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

Identification

Name
Desmethylsertraline
Accession Number
DB14071
Type
Small Molecule
Groups
Experimental
Description

Desmethylsertraline is a metabolite of sertraline.

Structure
Thumb
Synonyms
  • Demethylsertraline
  • N-Demethylsertraline
  • N-Desmethylsertraline
  • Norsertraline
External IDs
CP 62508 / CP-53261
Categories
UNII
CJJ71O9BE8
CAS number
87857-41-8
Weight
Average: 292.2
Monoisotopic: 291.0581549
Chemical Formula
C16H15Cl2N
InChI Key
SRPXSILJHWNFMK-ZBEGNZNMSA-N
InChI
InChI=1S/C16H15Cl2N/c17-14-7-5-10(9-15(14)18)11-6-8-16(19)13-4-2-1-3-12(11)13/h1-5,7,9,11,16H,6,8,19H2/t11-,16-/m0/s1
IUPAC Name
(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine
SMILES
[H][C@]1(N)CC[C@@]([H])(C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMultidrug resistance protein 1
inhibitor
Human
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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Desmethylsertraline.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Desmethylsertraline.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Desmethylsertraline.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Desmethylsertraline.
Ascorbic acidThe serum concentration of Ascorbic acid can be increased when it is combined with Desmethylsertraline.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Desmethylsertraline.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Desmethylsertraline.
ChlorambucilThe serum concentration of Chlorambucil can be increased when it is combined with Desmethylsertraline.
ChloroquineThe serum concentration of Chloroquine can be increased when it is combined with Desmethylsertraline.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Desmethylsertraline.
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
102729
BindingDB
50367182
ChEMBL
CHEMBL40733
Wikipedia
Desmethylsertraline

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 Solubility9.79e-05 mg/mLALOGPS
logP4.92ALOGPS
logP4.72ChemAxon
logS-6.5ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.97 m3·mol-1ChemAxon
Polarizability30.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. O'Brien FE, Dinan TG, Griffin BT, Cryan JF: Interactions between antidepressants and P-glycoprotein at the blood-brain barrier: clinical significance of in vitro and in vivo findings. Br J Pharmacol. 2012 Jan;165(2):289-312. doi: 10.1111/j.1476-5381.2011.01557.x. [PubMed:21718296]
  2. Wang JS, Zhu HJ, Gibson BB, Markowitz JS, Donovan JL, DeVane CL: Sertraline and its metabolite desmethylsertraline, but not bupropion or its three major metabolites, have high affinity for P-glycoprotein. Biol Pharm Bull. 2008 Feb;31(2):231-4. [PubMed:18239278]
  3. Gil-Ad I, Zolokov A, Lomnitski L, Taler M, Bar M, Luria D, Ram E, Weizman A: Evaluation of the potential anti-cancer activity of the antidepressant sertraline in human colon cancer cell lines and in colorectal cancer-xenografted mice. Int J Oncol. 2008 Aug;33(2):277-86. [PubMed:18636148]

Drug created on June 14, 2018 16:51 / Updated on October 01, 2018 15:42