Thiothixene
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MedKoo CAT#: 318866

CAS#: 3313-26-6 (Z-isomer)

Description: Tiotixene or Thiothixene is a typical antipsychotic drug of the thioxanthene class used in the treatment of psychoses like schizophrenia. It was introduced on July 24, 1967 by Pfizer. NSC 108165

Chemical Structure

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Thiothixene
CAS# 3313-26-6 (Z-isomer)
Instruction

Theoretical Analysis

MedKoo Cat#: 318866
Name: Thiothixene
CAS#: 3313-26-6 (Z-isomer)
Chemical Formula: C23H29N3O2S2
Exact Mass: 443.17
Molecular Weight: 443.624
Elemental Analysis: C, 62.27; H, 6.59; N, 9.47; O, 7.21; S, 14.45

Price and Availability

Size Price Availability Quantity
10mg USD -2 2 Weeks
50mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
1g USD -2 2 Weeks
2g USD -2 2 Weeks
5mg USD 325 2 Weeks
25mg USD 650 2 Weeks
100mg USD 1650 2 Weeks
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Related CAS #: 3313-26-6 (Z-isomer)   5591-45-7 (E-isomer)   3285-50-5 (maleate)   3285-54-9 (oxalate)   22189-31-7 (HCl)  

Synonym: CP 12,252-1; NSC 108165; P 4657B; Navane; Navan; Navaron; Orbinamo; Tiotixeno; Thixit; Thiothixene; Tiotixene; (Z)-Thiothixene; cis-​Thiothixene;

IUPAC/Chemical Name: (Z)-N,N-dimethyl-9-(3-(4-methylpiperazin-1-yl)propylidene)-9H-thioxanthene-2-sulfonamide

InChi Key: GFBKORZTTCHDGY-UWVJOHFNSA-N

InChi Code: InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3/b19-8-

SMILES Code: O=S(C1=CC(/C2=C\CCN3CCN(C)CC3)=C(SC4=C2C=CC=C4)C=C1)(N(C)C)=O

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, not in water

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO, not in water 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 443.62 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Leung JG, Dare FY, Flowers LM, Murphy LL, Sukiennik EM, Philbrick KL, Rasmussen KG. Thiothixene in the Management of Delirium: A Case Series. Psychosomatics. 2015 Sep-Oct;56(5):542-6. doi: 10.1016/j.psym.2015.02.003. Epub 2015 Feb 16. PubMed PMID: 26002225.

2: Xin C, Lihong W, Qiuyuan L, Hongzhuo L. Injectable long-term control-released in situ gels of hydrochloric thiothixene for the treatment of schizophrenia: preparation, in vitro and in vivo evaluation. Int J Pharm. 2014 Jul 20;469(1):23-30. doi: 10.1016/j.ijpharm.2014.04.044. Epub 2014 Apr 18. PubMed PMID: 24751344.

3: Juenke JM, Brown PI, Urry FM, Johnson-Davis KL, McMillin GA. Simultaneous UPLC-MS/MS assay for the detection of the traditional antipsychotics haloperidol, fluphenazine, perphenazine, and thiothixene in serum and plasma. Clin Chim Acta. 2013 Aug 23;423:32-4. doi: 10.1016/j.cca.2013.04.014. Epub 2013 Apr 23. PubMed PMID: 23618971.

4: Guthrie SK, Hariharan M, Kumar AA, Bader G, Tandon R. The effect of paroxetine on thiothixene pharmacokinetics. J Clin Pharm Ther. 1997 Jun;22(3):221-6. PubMed PMID: 9447478.

5: Markowitz JS, Gaulin BD, Good MI. Significance of plasma thiothixene concentrations. Ann Pharmacother. 1995 Jul-Aug;29(7-8):789-90. PubMed PMID: 8520104.

6: Merkl CO, Miller LJ. Intravenous thiothixene in the agitated patient. J Clin Psychiatry. 1994 Oct;55(10):456-7. PubMed PMID: 7961528.

7: Woodring JH, Martin CA, Keefer B. Esophageal atony and dilatation as a side effect of thiothixene and benztropine. Hosp Community Psychiatry. 1993 Jul;44(7):686-8. PubMed PMID: 8354511.

8: Buchsbaum MS, Potkin SG, Marshall JF, Lottenberg S, Teng C, Heh CW, Tafalla R, Reynolds C, Abel L, Plon L, et al. Effects of clozapine and thiothixene on glucose metabolic rate in schizophrenia. Neuropsychopharmacology. 1992 May;6(3):155-63. PubMed PMID: 1599606.

9: Ereshefsky L, Saklad SR, Watanabe MD, Davis CM, Jann MW. Thiothixene pharmacokinetic interactions: a study of hepatic enzyme inducers, clearance inhibitors, and demographic variables. J Clin Psychopharmacol. 1991 Oct;11(5):296-301. Erratum in: J Clin Psychopharmacol 1992 Apr;12(2):78. PubMed PMID: 1765572.

10: Bartlett EJ, Wolkin A, Brodie JD, Laska EM, Wolf AP, Sanfilipo M. Importance of pharmacologic control in PET studies: effects of thiothixene and haloperidol on cerebral glucose utilization in chronic schizophrenia. Psychiatry Res. 1991 Oct;40(2):115-24. PubMed PMID: 1763142.

11: Hariharan M, VanNoord T, Kindt EK, Tandon R. A simple, sensitive liquid chromatographic assay of cis-thiothixene in plasma with coulometric detection. Ther Drug Monit. 1991 Jan;13(1):79-85. PubMed PMID: 1676194.

12: Janicak PG, Bresnahan DB, Sharma R, Davis JM, Comaty JE, Malinick C. A comparison of thiothixene with chlorpromazine in the treatment of mania. J Clin Psychopharmacol. 1988 Feb;8(1):33-7. PubMed PMID: 3280617.

13: Davis CM, Harrington CA. Quantitation of thiothixene in plasma by high-performance thin-layer chromatography and fluorometric detection. Ther Drug Monit. 1988;10(2):215-23. PubMed PMID: 3381241.

14: Yesavage JA, Tanke ED, Sheikh JI. Tardive dyskinesia and steady-state serum levels of thiothixene. Arch Gen Psychiatry. 1987 Oct;44(10):913-5. PubMed PMID: 2889439.

15: Balon R, Berchou R, Han H. Priapism associated with thiothixene, chlorpromazine, and thioridazine. J Clin Psychiatry. 1987 May;48(5):216. PubMed PMID: 3571177.

16: Severin G. Comprehensive high-performance liquid chromatographic methodology for the determination of thiothixene in bulk drug, finished product, and dissolution testing samples. J Pharm Sci. 1987 Mar;76(3):231-4. PubMed PMID: 3585740.

17: Balon R, Berchou R, Zethelius M. Thrombocytopenia associated with chlorpromazine, haloperidol and thiothixene: a case report. Can J Psychiatry. 1987 Mar;32(2):149-50. PubMed PMID: 3567823.

18: Sarai K, Okada M. Comparison of efficacy of zotepine and thiothixene in schizophrenia in a double-blind study. Pharmacopsychiatry. 1987 Feb;20(1 Spec No):38-46. PubMed PMID: 2883680.

19: Goldberg SC, Schulz SC, Resnick RJ, Hamer RM, Schulz PM. Differential prediction of response to thiothixene and placebo in borderline and schizotypal personality disorders. Psychopharmacol Bull. 1987;23(3):342-6. PubMed PMID: 3324147.

20: Hollister LE, Lombrozo L, Huang CC. Plasma concentrations of thiothixene and clinical response in treatment-resistant schizophrenics. Int Clin Psychopharmacol. 1987 Jan;2(1):77-82. PubMed PMID: 3312399.