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Details

Stereochemistry RACEMIC
Molecular Formula C8H13N3O6
Molecular Weight 247.2053
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DORANIDAZOLE

SMILES

OC[C@@H](O)[C@H](CO)OCN1C=CN=C1[N+]([O-])=O

InChI

InChIKey=FIITXXIVUIXYMI-RQJHMYQMSA-N
InChI=1S/C8H13N3O6/c12-3-6(14)7(4-13)17-5-10-2-1-9-8(10)11(15)16/h1-2,6-7,12-14H,3-5H2/t6-,7+/m1/s1

HIDE SMILES / InChI

Description

PR-69 (Doranidazole) is a hypoxic radiosensitizer, and is a derivative of 2-nitroimidazole intended to reduce neurotoxicity due to its blood brain barrier (BBB) impermeability. Several studies have shown that doranidazole has a radiosensitizing effect under hypoxia, both in vitro and in vivo. Based on these studies, a phase III trial of doranidazole against advanced pancreatic cancer was performed; it was demonstrated that treatment with doranidazole following radiation significantly improved the tumor mass reduction rate and extended patient survival. Various results have suggested that doranidazole has promising potential for hypoxia-targeting chemoradiotherapy.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice: The radiation-induced growth delay of SCCVII tumors was significantly enhanced and the TCD(50/120) was reduced by a factor of 1.33 when 200 mg/kg PR-69 (Doranidazole) was injected, i.v., 20 min prior to tumor irradiation.
Route of Administration: Intravenous
In Vitro Use Guide
With the addition of 5 mmol/L doranidazole (PR-69), the cell killing by 30 Gy irradiation under hypoxic conditions was significantly increased from 22.2% to 36.4% in five colorectal cancer cell lines: VoLo, HT-29, DLD-1, Colo 201, SW 620.