U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C7H11N3O4
Molecular Weight 201.1799
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MISONIDAZOLE

SMILES

COCC(O)CN1C=CN=C1[N+]([O-])=O

InChI

InChIKey=OBBCSXFCDPPXOL-UHFFFAOYSA-N
InChI=1S/C7H11N3O4/c1-14-5-6(11)4-9-3-2-8-7(9)10(12)13/h2-3,6,11H,4-5H2,1H3

HIDE SMILES / InChI

Molecular Formula C7H11N3O4
Molecular Weight 201.1799
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Misonidazole is a nitroimidazole with radiosensitizing and antineoplastic properties. Exhibiting high electron affinity, misonidazole induces the formation of free radicals and depletes radioprotective thiols, thereby sensitizing hypoxic cells to the cytotoxic effects of ionizing radiation. This single-strand breaks in DNA induced by this agent result in the inhibition of DNA synthesis. The drug also possesses a substantial cytotoxic effect, independent of radiation, which is selectively expressed in hypoxic cells. Misonidazole may be cytotoxic to the normal hypoxic tissues in the human body, making this became a major concern in the clinical application of the drug. Misonidazole leads to strand breaks in cellular DNA and those cells which fail to survive also fail to repair these strand breaks. Misonidazole depletes intracellular glutathione and is more toxic in glutathione depleted cells.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
31.3 mg/L
600 mg/m² single, oral
MISONIDAZOLE plasma
Homo sapiens
125 mg/L
3 g/m² single, oral
MISONIDAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
348.5 mg × h/L
600 mg/m² single, oral
MISONIDAZOLE plasma
Homo sapiens
2150 mg × h/L
3 g/m² single, oral
MISONIDAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
18 min
3 g/m² single, oral
MISONIDAZOLE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Pelvic malignant disease: Oral Misonidazole at a dose of 4 gm/m2 was administered 4-6 hr prior to radiation (total dose 12 g/m2).
Route of Administration: Oral
In Vitro Use Guide
V-79 hamster cells, attached to permanox dishes, were gassed with known concentrations of oxygen (less than 10 to 200,000 ppm) and treated with 1 and 5 mM MISO for 4 h previous to exposure to the chemotherapy agent, melphalan.
Substance Class Chemical
Record UNII
8FE7LTN8XE
Record Status Validated (UNII)
Record Version