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Identification
NameColestipol
Accession NumberDB00375  (APRD00884)
TypeSmall Molecule
GroupsApproved
Description

Highly crosslinked and insoluble basic anion exchange resin used as anticholesteremic. It may also may reduce triglyceride levels. [PubChem]

Structure
Thumb
Synonyms
Colestipolum
Copolymer of bis(2-aminoethyl)amine and 2-(chloromethyl)oxirane
Epichlorohydrin-tetraethylenepentamine polymer
External Identifiers
  • U 26597 A
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Colestidgranule, for suspension5 g/5goralPharmacia and Upjohn Company1977-04-04Not applicableUs
Colestidtablet1 g/1oralPharmacia And Upjohn Company Llc1994-07-19Not applicableUs
Colestid Granulesgranules5 goralPfizer Canada Inc1985-12-31Not applicableCanada
Colestid Orange Granulesgranules5 goralPfizer Canada Inc1995-12-31Not applicableCanada
Colestid Tablets 1 Gtablet1 goralPfizer Canada Inc1995-12-31Not applicableCanada
Colestipol Hydrochloridetablet1 g/1oralCarilion Materials Management1994-07-19Not applicableUs
Colestipol Hydrochloridetablet1 g/1oralGreenstone LLC1994-07-19Not applicableUs
Colestipol Hydrochloridetablet1 g/1oralPhysicians Total Care, Inc.2007-02-28Not applicableUs
Colestipol Hydrochloridegranule, for suspension5 g/5goralGreenstone LLC1977-04-04Not applicableUs
Flavored Colestidgranule, for suspension5 g/7.5goralPharmacia and Upjohn Company1977-04-04Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Colestipol Hydrochloridetablet, film coated1 g/1oralImpax Generics2006-10-24Not applicableUs
Colestipol Hydrochloridesuspension5 g/1oralImpax Generics2006-05-02Not applicableUs
Colestipol Hydrochloridesuspension5 g/1oralImpax Generics2006-05-02Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CholestabylNot Available
LestidPfizer
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Colestipol hydrochloride
37296-80-3
ThumbNot applicableDBSALT001058
Categories
UNIIK50N755924
CAS number26658-42-4
WeightAverage: 281.826
Monoisotopic: 281.19823825
Chemical FormulaC11H28ClN5O
InChI KeyInChIKey=GMRWGQCZJGVHKL-UHFFFAOYSA-N
InChI
InChI=1S/C8H23N5.C3H5ClO/c9-1-3-11-5-7-13-8-6-12-4-2-10;4-1-3-2-5-3/h11-13H,1-10H2;3H,1-2H2
IUPAC Name
(2-aminoethyl)[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]amine; 2-(chloromethyl)oxirane
SMILES
ClCC1CO1.NCCNCCNCCNCCN
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as epoxides. These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassEpoxides
Sub ClassNot Available
Direct ParentEpoxides
Alternative Parents
Substituents
  • Oxacycle
  • Secondary amine
  • Ether
  • Oxirane
  • Secondary aliphatic amine
  • Dialkyl ether
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic heteromonocyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Pharmacology
IndicationFor use, as adjunctive therapy to diet, for the reduction of elevated serum total and LDL-C in patients with primary hypercholesterolemia (elevated LDL-C) who do not respond adequately to diet.
PharmacodynamicsCholesterol is the major, and probably the sole precursor of bile acids. During normal digestion, bile acids are secreted via the bile from the liver and gall bladder into the intestines. Bile acids emulsify the fat and lipid materials present in food, thus facilitating absorption. A major portion of the bile acids secreted is reabsorbed from the intestines and returned via the portal circulation to the liver, thus completing the enterohepatic cycle. Only very small amounts of bile acids are found in normal serum. Colestipol hydrochloride binds bile acids in the intestine forming a complex that is excreted in the feces. This nonsystemic action results in a partial removal of the bile acids from the enterohepatic circulation, preventing their reabsorption. Since colestipol hydrochloride is an anion exchange resin, the chloride anions of the resin can be replaced by other anions, usually those with a greater affinity for the resin than the chloride ion.
Mechanism of actionColestipol is a non-absorbed, lipid-lowering polymer that binds bile acids in the intestine, impeding their reabsorption. As the bile acid pool becomes depleted, the hepatic enzyme, cholesterol 7-(alpha)-hydroxylase, is upregulated, which increases the conversion of cholesterol to bile acids. This causes an increased demand for cholesterol in the liver cells, resulting in the dual effect of increasing transcription and activity of the cholesterol biosynthetic enzyme, hydroxymethyl-glutaryl-coenzyme A (HMG-CoA) reductase, and increasing the number of hepatic low-density lipoprotein (LDL) receptors. These compensatory effects result in increased clearance of LDL cholesterol (LDL-C) from the blood, resulting in decreased serum LDL-C levels. Serum triglyceride levels may increase or remain unchanged. The end result is increased clearance of LDL-cholesterol from the blood with decreased serum LDL-cholesterol.
Related Articles
AbsorptionNot absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot applicable (not hydrolyzed by digestive enzymes and not absorbed).
Metabolism

Not applicable (not hydrolyzed by digestive enzymes and not absorbed).

Route of eliminationColestipol hydrochloride binds bile acids in the intestine forming a complex that is excreted in the feces. In humans, less than 0.17% of a single 14C-labeled colestipol hydrochloride dose is excreted in the urine when given following 60 days of chronic dosing of 20 grams of colestipol hydrochloride per day. The increased fecal loss of bile acids due to colestipol hydrochloride administration leads to an increased oxidation of cholesterol to bile acids.
Half lifeNot Available
ClearanceNot Available
ToxicityOral LD50 in rats is > 1000 mg/kg. Symptoms of overdose may include eye irritation, constipation, abdominal cramps, nausea, vomiting, diarrhea, and hypersensitivity. However, as colestipol is not absorbed, the risk of systemic toxicity is low.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9221
Blood Brain Barrier+0.8825
Caco-2 permeable-0.5102
P-glycoprotein substrateSubstrate0.6506
P-glycoprotein inhibitor INon-inhibitor0.9435
P-glycoprotein inhibitor IINon-inhibitor0.956
Renal organic cation transporterNon-inhibitor0.6803
CYP450 2C9 substrateNon-substrate0.8931
CYP450 2D6 substrateNon-substrate0.7534
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.7178
CYP450 2C9 inhibitorNon-inhibitor0.8515
CYP450 2D6 inhibitorNon-inhibitor0.8411
CYP450 2C19 inhibitorNon-inhibitor0.7634
CYP450 3A4 inhibitorNon-inhibitor0.8919
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9404
Ames testAMES toxic0.9093
CarcinogenicityNon-carcinogens0.6451
BiodegradationNot ready biodegradable0.9346
Rat acute toxicity2.5333 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.508
hERG inhibition (predictor II)Non-inhibitor0.7601
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Impax laboratories inc
Packagers
Dosage forms
FormRouteStrength
Granule, for suspensionoral5 g/5g
Granulesoral5 g
Tabletoral1 g
Suspensionoral5 g/1
Tabletoral1 g/1
Tablet, film coatedoral1 g/1
Granule, for suspensionoral5 g/7.5g
Prices
Unit descriptionCostUnit
Colestid 90 5 gm Packets Box252.5USD box
Colestid 30 5 gm Packets Box81.11USD box
Colestid Flavored 5 gm/7.5 gm Packets3.29USD packet
Colestid 5 g Powder Packet1.04USD packet
Colestid Orange 5 g Powder Packet1.04USD packet
Colestid 1 gm tablet0.86USD tablet
Colestipol hcl 1 gm tablet0.66USD tablet
Colestid 5 gm Granules0.33USD gm
Colestid Flavored 5 gm Granules0.31USD gm
Colestid flavored granules0.3USD g
Colestid 1 g Tablet0.29USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5490987 No1993-02-132013-02-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP-2.206Not Available
Predicted Properties
PropertyValueSource
logP-2.5ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area88.13 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity56.04 m3·mol-1ChemAxon
Polarizability23.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Lednicer, D. and Peery,C.Y.; US. Patent 3,803,237; April 9, 1974; assigned to The Upjohn Co.

General ReferencesNot Available
External Links
ATC CodesC10AC02
AHFS Codes
  • 24:06.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (53.5 KB)
Interactions
Drug Interactions
Drug
AmiodaroneThe bioavailability of Amiodarone can be decreased when combined with Colestipol.
AtorvastatinThe serum concentration of Atorvastatin can be decreased when it is combined with Colestipol.
BudesonideColestipol can cause a decrease in the absorption of Budesonide resulting in a reduced serum concentration and potentially a decrease in efficacy.
Chenodeoxycholic acidThe serum concentration of Chenodeoxycholic acid can be decreased when it is combined with Colestipol.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Colestipol.
Cholic AcidColestipol can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
DeferasiroxThe serum concentration of Deferasirox can be decreased when it is combined with Colestipol.
DicoumarolColestipol can cause a decrease in the absorption of Dicoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
DigoxinColestipol can cause a decrease in the absorption of Digoxin resulting in a reduced serum concentration and potentially a decrease in efficacy.
DihydrotachysterolThe serum concentration of Dihydrotachysterol can be decreased when it is combined with Colestipol.
DiltiazemColestipol can cause a decrease in the absorption of Diltiazem resulting in a reduced serum concentration and potentially a decrease in efficacy.
EzetimibeColestipol can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.
FenofibrateColestipol can cause a decrease in the absorption of Fenofibrate resulting in a reduced serum concentration and potentially a decrease in efficacy.
InfliximabColestipol can cause a decrease in the absorption of Infliximab resulting in a reduced serum concentration and potentially a decrease in efficacy.
LeflunomideThe serum concentration of the active metabolites of Leflunomide can be reduced when Leflunomide is used in combination with Colestipol resulting in a loss in efficacy.
LiothyronineThe serum concentration of Liothyronine can be decreased when it is combined with Colestipol.
LomitapideColestipol can cause a decrease in the absorption of Lomitapide resulting in a reduced serum concentration and potentially a decrease in efficacy.
MethotrexateColestipol can cause a decrease in the absorption of Methotrexate resulting in a reduced serum concentration and potentially a decrease in efficacy.
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Colestipol.
NiacinColestipol can cause a decrease in the absorption of Niacin resulting in a reduced serum concentration and potentially a decrease in efficacy.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Colestipol.
OxytetracyclineColestipol can cause a decrease in the absorption of Oxytetracycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
PravastatinThe serum concentration of Pravastatin can be decreased when it is combined with Colestipol.
PropranololThe serum concentration of Propranolol can be decreased when it is combined with Colestipol.
RaloxifeneColestipol can cause a decrease in the absorption of Raloxifene resulting in a reduced serum concentration and potentially a decrease in efficacy.
TeriflunomideThe serum concentration of Teriflunomide can be decreased when it is combined with Colestipol.
TorasemideColestipol can cause a decrease in the absorption of Torasemide resulting in a reduced serum concentration and potentially a decrease in efficacy.
TrichlormethiazideColestipol can cause a decrease in the absorption of Trichlormethiazide resulting in a reduced serum concentration and potentially a decrease in efficacy.
Ursodeoxycholic acidThe serum concentration of Ursodeoxycholic acid can be decreased when it is combined with Colestipol.
VancomycinThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Colestipol.
Food Interactions
  • Take with food.

Targets

1. Bile acids
Kind
Group
Organism
Human
Pharmacological action
yes
Actions
binder
References
  1. LaRosa JC: The mechanism of action of lipid-lowering drugs. Angiology. 1982 Sep;33(9):562-76. [PubMed:7125296 ]
  2. Farmer JA, Gotto AM Jr: Currently available hypolipidaemic drugs and future therapeutic developments. Baillieres Clin Endocrinol Metab. 1995 Oct;9(4):825-47. [PubMed:8593127 ]
  3. Reiner Z: Combined therapy in the treatment of dyslipidemia. Fundam Clin Pharmacol. 2010 Feb;24(1):19-28. doi: 10.1111/j.1472-8206.2009.00764.x. Epub 2009 Aug 14. [PubMed:19682080 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23