NIMORAZOLE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H14N4O3.C4H4O4
Molecular Weight	342.3046
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.[O-][N+](=O)C1=CN=CN1CCN2CCOCC2

InChI

InChIKey=HIMDIGOBZNJDDV-BTJKTKAUSA-N

InChI=1S/C9H14N4O3.C4H4O4/c14-13(15)9-7-10-8-12(9)2-1-11-3-5-16-6-4-11;5-3(6)1-2-4(7)8/h7-8H,1-6H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

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	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
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
Nitroheterocyclic drugs with broad spectrum activity.	2003 Jun	12811546
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
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
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

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 `Sat Dec 16 13:44:13 GMT 2023` Edited by `admin` on `Sat Dec 16 13:44:13 GMT 2023`
Record UNII	DQ7IHI8234
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIMORAZOLE MALEATE

Common Name

English

MORPHOLINE, 4-(2-(5-NITRO-1H-IMIDAZOL-1-YL)ETHYL)-, (2Z)-2-BUTENEDIOATE

Systematic Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/12/952