Synonym
Tixocortol pivalate; Pivalone; JO 1016; JO-1016; JO1016;
IUPAC/Chemical Name
S-(2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) 2,2-dimethylpropanethioate
InChi Key
BISFDZNIUZIKJD-XDANTLIUSA-N
InChi Code
InChI=1S/C26H38O5S/c1-23(2,3)22(30)32-14-20(29)26(31)11-9-18-17-7-6-15-12-16(27)8-10-24(15,4)21(17)19(28)13-25(18,26)5/h12,17-19,21,28,31H,6-11,13-14H2,1-5H3/t17-,18-,19-,21+,24-,25-,26-/m0/s1
SMILES Code
C[C@@]12[C@](C(CSC(C(C)(C)C)=O)=O)(O)CC[C@@]1([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])[C@@H](O)C2)=O
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
>2 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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
462.64
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: Frankild S, Lepoittevin JP, Kreilgaard B, Andersen KE. Tixocortol pivalate contact allergy in the GPMT: frequency and cross-reactivity. Contact Dermatitis. 2001 Jan;44(1):18-22. doi: 10.1034/j.1600-0536.2001.440104.x. PMID: 11156006.
2: Rousselin Y, Yolka S, Clavel A. Crystal structures of two polymorphs of tixocortol pivalate. Acta Crystallogr E Crystallogr Commun. 2021 Jul 16;77(Pt 8):809-813. doi: 10.1107/S2056989021007167. PMID: 34422306; PMCID: PMC8340970.
3: Lutz ME, el-Azhary RA, Gibson LE, Fransway AF. Contact hypersensitivity to tixocortol pivalate. J Am Acad Dermatol. 1998 May;38(5 Pt 1):691-5. doi: 10.1016/s0190-9622(98)70197-5. PMID: 9591812.
4: Friedman G. Tixocortol Pivalate (JO 1016). Am J Gastroenterol. 1983 Aug;78(8):529-30. PMID: 6410909.
5: Larochelle P, Du Souich P, Bolte E, Lelorier J, Goyer R. Tixocortol pivalate, a corticosteroid with no systemic glucocorticoid effect after oral, intrarectal, and intranasal application. Clin Pharmacol Ther. 1983 Mar;33(3):343-50. doi: 10.1038/clpt.1983.43. PMID: 6402333.
6: Isaksson M. Corticosteroids. Dermatol Ther. 2004;17(4):314-20. doi: 10.1111/j.1396-0296.2004.04036.x. PMID: 15327476.
7: Mirshahpanah P, Maibach HI. Guinea pig maximization test assessment of hydrocortisone and tixocortol pivalate. Cutan Ocul Toxicol. 2007;26(4):375-82. doi: 10.1080/15569520701662775. PMID: 18058310.
8: Lelièvre V, Junien JL, Goyer R, Russo-Marie F. Affinity of tixocortol pivalate (JO 1016), tixocortol, cortisol acetate and cortisol for dexamethasone receptors of mouse thymus cells and rat renomedullary interstitial cells in culture. Correlation with their biological activities. J Steroid Biochem. 1984 Jan;20(1):363-6. doi: 10.1016/0022-4731(84)90234-6. PMID: 6584691.
9: Shaw DW, Maibach HI. Clinical relevance of tixocortol pivalate-positive patch tests and questionable bioequivalence of different hydrocortisone preparations. Contact Dermatitis. 2013 Jun;68(6):369-75. doi: 10.1111/cod.12066. PMID: 23692037.
10: Uphill PF, Poole A. A comparison of the effects of tixocortol pivalate (JO 1016), hydrocortisone acetate and beclomethasone dipropionate on the phagocytosis and lysis of microorganisms by alveolar macrophages. Arzneimittelforschung. 1981;31(3):462-6. PMID: 6784736.