Synonym
PNU-95666; PNU 95666; PNU95666; U 95666E; U-95666E; U95666E; Sumanirole maleate
IUPAC/Chemical Name
(R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one maleate
InChi Key
VOJRMYBBPKNLLI-ORHWHDKWSA-N
InChi Code
InChI=1S/C11H13N3O.C4H4O4/c1-12-8-5-7-3-2-4-9-10(7)14(6-8)11(15)13-9;5-3(6)1-2-4(7)8/h2-4,8,12H,5-6H2,1H3,(H,13,15);1-2H,(H,5,6)(H,7,8)/b;2-1-/t8-;/m1./s1
SMILES Code
O=C1NC2=C3N1C[C@H](NC)CC3=CC=C2.O=C(O)/C=C\C(O)=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
More Info
Related CAS#
179386-43-7 (Sumanirole free base).
179386-44-8 (Sumanirole maleate)
Biological target:
Sulforaphane is an inducer of Nrf2 and is also an inhibitor of histone deacetylase (HDAC) and NF-κB.
In vitro activity:
Dopamine homeostasis imbalance and dopamine receptors (DRs)-mediated AC/cAMP/PKA pathway activation might be vital mechanisms underlying aconitine-induced neurological injury. SCH23390 and sumanirole also reduced aconitine-induced cytotoxicity by inhibiting the AC/cAMP/PKA pathway in vitro.
Reference: Front Pharmacol. 2022 Mar 18;13:837810. https://pubmed.ncbi.nlm.nih.gov/35370746/
In vivo activity:
Sumanirole was compared to placebo and ropinirole in a study involving 614 early Parkinson's disease patients. Over 40 weeks, sumanirole and ropinirole showed significant improvement in UPDRS II + III scores compared to placebo. However, noninferiority of sumanirole to ropinirole was not established. Sumanirole exhibited better tolerability than ropinirole.
Reference: Mov Disord. 2007 Mar 15;22(4):476-82. https://pubmed.ncbi.nlm.nih.gov/17318839/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
12.5 |
39.15 |
| DMSO |
16.0 |
50.11 |
| PBS (pH 7.2) |
5.0 |
15.66 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
319.32
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 |
Formulation protocol:
1. Zhou J, Peng C, Li Q, Yan X, Yang L, Li M, Cao X, Xie X, Chen D, Rao C, Huang S, Peng F, Pan X. Dopamine Homeostasis Imbalance and Dopamine Receptors-Mediated AC/cAMP/PKA Pathway Activation are Involved in Aconitine-Induced Neurological Impairment in Zebrafish and SH-SY5Y Cells. Front Pharmacol. 2022 Mar 18;13:837810. doi: 10.3389/fphar.2022.837810. Erratum in: Front Pharmacol. 2023 May 16;14:1219561. PMID: 35370746; PMCID: PMC8971779.
2. Weissenrieder JS, Reed JL, Green MV, Moldovan GL, Koubek EJ, Neighbors JD, Hohl RJ. The Dopamine D2 Receptor Contributes to the Spheroid Formation Behavior of U87 Glioblastoma Cells. Pharmacology. 2020;105(1-2):19-27. doi: 10.1159/000502562. Epub 2019 Oct 23. PMID: 31645049; PMCID: PMC10777736.
3. Weber M, Chang WL, Breier MR, Yang A, Millan MJ, Swerdlow NR. The effects of the dopamine D2 agonist sumanirole on prepulse inhibition in rats. Eur Neuropsychopharmacol. 2010 Jun;20(6):421-5. doi: 10.1016/j.euroneuro.2010.02.011. Epub 2010 Mar 25. PMID: 20346635; PMCID: PMC2864324.
4. Singer C, Lamb J, Ellis A, Layton G; Sumanirole for Early Parkinson's Disease Study Group. A comparison of sumanirole versus placebo or ropinirole for the treatment of patients with early Parkinson's disease. Mov Disord. 2007 Mar 15;22(4):476-82. doi: 10.1002/mds.21361. PMID: 17318839.
In vitro protocol:
1. Zhou J, Peng C, Li Q, Yan X, Yang L, Li M, Cao X, Xie X, Chen D, Rao C, Huang S, Peng F, Pan X. Dopamine Homeostasis Imbalance and Dopamine Receptors-Mediated AC/cAMP/PKA Pathway Activation are Involved in Aconitine-Induced Neurological Impairment in Zebrafish and SH-SY5Y Cells. Front Pharmacol. 2022 Mar 18;13:837810. doi: 10.3389/fphar.2022.837810. Erratum in: Front Pharmacol. 2023 May 16;14:1219561. PMID: 35370746; PMCID: PMC8971779.
2. Weissenrieder JS, Reed JL, Green MV, Moldovan GL, Koubek EJ, Neighbors JD, Hohl RJ. The Dopamine D2 Receptor Contributes to the Spheroid Formation Behavior of U87 Glioblastoma Cells. Pharmacology. 2020;105(1-2):19-27. doi: 10.1159/000502562. Epub 2019 Oct 23. PMID: 31645049; PMCID: PMC10777736.
In vivo protocol:
1. Weber M, Chang WL, Breier MR, Yang A, Millan MJ, Swerdlow NR. The effects of the dopamine D2 agonist sumanirole on prepulse inhibition in rats. Eur Neuropsychopharmacol. 2010 Jun;20(6):421-5. doi: 10.1016/j.euroneuro.2010.02.011. Epub 2010 Mar 25. PMID: 20346635; PMCID: PMC2864324.
2. Singer C, Lamb J, Ellis A, Layton G; Sumanirole for Early Parkinson's Disease Study Group. A comparison of sumanirole versus placebo or ropinirole for the treatment of patients with early Parkinson's disease. Mov Disord. 2007 Mar 15;22(4):476-82. doi: 10.1002/mds.21361. PMID: 17318839.
1: Zou MF, Keck TM, Kumar V, Donthamsetti P, Michino M, Burzynski C, Schweppe C, Bonifazi A, Free RB, Sibley DR, Janowsky A, Shi L, Javitch JA, Newman AH. Novel Analogues of (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (Sumanirole) Provide Clues to Dopamine D2/D3 Receptor Agonist Selectivity. J Med Chem. 2016 Apr 14;59(7):2973-88. doi: 10.1021/acs.jmedchem.5b01612. Epub 2016 Apr 1. PubMed PMID: 27035329; PubMed Central PMCID: PMC4915350.
2: Weber M, Chang WL, Breier MR, Yang A, Millan MJ, Swerdlow NR. The effects of the dopamine D2 agonist sumanirole on prepulse inhibition in rats. Eur Neuropsychopharmacol. 2010 Jun;20(6):421-5. doi: 10.1016/j.euroneuro.2010.02.011. Epub 2010 Mar 25. PubMed PMID: 20346635; PubMed Central PMCID: PMC2864324.
3: Singer C, Lamb J, Ellis A, Layton G; Sumanirole for Early Parkinson's Disease Study Group. A comparison of sumanirole versus placebo or ropinirole for the treatment of patients with early Parkinson's disease. Mov Disord. 2007 Mar 15;22(4):476-82. PubMed PMID: 17318839.
4: Garcia-Borreguero D, Winkelman J, Adams A, Ellis A, Morris M, Lamb J, Layton G, Versavel M; Sumanirole in RLS Study Group. Efficacy and tolerability of sumanirole in restless legs syndrome: a phase II, randomized, double-blind, placebo-controlled, dose-response study. Sleep Med. 2007 Mar;8(2):119-27. Epub 2007 Jan 18. PubMed PMID: 17239657.
5: Barone P, Lamb J, Ellis A, Clarke Z. Sumanirole versus placebo or ropinirole for the adjunctive treatment of patients with advanced Parkinson's disease. Mov Disord. 2007 Mar 15;22(4):483-9. PubMed PMID: 17115380.
6: McCall RB, Lookingland KJ, Bédard PJ, Huff RM. Sumanirole, a highly dopamine D2-selective receptor agonist: in vitro and in vivo pharmacological characterization and efficacy in animal models of Parkinson's disease. J Pharmacol Exp Ther. 2005 Sep;314(3):1248-56. Epub 2005 Jun 24. PubMed PMID: 15980060.
7: de Paulis T. Sumanirole Pharmacia. Curr Opin Investig Drugs. 2003 Jan;4(1):77-82. Review. PubMed PMID: 12625034.
