Tioxolone | CAS#4991-65-5 | Carbonic Anhydrase I Inhibitor

MedKoo Cat#: 463104 | Name: Tioxolone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tioxolone is an inhibitor of carbonic anhydrase I. It is selective for CAI over CAII, -III, -IV, -VA, -VB, -VI, -VII, -IX, -XII, and -XIV. Tioxolone is active against Gram-positive or -negative bacteria, including M. tuberculosis. It is also active against dermatophytes, yeasts, and molds.

Chemical Structure

Tioxolone

CAS#4991-65-5

Theoretical Analysis

MedKoo Cat#: 463104

Name: Tioxolone

CAS#: 4991-65-5

Chemical Formula: C7H4O3S

Exact Mass: 167.9881

Molecular Weight: 168.17

Elemental Analysis: C, 50.00; H, 2.40; O, 28.54; S, 19.06

Price and Availability

Size	Price	Availability
1g	USD 150.00	2 Weeks
2g	USD 225.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 750.00	2 Weeks
25g	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Tioxolone; Thioxolone;

IUPAC/Chemical Name

6-hydroxybenzo[d][1,3]oxathiol-2-one

InChi Key

SLYPOVJCSQHITR-UHFFFAOYSA-N

InChi Code

InChI=1S/C7H4O3S/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3,8H

SMILES Code

O=C1OC2=CC(O)=CC=C2S1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 168.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Parizi MH, Farajzadeh S, Sharifi I, Pardakhty A, Parizi MHD, Sharifi H, Salarkia E, Hassanzadeh S. Antileishmanial Activity of Niosomal Combination Forms of Tioxolone along with Benzoxonium Chloride against Leishmania tropica. Korean J Parasitol. 2019 Aug;57(4):359-368. doi: 10.3347/kjp.2019.57.4.359. Epub 2019 Aug 31. PMID: 31533402; PMCID: PMC6753291. 2: Daie Parizi MH, Karvar M, Sharifi I, Bahrampour A, Heshmat Khah A, Rahnama Z, Baziar Z, Amiri R. The topical treatment of anthroponotic cutaneous leishmaniasis with the tincture of thioxolone plus benzoxonium chloride (Thio- Ben) along with cryotherapy: a single-blind randomized clinical trial. Dermatol Ther. 2015 May-Jun;28(3):140-6. doi: 10.1111/dth.12229. Epub 2015 Apr 6. PMID: 25847678. 3: Sippel KH, Genis C, Govindasamy L, Agbandje-McKenna M, Kiddle JJ, Tripp BC, McKenna R. Synchrotron Radiation Provides a Plausible Explanation for the Generation of a Free Radical Adduct of Thioxolone in Mutant Carbonic Anhydrase II. J Phys Chem Lett. 2010 Oct 7;1(19):2898-2902. doi: 10.1021/jz100954h. PMID: 20976122; PMCID: PMC2957018. 4: Miller K, Dunsmore CJ, Leeds JA, Patching SG, Sachdeva M, Blake KL, Stubbings WJ, Simmons KJ, Henderson PJ, De Los Angeles J, Fishwick CW, Chopra I. Benzothioxalone derivatives as novel inhibitors of UDP-N-acetylglucosamine enolpyruvyl transferases (MurA and MurZ). J Antimicrob Chemother. 2010 Dec;65(12):2566-73. doi: 10.1093/jac/dkq349. Epub 2010 Sep 22. PMID: 20861142. 5: Innocenti A, Maresca A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: thioxolone versus sulfonamides for obtaining isozyme-selective inhibitors? Bioorg Med Chem Lett. 2008 Jul 15;18(14):3938-41. doi: 10.1016/j.bmcl.2008.06.024. Epub 2008 Jun 12. PMID: 18572406. 6: Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK, Phillips E, Kiddle JJ, Tu C, Silverman DN, Govindasamy L, Agbandje-McKenna M, McKenna R, Tripp BC. Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry. 2008 Mar 11;47(10):3174-84. doi: 10.1021/bi702385k. Epub 2008 Feb 12. PMID: 18266323. 7: Iyer R, Barrese AA 3rd, Parakh S, Parker CN, Tripp BC. Inhibition profiling of human carbonic anhydrase II by high-throughput screening of structurally diverse, biologically active compounds. J Biomol Screen. 2006 Oct;11(7):782-91. doi: 10.1177/1087057106289403. Epub 2006 Jul 20. PMID: 16858005. 8: Villas Martinez F, Joral Badas A, Garmendia Goitia JF. Contact dermatitis from thioxolone. Contact Dermatitis. 1993 Aug;29(2):96. doi: 10.1111/j.1600-0536.1993.tb03492.x. PMID: 8365186. 9: Varga JM, Kalchschmid G, Klein GF, Fritsch P. Mechanism of allergic cross- reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody. Mol Immunol. 1991 Jun;28(6):641-54. doi: 10.1016/0161-5890(91)90133-5. PMID: 1650428. 10: Näher H, Frosch PJ. Contact dermatitis to thioxolone. Contact Dermatitis. 1987 Oct;17(4):250-1. doi: 10.1111/j.1600-0536.1987.tb02728.x. PMID: 2962826. 11: Camarasa JG. Contact dermatitis to thioxolone. Contact Dermatitis. 1981 Jul;7(4):213-4. doi: 10.1111/j.1600-0536.1981.tb04048.x. PMID: 7326929. 12: Lius V, Sennerfeldt P. Lokal behandling av akne med tioxolon [Local treatment of acne with tioxolone]. Lakartidningen. 1979 Jan 3;76(1-2):39-41. Swedish. PMID: 153995. 13: Thiers H, Fayolle J, Michel Y. Le gel alcoolique de thioxolone dans le traitement de l'acné juvénile. A propos de 36 observations [Alcoholized gel of thioxolone in treatment of juvenile acne. Apropos of 36 cases]. Lyon Med. 1969 Jan 5;221(1):27-30. French. PMID: 4238443. 14: SUGII A, KABASAWA Y, INABA T. [POLAROGRAPHY OF THIOXOLONE DERIVATIVES. 3. DECOMPOSITION OF CHLOROTHIOXOLONE IN ALKALINE SOLUTION]. Yakugaku Zasshi. 1965 Mar;85:266-70. Japanese. PMID: 14322092. 15: SUGII A, KABASAWA Y. [POLAROGRAPHY OF THIOXOLONE DERIVATIVES. II. DETERMINATION OF THIOXOLONE IN THE DRUGS]. Yakugaku Zasshi. 1964 Nov;84:1138-40. Japanese. doi: 10.1248/yakushi1947.84.11_1138. PMID: 14265141. 16: SUGII A, KABASAWA Y. [POLAROGRAPHY OF THIOXOLONE DERIVATIVES. I. DECOMPOSITION OF THIOXOLONE IN ALKALINE SOLUTION]. Yakugaku Zasshi. 1964 Aug;84:691-5. Japanese. PMID: 14236229. 17: TOYOSHIMA S, SHIMADA K, TANAKA S, KANAZAWA T, KAWABE K. [STUDIES ON CHEMOTHERAPEUTICAL DRUGS. I. STUDIES ON THIOXOLONE DERIVATIVES]. Yakugaku Zasshi. 1964 Feb;84:187-91. Japanese. doi: 10.1248/yakushi1947.84.2_187. PMID: 14140144.