Metronidazole

A synthetic 5-nitroimidazole antimicrobial agent used to treat infections caused by susceptible anaerobic bacteria and protozoa, including bacterial vaginosis, trichomoniasis, giardiasis, and amebiasis. Metronidazole undergoes reductive activation in susceptible organisms, generating reactive intermediates that damage DNA and inhibit nucleic acid synthesis. It is available in oral, intravenous, vaginal, and topical formulations. Important adverse effects include nausea, metallic taste, and peripheral neuropathy, particularly with prolonged or repeated treatment. It is also used in combination regimens for selected Helicobacter pylori infections

CAS Number: 443-48-1

Molecular Mass: 171.15 g/mol

Formula: C₆H₉N₃O₃

Smiles: Cc1ncc([N+](=O)[O-])n1CCO

Synonymes:

Metronidazole, metronidazole, 443-48-1, Metronidazol, 2-Methyl-5-nitroimidazole-1-ethanol, Gineflavir, Deflamon, Orvagil, Anagiardil, Trichazol, MetroGel, Bayer 5360, Sanatrichom, Danizol, Meronidal, Metronidaz, Mexibol, Trichocide, Tricocet, Trivazol, Vagilen, Vagimid, Arilin, Clont, Klion, Metronidazolo, Acromona, Flagemona, Flagesol, Giatricol, Novonidazol, Protostat, Takimetol, Trichomol, Trichopol, Trikacide, Trikamon, Trikojol, Trikozol, Vertisal, Atrivyl, Efloran, Entizol, Flagil, Monagyl, Trichex, Tricom, Trimeks, Bexon, Eumin, Klont, MetroCream, MetroLotion, Nalox, 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol, neo-Tric, Tricowas B, MetroGel-Vaginal, Metromidol, Deflamon-wirkstoff, Fossyol, CONT, Noritate, Trichopal, Flagyl Er, Metro I.V., Metronidazolum, Zadstat, Metrolyl, Vandazole, RP 8823, Metric 21, NSC-50364, 2-(2-methyl-5-nitroimidazol-1-yl)ethanol, 1H-Imidazole-1-ethanol, 2-methyl-5-nitro-, Metrotop, 1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole, Metronidazole in Plastic Container, SC 10295, 2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazole, 2-Methyl-3-(2-hydroxyethyl)-4-nitroimidazole, Zidoval, 1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrrole, Flagyl I.V. RTU, Flagyl 375, 1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazole, Metro I.V. In Plastic Container, 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol, 1-Hydroxyethyl-2-methyl-5-nitroimidazole, LIKMEZ, 1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazole, FLAGYL I.V. RTU IN PLASTIC CONTAINER, 1-(beta-Oxyethyl)-2-methyl-5-nitroimidazole, Imidazole-1-ethanol, 2-methyl-5-nitro-, BAY-5360, NSC69587, NSC-69587, RP-8823, BAYER-5360, DTXSID2020892, 140QMO216E, NSC50364, DTXCID20892, CHEBI:6909, 5-23-05-00063 (Beilstein Handbook Reference), Anabact, Drazifon, Metroplex, Metrosa, Neutratop, Nuvessa, Rosiced, Vaginyl, MetroCleanse, Norzol, Zyomet, Flagyl compak, Flagyl-s, Rosaclear System, Metronidazole Oral, metronidazole vaginal, Metronidazole Topical, AYRADIA, Metronidazole250 mg, Metronidazole500 mg, Flagyl-400, RefChem:6037, Trichomonacid'pharmachim', Metronidazole Topical Gel, Metronidazole Vaginal Gel, Metronidazole Topical Cream, Metronidazole250 mg 250 mg, Metronidazole500 mg 500 mg, A01AB17, D06BX01, G01AF01, J01XD01, P01AB01, Metronidazole vaginal gel, 1.3 %, Metronidazole Vaginal Gel, 0.75%, 2 Methyl 5 nitroimidazole 1 ethanol, B7-1, ICAM-1, LFA-3, B7-1, intercellular adhesion molecule-1, and leukocyte function-associated antigen-3, 207-136-1, Rozex, Flagyl, Monasin, Wagitran, Elyzol, Satric, NIDA, Methronidazole, Trichomonacid 'pharmachim', MFCD00009750, 2-Methyl-5-nitro-1H-imidazole-1-ethanol, 2-(2-methyl-5-nitro-1-imidazolyl)ethanol, 2-(2-methyl-5-nitro-imidazol-1-yl)ethanol, NSC 50364, MLS000028590, Tricho cordes, Tricho-gynaedron, Metro Gel, s1907, NCGC00016446-06, CAS-443-48-1, Metrolag, Rathimed, SMR000058175, 2-(2-methyl-5-nitroimidazolyl)ethan-1-ol, Metronidazolo [DCIT], Mexibol 'silanes', 1-(.beta.-Ethylol)-2-methyl-5-nitro-3-azapyrrole, 1-(.beta.-Hydroxyethyl)-2-methyl-5-nitroimidazole, Metronidazol [INN-Spanish], Metronidazolum [INN-Latin], Trichobrol, Florazole, Mepagyl, Nidagyl, Rosased, Caswell No. 579AA, WLN: T5N CNJ A2Q B1 ENW, Noritate (TN), CCRIS 410, Metro cream & gel, Flagyl (TN), HSDB 3129, WLN: T6NTJ DQ ANU1- ET5N CNJ A1 BNW, SR-01000000244, EINECS 207-136-1, NSC 69587, EPA Pesticide Chemical Code 120401, BRN 0611683, Polibiotic, Trikhopol, Donnan, Flazol, UNII-140QMO216E, Metrotop, , Midazol, , Metronidazole RS, Elyzol, , Flagyl, , Torgyl, , CB-01-14 MMX, Metronidazole CRS, Metro IV, Vandazole (TN), Prestwick_334, Nuvessa (TN), IDR-90105, Cimetrol 500LPCI, Metronidazole, BioXtra, Metronidazole (Flagyl), Metronidazole Micronized, Spectrum_001035, Metronidazole [USAN:USP:INN:BAN:JAN], HELIDAC (Salt/Mix), Metronidazole (Standard), Maybridge1_001999, Opera_ID_1585, Prestwick0_000081, Prestwick1_000081, Prestwick2_000081, Prestwick3_000081, Spectrum2_000883, Spectrum3_000506, Spectrum4_000060, Spectrum5_001289, M0924, METRONIDAZOLE [MI], CHEMBL137, METRONIDAZOLE [INN], METRONIDAZOLE [JAN], METRONIDAZOLE [HSDB], METRONIDAZOLE [IARC], METRONIDAZOLE [USAN], NCIOpen2_000337, SCHEMBL23042, BSPBio_000002, BSPBio_002031, KBioGR_000559, KBioSS_001515, METRONIDAZOLE [VANDF], MLS000758286, MLS001424018, BIDD:GT0107, DivK1c_000007, METRONIDAZOLE [MART.], SPECTRUM1500412, SPBio_000666, SPBio_001941, METRONIDAZOLE [USP-RS], METRONIDAZOLE [WHO-DD], METRONIDAZOLE [WHO-IP], BPBio1_000004, orb1309838, orb3139877, Flagyl I.V. RTU (Salt/Mix), BCBcMAP01_000184, GTPL10914, HMS500A09, HMS547C19, HY-B0318R, KBio1_000007, KBio2_001515, KBio2_004083, KBio2_006651, KBio3_001531, Metronidazole (JP18/USP/INN), MSK5554, Metronidazole, analytical standard, NINDS_000007, GLXC-07994, HMS1568A04, HMS1920N19, HMS2051G07, HMS2090B19, HMS2091F14, HMS2095A04, HMS2231E11, HMS3373O05, HMS3393G07, HMS3655E22, HMS3712A04, HMS5080F03, Pharmakon1600-01500412, METRONIDAZOLE [EP IMPURITY], METRONIDAZOLE [ORANGE BOOK], ALBB-038642, HY-B0318, LAC39247, METRONIDAZOLE [EP MONOGRAPH], METRONIDAZOLE [USP IMPURITY], Tox21_110441, Tox21_202413, Tox21_302794, BBL005452, BDBM50375309, CCG-40016, EBC-03271, FP-250, METRONIDAZOLE [USP MONOGRAPH], MSK5554-100M, NSC757118, PYLERA COMPONENT METRONIDAZOLE, SBB001486, SBB041018, STK177359, HELIDAC COMPONENT METRONIDAZOLE, Metronidazole 2.0 mg/ml in Methanol, AKOS000269646, AKOS005169650, MSK5554-1000M, Tox21_110441_1, AM01526, DB00916, KS-5140, NC00020, NSC-757118, IDI1_000007, SMP1_000189, NCGC00016446-01, NCGC00016446-02, NCGC00016446-03, NCGC00016446-04, NCGC00016446-05, NCGC00016446-07, NCGC00016446-08, NCGC00016446-09, NCGC00016446-11, NCGC00016446-12, NCGC00016446-17, NCGC00022059-03, NCGC00022059-04, NCGC00022059-05, NCGC00256513-01, NCGC00259962-01, AC-23968, ST024769, SY002821, SBI-0051447.P003, DB-051212, Metronidazole, SAJ first grade, >=99.0%, AB00052046, NS00000210, SW196613-4, EN300-16851, Metronidazole Solution in Methanol, 100ug/mL, C07203, D00409, Metronidazole Solution in Methanol, 1000ug/mL, AB00052046-17, AB00052046_18, AB00052046_19, F222567, imidazole, 1-(2-hydroxyethyl)-2-methyl-5-nitro-, Metronidazole, VETRANAL(TM), analytical standard, Q169569, 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol #, SR-01000000244-4, SR-01000000244-5, BRD-K52020312-001-05-2, BRD-K52020312-001-15-1, BRD-K52020312-001-25-0, BRD-K52020312-001-26-8, METRONIDAZOLE BENZOATE IMPURITY A [EP IMPURITY], Z87001124, F1773-0073, Metronidazole, certified reference material, TraceCERT(R), Metronidazole, British Pharmacopoeia (BP) Reference Standard, Metronidazole, European Pharmacopoeia (EP) Reference Standard, Metronidazole, United States Pharmacopeia (USP) Reference Standard, Metronidazole, Pharmaceutical Secondary Standard, Certified Reference Material, 56010-45-8

Bioactivity: Nitroimidazole antibacterial and antiprotozoal agent; DNA-damaging antimicrobial activated by reductive metabolism in anaerobic organisms

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	293.15	-	10.01	[165]
1-Butanol	297.55	-	10.78	[165]
1-Butanol	302.55	-	12.91	[165]
1-Butanol	307.55	-	17.01	[165]
1-Butanol	312.35	-	20.68	[165]
1-Butanol	317.85	-	24.46	[165]
1-Butanol	322.35	-	30.22	[165]
Chloroform	293.15	-	2.731	[165]
Chloroform	297.55	-	3.4	[165]
Chloroform	302.55	-	4.775	[165]
Chloroform	307.55	-	6.057	[165]
Chloroform	312.35	-	7.52	[165]
Chloroform	317.85	-	8.672	[165]
Diethylene Glycol Monoethyl Ether	298.15	-	26.51	[166]
Diethylene Glycol Monoethyl Ether	303.15	-	29.0	[166]
Diethylene Glycol Monoethyl Ether	308.15	-	31.08	[166]
Diethylene Glycol Monoethyl Ether	313.15	-	33.41	[166]
Diethylene Glycol Monoethyl Ether	318.15	-	35.86	[166]
Diethylene Glycol Monoethyl Ether	323.15	-	38.29	[166]
Diethylene Glycol Monoethyl Ether	328.15	-	41.6	[166]
Diethylene Glycol Monoethyl Ether	333.15	-	45.46	[166]
Ethanol	293.15	-	12.75	[165]
Ethanol	297.55	-	17.49	[165]
Ethanol	302.55	-	18.71	[165]
Ethanol	307.55	-	22.18	[165]
Ethanol	312.35	-	28.35	[165]
Ethanol	317.85	-	34.95	[165]
Ethanol	322.35	-	41.64	[165]
Ethyl acetate	293.15	-	5.248	[165]
Ethyl acetate	297.55	-	6.899	[165]
Ethyl acetate	302.55	-	8.597	[165]
Ethyl acetate	307.55	-	10.44	[165]
Ethyl acetate	312.35	-	12.23	[165]
Ethyl acetate	317.85	-	15.12	[165]
Ethyl acetate	322.35	-	20.51	[165]
Isopropanol	293.15	-	8.899	[165]
Isopropanol	297.55	-	10.34	[165]
Isopropanol	302.55	-	12.44	[165]
Isopropanol	307.55	-	13.61	[165]
Isopropanol	312.35	-	17.53	[165]
Isopropanol	317.85	-	22.37	[165]
Isopropanol	322.35	-	27.39	[165]
Methanol	293.15	-	27.25	[165]
Methanol	297.55	-	32.2	[165]
Methanol	302.55	-	38.99	[165]
Methanol	307.55	-	47.13	[165]
Methanol	312.35	-	57.59	[165]
Methanol	317.85	-	71.1	[165]
Methanol	322.35	-	83.54	[165]
Water	293.15	-	8.277	[165]
Water	298.15	-	10.53	[166]
Water	298.45	-	9.908	[165]
Water	303.15	-	11.27	[166]
Water	306.95	-	13.79	[165]
Water	308.15	-	12.1	[166]
Water	308.65	-	14.38	[165]
Water	313.15	-	17.05	[165]
Water	313.15	-	12.93	[166]
Water	318.05	-	20.37	[165]
Water	318.15	-	13.85	[166]
Water	322.95	-	24.9	[165]
Water	323.15	-	14.95	[166]
Water	328.15	-	15.9	[166]
Water	333.15	-	17.03	[166]

Molecule 3D descriptors

Descriptor	Value
PMI1	414.6769
PMI2	553.9450
PMI3	823.1147
NPR1	0.5038
NPR2	0.6730
RadiusOfGyration	2.2878
InertialShapeFactor	0.0016
Eccentricity	0.8638
Asphericity	0.1611
SpherocityIndex	0.3097
PBF	0.6701