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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H13N3O6
Molecular Weight 247.2053
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PR-69

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
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

Description
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.

CNS Activity

CNS Non-penetrant
1040
Curator's Comment: In the normal brain, doranidazole does not penetrate into intrabrain regions through the BBB via its hydrophilic residue.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
Dihydropyrimidine dehydrogenase [NADP(+)]
4
Target ID: O89000
Gene ID: 81656.0
Gene Symbol: Dpyd
Target Organism: Rattus norvegicus (Rat)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/11272282/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/11272282/
Sources:
https://pubmed.ncbi.nlm.nih.gov/11272282/
2000 mg/m2 single, intravenous
Highest studied dose
Dose: 2000 mg/m2
Route: intravenous
Route: single
Dose: 2000 mg/m2
Sources:
https://pubmed.ncbi.nlm.nih.gov/11272282/
unhealthy
Health Status: unhealthy
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/11272282/
Sources:
https://pubmed.ncbi.nlm.nih.gov/11272282/
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

20100076042
2
20100130576
2
20120136295
2
8202898
2
8258165
2
8420687
2
8450356
2

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:33:55 GMT 2025
Edited
by admin
on Mon Mar 31 22:33:55 GMT 2025
Record UNII
4BLU68P76A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,2,4-BUTANETRIOL, 3-((2-NITRO-1H-IMIDAZOL-1-YL)METHOXY)-, (2R,3S)-
Preferred Name English
PR-69
Code English
(2R,3S)-3-((2-NITRO-1H-IMIDAZOL-1-YL)METHOXY)-1,2,4-BUTANETRIOL
Common Name English
1,2,4-BUTANETRIOL, 3-((2-NITRO-1H-IMIDAZOL-1-YL)METHOXY)-, (S-(R*,S*))-
Systematic Name English
Code System Code Type Description
CAS
161903-10-2
Created by admin on Mon Mar 31 22:33:55 GMT 2025 , Edited by admin on Mon Mar 31 22:33:55 GMT 2025
PRIMARY
PUBCHEM
164486
Created by admin on Mon Mar 31 22:33:55 GMT 2025 , Edited by admin on Mon Mar 31 22:33:55 GMT 2025
PRIMARY
FDA UNII
4BLU68P76A
Created by admin on Mon Mar 31 22:33:55 GMT 2025 , Edited by admin on Mon Mar 31 22:33:55 GMT 2025
PRIMARY
Related Record Type Details
Structure of DORANIDAZOLE
RACEMATE -> ENANTIOMER
Related Record Type Details
Structure of PR-69
ACTIVE MOIETY
NIH
NCATS
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