Synonym
SSR-69071; SSR 69071; SSR69071
IUPAC/Chemical Name
2-[[6-methoxy-4-(1-methylethyl)-1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl]methoxy]-9-[2-(1-piperidinyl)ethoxy]-4H-pyrido[1,2-a]pyrimidin-4-one
InChi Key
DRZXDZYWZSKFDL-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H32N4O7S/c1-18(2)20-14-19(36-3)15-22-25(20)27(33)31(39(22,34)35)17-38-23-16-24(32)30-11-7-8-21(26(30)28-23)37-13-12-29-9-5-4-6-10-29/h7-8,11,14-16,18H,4-6,9-10,12-13,17H2,1-3H3
SMILES Code
O=C1N(C2=NC(OCN3S(C(C=C(OC)C=C4C(C)C)=C4C3=O)(=O)=O)=C1)C=CC=C2OCCN5CCCCC5
Purity
>95% (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
>3 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
Biological target:
SSR-69071 is a potent inhibitor of neutrophil elastase (Ki = 0.0168 nM for the human enzyme). It is selective for human neutrophil elastase over rat, mouse, and rabbit elastases (Kis = 3, 1.8, 58 nM, respectively).
In vivo activity:
This study demonstrates that SSR-69071 is a selective, orally active, and potent inhibitor of human leukocyte elastase (HLE) with good penetration in respiratory tissues. Bronchoalveolar lavage fluid from mice orally treated with SSR69071 inhibits HLE. SSR-69071 significantly decreased the acute lung hemorrhage induced by HLE (ED(50) = 2.8 mg/kg p.o.) in mice. SSR-69071 also prevented carrageenan- (ED(30) = 2.2 mg/kg) and HLE-induced (ED(30) = 2.7 mg/kg) paw edema in rats after p.o. administration.
Reference: J Pharmacol Exp Ther. 2003 May;305(2):451-9. https://pubmed.ncbi.nlm.nih.gov/12606659/
|
Solvent |
mg/mL |
mM |
comments |
Solubility |
DMSO |
25.0 |
44.91 |
|
Ethanol |
10.0 |
17.97 |
|
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
556.63
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. Kapui Z, Varga M, Urban-Szabo K, Mikus E, Szabo T, Szeredi J, Batori S, Finance O, Aranyi P. Biochemical and pharmacological characterization of 2-(9-(2-piperidinoethoxy)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yloxymethyl)-4-(1-methylethyl)-6-methoxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide (SSR69071), a novel, orally active elastase inhibitor. J Pharmacol Exp Ther. 2003 May;305(2):451-9. doi: 10.1124/jpet.102.044263. Epub 2003 Feb 11. PMID: 12606659.
2. Bidouard JP, Duval N, Kapui Z, Herbert JM, O'Connor SE, Janiak P. SSR69071, an elastase inhibitor, reduces myocardial infarct size following ischemia-reperfusion injury. Eur J Pharmacol. 2003 Feb 7;461(1):49-52. doi: 10.1016/s0014-2999(03)01298-6. PMID: 12568915.
In vivo protocol:
1. Kapui Z, Varga M, Urban-Szabo K, Mikus E, Szabo T, Szeredi J, Batori S, Finance O, Aranyi P. Biochemical and pharmacological characterization of 2-(9-(2-piperidinoethoxy)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yloxymethyl)-4-(1-methylethyl)-6-methoxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide (SSR69071), a novel, orally active elastase inhibitor. J Pharmacol Exp Ther. 2003 May;305(2):451-9. doi: 10.1124/jpet.102.044263. Epub 2003 Feb 11. PMID: 12606659.
2. Bidouard JP, Duval N, Kapui Z, Herbert JM, O'Connor SE, Janiak P. SSR69071, an elastase inhibitor, reduces myocardial infarct size following ischemia-reperfusion injury. Eur J Pharmacol. 2003 Feb 7;461(1):49-52. doi: 10.1016/s0014-2999(03)01298-6. PMID: 12568915.
1: Wen Z, Ablimit A. Comprehensive analysis of scRNA-Seq and bulk RNA-Seq reveals ubiquitin promotes pulmonary fibrosis in chronic pulmonary diseases. Sci Rep. 2024 Sep 11;14(1):21195. doi: 10.1038/s41598-024-70659-1. PMID: 39261509; PMCID: PMC11390722.
2: Bali KK, Kuner R. Therapeutic potential for leukocyte elastase in chronic pain states harboring a neuropathic component. Pain. 2017 Nov;158(11):2243-2258. doi: 10.1097/j.pain.0000000000001032. PMID: 28837503; PMCID: PMC5642338.
3: De Muynck L, Herdewyn S, Beel S, Scheveneels W, Van Den Bosch L, Robberecht W, Van Damme P. The neurotrophic properties of progranulin depend on the granulin E domain but do not require sortilin binding. Neurobiol Aging. 2013 Nov;34(11):2541-7. doi: 10.1016/j.neurobiolaging.2013.04.022. Epub 2013 May 24. PMID: 23706646.
4: Varga M, Kapui Z, Bátori S, Nagy LT, Vasvári-Debreczy L, Mikus E, Urbán-Szabó K, Arányi P. A novel orally active inhibitor of HLE. Eur J Med Chem. 2003 Apr;38(4):421-5. doi: 10.1016/s0223-5234(03)00046-1. PMID: 12750030.
5: Kapui Z, Varga M, Urban-Szabo K, Mikus E, Szabo T, Szeredi J, Batori S, Finance O, Aranyi P. Biochemical and pharmacological characterization of 2-(9-(2 -piperidinoethoxy)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yloxymethyl)-4-(1-methyleth yl)-6-methoxy-1,2-benzisothiazol-3(2H)-one-1,1-dioxide (SSR69071), a novel, orally active elastase inhibitor. J Pharmacol Exp Ther. 2003 May;305(2):451-9. doi: 10.1124/jpet.102.044263. Epub 2003 Feb 11. PMID: 12606659.
6: Bidouard JP, Duval N, Kapui Z, Herbert JM, O'Connor SE, Janiak P. SSR69071, an elastase inhibitor, reduces myocardial infarct size following ischemia- reperfusion injury. Eur J Pharmacol. 2003 Feb 7;461(1):49-52. doi: 10.1016/s0014-2999(03)01298-6. PMID: 12568915.