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
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
| Molecular Formula | C8H13N3O6 |
| Molecular Weight | 247.2053 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12056332 and http://www.ncbi.nlm.nih.gov/pubmed/7642409
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12056332 and http://www.ncbi.nlm.nih.gov/pubmed/7642409
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04210 |
|||
Target ID: O89000 Gene ID: 81656.0 Gene Symbol: Dpyd Target Organism: Rattus norvegicus (Rat) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
38 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
400 mg/m² single, intravenous dose: 400 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
89 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
800 mg/m² single, intravenous dose: 800 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
DORANIDAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
117 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
1300 mg/m² single, intravenous dose: 1300 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
172 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
2000 mg/m² single, intravenous dose: 2000 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
101 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
400 mg/m² single, intravenous dose: 400 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
248 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
800 mg/m² single, intravenous dose: 800 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
DORANIDAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
319 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
1300 mg/m² single, intravenous dose: 1300 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
502 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
2000 mg/m² single, intravenous dose: 2000 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.5 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
400 mg/m² single, intravenous dose: 400 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.4 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
800 mg/m² single, intravenous dose: 800 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
DORANIDAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.9 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
1300 mg/m² single, intravenous dose: 1300 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.2 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/11272282/ |
2000 mg/m² single, intravenous dose: 2000 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
PR-69 serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
2000 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 2000 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 2000 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
|
2000 mg/m2 single, intravenous Highest studied dose Dose: 2000 mg/m2 Route: intravenous Route: single Dose: 2000 mg/m2 Sources: |
unhealthy Health Status: unhealthy Sex: unknown Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The prospective application of a hypoxic radiosensitizer, doranidazole to rat intracranial glioblastoma with blood brain barrier disruption. | 2013-03-08 |
|
| Phase I/II trial of sequential chemoradiotherapy using a novel hypoxic cell radiosensitizer, doranidazole (PR-350), in patients with locally advanced non-small-cell lung Cancer (WJTOG-0002). | 2007-11-01 |
|
| The radiosensitizing effect of doranidazole on human colorectal cancer cells exposed to high doses of irradiation. | 2007-10-06 |
|
| Phase III trial of radiosensitizer PR-350 combined with intraoperative radiotherapy for the treatment of locally advanced pancreatic cancer. | 2004-04 |
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
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Edited
Mon Mar 31 18:17:36 GMT 2025
by
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Mon Mar 31 18:17:36 GMT 2025
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| Record UNII |
911XR034RX
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| Record Status |
Validated (UNII)
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| Record Version |
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FDA ORPHAN DRUG |
665218
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NCI_THESAURUS |
C277
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CHEMBL2107741
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DTXSID3048817
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C106738
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300000034129
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C65469
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911XR034RX
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149838-23-3
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8431
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