Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H9N3O3.ClH |
Molecular Weight | 207.615 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=NC=C(N1CCO)[N+]([O-])=O
InChI
InChIKey=FPTPAIQTXYFGJC-UHFFFAOYSA-N
InChI=1S/C6H9N3O3.ClH/c1-5-7-4-6(9(11)12)8(5)2-3-10;/h4,10H,2-3H2,1H3;1H
DescriptionCurator's Comment: description was created based on several sources, including
http://www.emedexpert.com/facts/metronidazole-facts.shtml
Curator's Comment: description was created based on several sources, including
http://www.emedexpert.com/facts/metronidazole-facts.shtml
Metronidazole was synthesized by France's Rhone-Poulenc laboratories and introduced in the mid-1950s under the brand name Flagel in the US, while Sanofi-Aventis markets metronidazole globally under the same trade name, Flagyl, and also by various generic manufacturers. Metronidazole is one of the rare examples of a drug developed as ant parasitic, which has since gained broad use as an antibacterial agent. Metronidazole, a nitroimidazole, exerts antibacterial effects in an anaerobic environment against most obligate anaerobes. Metronidazole is indicated for the treatment of the following infections due to susceptible strains of sensitive organisms: Trichomoniasis: symptomatic, asymptomatic, asymptomatic consorts; Amebiasis: acute intestinal amebiasis (amebic dysentery) and amebic liver abscess; Anaerobic bacterial infections; Intra-abdominal infections, including peritonitis, intra-abdominal abscess, and liver abscess; Skin and skin structure infections; Gynecologic infections, including endometritis, endomyometritis, tubo-ovarian abscess, and postsurgical vaginal cuff infection; Bacterial septicemia; Bone and joint infections, as adjunctive therapy; Central Nervous System infections, including meningitis and brain abscess; Lower Respiratory Tract infections, including pneumonia, empyema, and lung abscess; Endocarditis. Metronidazole is NOT effective for infections caused by aerobic bacteria that can survive in the presence of oxygen. Metronidazole is only effective against anaerobic bacterial infections because the presence of oxygen will inhibit the nitrogen-reduction process that is crucial to the drug's mechanism of action. Once metronidazole enters the organism by passive diffusion and activated in the cytoplasm of susceptible anaerobic bacteria, it is reduced; this process includes intracellular electron transport proteins such as ferredoxin, transfer of an electron to the nitro group of the metronidazole, and formation of a short-lived nitroso free radical. Because of this alteration of the metronidazole molecule, a concentration gradient is created and maintained which promotes the drug’s intracellular transport. The reduced form of metronidazole and free radicals can interact with DNA leading to inhibition of DNA synthesis and DNA degradation leading to death of the bacteria. The precise mechanism of action of metronidazole is unknown. Metronidazole has a limited spectrum of activity that encompasses various protozoans and most Gram-negative and Gram-positive anaerobic bacteria. Metronidazole has activity against protozoans like Entamoeba histolytica, Giardia lamblia and Trichomonas vaginalis, for which the drug was first approved as an effective treatment.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20930076
Curator's Comment: In animal studies, metronidazole readily penetrated the blood-CSF/blood-brain barrier, and data regarding the entry into human CSF and brain abscess confirmed this finding
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364041 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | FLAGYL Approved UseINDICATIONS & USAGE Metronidazole vaginal gel USP, 0.75% is indicated in the treatment of bacterial vaginosis (formerly referred to as Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). NOTE: For purposes of this indication, a clinical diagnosis of bacterial vaginosis is usually defined by the presence of a homogeneous vaginal discharge that (a) has a pH of greater than 4.5, (b) emits a “fishy” amine odor when mixed with a 10% KOH solution, and (c) contains clue cells on microscopic examination. Gram’s stain results consistent with a diagnosis of bacterial vaginosis include (a) markedly reduced or absent Lactobacillus morphology, (b) predominance of Gardnerella morphotype, and (c) absent or few white blood cells. Other pathogens commonly associated with vulvovaginitis, e.g., Trichomonas vaginalis, Chlamydia trachomatis, N. gonorrhoeae, Candida albicans, and Herpes simplex virus should be ruled out. Launch Date1963 |
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Curative | FLAGYL Approved UseINDICATIONS & USAGE Metronidazole vaginal gel USP, 0.75% is indicated in the treatment of bacterial vaginosis (formerly referred to as Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). NOTE: For purposes of this indication, a clinical diagnosis of bacterial vaginosis is usually defined by the presence of a homogeneous vaginal discharge that (a) has a pH of greater than 4.5, (b) emits a “fishy” amine odor when mixed with a 10% KOH solution, and (c) contains clue cells on microscopic examination. Gram’s stain results consistent with a diagnosis of bacterial vaginosis include (a) markedly reduced or absent Lactobacillus morphology, (b) predominance of Gardnerella morphotype, and (c) absent or few white blood cells. Other pathogens commonly associated with vulvovaginitis, e.g., Trichomonas vaginalis, Chlamydia trachomatis, N. gonorrhoeae, Candida albicans, and Herpes simplex virus should be ruled out. Launch Date1963 |
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Curative | FLAGYL Approved UseINDICATIONS & USAGE Metronidazole vaginal gel USP, 0.75% is indicated in the treatment of bacterial vaginosis (formerly referred to as Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). NOTE: For purposes of this indication, a clinical diagnosis of bacterial vaginosis is usually defined by the presence of a homogeneous vaginal discharge that (a) has a pH of greater than 4.5, (b) emits a “fishy” amine odor when mixed with a 10% KOH solution, and (c) contains clue cells on microscopic examination. Gram’s stain results consistent with a diagnosis of bacterial vaginosis include (a) markedly reduced or absent Lactobacillus morphology, (b) predominance of Gardnerella morphotype, and (c) absent or few white blood cells. Other pathogens commonly associated with vulvovaginitis, e.g., Trichomonas vaginalis, Chlamydia trachomatis, N. gonorrhoeae, Candida albicans, and Herpes simplex virus should be ruled out. Launch Date1963 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12 μg/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
25 μg/mL |
7.5 mg/kg 4 times / day steady-state, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
40 μg/mL |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6 μg/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.77 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22918856 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.54 mg/L Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01222585 |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: intravenous experiment type: single co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: unhealthy age: ∞ants sex: food status: |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75.23 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22918856 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8 h |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
8 h |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
8 h |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
8 h |
unknown, oral |
METRONIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.76 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22918856 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METRONIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
unknown, oral |
METRONIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
12.5 g single, oral Overdose |
unhealthy, 58 years n = 1 Health Status: unhealthy Condition: chronic depressive illness Age Group: 58 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity (9.6%) Sources: |
8.5 g single, oral Overdose |
unhealthy, 62 years n = 1 Health Status: unhealthy Condition: extensive past medical history, including end-stage renal disease Age Group: 62 years Sex: M Population Size: 1 Sources: |
|
1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
DLT: Nausea and vomiting, Generalised onset motor seizure... Dose limiting toxicities: Nausea and vomiting (13.5%) Sources: Generalised onset motor seizure (12.8%) Neurotoxicity NOS (10.9%) |
5.3 mg/m2 3 times / week multiple, oral (mean) Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Co-administed with:: radiotherapy Sources: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: |
DLT: Gastrointestinal toxicity, Central nervous system toxicity... Dose limiting toxicities: Gastrointestinal toxicity (14.5%) Sources: Central nervous system toxicity (13.7%) |
1350 mg 3 times / day steady, oral Overdose Dose: 1350 mg, 3 times / day Route: oral Route: steady Dose: 1350 mg, 3 times / day Sources: |
unhealthy, preterm newborn n = 1 Health Status: unhealthy Condition: bloody stools and apnoea Age Group: preterm newborn Sex: F Population Size: 1 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hepatotoxicity | 9.6% Disc. AE |
12.5 g single, oral Overdose |
unhealthy, 58 years n = 1 Health Status: unhealthy Condition: chronic depressive illness Age Group: 58 years Sex: F Population Size: 1 Sources: |
Neurotoxicity NOS | 10.9% DLT |
1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
Generalised onset motor seizure | 12.8% DLT |
1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
Nausea and vomiting | 13.5% DLT |
1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
Central nervous system toxicity | 13.7% DLT |
5.3 mg/m2 3 times / week multiple, oral (mean) Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Co-administed with:: radiotherapy Sources: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: |
Gastrointestinal toxicity | 14.5% DLT |
5.3 mg/m2 3 times / week multiple, oral (mean) Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Co-administed with:: radiotherapy Sources: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
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PubMed
Title | Date | PubMed |
---|---|---|
Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants. | 1992 |
|
The effect of therapeutic drugs used in inflammatory bowel disease on the incidence and growth of colonic cancer in the dimethylhydrazine rat model. | 1992 Nov |
|
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
|
Concordance between genetic relatedness and phenotypic similarities of Trichomonas vaginalis strains. | 2001 |
|
Technology evaluation: CEA-TRICOM, Therion Biologics Corp. | 2001 Aug |
|
[A comparative study on wound healing treated by different doses of bovine basic fibroblast growth factor (bFGF)]. | 2001 Feb |
|
Metronidazole-induced encephalopathy in a uremic patient: a case report. | 2001 Sep |
|
[Treatment of bacterial vaginosis with high dosage metronidazole and lactic acid]. | 2002 |
|
[Fromilid (clarithromycin) in eradication patients in patients with duodenal ulcer associated with Helicobacter pylori (comparison of two treatment variations)]. | 2002 |
|
[The efficacy of the Helicobacter pylori eradication in people of an advanced age]. | 2002 |
|
Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase. | 2002 Apr 11 |
|
Role of P53 functionality in the genotoxicity of metronidazole and its hydroxy metabolite. | 2002 Apr 25 |
|
Vaccine-based therapy directed against carcinoembryonic antigen demonstrates antitumor activity on spontaneous intestinal tumors in the absence of autoimmunity. | 2002 Dec 1 |
|
[Comparative study of combined local treatment (sulfadimidine, metronidazole and nystatin) and the standard monotherapy in uncomplicated bacterial vaginosis]. | 2002 Dec 22 |
|
Metronidazol as a probable cause of severe liver injury. | 2002 Jan-Feb |
|
[Antibiotic prophylaxys in pediatric surgery of genito-urinary abnormalities]. | 2002 Jun |
|
Local antimicrobial therapy after initial periodontal treatment. | 2002 Jun |
|
Lack of disulfiram-like reaction with metronidazole and ethanol. | 2002 Jun |
|
Effectiveness of metronidazole gel on cyclosporine-induced gingival overgrowth in heart transplant patients. | 2002 Mar |
|
Effects of non-surgical treatment modalities on peri-implantitis. | 2002 May |
|
[Antiamebic effect of metronidazole proved in a study conducted in Cienfuegos province]. | 2002 May-Aug |
|
[Long-term curative effects of suture plus proximal gastric vagotomy or triad-therapy for duodenal ulcer with acute perforation]. | 2002 Sep |
|
[Anaerobic bacteria in bronchoalveolar lavage fluid (BAL) after thoracic surgery]. | 2003 |
|
[Comparative clinical and epidemiological evaluation of beta-lactam antibiotics in the treatment of intraabdominal infections]. | 2003 |
|
An unexpected and severe neurological disorder with permanent disability acquired during short-course treatment with metronidazole. | 2003 |
|
Metronidazole and mental confusion. | 2003 Apr |
|
Antitumor immunity after vaccination with B lymphoma cells overexpressing a triad of costimulatory molecules. | 2003 Apr 2 |
|
Superior mesenteric vein thrombosis following laparoscopic Nissen fundoplication. | 2003 Apr-Jun |
|
An open label crossover trial of effects of metronidazol on hyperlipidaemia. | 2003 Aug |
|
Complete remission of Crohn's disease after high-dose cyclophosphamide and autologous stem cell transplantation. | 2003 Aug |
|
Renal papillary necrosis induced by naproxen. | 2003 Aug |
|
Analysis of antimicrobial susceptibility and virulence factors in Helicobacter pylori clinical isolates. | 2003 Aug 11 |
|
Solvent effects in permeation assessed in vivo by skin surface biopsy. | 2003 Dec 18 |
|
[Vulvar amebiasis. Report of a case and review of the literature]. | 2003 Feb |
|
Role of bacteria and inducible nitric oxide synthase activity in the systemic inflammatory microvascular response provoked by indomethacin in the rat. | 2003 Feb 7 |
|
Penetration of capecitabine and its metabolites into malignant and healthy tissues of patients with advanced breast cancer. | 2003 Mar 10 |
|
A triad of costimulatory molecules synergize to amplify T-cell activation in both vector-based and vector-infected dendritic cell vaccines. | 2003 May |
|
[Evaluation on monkeys of reactogenicity and effectiveness of the complex immunoglobulin preparation formulation]. | 2003 May-Jun |
|
Diazepam as a treatment for metronidazole toxicosis in dogs: a retrospective study of 21 cases. | 2003 May-Jun |
|
Bone defects of the facial skeleton - replacement with biomaterials. | 2003 Nov |
|
Bronchospasm and laryngeal stridor as an adverse effect of oxytocin treatment. | 2003 Oct |
|
Cardiac diphtheria in a previously immunized individual. | 2003 Sep |
|
MR imaging and diffusion-weighted imaging changes in metronidazole (Flagyl)-induced cerebellar toxicity. | 2003 Sep |
|
TRICOM: enhanced vaccines as anticancer therapy. | 2004 Aug |
|
Nitazoxanide: a new broad spectrum antiparasitic agent. | 2004 Feb |
|
Reduced stem cell mobilization in mice receiving antibiotic modulation of the intestinal flora: involvement of endotoxins as cofactors in mobilization. | 2004 Jan 1 |
|
A case of clarithromycin-induced manic episode (antibiomania). | 2004 Mar |
|
Reversible cerebellar lesions induced by metronidazole therapy for helicobacter pylori. | 2004 Oct |
|
Abnormal enhancing lesion of dentate nuclei causing neurologic symptoms induced by metronidazole toxicity. | 2005 Mar |
|
Can antibiotics prevent preterm birth--the pro and con debate. | 2005 Mar |
Sample Use Guides
Trichomoniasis:
In the Female: One-day treatment − two grams of FLAGYL, given ither as a single dose or in two divided doses of one gram each, given in the same day.
Anaerobic Bacterial Infections: In the treatment of most serious anaerobic infections, intravenous metronidazole is usually administered initially. The usual adult oral dosage is 7.5 mg/kg every six hours (approx. 500 mg for a 70-kg adult). A maximum of 4 g should not be exceeded during a 24-hour period.
Amebiasis:
Adults: For acute intestinal amebiasis (acute amebic dysentery): 750 mg orally three times daily for 5 to 10 days.
For amebic liver abscess: 500 mg or 750 mg orally three times daily for 5 to 10 days. Pediatric patients: 35 to 50 mg/kg/24 hours, divided into three doses, orally for 10 days.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25681616
Cells incubated with lethal drug (Metronidazole (MTZ)) concentration exhibit unchanged DNA profile, only about 50% of cells are positive for γH2A and lose an ability to attach to a surface after few hours of incubation. It is likely that the early reaction of cells to lethal concentration of MTZ is not primarily initiated by the reaction to DNA damage but rather by the immediate interaction of MTZ with biomolecules where activated MTZ is generated.
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NCI_THESAURUS |
C279
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NCI_THESAURUS |
C784
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69198-10-3
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SUB14570MIG
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DTXSID70219228
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C48005
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82047
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50687
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CHEMBL137
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100000076224
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68592
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DBSALT000362
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76JC1633UF
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m7506
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PRIMARY | Merck Index |
ACTIVE MOIETY
SUBSTANCE RECORD