TREOSULFAN

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 Search

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
Sources: https://monographs.iarc.fr/ENG/Monographs/vol100A/mono100A-15.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
cell growth 21 Target ID: GO:0016049 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18246351	Inhibitor 8504	13.0 µM [IC50]
Apoptosis 156 Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12956758	Activator 1447
cell growth 21 Target ID: GO:0016049 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17823799	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Ovarian cancer 160 Sources: http://www.bccancer.bc.ca/drug-database-site/Drug%20Index/Treosulfaninterim_monograph_14Jul2011.pdf	Palliative	Approved 8583	Treosulfan Approved Use Palliative therapy for advanced ovarian or primary peritoneal cancer. Launch Date 2012
Acute myeloid leukemia 141 Sources: https://clinicaltrials.gov/ct2/show/NCT00822393	Palliative	Phase III 665	Unknown Approved Use Unknown
Ewing’s sarcoma 8 Sources: https://clinicaltrials.gov/ct2/show/NCT00987636	Palliative	Phase III 665	Unknown Approved Use Unknown
Melanoma 88 Sources: https://clinicaltrials.gov/ct2/show/NCT00779714	Palliative	Phase III 665	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://clinicaltrials.gov/ct2/show/NCT01010243	Palliative	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
306 μg/mL DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/trecondi-epar-product-information_en.pdf	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
461 μg/mL DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/trecondi-epar-product-information_en.pdf	12 g/m² single, intravenous dose: 12 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
494 μg/mL DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/trecondi-epar-product-information_en.pdf	14 g/m² single, intravenous dose: 14 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
465 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	8 g/m² single, intravenous dose: 8 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
597 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
181 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	8 g/m² single, intravenous dose: 8 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
306 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1520 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11106234/	56 g/m² single, intravenous dose: 56 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
1297 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11106234/	47 g/m² single, intravenous dose: 47 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
708 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	8 g/m² single, intravenous dose: 8 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
977 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
541 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	8 g/m² single, intravenous dose: 8 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
940 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8040 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11106234/	56 g/m² single, intravenous dose: 56 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
5980 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11106234/	47 g/m² single, intravenous dose: 47 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.94 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	8 g/m² single, intravenous dose: 8 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.87 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	8 g/m² single, intravenous dose: 8 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
1.99 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654108/	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11106234/	56 g/m² single, intravenous dose: 56 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2.16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11106234/	47 g/m² single, intravenous dose: 47 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
100% DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/trecondi-epar-product-information_en.pdf	10 g/m² single, intravenous dose: 10 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
100% DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/trecondi-epar-product-information_en.pdf	12 g/m² single, intravenous dose: 12 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
100% DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/trecondi-epar-product-information_en.pdf	14 g/m² single, intravenous dose: 14 g/m² route of administration: Intravenous experiment type: SINGLE co-administered:	TREOSULFAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
56 g/m2 single, intravenous Highest studied dose Dose: 56 g/m2 Route: intravenous Route: single Dose: 56 g/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/11106234/	unhealthy Health Status: unhealthy Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11106234/	Other AEs: diarrhea, stomatitis... Other AEs: diarrhea (grade 3-4, 3 patients) stomatitis (grade 3, 1 pt) stomatitis (grade 4, 1 pt) acidosis (grade 3, 1 pt) Vomiting (grade 2, 2 patients) Fever (grade 2-3, 3 patients) pain (grade 2, 3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11106234/
47 g/m2 single, intravenous MTD Dose: 47 g/m2 Route: intravenous Route: single Dose: 47 g/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/11106234/	unhealthy Health Status: unhealthy Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11106234/	Other AEs: Fever, Diarrhea... Other AEs: Fever (grade 2, 1 pt) Diarrhea (grade 2, 2 patients) pain (grade 2, 1 pt) Skin infection (grade 2, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11106234/
600 mg/m2 1 times / day multiple, oral Studied dose Dose: 600 mg/m2, 1 times / day Route: oral Route: multiple Dose: 600 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27896440/	unhealthy Health Status: unhealthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27896440/	Other AEs: Nausea, Vomiting... Other AEs: Nausea (grade 1-3, 32%) Vomiting (all grades, 22.1%) Constipation (grade 1-3, 15.6%) Diarrhea (grade 1-2, 15.6%) Ileus (grade 3-4, 8.2%) Fatigue (grade 1-3, 29.5%) Abdominal pain (grade 1-3, 22.1%) Dyspnea (grade 1-3, 13.9%) Arthralgia (grade 1-2, 5.7%) Headache (grade 1-2, 5.7%) Neuropathy (grade 1-2, 9%) Febrile neutropenia (grade 1-3, 13.1%) Renal infections and inflammations (excl nephritis) (grade 1-4, 12.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/27896440/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8 1057 CYP2B6 926 CYP2C19 2057 MATE1 415 BSEP 550 MATE2-K 77 P-gp 1741 OATP1B1 1079 CYP19A1 429 OAT3 747 OATP1B3 961 OAT1 725 OCT2 779 OCT1 620

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no [IC50 1870 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no [IC50 972 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206310	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346984#sid=144206310	no
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	yes [IC50 3000 uM]
MATE2-K 77	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34519068/	yes [IC50 8210 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=144206310

PubMed

Title	Date	PubMed
Progression of Parkinson's disease with impairment of vision under carboplatin/cyclophosphamide therapy for ovarian cancer.	1998	9523741
Neoadjuvant gemcitabine/treosulfan chemotherapy for newly diagnosed glioblastoma: a phase II study.	2002 Sep	12241108
Treosulfan/fludarabine as an allogeneic hematopoietic stem cell transplant conditioning regimen for high-risk patients.	2008 Sep	18626885

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 Created by `admin` on `Mon Mar 31 17:54:41 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:41 GMT 2025`
Record UNII	CO61ER3EPI
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TREOSULFAN

Official Name

English

OVASTAT

Preferred 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

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