This document discusses the chemical metronidazole, including its molecular formula, structure, alternative names, history of development and uses. Metronidazole is a synthetic antibiotic and antiprotozoal agent used to treat various infections caused by anaerobic bacteria and protozoa. It works by being selectively reduced inside anaerobic cells and binding to DNA. Common side effects include nausea and neurological symptoms. The document compares metronidazole to other drugs for specific conditions, finding ciprofloxacin and vancomycin more effective than metronidazole for some infections. Metronidazole is recommended for completing the prescribed dosage to avoid antibiotic resistance.

1. East West University
Course: Chemistry for Biologist II
Course Code: CHE208
Topic: Metronidazole
Submitted by: Md. Shabab Mehebub,
Department of Genetic engineering and biotechnology.

2. Company Name: WATSON LABS
Chemical Component
Name: Metronidazole
Molecular Formula: C6H9N3O3
Structure:
2D Structure of Metronidazole 3D Structure of Metronidazole

3. Alternative Name:
1. 2 Methyl 5 nitroimidazole 1 ethanol
2. 2-Methyl-5-nitroimidazole-1-ethanol
3. Bayer 5360
4. Clont
5. Danizol
6. Flagyl
7. Gineflavir
8. Hydrochloride, Metronidazole
9. Metric
10. Metrodzhil
11. MetroGel
12. Metrogyl
13. Metronidazole
14. Metronidazole Hydrochloride
15. Metronidazole Monohydrochloride
16. Metronidazole Phosphate
17. Metronidazole Phosphoester
18. Monohydrochloride, Metronidazole
19. Phosphate, Metronidazole
20. Phosphoester, Metronidazole
21. Satric
22. Trichazol
23. Trichopol
24. Trivazol
25. Vagilen

4. History:
Metronidazole was synthesized by France's Rhone-Poulenc laboratories and introduced in the
mid-1950s under the brand name Flagyl. It was the first member of the group of drugs that are
now called nitroimidazoles. In the US it was licensed to Searle. Metronidazole is one of the rare
examples of a drug developed as antiparasitic which has since gained broad use as an
antibacterial agent. Briefly, at Rhone-Poulenc labs, extracts of Streptomyces spp. were
screened for activity against Trichomonas vaginalis, a cause of vaginal itching.
Azomycin, a nitroimidazole, was identified, and metronidazole, a synthetic derivative, was used
to treat chronic trichomonad infections, beginning in 1959.
The antibacterial activity of metronidazole was discovered by accident in 1962 when
metronidazole cured a patient of both trichomonad vaginitis and bacterial gingivitis. However,
it was not until the 1970s that metronidazole was popularized for treatment of infections
caused by gram-negative anaerobes such as bacteroides or gram-positive anaerobes such as
clostridia. Currently, metronidazole is on the formulary at most hospitals for prophylaxis against
anaerobic infection after bowel surgery, for treatment of wound abscess, and for treatment of
antibiotic-associated colitis caused by Clostridium difficile. Metronidazole in combination with
other agents is widely used against Helicobacter pylori, a major cause of gastritis and a risk
factor for stomach cancer.
Mode of Action
Target: Metronidazole, a synthetic antibacterial and antiprotozoal agent of
the nitroimidazole class, is used against protozoa such asTrichomonas 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.

5. Mechanism: 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.
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.
Side effects: Symptoms of exposure to this chemical may include nerve or sheath structural
changes, eye changes, tremors, fever, jaundice and other liver changes. It may cause convulsive
seizures, numbness, nausea, vomiting, abdominal discomfort, diarrhea, sharp, unpleasant
metallic taste, erythematous rash, pruritus, dizziness, syncope, ataxia, thrombophlebitis after
intravenous infusion, darkened urine, anorexia, epigastric distress, constipation, glossitis,
stomatitis, reversible thrombocytopenia and vertigo. Flattening of the T-wave may be seen in
electrocardiographic tracings. It may also cause incoordination, irritability, depression,
weakness, insomnia, nasal congestion dysuria, cystitus, polyuria, incontinence, a sense of pelvic
pressure, dyspareunia, decrease of libido, proctitis and fleeting joint pains sometimes
resembling serum sickness. It may cause skin rash and drowsiness. Other symptoms of
exposure include malaise, transient rashes, gastrointestinal disturbances and peripheral
neuropathy. It may cause coated tongue, dry mouth, urethral discomfort, temporary
leukopenia, increase in chromosome aberrations, candidal vaginitis, lethargy and sore furred
tongue. In conjunction with alcohol it may provoke a disulfuram-like reaction. Pregnant women
expose to this compound have given birth to premature, stillborn infants. One infant has died
of white asphyxia. It may cause epigastric distress, abdominal cramping, numbness or
paresthesia of an extremity, urticaria, flushing, dryness of vagina or vulva, abdominal distress,
headache (if ingested with alcohol), confusional and psychotic states, blood dyscrasias,

6. temporary neutropenia which reverses after therapy, and low concentrations of lipids in
plasma. ACUTE/CHRONIC HAZARDS: This compound is harmful by ingestion, inhalation or skin
absorption. It may cause irritation. When heated to decomposition it emits toxic fumes
of carbon monoxide,carbon dioxide and nitrogen oxides. (NTP, 1992)
Discussion:
Comparison with related Drug
1. Metronidazole vs. Ciprofloxacin (Cipro)
Pouchitis
Ciprofloxacin is preferable to metronidazole, because treatment with ciprofloxacin eradicates
both pathogens (Clostridium perfringens and E. coli) and results in an optimal restoration of
normal pouch flora. Also, ciprofloxacin is better tolerated than metronidazole.
2. Metronidazole vs. Albendazole
Giardiasis
Albendazole and metronidazole are equally effective in the treatment of giardiasis. Albendazole
is better tolerated than metronidazole.
Results of randomized, double-blind, clinical trial of
albendazole versus metronidazolefor adult giardiasis Metronidazole Albendazole
Regimen
250 mg 3 times daily for 5
days
400 mg daily for
5 days
Efficacy rate 85.3% 82.6%

7. Most common side effects
bitter taste, headache,
vomiting and dizziness abdominal pain
3. Metronidazole vs. Vancomycin
Clostridium difficile-associated diarrhea
Metronidazole and vancomycin are equally effective for mild Clostridium difficile-associated
diarrhea (CDAD), but vancomycin is superior for treating severe CDAD.
In the prospective observational study among the patients with mild CDAD, treatment with
metronidazole or vancomycin resulted in clinical cure in 90% and 98% of the patients. However,
in severe CDAD clinical cure was 76% in metronidazole group and 97% in vancomycin group.
Results from 2 randomized, controlled trials of vancomycin, metronidazole,
or tolevamer for Clostridium difficile Infection (CDI) 7 Metronidazole Vancomycin
Clinical success 72.7% 81.1%
Clinical success in patients with severe CDI 66.3% 78.5%
Conclusion: Metronidazole is primarily used to treat: bacterial vaginosis, pelvic inflammatory
disease (along with other antibacterials likeceftriaxone), pseudomembranous colitis, aspiration
pneumonia, rosacea (topical), fungating wounds (topical), intra-abdominal infections, lung
abscess, periodontitis, amoebiasis, oral infections, giardiasis, trichomoniasis, and infections
caused by susceptible anaerobic organisms such
as Bacteroides, Fusobacterium, Clostridium, Peptostreptococcus, and Prevotella species. It is

8. also often used to eradicate Helicobacter pylori along with other drugs and to prevent infection
in people recovering from surgery.
This is an antibiotic drug so dosage should be completed. If the dosage is not completed by the
patient he/she can become bacteria resistance. Metronidazole is a good antibiotic. It is a broad
spectrum antibiotic. Vancomycin works better than metronidazole as an alternative drug.