tioxolone

Names

[ Name ]:
tioxolone

[Synonym ]:
1,3-Benzoxathiol-2-one, 6-hydroxy-
6-Hydroxy-2-oxo-1,3-benzoxathiole
Camyna
Stepin
MFCD00005859
Acnosan
6-Hydroxybenzo[d][1,3]oxathiol-2-one
EINECS 225-653-0
tioxolone
6-Hydroxy-1,3-benzoxathiol-2-one

Biological Activity

[Description]:

Tioxolone, a metalloenzyme carbonic anhydrase I inhibitor, is an anti-acne preparation.Target: Carbonic Anhydrase Tioxolone is a metalloenzyme carbonic anhydrase I inhibitor with a Ki of 91 nM. Tioxolone lacks sulfonamide, sulfamate, or hydroxamate functional groups that are typically found in therapeutic carbonic anhydrase (CA) inhibitors, such as acetazolamide. Tioxolone is proposed to be a prodrug inhibitor that is cleaved via a CA II zinc-hydroxide mechanism known to catalyze the hydrolysis of esters. When tioxolone binds in the active site of CA II, it is cleaved and forms 4-mercaptobenzene-1,3-diol via the intermediate S-(2,4-thiophenyl) hydrogen thiocarbonate. The esterase cleavage product binds to the zinc active site via the thiol group and is therefore the active CA inhibitor, while the intermediate is located at the rim of the active-site cavity. From Wikipedia.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase

Research Areas >> Metabolic Disease

[References]

[1]. http://en.wikipedia.org/wiki/Tioxolone

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
377.8±44.0 °C at 760 mmHg

[ Melting Point ]:
158-160 °C(lit.)

[ Molecular Formula ]:
C₇H₄O₃S

[ Molecular Weight ]:
168.170

[ Flash Point ]:
182.3±28.4 °C

[ Exact Mass ]:
167.988113

[ PSA ]:
78.68000

[ LogP ]:
1.77

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.718

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DM2953750

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

The supramolecular structure of 6-hydroxy-1,3-benzoxathiol-2-one (tioxolone).

Acta Crystallogr. C 60(Pt 6) , o395-6, (2004)

The planar molecules of 6-hydroxy-1,3-benzoxathiol-2-one, C(7)H(4)O(3)S, are linked by extensive O-H.O and C-H.O hydrogen bonding and are further stablilized by face-to-face pi-pi interactions.

[Antimicrobial and cytostatic properties of 6-hydroxy-1,3-benzoxathiol-2-one (01 1)].

Arzneimittelforschung 19(8) , 1298-304, (1969)

Contact dermatitis from thioxolone.

Contact Dermatitis 29(2) , 96, (1993)

Related Compounds

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