritis, Gastric Ulcer, and Duodenal Ulcer1
4Unknown StatusTreatmentHelicobacter Pylori1
4Unknown StatusTreatmentPancreatitis,Acute Necrotizing1
4WithdrawnTreatmentAppendicitis1
Not AvailableActive Not RecruitingTreatmentSimple Diverticular Disease1
Not AvailableCompletedNot AvailableAntibiotic-Associated Colitis / Clostridium Enterocolitis / Pseudomembranous Colitis1
Not AvailableCompletedNot AvailableBacterial Vaginosis (BV) / Trichomonal Vaginitis / Vaginal Candidiasis1
Not AvailableCompletedNot AvailableC. Difficile / Diarrhea / Enterocolitis1
Not AvailableCompletedNot AvailablePeriodontitis, Chronic1
Not AvailableCompletedNot AvailableRosaceas2
Not AvailableCompletedBasic ScienceEndotoxaemia1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Sepsis1
Not AvailableCompletedDiagnosticIron Deficiency / Malabsorption1
Not AvailableCompletedOtherFlu caused by Influenza1
Not AvailableCompletedPreventionBacterial Vaginosis (BV) / Vaginal Discharge1
Not AvailableCompletedPreventionFirst Trimester Abortion1
Not AvailableCompletedSupportive CareBacterial Vaginosis (BV)1
Not AvailableCompletedTreatmentAppendicitis / Children1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)5
Not AvailableCompletedTreatmentBacterial Vaginosis (BV)2
Not AvailableCompletedTreatmentHepatitis, Autoimmune / Overlap Syndrome / Primary Sclerosing Cholangitis (PSC)1
Not AvailableCompletedTreatmentPerforated Appendicitis1
Not AvailableCompletedTreatmentPeritonsillar Abscess1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableEnrolling by InvitationOtherAppendicitis Acute1
Not AvailableEnrolling by InvitationTreatmentAppendicitis Acute1
Not AvailableNot Yet RecruitingPreventionAppendicitis1
Not AvailableNot Yet RecruitingPreventionColostomy Stoma / Hirschprung's Disease / Ileostomy - Stoma / Inflammatory Bowel Diseases (IBD) / Intestinal Obstruction / Jejunostomy Stoma / Meconium Ileus / NEC1
Not AvailableRecruitingPreventionForeskin HIV Susceptibility1
Not AvailableRecruitingPreventionRectal Carcinoma1
Not AvailableRecruitingTreatmentAbnormal Vaginal Flora / Clindamycin Vs Metronidazole / High Risk Pregnancies for Preterm Labor1
Not AvailableRecruitingTreatmentAppendicitis Acute1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
Not AvailableRecruitingTreatmentChronic Periodontitis Complex1
Not AvailableRecruitingTreatmentHelicobacter Infection2
Not AvailableRecruitingTreatmentPeriodontitis, Chronic / Probiotics1
Not AvailableTerminatedPreventionLength of Pregnancy Prolongation in Hours1
Not AvailableTerminatedTreatmentAbortions spontaneous / Bacterial Vaginosis (BV) / Infertilities1
Not AvailableTerminatedTreatmentSeptic Abortion1
Not AvailableTerminatedTreatmentUlcerative Colitis (UC)1
Not AvailableUnknown StatusDiagnosticC. Difficile Infection1
Not AvailableUnknown StatusPreventionAppendicitis1
Not AvailableUnknown StatusPreventionSurgical Site Infection in Obese Women Undergoing C-section1
Not AvailableUnknown StatusTreatmentBMI >30 kg/m2 / Periodontal Diseases / Periodontitis1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1

Pharmacoeconomics

Manufacturers
  • Gd searle llc
  • Able laboratories inc
  • Alembic ltd
  • Par pharmaceutical inc
  • Galderma laboratories lp
  • Altana inc
  • G and w laboratories inc
  • Sanofi aventis us llc
  • Taro pharmaceutical industries ltd
  • Tolmar inc
  • Graceway pharmaceuticals llc
  • Teva pharmaceuticals usa
  • Baxter healthcare corp
  • B braun medical inc
  • Abbott laboratories pharmaceutical products div
  • Abraxis pharmaceutical products
  • Elkins sinn div ah robins co inc
  • International medication systems ltd
  • Watson laboratories inc
  • Claris lifesciences ltd
  • Hospira inc
  • Laboratorios aplicaciones farmaceuticas sa de cv
  • Halsey drug co inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lnk international inc
  • Mutual pharmaceutical co inc
  • Pliva inc
  • Sandoz inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • World gen llc
  • Ortho mcneil pharmaceutical inc
  • Savage laboratories inc div altana inc
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • American Pharmaceutical Association
  • Ameri-Pac Inc.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apace Packaging
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • B. Braun Melsungen AG
  • Baxter International Inc.
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Central Texas Community Health Centers
  • Claris Lifesciences Inc.
  • Community Action Inc. Community Health Services
  • Comprehensive Consultant Services Inc.
  • Contract Pharm
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • Dermik Labs
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DPT Laboratories Ltd.
  • Dudley Corp.
  • E. Fougera and Co.
  • G & W Labs
  • Galderma Laboratories
  • GD Searle LLC
  • GlaxoSmithKline Inc.
  • Golden State Medical Supply Inc.
  • Graceway Pharmaceuticals
  • Group Health Cooperative
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Harris Pharmaceutical Inc.
  • Hawkins Inc.
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Medvantx Inc.
  • Mississippi State Dept Health
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Nord Ost Corp.
  • Nucare Pharmaceuticals Inc.
  • Nycomed Inc.
  • Obagi Medical Products Inc.
  • Palmetto Pharmaceuticals Inc.
  • Pangeo Pharma Quebec Inc.
  • Par Pharmaceuticals
  • Patheon Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmacia Inc.
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Prasco Labs
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Raz Co. Inc.
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Rochester Pharmaceuticals
  • Sagent Pharmaceuticals
  • Sandhills Packaging Inc.
  • Sandoz
  • Sanofi-Aventis Inc.
  • SCS Pharmaceuticals
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • Tolmar Inc.
  • UDL Laboratories
  • Upsher Smith Laboratories
  • Vangard Labs Inc.
  • Veratex Corp.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
CapsuleOral375 mg/1
CreamVaginal10 %
SuppositoryVaginal500 mg
CreamVaginal
SuppositoryVaginal
Tablet, extended releaseOral750 mg
KitOral
CreamTopical.75 %
GelTopical10 mg/1g
GelVaginal7.5 mg/1g
GelTopical0.75 %
GelTopical1 %
LotionTopical0.75 %
CreamTopical10 mg/1g
CreamTopical7.5 mg/1g
GelTopical7.5 mg/1g
GelVaginal13 mg/1g
InjectionIntravenous500 mg/100mL
Injection, solutionIntravenous500 mg/100mL
LotionTopical7.5 mg/1g
LotionTopical7.5 mg/1mL
SolutionIntravenous500 mg/100mL
TabletOral250 mg/1
TabletOral250 mg
TabletOral500 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral500 1/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coated, extended releaseOral750 mg/1
LiquidIntravenous5 mg
SolutionIntravenous5 mg
GelVaginal0.75 %
CreamTopical1 %
CreamTopical10 mg/60g
GelTopical65 mg/5g
GelVaginal65 mg/5g
CapsuleOral500 mg
CapsuleOral
Kit7.5 mg/1g
CreamTopical
Prices
Unit descriptionCostUnit
MetroLotion 0.75% Lotion 59ml Bottle292.66USD bottle
MetroCream 0.75% Cream 45 gm Tube281.09USD tube
Metrogel 1% Gel 60 gm Tube200.93USD tube
Metrogel 1% Kit Box200.93USD box
Metrogel 1% kit193.2USD kit
Noritate 1% Cream 60 gm Tube156.44USD tube
MetroNIDAZOLE 0.75% Lotion 59ml Bottle89.86USD bottle
MetroNIDAZOLE 0.75% Cream 45 gm Tube80.87USD tube
MetroNIDAZOLE 0.75% Gel 45 gm Tube74.0USD tube
MetroNIDAZOLE 0.75% Gel 70 gm Tube68.53USD tube
Flagyl ER 750 mg 24 Hour tablet13.2USD tablet
Flagyl er 750 mg tablet12.7USD tablet
MetroNIDAZOLE 750 mg 24 Hour tablet8.07USD tablet
Flagyl 500 mg tablet6.24USD tablet
Metrocream 0.75% cream5.99USD g
Danazol 200 mg capsule5.63USD capsule
Flagyl 375 mg capsule5.45USD capsule
Metrolotion topical 0.75%4.77USD ml
Metronidazole benz powder4.74USD g
Flagyl 250 mg tablet3.49USD tablet
Danazol 100 mg capsule2.98USD capsule
Noritate 1% cream2.51USD g
Danazol 50 mg capsule1.99USD capsule
Metronidazole powder1.65USD g
Metronidazole 0.75% cream1.34USD g
Metronidazole vaginal 0.75% gl0.94USD g
Metronidazole 500 mg tablet0.72USD tablet
Metrogel 0.75 % Gel0.69USD g
Metrogel 1 % Gel0.63USD g
Noritate 1 % Cream0.58USD g
Rosasol 1 % Cream0.57USD g
Metrocream 0.75 % Cream0.52USD g
Metrolotion 0.75 % Lotion0.52USD g
Metrogel-vaginal 0.75% gel0.51USD g
Vandazole vaginal 0.75% gel0.48USD g
Metronidazole 250 mg tablet0.44USD tablet
Flagyl 10 % Cream0.25USD g
Apo-Metronidazole 250 mg Tablet0.06USD tablet
Flagyl 5 mg/ml0.03USD ml
Metro iv 500 mg/100 ml0.03USD ml
Metronidazole 5 mg/ml0.03USD ml
Metronidazole 500 mg/100 ml0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5536743No1993-07-162013-07-16Us
CA2470492No2010-02-232022-11-07Canada
CA2161737No1998-10-202015-10-30Canada
US6881726No2002-02-212022-02-21Us
US7348317No2002-02-212022-02-21Us
US7456207No2004-09-222024-09-22Us
US6350468No1998-12-142018-12-14Us
US8946276No2012-06-282032-06-28Us
US8658678No2008-06-272028-06-27Us
US9198858No2012-06-282032-06-28Us
US8877792No2008-02-022028-02-02Us
US7893097No2008-02-192028-02-19Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)160.5 °CPhysProp
water solubility9500 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.02HANSCH,C ET AL. (1995)
logS-1.26ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility5.92 mg/mLALOGPS
logP-0.15ALOGPS
logP-0.46ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)3.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.87 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.22 m3·mol-1ChemAxon
Polarizability15.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9805
Blood Brain Barrier+0.9297
Caco-2 permeable-0.5365
P-glycoprotein substrateNon-substrate0.5141
P-glycoprotein inhibitor INon-inhibitor0.8954
P-glycoprotein inhibitor IINon-inhibitor0.8755
Renal organic cation transporterNon-inhibitor0.7762
CYP450 2C9 substrateNon-substrate0.7318
CYP450 2D6 substrateNon-substrate0.8815
CYP450 3A4 substrateNon-substrate0.6767
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9242
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9401
CYP450 3A4 inhibitorNon-inhibitor0.9242
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8483
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7471
BiodegradationNot ready biodegradable0.5941
Rat acute toxicity2.0422 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Non-inhibitor0.8272
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.68 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0ul0-9300000000-2268b08f47fed3f6d263
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-1900000000-659f2bbb83f8ef5a85d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-50c7cfe79eb17c4440a8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-b06d808767cc01c0d494
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00fr-0900000000-e9c07cc448b8fb519022
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-8ad03b44aa7557127e34
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-ed7ba5c872a6309a31d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-e0ead4b0eec72b9c44b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-5900000000-2da8a7b45537f9063220
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-24d94f1704e577b05eb7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00fr-0900000000-fbb1c4e8457cd3d799b9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-fd6166313a17f944f530
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-5ebb32a580e1f5d00170
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-811a6e7e45b7ea1a6184
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-5900000000-082e6de6c0fa3f382d84
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-baf9e195c01d875e77b5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-ec181c008a10dac8040b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-1900000000-2a218e19a8fadb9c66d6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-003r-9500000000-ed02acd36b190c189cc9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-71ea79659ccd75c64bef
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-3f7795597c6629540426
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Nitroimidazoles
Alternative Parents
Nitroaromatic compounds / 1,2,5-trisubstituted imidazoles / N-substituted imidazoles / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Azacyclic compounds / Alkanolamines / Primary alcohols / Organopnictogen compounds
show 3 more
Substituents
1,2,5-trisubstituted-imidazole / Nitroaromatic compound / Nitroimidazole / Trisubstituted imidazole / N-substituted imidazole / Heteroaromatic compound / Organic nitro compound / C-nitro compound / Alkanolamine / Azacycle
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
C-nitro compound, imidazoles, primary alcohol (CHEBI:6909)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Binder
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Salles JM, Salles MJ, Moraes LA, Silva MC: Invasive amebiasis: an update on diagnosis and management. Expert Rev Anti Infect Ther. 2007 Oct;5(5):893-901. [PubMed:17914922]
  2. Li AQ, Dai N, Yan J, Zhu YL: [Screening for metronidazole-resistance associated gene fragments of Helicobacter pylori by suppression subtractive hybridization]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2007 Sep;36(5):465-9. [PubMed:17924465]
  3. Edwards DI: Nitroimidazole drugs--action and resistance mechanisms. I. Mechanisms of action. J Antimicrob Chemother. 1993 Jan;31(1):9-20. [PubMed:8444678]
Kind
Protein
Organism
Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action
Yes
Actions
Potentiator
General Function
Oxidoreductase activity
Specific Function
Reduction of a variety of nitroaromatic compounds using NADPH as source of reducing equivalents; two electrons are transferred (By similarity). Capable of reducing metronidazole; inactive RdxA rend...
Gene Name
rdxA
Uniprot ID
O25608
Uniprot Name
Oxygen-insensitive NADPH nitroreductase
Molecular Weight
24067.775 Da
References
  1. Sisson G, Jeong JY, Goodwin A, Bryden L, Rossler N, Lim-Morrison S, Raudonikiene A, Berg DE, Hoffman PS: Metronidazole activation is mutagenic and causes DNA fragmentation in Helicobacter pylori and in Escherichia coli containing a cloned H. pylori RdxA(+) (Nitroreductase) gene. J Bacteriol. 2000 Sep;182(18):5091-6. [PubMed:10960092]
  2. Chisholm SA, Owen RJ: Mutations in Helicobacter pylori rdxA gene sequences may not contribute to metronidazole resistance. J Antimicrob Chemother. 2003 Apr;51(4):995-9. Epub 2003 Mar 13. [PubMed:12654749]
  3. Debets-Ossenkopp YJ, Pot RG, van Westerloo DJ, Goodwin A, Vandenbroucke-Grauls CM, Berg DE, Hoffman PS, Kusters JG: Insertion of mini-IS605 and deletion of adjacent sequences in the nitroreductase (rdxA) gene cause metronidazole resistance in Helicobacter pylori NCTC11637. Antimicrob Agents Chemother. 1999 Nov;43(11):2657-62. [PubMed:10543743]
  4. Pisharath H, Parsons MJ: Nitroreductase-mediated cell ablation in transgenic zebrafish embryos. Methods Mol Biol. 2009;546:133-43. doi: 10.1007/978-1-60327-977-2_9. [PubMed:19378102]
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Clostridium pasteurianum
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Iron ion binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P29166
Uniprot Name
Iron hydrogenase 1
Molecular Weight
63827.595 Da
References
  1. Kutty R, Bennett GN: Studies on inhibition of transformation of 2,4,6-trinitrotoluene catalyzed by Fe-only hydrogenase from Clostridium acetobutylicum. J Ind Microbiol Biotechnol. 2006 May;33(5):368-76. Epub 2006 Jan 28. [PubMed:16550436]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name
CYP51A1
Uniprot ID
Q16850
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
56805.26 Da
References
  1. Ekins S, Mankowski DC, Hoover DJ, Lawton MP, Treadway JL, Harwood HJ Jr: Three-dimensional quantitative structure-activity relationship analysis of human CYP51 inhibitors. Drug Metab Dispos. 2007 Mar;35(3):493-500. Epub 2006 Dec 28. [PubMed:17194716]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [PubMed:25470432]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [PubMed:25470432]
  2. Michalets EL: Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112. [PubMed:9469685]
  3. Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [PubMed:8877250]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Kudo T, Endo Y, Taguchi R, Yatsu M, Ito K: Metronidazole reduces the expression of cytochrome P450 enzymes in HepaRG cells and cryopreserved human hepatocytes. Xenobiotica. 2015 May;45(5):413-9. doi: 10.3109/00498254.2014.990948. Epub 2014 Dec 3. [PubMed:25470432]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2018 04:36