NIMORAZOLE HYDROCHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H14N4O3.ClH
Molecular Weight	262.693
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[O-][N+](=O)C1=CN=CN1CCN2CCOCC2

InChI

InChIKey=YNZSADJOMNVVST-UHFFFAOYSA-N

InChI=1S/C9H14N4O3.ClH/c14-13(15)9-7-10-8-12(9)2-1-11-3-5-16-6-4-11;/h7-8H,1-6H2;1H

HIDE SMILES / InChI

Molecular Formula	C9H14N4O3
Molecular Weight	226.2325
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB12172 | http://www.mims.com/india/drug/info/nimorazole?type=full&mtype=generic | http://adisinsight.springer.com/drugs/800042156

Nimorazole is an antimicrobial with activity against anaerobic bacteria and protozoa. Its actions and properties are similar to metronidazole. It has also been used in trials studying the treatment of Hypoxia, Radiotherapy, Hypoxic Modification, Gene Profile, Gene Signature, and Head and Neck Squamous Cell Carcinoma, among others. Azanta is developing, nimorazole, as an oral hypoxic radio-sensitiser for the treatment of patients with head and neck cancer who are undergoing radiotherapy. Previously, nimorazole has been approved for use as an anti-protozoal agent and has been launched worldwide. Nimorazole, for the treatment of head and neck cancer patients undergoing radiotherapy received orphan designation by EMA in 2011.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Trichomonas vaginalis 11 Target ID: CHEMBL612884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/211235	Inhibitor 8504
DNA replication 10 Target ID: map03030 Sources: http://adisinsight.springer.com/drugs/800042156	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Trichomoniasis 18 Sources: http://www.mims.com/india/drug/info/nimorazole?type=full&mtype=generic http://www.druginfosys.com/drug.aspx?drugcode=2009&type=1	Curative	Approved 8583	Nimorazole Approved Use Trichomoniasis
Amoebiasis 12 Sources: http://www.mims.com/india/drug/info/nimorazole?type=full&mtype=generic http://www.druginfosys.com/drug.aspx?drugcode=2009&type=1	Curative	Approved 8583	Nimorazole Approved Use Amoebiasis
Giardiasis 13 Sources: http://www.mims.com/india/drug/info/nimorazole?type=full&mtype=generic http://www.druginfosys.com/drug.aspx?drugcode=2009&type=1	Curative	Approved 8583	Nimorazole Approved Use Giardiasis
Gingivitis 45 Sources: http://www.mims.com/india/drug/info/nimorazole?type=full&mtype=generic http://www.druginfosys.com/drug.aspx?drugcode=2009&type=1	Curative	Approved 8583	Nimorazole Approved Use Gingivitis
Head and neck cancer 50 Sources: http://adisinsight.springer.com/drugs/800042156	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
5.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
14.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FED
10 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
22.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
49.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
41 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
69.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
79.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3.5 g single, oral dose: 3.5 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
64 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480460/	3 g 1 times / day multiple, oral dose: 3 g route of administration: Oral experiment type: MULTIPLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
26 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
91 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FED
40 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
122 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
293 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
262 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
469 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
376 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3.5 g single, oral dose: 3.5 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
295 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480460/	3 g 1 times / day multiple, oral dose: 3 g route of administration: Oral experiment type: MULTIPLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FED
2.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6871077/	3.5 g single, oral dose: 3.5 g route of administration: Oral experiment type: SINGLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
3.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480460/	3 g 1 times / day multiple, oral dose: 3 g route of administration: Oral experiment type: MULTIPLE co-administered:	NIMORAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2.7 g/m2 1 times / day multiple, oral Studied dose Dose: 2.7 g/m2, 1 times / day Route: oral Route: multiple Dose: 2.7 g/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	Disc. AE: Coma, Encephalopathy... Other AEs: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Coma (grade 5, 1.6%) Encephalopathy (grade 5, 1.6%) Grand mal seizure (grade 5, 1.6%) Other AEs: Nausea (grade 3, 22%) Vomiting (grade 3, 5%) Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/

AEs

AE	Significance	Dose	Population
Nausea	grade 3, 22%	2.7 g/m2 1 times / day multiple, oral Studied dose Dose: 2.7 g/m2, 1 times / day Route: oral Route: multiple Dose: 2.7 g/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/
Vomiting	grade 3, 5%	2.7 g/m2 1 times / day multiple, oral Studied dose Dose: 2.7 g/m2, 1 times / day Route: oral Route: multiple Dose: 2.7 g/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/
Coma	grade 5, 1.6% Disc. AE	2.7 g/m2 1 times / day multiple, oral Studied dose Dose: 2.7 g/m2, 1 times / day Route: oral Route: multiple Dose: 2.7 g/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/
Encephalopathy	grade 5, 1.6% Disc. AE	2.7 g/m2 1 times / day multiple, oral Studied dose Dose: 2.7 g/m2, 1 times / day Route: oral Route: multiple Dose: 2.7 g/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/
Grand mal seizure	grade 5, 1.6% Disc. AE	2.7 g/m2 1 times / day multiple, oral Studied dose Dose: 2.7 g/m2, 1 times / day Route: oral Route: multiple Dose: 2.7 g/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12559522/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23009#section=Biological-Test-Results Page: 3.0	inconclusive [IC50 7.7619 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23009#section=Biological-Test-Results Page: 139.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23009#section=Biological-Test-Results Page: 140.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23009#section=Biological-Test-Results Page: 134.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23009#section=Biological-Test-Results Page: 133.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/23009#section=Biological-Test-Results Page: 140.0

PubMed

Title	Date	PubMed
Tinidazole in the treatment of bacterial vaginosis.	2010-08-09	21072275
HPV-associated p16-expression and response to hypoxic modification of radiotherapy in head and neck cancer.	2010-01	19910068
Enhanced local tumour control after single or fractionated radiation treatment using the hypoxic cell radiosensitizer doranidazole.	2008-06	18375007
[The Oxygen effect: an old new target?].	2008-01	18261946
Erythropoiesis-stimulating agents: benefits and risks in supportive care of cancer.	2008-01	18231643
Carbonic anhydrase IX and response to postmastectomy radiotherapy in high-risk breast cancer: a subgroup analysis of the DBCG82 b and c trials.	2008	18355402
The nimorazole regimen in patients with head and neck cancer can increase the effect of vitamin K antagonists.	2008	17851836
Evidence-based radiation oncology in head and neck squamous cell carcinoma.	2007-10	17482300
Chemical radiosensitizers for use in radiotherapy.	2007-08	17478086
The importance of radiobiology to cancer therapy: current practice and future perspectives.	2007-08	17451922
Lack of prognostic and predictive value of CA IX in radiotherapy of squamous cell carcinoma of the head and neck with known modifiable hypoxia: an evaluation of the DAHANCA 5 study.	2007-06	17543403
Differential risk assessments from five hypoxia specific assays: The basis for biologically adapted individualized radiotherapy in advanced head and neck cancer patients.	2007-06	17499868
Motexafin gadolinium injection for the treatment of brain metastases in patients with non-small cell lung cancer.	2007	17722515
Plasma osteopontin levels in patients with head and neck cancer and cervix cancer are critically dependent on the choice of ELISA system.	2006-08-15	16911785
Evaluation of hypoxic cell radio-sensitizers in terms of radio-sensitizing and repair-inhibiting potential. Dependency on p53 status of tumor cells and the effects on intratumor quiescent cells.	2006-04-20	16619533
Update on clinical radiobiology.	2006-01	21614219
Reevaluation of the radiosensitizing effects of sanazole and nimorazole in vitro and in vivo.	2005-12	16394636
Plasma osteopontin, hypoxia, and response to the hypoxia sensitiser nimorazole in radiotherapy of head and neck cancer: results from the DAHANCA 5 randomised double-blind placebo-controlled trial.	2005-10	16198981
Nimorazole may increase the effect of phenprocoumon.	2005-03	15763317
Probing NMR parameters, structure and dynamics of 5-nitroimidazole derivatives. Density functional study of prototypical radiosensitizers.	2005-02	15558660
Microenvironmental adaptation of experimental tumours to chronic vs acute hypoxia.	2004-09-13	15305198
Targeted radiosensitisation by pegylated liposome-encapsulated 3', 5'-O-dipalmitoyl 5-iodo-2'-deoxyuridine in a head and neck cancer xenograft model.	2004-07-19	15199395
Effect of the hypoxic cell sensitizer isometronidazole on local control of two human squamous cell carcinomas after fractionated irradiation.	2004-06	15175873
Five compared with six fractions per week of conventional radiotherapy of squamous-cell carcinoma of head and neck: DAHANCA 6 and 7 randomised controlled trial.	2003-09-20	14511925
Nitroheterocyclic drugs with broad spectrum activity.	2003-06	12811546
Treatment of head and neck cancer with CHART and nimorazole: phase II study.	2003-01	12559522
A systematic overview of radiation therapy effects in head and neck cancer.	2003	14596506
Structure/activity relationships for the enhancement by electron-affinic drugs of the anti-tumour effect of CCNU.	1982-08	7150475

Patents

Sample Use Guides

In Vivo Use Guide

Oral Trichomoniasis Adult: 2 g as a single dose. Alternatively, 1 g every 12 hr for 3 doses or 250 mg tid for 5-7 days. Sexual partners should be treated concomitantly. Oral Amoebiasis Adult: 1 g bid for 5-10 days. Oral Giardiasis Adult: 500 mg bid for 5-7 days. Oral Acute ulcerative gingivitis Adult: 500 mg bid for 2 days.

Route of Administration: Oral

In Vitro Use Guide

Nimorazole inhibited Trichomonas vaginalis with MIC 12.5 ug/ml

Substance Class	Chemical Created by `admin` on `Tue Apr 01 19:10:56 GMT 2025` Edited by `admin` on `Tue Apr 01 19:10:56 GMT 2025`
Record UNII	NX491H5YCU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIMORAZOLE HYDROCHLORIDE

Common Name

English

4-(2-(5-NITRO-1H-IMIDAZOLE-1-YL)ETHYL)MORPHOLINE MONOHYDROCHLORIDE

Preferred Name

English

Code System Code Type Description

PUBCHEM

3023540