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MedKoo Cat#: 329628 | Name: Tirilazad mesylate

Description:

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

Tirilazad, also known as U 74006F, is a lazaroid and potent inhibitor of iron-dependent lipid peroxidation. Tirilazad has shown excellent activity in in vivo models of experimental central nervous system trauma & ischemia. Tirilazad is a drug that has been proposed to treat acute ischaemic stroke. When tested on animal models, tirilazad protects brain tissue, and reduces brain damage. However, the drug fails to treat, and even worsens a stroke when studied on a human being. Tirilazad currently has no usage in the clinical treatment of stroke.

Chemical Structure

Tirilazad mesylate
Tirilazad mesylate
CAS#110101-67-2 (mesylate)

Theoretical Analysis

MedKoo Cat#: 329628

Name: Tirilazad mesylate

CAS#: 110101-67-2 (mesylate)

Chemical Formula: C39H56N6O5S

Exact Mass:

Molecular Weight: 720.97

Elemental Analysis: C, 64.97; H, 7.83; N, 11.66; O, 11.10; S, 4.45

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
110101-66-1 (free base) 110101-67-2 (mesylate) 111793-42-1 (mesylate hydrate)
Synonym
U 74006F; U74006F; U-74006F; U 74006; U74006; U-74006; Tirilazad mesylate; tradename Freedox.
IUPAC/Chemical Name
21-(4-(2,6-di-1-Pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl)-16-methylpregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate
InChi Key
HPZOOQSXPMEJBV-CAGOZALDSA-N
InChi Code
InChI=1S/C38H52N6O2.CH4O3S/c1-26-22-31-29-9-8-27-23-28(45)10-12-37(27,2)30(29)11-13-38(31,3)35(26)32(46)25-41-18-20-43(21-19-41)34-24-33(42-14-4-5-15-42)39-36(40-34)44-16-6-7-17-44;1-5(2,3)4/h10-12,23-24,26,29,31,35H,4-9,13-22,25H2,1-3H3;1H3,(H,2,3,4)/t26?,29-,31+,35-,37+,38+;/m1./s1
SMILES Code
C[C@@]12[C@@H](C(CN3CCN(C4=NC(N5CCCC5)=NC(N6CCCC6)=C4)CC3)=O)C(C)C[C@@]1([H])[C@]7([H])CCC8=CC(C=C[C@]8(C)C7=CC2)=O.CS(=O)(O)=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 720.97 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
1: Bracken MB, Shepard MJ, Holford TR, Leo-Summers L, Aldrich EF, Fazl M, Fehlings M, Herr DL, Hitchon PW, Marshall LF, Nockels RP, Pascale V, Perot PL Jr, Piepmeier J, Sonntag VK, Wagner F, Wilberger JE, Winn HR, Young W. Administration of methylprednisolone for 24 or 48 hours or tirilazad mesylate for 48 hours in the treatment of acute spinal cord injury. Results of the Third National Acute Spinal Cord Injury Randomized Controlled Trial. National Acute Spinal Cord Injury Study. JAMA. 1997 May 28;277(20):1597-604. PubMed PMID: 9168289. 2: Zhang S, Wang L, Liu M, Wu B. Tirilazad for aneurysmal subarachnoid haemorrhage. Cochrane Database Syst Rev. 2010 Feb 17;(2):CD006778. doi: 10.1002/14651858.CD006778.pub2. Review. PubMed PMID: 20166088. 3: Fleishaker JC, Pearson PG, Wienkers LC, Pearson LK, Moore TA, Peters GR. Biotransformation of tirilazad in human: 4. effect of finasteride on tirilazad clearance and reduced metabolite formation. J Pharmacol Exp Ther. 1998 Nov;287(2):591-7. PubMed PMID: 9808685. 4: Jang YG, Ilodigwe D, Macdonald RL. Metaanalysis of tirilazad mesylate in patients with aneurysmal subarachnoid hemorrhage. Neurocrit Care. 2009;10(1):141-7. doi: 10.1007/s12028-008-9147-y. Epub 2008 Sep 23. PubMed PMID: 18810661. 5: Fleishaker JC, Pearson PG, Wienkers LC, Pearson LK, Peters GR. Biotransformation of tirilazad in human: 2. Effect of ketoconazole on tirilazad clearance and oral bioavailability. J Pharmacol Exp Ther. 1996 May;277(2):991-8. PubMed PMID: 8627582. 6: Fleishaker JC, Peters GR. Pharmacokinetics of tirilazad and U-89678 in ischemic stroke patients receiving a loading regimen and maintenance regimen of 10 mg/kg/day of tirilazad. J Clin Pharmacol. 1996 Sep;36(9):809-13. PubMed PMID: 8889901. 7: Wang Y, Cory AL. A novel stable supersaturated submicron lipid emulsion of tirilazad. Pharm Dev Technol. 1999 Aug;4(3):333-45. PubMed PMID: 10434279. 8: Fleishaker JC, Hulst LK, Peters GR. Multiple-dose tolerability and pharmacokinetics of tirilazad mesylate at doses of up to 10 mg/kg/day administered over 5-10 days in healthy volunteers. Int J Clin Pharmacol Ther. 1994 May;32(5):223-30. PubMed PMID: 7921515. 9: Wienkers LC, Steenwyk RC, Hauer MJ, Fleishaker JC, Pearson PG. Biotransformation of tirilazad in human: 3. tirilazad A-ring reduction by human liver microsomal 5alpha-reductase type 1 and type 2. J Pharmacol Exp Ther. 1998 Nov;287(2):583-90. PubMed PMID: 9808684. 10: Fleishaker JC, Pearson LK, Peters GR. Induction of tirilazad clearance by phenytoin. Biopharm Drug Dispos. 1998 Mar;19(2):91-6. PubMed PMID: 9533108. 11: Fleishaker JC, Pearson LK, Pearson PG, Wienkers LC, Hopkins NK, Peters GR. Hormonal effects on tirilazad clearance in women: assessment of the role of CYP3A. J Clin Pharmacol. 1999 Mar;39(3):260-7. PubMed PMID: 10073325. 12: Fleishaker JC, Straw RN, Cross CJ. Pharmacokinetics of tirilazad and U-89678, an active, reduced metabolite, following acute head trauma in adults. J Pharm Sci. 1997 Apr;86(4):434-7. PubMed PMID: 9109044. 13: Kassell NF, Haley EC Jr, Apperson-Hansen C, Alves WM. Randomized, double-blind, vehicle-controlled trial of tirilazad mesylate in patients with aneurysmal subarachnoid hemorrhage: a cooperative study in Europe, Australia, and New Zealand. J Neurosurg. 1996 Feb;84(2):221-8. PubMed PMID: 8592224. 14: Suzuki H, Kanamaru K, Kuroki M, Sun H, Waga S, Miyazawa T. Effects of tirilazad mesylate on vasospasm and phospholipid hydroperoxides in a primate model of subarachnoid hemorrhage. Stroke. 1999 Feb;30(2):450-5; discussion 455-6. PubMed PMID: 9933286. 15: Tirilazad mesylate in acute ischemic stroke: A systematic review. Tirilazad International Steering Committee. Stroke. 2000 Sep;31(9):2257-65. Erratum in: Stroke 2001 Jan;32(1):279. PubMed PMID: 10978061. 16: Fleishaker JC, Pearson LK, Peters GR. Gender does not affect the degree of induction of tirilazad clearance by phenobarbital. Eur J Clin Pharmacol. 1996;50(1-2):139-45. PubMed PMID: 8739825. 17: Fleishaker JC, Peters GR, Cathcart KS. Evaluation of the pharmacokinetics and tolerability of tirilazad mesylate, a 21-aminosteroid free radical scavenger: I. Single-dose administration. J Clin Pharmacol. 1993 Feb;33(2):175-81. PubMed PMID: 8382708. 18: Fleishaker JC, Hulst-Pearson LK, Peters GR. Effect of Gender and Menopausal Status on the Pharmacokinetics of Tirilazad Mesylate in Healthy Subjects. Am J Ther. 1995 Aug;2(8):553-560. PubMed PMID: 11854826. 19: Marshall LF, Maas AI, Marshall SB, Bricolo A, Fearnside M, Iannotti F, Klauber MR, Lagarrigue J, Lobato R, Persson L, Pickard JD, Piek J, Servadei F, Wellis GN, Morris GF, Means ED, Musch B. A multicenter trial on the efficacy of using tirilazad mesylate in cases of head injury. J Neurosurg. 1998 Oct;89(4):519-25. PubMed PMID: 9761043. 20: Nakayama M, Hasegawa N, Oka Y, Lutzke B, McCall JM, Raffin TA. Effects of the lazaroid, tirilazad mesylate, on sepsis-induced acute lung injury in minipigs. Crit Care Med. 1998 Mar;26(3):538-47. PubMed PMID: 9504584.