NIMORAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H14N4O3
Molecular Weight	226.2325
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MDJFHRLTPRPZLY-UHFFFAOYSA-N

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

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

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 8297
DNA replication 10 Target ID: map03030 Sources: http://adisinsight.springer.com/drugs/800042156	Inhibitor 8297

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 8429	Nimorazole Approved Use Trichomoniasis
Amoebiasis 11 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 8429	Nimorazole Approved Use Amoebiasis
Giardiasis 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 8429	Nimorazole Approved Use Giardiasis
Gingivitis 44 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 8429	Nimorazole Approved Use Gingivitis
Head and neck cancer 50 Sources: http://adisinsight.springer.com/drugs/800042156	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Structure/activity relationships for the enhancement by electron-affinic drugs of the anti-tumour effect of CCNU.	1982 Aug	7150475
A systematic overview of radiation therapy effects in head and neck cancer.	2003	14596506
Treatment of head and neck cancer with CHART and nimorazole: phase II study.	2003 Jan	12559522
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 Sep 20	14511925
Targeted radiosensitisation by pegylated liposome-encapsulated 3', 5'-O-dipalmitoyl 5-iodo-2'-deoxyuridine in a head and neck cancer xenograft model.	2004 Jul 19	15199395
Effect of the hypoxic cell sensitizer isometronidazole on local control of two human squamous cell carcinomas after fractionated irradiation.	2004 Jun	15175873
Microenvironmental adaptation of experimental tumours to chronic vs acute hypoxia.	2004 Sep 13	15305198
Reevaluation of the radiosensitizing effects of sanazole and nimorazole in vitro and in vivo.	2005 Dec	16394636
Probing NMR parameters, structure and dynamics of 5-nitroimidazole derivatives. Density functional study of prototypical radiosensitizers.	2005 Feb	15558660
Nimorazole may increase the effect of phenprocoumon.	2005 Mar	15763317
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 Oct	16198981
Plasma osteopontin levels in patients with head and neck cancer and cervix cancer are critically dependent on the choice of ELISA system.	2006 Aug 15	16911785
Update on clinical radiobiology.	2006 Jan	21614219
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 Mar-Apr	16619533
Motexafin gadolinium injection for the treatment of brain metastases in patients with non-small cell lung cancer.	2007	17722515
Chemical radiosensitizers for use in radiotherapy.	2007 Aug	17478086
The importance of radiobiology to cancer therapy: current practice and future perspectives.	2007 Aug	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 Jun	17543403
Differential risk assessments from five hypoxia specific assays: The basis for biologically adapted individualized radiotherapy in advanced head and neck cancer patients.	2007 Jun	17499868
Evidence-based radiation oncology in head and neck squamous cell carcinoma.	2007 Oct	17482300
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
[The Oxygen effect: an old new target?].	2008 Jan	18261946
Erythropoiesis-stimulating agents: benefits and risks in supportive care of cancer.	2008 Jan	18231643
Enhanced local tumour control after single or fractionated radiation treatment using the hypoxic cell radiosensitizer doranidazole.	2008 Jun	18375007
Tinidazole in the treatment of bacterial vaginosis.	2010 Aug 9	21072275
HPV-associated p16-expression and response to hypoxic modification of radiotherapy in head and neck cancer.	2010 Jan	19910068

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 `Fri Dec 15 16:13:20 UTC 2023` Edited by `admin` on `Fri Dec 15 16:13:20 UTC 2023`
Record UNII	469ULX0H4G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIMORAZOLE

Official Name

English

Nimorazole [WHO-DD]

Common Name

English

K-1900

Code

English

4-(2-(5-NITROIMIDAZOL-1-YL)ETHYL)MORPHOLINE

Systematic Name

English

NAXOGIN

Brand Name

English

nimorazole [INN]

Common Name

English

NSC-107524

Code

English

NIMORAZOLE [MART.]

Common Name

English

NIMORAZOLE [MI]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/10/842