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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H10O4
Molecular Weight 146.1412
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIANHYDROGALACTITOL

SMILES

O[C@@H]([C@@H](O)[C@H]1CO1)[C@@H]2CO2

InChI

InChIKey=AAFJXZWCNVJTMK-GUCUJZIJSA-N
InChI=1S/C6H10O4/c7-5(3-1-9-3)6(8)4-2-10-4/h3-8H,1-2H2/t3-,4+,5+,6-

HIDE SMILES / InChI
Molecular Formula C6H10O4
Molecular Weight 146.1412
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dianhydrogalactitol (VAL-083 or NSC-132313) a cytostatic sugar derivative, is alpha,omega-substituted hexitol acting as bifunctional alkylating agent. It induces interstrand crosslinks at N7 guanines leading to doublestrand breaks and HR activation independent of MGMT, and mediating cell cycle arrest through p53-dependent and p53-independent pathways. Dianhydrogalactitol is approved as a cancer chemotherapeutic in China for the treatment of chronic myelogenous leukemia and lung cancer. The drug has not been approved for any indication outside of China. DelMar Pharmaceuticals is developing dianhydrogalactitol for the treatment of intracranial tumors.

CNS Activity

Originator

Vargha, L. et al.
2
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/6784907

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
DNA
282
Target ID: CHEMBL2311221
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Approved
8583
DIANHYDROGALACTITOL

Approved Use

Dianhydrogalactitol (VAL-083) is approved as a cancer chemotherapeutic in China for the treatment of chronic myelogenous leukemia ("CML") and lung cancer.
Primary
Approved
8583
DIANHYDROGALACTITOL

Approved Use

Dianhydrogalactitol (VAL-083) is approved as a cancer chemotherapeutic in China for the treatment of chronic myelogenous leukemia ("CML") and lung cancer.
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3699079/
0.7 mg/kg single, intravenous
dose: 0.7 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DIANHYDROGALACTITOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
40 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 40 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
DLT: Thrombocytopenia...
Other AEs: nausea, vomiting...
Dose limiting toxicities:
Thrombocytopenia (11 patient)
Other AEs:
nausea (5 patients)
vomiting (2 patients)
leukopenia (13 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
16 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 16 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 16 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
DLT: Thrombocytopenia...
Other AEs: Nausea, vomiting...
Dose limiting toxicities:
Thrombocytopenia (3 patients)
Other AEs:
Nausea (3 patients)
vomiting (1 pt)
leukopenia (5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
DLT: Thrombocytopenia...
Other AEs: Nausea, vomiting...
Dose limiting toxicities:
Thrombocytopenia (4 patients)
Other AEs:
Nausea (5 patients)
vomiting (2 patients)
leukopenia (3 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
30 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 30 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 30 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
DLT: Thrombocytopenia...
Other AEs: Nausea, vomiting...
Dose limiting toxicities:
Thrombocytopenia (8 patients)
Other AEs:
Nausea (4 patients)
vomiting (2 patients)
leukopenia (7 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
AEs

AEs

AESignificanceDosePopulation
Thrombocytopenia 11 patient
DLT
40 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 40 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
leukopenia 13 patients
40 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 40 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
vomiting 2 patients
40 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 40 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
nausea 5 patients
40 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 40 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
vomiting 1 pt
16 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 16 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 16 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
Nausea 3 patients
16 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 16 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 16 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
Thrombocytopenia 3 patients
DLT
16 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 16 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 16 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
leukopenia 5%
16 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 16 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 16 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
vomiting 2 patients
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
leukopenia 3 patients
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
Thrombocytopenia 4 patients
DLT
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
Nausea 5 patients
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
vomiting 2 patients
30 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 30 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 30 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
Nausea 4 patients
30 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 30 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 30 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
leukopenia 7 patients
30 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 30 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 30 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
Thrombocytopenia 8 patients
DLT
30 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 30 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 30 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/943554/
PubMed

PubMed

TitleDatePubMed
L-phenylalanine mustard-dianhydrogalactitol and hyponatremia.
1986
Clinical trials with the hexitol derivatives in the U.S.
1981-02-01
Patents

Patents

20140315318
1

Sample Use Guides

In Vivo Use Guide
In a Phase 3 clinical trial a total of up to 180 eligible patients with recurrent/progressive patients with glioblastoma multiforme (GBM) or gliosarcoma (GS) will be randomized to receive either dianhydrogalactitol (VAL-083) or "Investigator's choice of salvage therapy" as a contemporaneous control, in a 2:1 fashion. Up to 120 eligible patients will be randomized to receive VAL-083 at 40 mg/m2 IV on days 1, 2, and 3 of a 21-day treatment-cycle, for up to 12, 21-day treatment cycles or until they fulfill one of the criteria for study discontinuation.
Route of Administration: Intravenous
In Vitro Use Guide
Treatment with 1,2:5,6-dianhydrogalactitol (DAG) (120 μmol/L) dose-dependently inhibited the proliferation and colony formation in human glioma cell lines LN229, U251, and U87MG in vitro. DAG (1, 2, 5 μmol/L) induced cell cycle arrest at G2/M phase in the 3 glioma cell lines in a dose-dependent manner.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:02:56 GMT 2025
Edited
by admin
on Mon Mar 31 18:02:56 GMT 2025
Record UNII
4S465RYF7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
dianhydrogalactitol [INN]
Preferred Name English
DIANHYDROGALACTITOL
INN   USAN  
USAN   INN  
Official Name English
1,2:5,6-DIANHDROGALACTITOL
Common Name English
NSC-132313
Code English
1,2:5,6-DIANHYDROGALACTITOL
Common Name English
VAL-083
Code English
DIANHYDROGALACTITOL [USAN]
Common Name English
GALACTITOL, 1,2:5,6-DIANHYDRO-
Systematic Name English
meso-(1R,2S)-1-[(2R)-Oxiran-2-yl]-2-[(2S)-oxiran-2-yl]ethane-1,2-diol
Systematic Name English
Dianhydrogalactitol [WHO-DD]
Common Name English
DULCITOL DIEPOXIDE
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/12/1093
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
FDA ORPHAN DRUG 903822
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
FDA ORPHAN DRUG 361311
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
FDA ORPHAN DRUG 514915
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
NCI_THESAURUS C475
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
FDA ORPHAN DRUG 512515
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
Code System Code Type Description
NSC
132313
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
USAN
AB-48
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
CAS
23261-20-3
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
INN
9908
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
MESH
D003961
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
NCI_THESAURUS
C425
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
ChEMBL
CHEMBL3137322
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
SMS_ID
100000178203
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
EPA CompTox
DTXSID90878831
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
DRUG BANK
DB12873
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
FDA UNII
4S465RYF7M
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
PUBCHEM
15942827
Created by admin on Mon Mar 31 18:02:56 GMT 2025 , Edited by admin on Mon Mar 31 18:02:56 GMT 2025
PRIMARY
Related Record Type Details
Structure of DIANHYDROGALACTITOL
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966