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50925-79-6 molecular structure
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(2-aminoethyl)[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]amine; 2-(chloromethyl)oxirane

ChemBase ID: 259
Molecular Formular: C11H28ClN5O
Molecular Mass: 281.82592
Monoisotopic Mass: 281.19823822
SMILES and InChIs

SMILES:
ClCC1OC1.N(CCNCCN)CCNCCN
Canonical SMILES:
ClCC1OC1.NCCNCCNCCNCCN
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
InChIKey:
GMRWGQCZJGVHKL-UHFFFAOYSA-N

Cite this record

CBID:259 http://www.chembase.cn/molecule-259.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2-aminoethyl)[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]amine; 2-(chloromethyl)oxirane
IUPAC Traditional name
epichlorohydrin; tetraethylenepentamine
Brand Name
Cholestabyl
Colestid
Synonyms
Colestipolum [INN-Latin]
Colestipol
CAS Number
50925-79-6
PubChem SID
160963722
46505777
PubChem CID
62816

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00375 external link
PubChem 62816 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -11.474277  LogD (pH = 7.4) -7.797468 
Log P -2.515653  Molar Refractivity 56.0418 cm3
Polarizability 23.113699 Å3 Polar Surface Area 88.13 Å2
Rotatable Bonds 11  Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Insoluble expand Show data source
Hydrophobicity(logP)
-2.206 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00375 external link
Item Information
Drug Groups approved
Description Highly crosslinked and insoluble basic anion exchange resin used as anticholesteremic. It may also may reduce triglyceride levels. [PubChem]
Indication For 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.
Pharmacology Cholesterol 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.
Toxicity Oral 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
Biotransformation Not applicable (not hydrolyzed by digestive enzymes and not absorbed).
Absorption Not absorbed from the gastrointestinal tract.
Protein Binding Not applicable (not hydrolyzed by digestive enzymes and not absorbed).
Elimination Colestipol 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.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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