2-(chloromethyl)oxirane; prop-2-en-1-amine

• ChemBase ID: 540
• Molecular Formular: C6H12ClNO
• Molecular Mass: 149.61858
• Monoisotopic Mass: 149.06074169
• SMILES: ClCC1OC1.NCC=C
• Canonical SMILES: ClCC1CO1.C=CCN
• InChI: InChI=1S/C3H5ClO.C3H7N/c4-1-3-2-5-3;1-2-3-4/h3H,1-2H2;2H,1,3-4H2
• InChIKey: ZNSIZMQNQCNRBW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(chloromethyl)oxirane; prop-2-en-1-amine
• IUPAC Traditional name: allylamine; epichlorohydrin
• Brand Name: Renagel
• Synonyms: Sevelamer; 2-Propen-1-amine Hydrochloride polymer with 2-(Chloromethyl)oxirane; 2-Propen-1-amine Hydrochloride polymer with (Chloromethyl)oxirane; (Chloromethyl)oxirane polymer with 2-Propen-1-amine Hydrochloride; Allylamine Hydrochloride-epichlorhydrin Copolymer; Allylamine Hydrochloride-epichlorohydrin Copolymer; GT 16-026A; Phosblock; RenaGel; Sevelamer Hydrochloride

Database IDs

• CAS Number: 152751-57-0
• PubChem SID: 46505951; 160964003
• PubChem CID: 3085017

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6772814
• LogD (pH = 7.4): 0.6772814
• Log P: 0.6772814
• Molar Refractivity: 20.057 cm^3
• Polarizability: 8.123073 Å^3
• Polar Surface Area: 12.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 0.559

DETAILS

DrugBank - DB00658

• Drug Groups: approved
• Description: Sevelamer is a phosphate binding drug used to prevent hyperphosphataemia in patients with chronic renal failure. When taken with meals, sevelamer binds to dietary phosphate and prevents its absorption. It is marketed by Genzyme under the trade name Renagel.
• Indication: For the control of serum phosphorus in patients with Chronic Kidney Disease (CKD) on hemodialysis.
• Pharmacology: Patients with end-stage renal disease (ESRD) retain phosphorus and can develop hyperphosphatemia. High serum phosphorus can precipitate serum calcium resulting in ectopic calcification. When the product of serum calcium and phosphorus concentrations (Ca x P) exceeds 55 mg^2/dL^2, there is an increased risk that ectopic calcification will occur. Hyperphosphatemia plays a role in the development of secondary hyperparathyroidism in renal insufficiency. An increase in parathyroid hormone (PTH) levels is characteristic of patients with chronic renal failure. Increased levels of PTH can lead to osteitis fibrosa, a bone disease. A decrease in serum phosphorus may decrease serum PTH levels. Treatment of hyperphosphatemia includes reduction in dietary intake of phosphate, inhibition of intestinal phosphate absorption with phosphate binders, and removal of phosphate with dialysis. Sevelamer taken with meals has been shown to decrease serum phosphorus concentrations in patients with ESRD who are on hemodialysis. In vitro studies have shown that the capsule and tablet formulations bind phosphate to a similar extent. Sevelamer treatment also results in a lowering of low-density lipoprotein (LDL) and total serum cholesterol levels.
• Toxicity: Sevelamer has been given to normal healthy volunteers in doses of up to 14 grams per day for eight days with no adverse effects. Sevelamer has been given in average doses up to 13 grams per day to hemodialysis patients. There are no reported overdosages of sevelamer in patients. Since sevelamer is not absorbed, the risk of systemic toxicity is low.
• Affected Organisms: Humans and other mammals
• Absorption: Not absorbed following oral administration, however no absorption studies have been performed in patients with renal disease.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - S256000

Sevelamer hydrochloride is a noncalcemic phosphate binder for the treatment of hyperphosphatemia in chronic renal failure.

REFERENCES

• Wells, K., et al.: Am. J. Psychiatry, 156, 5 (1999)
• Finn, W., et al.: Clin. Nephrol., 65, 191 (1999)
• Hutchison, A., et al.: Nephrol. Clin. Pract., 102, 61 (1999)