Treosulfan

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Treosulfan are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Treosulfan?

The molecule Treosulfan presents a molecular formula of C6H14O8S2 and its IUPAC name is [(2S,3S)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate.

Treosulfan (INN) is an alkylating antineoplastic agent used in cancer chemotherapy. It is a member of the class of drugs known as cross-linking agents..

Treosulfan is a prodrug, which is metabolised in vivo to the active sulfonate. The active sulfonate is a cross-linking agent, which reacts with DNA, causing cross-linking of DNA strands. This inhibits DNA replication and leads to cell death..

Treosulfan is used to treat a variety of solid tumours, including ovarian cancer, breast cancer, and head and neck cancer. It is typically given as an intravenous infusion over 30-60 minutes..

The most common side effects of treosulfan include nausea, vomiting, diarrhoea, hair loss, fatigue, and low blood counts. More serious side effects include liver damage, kidney damage, and severe allergic reactions..

Treosulfan is a potentially toxic drug and should be used with caution in patients with pre-existing liver or kidney damage. It is also important to monitor blood counts during treatment with treosulfan, as the drug can cause a decrease in white blood cells, red blood cells, and platelets..

3D structure

Cartesian coordinates

Geometry of Treosulfan in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Treosulfan YCPOZVAOBBQLRI-WDSKDSINSA-N chemical compound 2D structure molecule svg
Treosulfan

 

Molecule descriptors

 
IUPAC name[(2S,3S)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate
InChI codeInChI=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
InChI KeyYCPOZVAOBBQLRI-WDSKDSINSA-N
SMILESCS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2S,3S)-2,3-dihydroxy-4-(methanesulfonyloxy)butyl methanesulfonate
  • (2S,3S)-2,3-dihydroxybutane-1,4-diyl dimethanesulfonate
  • (2S,3S)-Threitol 1,4-bismethanesulfonate
  • (S)-3-BOC-AMINO-1-DIAZO-3-(4-BENZYLOXY)PHENYL-2-BUTANONE
  • (S-(R*,R*))-1,2,3,4-Butanetetrol, 1,4-dimethanesulfonate
  • 1,2,3,4-Butanetetrol, 1,4-dimethanesulfonate, (S-(R*,R*))-
  • 299-75-2
  • A912763
  • C19557
  • CB 40067
  • CCRIS 2781
  • CO61ER3EPI
  • CS-3889
  • D07253
  • DB11678
  • DHB
  • Dihydroxybusulfan
  • GRAFAPEX
  • GRAFTREVO
  • HSDB 6963
  • HY-16503
  • KEPCONDI
  • L-THREITOL 1,4-DIMETHANESULPHONATE
  • L-Threitol 1,4-dimethanesulfonate
  • L-Threitol, 1,4-bis(methanesulfonate)
  • L-Threitol, 1,4-bismethanesulfonate
  • L-threitol 1,4-bis(methanesulfonate)
  • MFCD02258964
  • NSC 39069
  • NSC-39069
  • Ovastat
  • PS-12126
  • TRECONDYV
  • TREOGRAFT
  • Threitol, 1,4-dimethanesulfonate, (2S,3S)-
  • Threitol, 1,4-dimethanesulfonate, L-(+)-
  • Trecondi
  • Treosulfan
  • Treosulfan (INN)
  • Treosulfano
  • Treosulfanum
  • Treosulphan
  • TreosulphanNSC 39069
  • WHO 3103
  • [(2S,3S)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate
  • l-Threitol-1,4-bis(methanesulfonate)
  • l-threitol-1,4-bis-methanesulfonate
  • s6958
  • threosulphan

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1671094
  • UNII-CO61ER3EPI
  • DTXSID0026173
  • CHEMBL455186
  • CHEBI:82557
  • EINECS 206-081-0
  • SCHEMBL5399430

Physico-Chemical properties

IUPAC name[(2S,3S)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate
Molecular formulaC6H14O8S2
Molecular weight278.301
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity53.38
LogP-0.2
Topological polar surface area144.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.