NAV

Desmethylsertraline

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

Identification

Generic Name
Desmethylsertraline
DrugBank Accession Number
DB14071
Background

Desmethylsertraline is a metabolite of sertraline.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 292.2
Monoisotopic: 291.0581549
Chemical Formula
C16H15Cl2N
Synonyms
  • Demethylsertraline
  • N-Demethylsertraline
  • N-Desmethylsertraline
  • Norsertraline
External IDs
  • CP 62508
  • CP-53261
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UP-glycoprotein 1
inhibitor
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Desmethylsertraline.
AmifampridineThe risk or severity of seizure can be increased when Desmethylsertraline is combined with Amifampridine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Desmethylsertraline.
BrexanoloneThe therapeutic efficacy of Brexanolone can be decreased when used in combination with Desmethylsertraline.
BrivaracetamThe therapeutic efficacy of Brivaracetam can be decreased when used in combination with Desmethylsertraline.
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
CJJ71O9BE8
CAS number
87857-41-8
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

References

General References
Not Available
ChemSpider
102729
BindingDB
50367182
ChEMBL
CHEMBL40733
ZINC
ZINC000006117444
Wikipedia
Desmethylsertraline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-c8a27cf2eba278da49c8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-e1a38ee1a8d44b01457f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-60bd5193d0ba3e1f0eae
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-1090000000-5818a0d7e4e606cd95db
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002u-0690000000-259869c84c9f44398681
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9340000000-ef0b6a5d7b4c2dd3444a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 14, 2018 22:51 / Updated at June 12, 2020 16:53