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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

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

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
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.

Originator

Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/6784907

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
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
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.
PubMed

PubMed

TitleDatePubMed
Clinical trials with the hexitol derivatives in the U.S.
1981 Feb 1
L-phenylalanine mustard-dianhydrogalactitol and hyponatremia.
1986
Patents

Patents

Sample Use Guides

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
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.
Name Type Language
DIANHYDROGALACTITOL
INN   USAN  
USAN   INN  
Official Name English
dianhydrogalactitol [INN]
Common 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 Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
FDA ORPHAN DRUG 903822
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
FDA ORPHAN DRUG 361311
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
FDA ORPHAN DRUG 514915
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
NCI_THESAURUS C475
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
FDA ORPHAN DRUG 512515
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
Code System Code Type Description
NSC
132313
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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USAN
AB-48
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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CAS
23261-20-3
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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INN
9908
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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MESH
D003961
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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NCI_THESAURUS
C425
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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ChEMBL
CHEMBL3137322
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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SMS_ID
100000178203
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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EPA CompTox
DTXSID90878831
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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DRUG BANK
DB12873
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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FDA UNII
4S465RYF7M
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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PUBCHEM
15942827
Created by admin on Fri Dec 15 15:36:46 UTC 2023 , Edited by admin on Fri Dec 15 15:36:46 UTC 2023
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