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MedKoo Cat#: 529901 | Name: Repinotan HCl

Description:

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

Repinotan HCl is a 5-HT1A receptor agonist potentially for the treatment of stroke. It is a selective 5-HT(1A)-R-agonist repinotan that prevents remifentanil-induced ventilatory depression and prolongs antinociception. It has also been shown to antagonize morphine-induced ventilatory depression in anesthetized rats.

Chemical Structure

Repinotan HCl
Repinotan HCl
CAS#144980-77-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 529901

Name: Repinotan HCl

CAS#: 144980-77-8 (HCl)

Chemical Formula: C21H25ClN2O4S

Exact Mass:

Molecular Weight: 436.95

Elemental Analysis: C, 57.73; H, 5.77; Cl, 8.11; N, 6.41; O, 14.65; S, 7.34

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 #
144980-29-0 (free base) 144980-77-8 (HCl)
Synonym
Bay-x-3702; X-3702; Bayx3702; X3702; Bay x 3702; X 3702; Repinotan HCl
IUPAC/Chemical Name
2-(4-((chroman-2-ylmethyl)amino)butyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide hydrochloride
InChi Key
IGKYREHZJIHPML-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H24N2O4S.ClH/c24-21-18-8-2-4-10-20(18)28(25,26)23(21)14-6-5-13-22-15-17-12-11-16-7-1-3-9-19(16)27-17;/h1-4,7-10,17,22H,5-6,11-15H2;1H
SMILES Code
O=C(C1=C2C=CC=C1)N(CCCCNCC3CCC4=CC=CC=C4O3)S2(=O)=O.[H]Cl
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
Related CAS# 144980-29-0(Repinotan free base) 144980-77-8(Repinotan HCl)

Preparing Stock Solutions

The following data is based on the product molecular weight 436.95 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: Guenther U, Theuerkauf NU, Huse D, Boettcher MF, Wensing G, Putensen C, Hoeft A. Selective 5-HT(1A)-R-agonist repinotan prevents remifentanil-induced ventilatory depression and prolongs antinociception. Anesthesiology. 2012 Jan;116(1):56-64. doi: 10.1097/ALN.0b013e31823d08fa. PubMed PMID: 22082683. 2: Guenther U, Wrigge H, Theuerkauf N, Boettcher MF, Wensing G, Zinserling J, Putensen C, Hoeft A. Repinotan, a selective 5-HT1A-R-agonist, antagonizes morphine-induced ventilatory depression in anesthetized rats. Anesth Analg. 2010 Oct;111(4):901-7. doi: 10.1213/ANE.0b013e3181eac011. PubMed PMID: 20802053. 3: Teal P, Davis S, Hacke W, Kaste M, Lyden PD; Modified Randomized Exposure Controlled Trial Study Investigators., Fierus M; Bayer HealthCare AG.. A randomized, double-blind, placebo-controlled trial to evaluate the efficacy, safety, tolerability, and pharmacokinetic/pharmacodynamic effects of a targeted exposure of intravenous repinotan in patients with acute ischemic stroke: modified Randomized Exposure Controlled Trial (mRECT). Stroke. 2009 Nov;40(11):3518-25. doi: 10.1161/STROKEAHA.109.551382. PubMed PMID: 19745176. 4: Heinig R, Sundaresan P, Shah A, Boettcher M. Effect of gender and age on the pharmacokinetics of repinotan. Clin Drug Investig. 2005;25(2):125-34. PubMed PMID: 17523762. 5: Schwarz T, Beckermann B, Buehner K, Mauler F, Schuhmacher J, Seidel D, Steinke W, Weinz C, Zimmerd D. Pharmacokinetics of repinotan in healthy and brain injured animals. Biopharm Drug Dispos. 2005 Sep;26(6):259-68. PubMed PMID: 15966026. 6: Mauler F, Horváth E. Neuroprotective efficacy of repinotan HCl, a 5-HT1A receptor agonist, in animal models of stroke and traumatic brain injury. J Cereb Blood Flow Metab. 2005 Apr;25(4):451-9. PubMed PMID: 15674237. 7: Teal P, Silver FL, Simard D. The BRAINS study: safety, tolerability, and dose-finding of repinotan in acute stroke. Can J Neurol Sci. 2005 Feb;32(1):61-7. PubMed PMID: 15825548. 8: Heinig R, Böttcher MF. Pharmacokinetics of escalating doses of intravenous repinotan in healthy male volunteers. Clin Drug Investig. 2005;25(2):115-23. PubMed PMID: 17523761. 9: Berends AC, Luiten PG, Nyakas C. A review of the neuroprotective properties of the 5-HT1A receptor agonist repinotan HCl (BAYx3702) in ischemic stroke. CNS Drug Rev. 2005 Winter;11(4):379-402. Review. PubMed PMID: 16614737. 10: Tanigawa T, Heinig R, Kuroki Y, Higuchi S. Evaluation of interethnic differences in repinotan pharmacokinetics by using population approach. Drug Metab Pharmacokinet. 2006 Feb;21(1):61-9. PubMed PMID: 16547395. 11: Kline AE, Yu J, Horváth E, Marion DW, Dixon CE. The selective 5-HT(1A) receptor agonist repinotan HCl attenuates histopathology and spatial learning deficits following traumatic brain injury in rats. Neuroscience. 2001;106(3):547-55. PubMed PMID: 11591455. 12: Harkany T, Mulder J, Horvath KM, Keijser J, van der Meeberg EK, Nyakas C, Luiten PG. Oral post-lesion administration of 5-HT(1A) receptor agonist repinotan hydrochloride (BAY x 3702) attenuates NMDA-induced delayed neuronal death in rat magnocellular nucleus basalis. Neuroscience. 2001;108(4):629-42. PubMed PMID: 11738499. 13: Ohman J, Braakman R, Legout V; Traumatic Brain Injury Study Group.. Repinotan (BAY x 3702): a 5HT1A agonist in traumatically brain injured patients. J Neurotrauma. 2001 Dec;18(12):1313-21. PubMed PMID: 11780862. 14: Lutsep HL. Repinotan, A 5-HT1A agonist, in the treatment of acute ischemic stroke. Curr Drug Targets CNS Neurol Disord. 2005 Apr;4(2):119-20. Review. PubMed PMID: 15857296. 15: Lutsep HL. Repinotan Bayer. Curr Opin Investig Drugs. 2002 Jun;3(6):924-7. Review. PubMed PMID: 12137415. 16: Bezard E, Gerlach I, Moratalla R, Gross CE, Jork R. 5-HT1A receptor agonist-mediated protection from MPTP toxicity in mouse and macaque models of Parkinson's disease. Neurobiol Dis. 2006 Jul;23(1):77-86. PubMed PMID: 16545572. 17: Cheng JP, Leary JB, Sembhi A, Edwards CM, Bondi CO, Kline AE. 5-hydroxytryptamine1A (5-HT1A) receptor agonists: A decade of empirical evidence supports their use as an efficacious therapeutic strategy for brain trauma. Brain Res. 2016 Jun 1;1640(Pt A):5-14. doi: 10.1016/j.brainres.2015.11.026. Review. PubMed PMID: 26612522; PubMed Central PMCID: PMC4870091. 18: Adayev T, Ray I, Sondhi R, Sobocki T, Banerjee P. The G protein-coupled 5-HT1A receptor causes suppression of caspase-3 through MAPK and protein kinase Calpha. Biochim Biophys Acta. 2003 Apr 7;1640(1):85-96. PubMed PMID: 12676358. 19: Ferro JM, Dávalos A. Other neuroprotective therapies on trial in acute stroke. Cerebrovasc Dis. 2006;21 Suppl 2:127-30. PubMed PMID: 16651823. 20: de Boer SF, Koolhaas JM. 5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis. Eur J Pharmacol. 2005 Dec 5;526(1-3):125-39. Review. PubMed PMID: 16310183.