This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Avasimibe
Accession Number
DB06442
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
CI-1011
Product Ingredients
IngredientUNIICASInChI Key
Avasimibe Sodium32035QP3VQ166518-61-2LENDCHCWVCXELL-UHFFFAOYSA-M
Categories
UNII
28LQ20T5RC
CAS number
166518-60-1
Weight
Average: 501.73
Monoisotopic: 501.291280043
Chemical Formula
C29H43NO4S
InChI Key
PTQXTEKSNBVPQJ-UHFFFAOYSA-N
InChI
InChI=1S/C29H43NO4S/c1-17(2)22-14-25(20(7)8)27(26(15-22)21(9)10)16-28(31)30-35(32,33)34-29-23(18(3)4)12-11-13-24(29)19(5)6/h11-15,17-21H,16H2,1-10H3,(H,30,31)
IUPAC Name
1-({[2,6-bis(propan-2-yl)phenoxy]sulfonyl}amino)-2-[2,4,6-tris(propan-2-yl)phenyl]ethan-1-one
SMILES
CC(C)C1=CC(C(C)C)=C(CC(=O)NS(=O)(=O)OC2=C(C=CC=C2C(C)C)C(C)C)C(=C1)C(C)C

Pharmacology

Indication

Investigated for use/treatment in peripheral vascular disease.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULiver carboxylesterase 1Not AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Avasimibe.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Avasimibe.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Avasimibe.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Avasimibe.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Avasimibe.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Avasimibe.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be increased when combined with Avasimibe.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Avasimibe.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Avasimibe.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Avasimibe.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Sahi J, Stern RH, Milad MA, Rose KA, Gibson G, Zheng X, Stilgenbauer L, Sadagopan N, Jolley S, Gilbert D, LeCluyse EL: Effects of avasimibe on cytochrome P450 2C9 expression in vitro and in vivo. Drug Metab Dispos. 2004 Dec;32(12):1370-6. Epub 2004 Aug 27. [PubMed:15333513]
External Links
ChemSpider
145759
BindingDB
50069900
ChEMBL
CHEMBL101309

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.63e-05 mg/mLALOGPS
logP5.98ALOGPS
logP8.67ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.47 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity144.81 m3·mol-1ChemAxon
Polarizability57.13 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Aromatic monoterpenoids
Alternative Parents
Phenylacetamides / Monocyclic monoterpenoids / Phenylpropanes / Cumenes / Phenoxy compounds / Organic sulfuric acids and derivatives / Carboxylic acids and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
P-cymene / Aromatic monoterpenoid / Phenylacetamide / Monocyclic monoterpenoid / Cumene / Phenylpropane / Phenoxy compound / Monocyclic benzene moiety / Benzenoid / Organic sulfuric acid or derivatives
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Delsing DJ, Offerman EH, van Duyvenvoorde W, van Der Boom H, de Wit EC, Gijbels MJ, van Der Laarse A, Jukema JW, Havekes LM, Princen HM: Acyl-CoA:cholesterol acyltransferase inhibitor avasimibe reduces atherosclerosis in addition to its cholesterol-lowering effect in ApoE*3-Leiden mice. Circulation. 2001 Apr 3;103(13):1778-86. [PubMed:11282910]
  2. Sudhop T, von Bergmann K: Cholesterol absorption inhibitors for the treatment of hypercholesterolaemia. Drugs. 2002;62(16):2333-47. [PubMed:12396226]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Sahi J, Milad MA, Zheng X, Rose KA, Wang H, Stilgenbauer L, Gilbert D, Jolley S, Stern RH, LeCluyse EL: Avasimibe induces CYP3A4 and multiple drug resistance protein 1 gene expression through activation of the pregnane X receptor. J Pharmacol Exp Ther. 2003 Sep;306(3):1027-34. Epub 2003 May 23. [PubMed:12766253]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
There are limited data supporting this enzyme action in the literature.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Sahi J, Stern RH, Milad MA, Rose KA, Gibson G, Zheng X, Stilgenbauer L, Sadagopan N, Jolley S, Gilbert D, LeCluyse EL: Effects of avasimibe on cytochrome P450 2C9 expression in vitro and in vivo. Drug Metab Dispos. 2004 Dec;32(12):1370-6. Epub 2004 Aug 27. [PubMed:15333513]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Sahi J, Stern RH, Milad MA, Rose KA, Gibson G, Zheng X, Stilgenbauer L, Sadagopan N, Jolley S, Gilbert D, LeCluyse EL: Effects of avasimibe on cytochrome P450 2C9 expression in vitro and in vivo. Drug Metab Dispos. 2004 Dec;32(12):1370-6. Epub 2004 Aug 27. [PubMed:15333513]

Drug created on March 19, 2008 10:33 / Updated on May 01, 2019 13:20