Rilmenidine phosphate

Names

[ Name ]:
Rilmenidine phosphate

[Synonym ]:
2-Oxazolamine, N-(dicyclopropylmethyl)-4,5-dihydro-, phosphate (1:1)
N-(Dicyclopropylmethyl)-4,5-dihydro-1,3-oxazol-2-amine phosphate (1:1)
Rilmenidine phosphate
2-Oxazolamine, 4,5-dihydro-N-(dicyclopropylmethyl)-, phosphate (1:1)
S 3341-3 {Phosphate}
Rilmenidine dihydrogen phosphate
S 3341-3
EINECS 287-106-2
4,5-Dihydro-N-(dicyclopropylmethyl)-2-oxazolamine phosphate (1:1)
Hyperium

Biological Activity

[Description]:

Rilmenidine phosphate, an antihypertensive agent, is an orally active, selective I1 imidazoline receptor agonist. Rilmenidine phosphate acts both centrally by reducing sympathetic overactivity and in the kidney by inhibiting the Na+/H+ antiport. Rilmenidine phosphate induces autophagy. Rilmenidine phosphate is also an alpha 2-adrenoceptor agonist. Rilmenidine phosphate modulates proliferation and stimulates the proapoptotic protein Bax thus inducing the perturbation of the mitochondrial pathway and apoptosis in human leukemic K562 cells[1][2][3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Imidazoline Receptor

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cardiovascular Disease

Signaling Pathways >> GPCR/G Protein >> Imidazoline Receptor

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

[In Vitro]

Rilmenidine phosphate (25-100 μM; 24 hours) inhibits K562 cell proliferation[2].Rilmenidine provides antihypertensive efficacy comparable with that of diuretics, beta-blockers, calcium channel blockers, and angiotensin-converting enzyme (ACE) inhibitors[3]. Cell Proliferation Assay[2] Cell Line: K562 cells Concentration: 25, 50, 100 μM Incubation Time: 24 hours Result: Dose-dependently inhibited K562 colony formation.

[In Vivo]

Rilmenidine phosphate-treated N171-82Q mice (i.p.; 4-times a week) displays significant improved forelimb grip strength and all limbs grip strength from 12 to 22 weeks of age[4]. Rilmenidine phosphate decreases levels of mutant huntingtin[4].

[References]

[1]. Reid JL. Rilmenidine: a clinical overview. Am J Hypertens. 2000;13(6 Pt 2):106S-111S.

[2]. Srdic-Rajic T, et al. Rilmenidine suppresses proliferation and promotes apoptosis via the mitochondrial pathway in human leukemic K562 cells. Eur J Pharm Sci. 2016;81:172-180.

[3]. Reid JL. Rilmenidine: a clinical overview. Am J Hypertens. 2000;13(6 Pt 2):106S-111S.

[4]. Rose C, et al. Rilmenidine attenuates toxicity of polyglutamine expansions in a mouse model of Huntington's disease. Hum Mol Genet. 2010;19(11):2144-2153.

Chemical & Physical Properties

[ Boiling Point ]:
609.1ºC at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₉N₂O₅P

[ Molecular Weight ]:
278.242

[ Flash Point ]:
322.1ºC

[ Exact Mass ]:
278.103149

[ PSA ]:
121.19000

[ LogP ]:
0.04870

[ Storage condition ]:
-20℃

[ Water Solubility ]:
Freely soluble in water, slightly soluble in alcohol, practically insoluble in methylene chloride.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RP6744000

CAS REGISTRY NUMBER :: 85409-38-7

LAST UPDATED :: 199512

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H16-N2-O.H3-O4-P

MOLECULAR WEIGHT :: 278.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 295 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CDREEA Cardiovascular Drug Reviews. (Raven Press, 1185 Avenue of the Americas, New York, NY 10036) V.6- 1988- Volume(issue)/page/year: 8,56,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 375 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CDREEA Cardiovascular Drug Reviews. (Raven Press, 1185 Avenue of the Americas, New York, NY 10036) V.6- 1988- Volume(issue)/page/year: 8,56,1990

Safety Information

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%