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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14O8S2
Molecular Weight 278.301
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TREOSULFAN

SMILES

CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O

InChI

InChIKey=YCPOZVAOBBQLRI-WDSKDSINSA-N
InChI=1S/C6H14O8S2/c1-15(9,10)13-3-5(7)6(8)4-14-16(2,11)12/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1

HIDE SMILES / InChI
Molecular Formula C6H14O8S2
Molecular Weight 278.301
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description is created based on several sources, including http://medacuk.com/assets/files/SPC%20Treosulfan%20injection%2001_2015.pdf

Treosulfan (l-threitol-1,4-bis-methanesulfonate; dihydroxybusulfan) is a prodrug of a bifunctional alkylating cytotoxic agent that is approved for the treatment of ovarian carcinomas in a number of European countries. The antitumor activity of treosulfan has been shown in a variety of solid tumors. It is used for the treatment of all types of ovarian cancer, either supplementary to surgery or palliatively. Treosulfan is a prodrug that is converted nonenzymatically first to a mono-epoxide – (2S,3S)- 1,2-epoxy-3,4-butanediol-4-methanesulfonate – and then to a diepoxide – l-diepoxybutane, which is also a metabolite of butadiene – under physiological conditions. Such conversions are assumed to account for the alkylating and therapeutic activities of treosulfan.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Treosulfan demonstrated poor and sex-independent penetration into CNS. However, the brain exposure was greater in juvenile rats, so very young children might potentially be more susceptible to high-dose Treosulfan-related CNS exposure than young adults.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 13.0 µM [IC50]
Activator
1430
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
Treosulfan

Approved Use

Palliative therapy for advanced ovarian or primary peritoneal cancer.

Launch Date

1.327104E12
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Progression of Parkinson's disease with impairment of vision under carboplatin/cyclophosphamide therapy for ovarian cancer.
1998
Neoadjuvant gemcitabine/treosulfan chemotherapy for newly diagnosed glioblastoma: a phase II study.
2002 Sep
Treosulfan/fludarabine as an allogeneic hematopoietic stem cell transplant conditioning regimen for high-risk patients.
2008 Sep
Patents

Patents

US 20160009687
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can be given orally or by intravenous or intraperitoneal administration
Treosulfan is given orally or by intravenous or intraperitoneal administration. Treosulfan is available as 1 g and 5 g powders for reconstitution for injection or as a 250 mg capsule
Route of Administration: Intravenous
In Vitro Use Guide
100 umol/l treosulfan was capable of inducing cell death in 63.6 +/- 23.9% of human primary myeloma cells
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:42 UTC 2023
Edited
by admin
on Fri Dec 15 15:20:42 UTC 2023
Record UNII
CO61ER3EPI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TREOSULFAN
HSDB   INN   MART.   WHO-DD  
USAN   INN  
Official Name English
TREOSULFAN [USAN]
Common Name English
treosulfan [INN]
Common Name English
KEPCONDI
Brand Name English
NSC-39069
Code English
L-THREITOL 1,4-DIMETHANESULPHONATE
Common Name English
DIHYDROXYBUSULFAN
Systematic Name English
THREOSULPHAN
Common Name English
GRAFTREVO
Brand Name English
TREOSULFAN [IARC]
Common Name English
GRAFAPEX
Common Name English
TREOSULFAN [MART.]
Common Name English
OVASTAT
Brand Name English
TREOSULFAN [HSDB]
Common Name English
TREOGRAFT
Brand Name English
Treosulfan [WHO-DD]
Common Name English
L-THREITOL 1,4-DIMETHANESULFONATE
Common Name English
TRECONDYV
Brand Name English
TRECONDI
Brand Name English
Classification Tree Code System Code
WHO-VATC QL01AB02
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
EU-Orphan Drug EU/3/04/186
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
FDA ORPHAN DRUG 81294
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
NCI_THESAURUS C222
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
FDA ORPHAN DRUG 468014
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
WHO-ATC L01AB02
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
Code System Code Type Description
HSDB
6963
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
FDA UNII
CO61ER3EPI
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
INN
3103
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
RXCUI
38508
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY RxNorm
MESH
C018404
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID0026173
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
DRUG CENTRAL
2718
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
PUBCHEM
9882105
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL455186
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-081-0
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
WIKIPEDIA
TREOSULFAN
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
NCI_THESAURUS
C1257
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
NSC
39069
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
DRUG BANK
DB11678
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
CAS
299-75-2
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
SMS_ID
100000077502
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
USAN
JK-167
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
EVMPD
SUB11235MIG
Created by admin on Fri Dec 15 15:20:42 UTC 2023 , Edited by admin on Fri Dec 15 15:20:42 UTC 2023
PRIMARY
Related Record Type Details
Structure of TREOSULFAN
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