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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
13.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Treosulfan
Palliative
Unknown
Palliative
Unknown
Palliative
Unknown
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
306 μg/mL
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
461 μg/mL
12 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
494 μg/mL
14 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
465 μg/mL
8 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
597 μg/mL
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
181 μg/mL
8 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
306 μg/mL
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
1520 μg/mL
56 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
1297 μg/mL
47 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
708 μg × h/mL
8 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
977 μg × h/mL
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
541 μg × h/mL
8 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
940 μg × h/mL
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
8040 μg × h/mL
56 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
5980 μg × h/mL
47 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.94 h
8 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
1.87 h
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
1.75 h
8 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
1.99 h
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
3.06 h
56 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
2.16 h
47 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
10 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
100%
12 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens
100%
14 g/m² single, intravenous
TREOSULFAN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
CO61ER3EPI
Record Status Validated (UNII)
Record Version