NAV

4-(1R,3AS,4R,8AS,8BR)-[1-DIFLUOROMETHYL-2-(4-FLUOROBENZYL)-3-OXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZAMIDINE

Identification

Generic Name
4-(1R,3AS,4R,8AS,8BR)-[1-DIFLUOROMETHYL-2-(4-FLUOROBENZYL)-3-OXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZAMIDINE
DrugBank Accession Number
DB07741
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 444.4926
Monoisotopic: 444.213696121
Chemical Formula
C24H27F3N4O
Synonyms
Not Available
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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
UProthrombinNot AvailableHumans
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Pyrrolizidines / Aralkylamines / Fluorobenzenes / Pyrrolidine-2-ones / Aryl fluorides / N-alkylpyrrolidines / Tertiary carboxylic acid amides / Pyrroles / Trialkylamines / Amino acids and derivatives
show 9 more
Substituents
2-phenylpyrrolidine / 2-pyrrolidone / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VPNYXOTTXAXSIH-SXYSDOLCSA-N
InChI
InChI=1S/C24H27F3N4O/c25-16-9-3-13(4-10-16)12-31-21(22(26)27)18-17-2-1-11-30(17)20(19(18)24(31)32)14-5-7-15(8-6-14)23(28)29/h3-10,17-23H,1-2,11-12,28-29H2/t17-,18-,19-,20-,21-/m0/s1
IUPAC Name
(1S,3aS,4R,8aS,8bR)-4-[4-(diaminomethyl)phenyl]-1-(difluoromethyl)-2-[(4-fluorophenyl)methyl]-decahydropyrrolo[3,4-a]pyrrolizin-3-one
SMILES
[H][C@@]12CCC[N@@]1[C@@]([H])(C1=CC=C(C=C1)C(N)N)[C@@]1([H])C(=O)N(CC3=CC=C(F)C=C3)[C@]([H])(C(F)F)[C@@]21[H]

References

General References
Not Available
PubChem Compound
46937090
PubChem Substance
99444212
ChemSpider
25060827
ZINC
ZINC000038444302
PDBe Ligand
F25
PDB Entries
2cn0

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 Solubility0.046 mg/mLALOGPS
logP2.23ALOGPS
logP2.4Chemaxon
logS-4ALOGPS
pKa (Strongest Basic)9.74Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.59 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity114.99 m3·mol-1Chemaxon
Polarizability44.06 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9848
Caco-2 permeable-0.6453
P-glycoprotein substrateSubstrate0.5857
P-glycoprotein inhibitor INon-inhibitor0.5774
P-glycoprotein inhibitor IIInhibitor0.7537
Renal organic cation transporterInhibitor0.5999
CYP450 2C9 substrateNon-substrate0.8166
CYP450 2D6 substrateNon-substrate0.7033
CYP450 3A4 substrateSubstrate0.5185
CYP450 1A2 substrateInhibitor0.6605
CYP450 2C9 inhibitorNon-inhibitor0.534
CYP450 2D6 inhibitorInhibitor0.578
CYP450 2C19 inhibitorInhibitor0.6859
CYP450 3A4 inhibitorNon-inhibitor0.8069
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7547
Ames testNon AMES toxic0.6014
CarcinogenicityNon-carcinogens0.9068
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5677 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9682
hERG inhibition (predictor II)Inhibitor0.8357
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-24dd55a98fdaa0cab351
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-e5083dbba97c2d1dcdfc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-d4f4d9d65801262bd091
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-0013900000-af7905d96ed97362bd93
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0203900000-0683c66ced187d595eb4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02vi-1098400000-73b02b38bfbd8ed7d9e7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-202.4225
predicted
DeepCCS 1.0 (2019)
[M+H]+204.63997
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.38037
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prothrombin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thrombospondin receptor activity
Specific Function
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
Molecular Weight
70036.295 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52