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Identification
Name Sevelamer
Accession Number DB00658 (APRD01226)
Type small molecule
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Renagel
Brand name mixtures Not Available
Categories
  • Phosphate Binders
CAS number 152751-57-0
Weight Average: 149.619
Monoisotopic: 149.060741718
Chemical Formula C6H12ClNO
InChI Key InChIKey=ZNSIZMQNQCNRBW-UHFFFAOYSA-N
InChI
InChI=1S/C3H5ClO.C3H7N/c4-1-3-2-5-3;1-2-3-4/h3H,1-2H2;2H,1,3-4H2
Plain Text
IUPAC Name
2-(chloromethyl)oxirane; prop-2-en-1-amine
SMILES
NCC=C.ClCC1CO1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aliphatic and Aryl Amines
Substructures
  • Alkanes and Alkenes
  • Aliphatic and Aryl Amines
  • Ethers
  • Alkyl Halides
  • Heterocyclic compounds
  • Epoxides
Pharmacology
Indication For the control of serum phosphorus in patients with Chronic Kidney Disease (CKD) on hemodialysis.
Pharmacodynamics 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 mg2/dL2, 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.
Mechanism of action Sevelamer prevents hyperphosphatemia by binding to dietary phosphate in the gut, preventing its absorption and thus decreasing serum parathyroid hormone levels.
Absorption Not absorbed following oral administration, however no absorption studies have been performed in patients with renal disease.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Genzyme corp
  • Genzyme Corporation
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Renagel 800 mg tablet 2.41 USD tablet
Renvela 800 mg tablet 2.17 USD tablet
Renagel 400 mg tablet 1.66 USD tablet
Patents
Country Patent Number Approved Expires
United States 6733780 2000-10-18 2020-10-18
United States 5496545 1993-08-11 2013-08-11
Canada 2310960 2003-05-27 2014-08-10
Canada 2169356 2000-07-04 2014-08-10
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Insoluble PhysProp
logP 0.559 PhysProp
Predicted Properties
Property Value Source
water solubility ALOGPS
logP ALOGPS
logP 0.11 ChemAxon Molconvert
logS ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 1 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 26.02 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 19.08 ChemAxon Molconvert
polarizability 6.89 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01983 Link_out
PubChem Compound 3085017 Link_out
PubChem Substance 46505951 Link_out
ChemSpider 2341997 Link_out
PharmGKB PA451339 Link_out
Drug Product Database 2244310 Link_out
RxList http://www.rxlist.com/cgi/generic2/sevel.htm Link_out
Drugs.com http://www.drugs.com/cdi/sevelamer.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Sevelamer Link_out
ATC Codes
  • V03AE02
AHFS Codes
  • 92:00.00
PDB Entries Not Available
FDA label show (36.4 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Phosphate

Pharmacological action: yes
Actions: binder

References:
  1. Cannata-Andia JB, Rodriguez-Garcia M, Roman-Garcia P, Tunon-le Poultel D, Lopez-Hernandez F, Rodriguez-Puyol D: New therapies: calcimimetics, phosphate binders and vitamin D receptor activators. Pediatr Nephrol. 2010 Apr;25(4):609-16. Epub 2010 Feb 12. Pubmed
  2. Novak JE, Szczech LA: Phosphate binders in chronic kidney disease and end-stage renal disease: a patient-centered approach. Semin Dial. 2009 Jan-Feb;22(1):56-63. Epub 2008 Oct 16. Pubmed
  3. Salusky IB: A new era in phosphate binder therapy: what are the options? Kidney Int Suppl. 2006 Dec;(105):S10-5. Pubmed
  4. Schucker JJ, Ward KE: Hyperphosphatemia and phosphate binders. Am J Health Syst Pharm. 2005 Nov 15;62(22):2355-61. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:41

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.