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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N7O2
Molecular Weight 395.4582
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Edelinontrine

SMILES

C[C@@H]1CN(CC2=NC=CC=N2)C[C@H]1C3=NC4=C(C=NN4C5CCOCC5)C(=O)N3

InChI

InChIKey=IWXUVYOOUMLUTQ-CZUORRHYSA-N
InChI=1S/C20H25N7O2/c1-13-10-26(12-17-21-5-2-6-22-17)11-16(13)18-24-19-15(20(28)25-18)9-23-27(19)14-3-7-29-8-4-14/h2,5-6,9,13-14,16H,3-4,7-8,10-12H2,1H3,(H,24,25,28)/t13-,16-/m1/s1

HIDE SMILES / InChI
Molecular Formula C20H25N7O2
Molecular Weight 395.4582
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22780914

PF-04447943 is a potent, selective brain penetrant PDE9 inhibitor (Ki of 2.8, 4.5 and 18 nM) for human, rhesus and rat recombinant PDE9 respectively and high selectivity for PDE9 versus PDEs1-8 and 10-11. PF-04447943 was being developed by Pfizer for the treatment of cognitive disorders. PF-04447943 attenuates a scopolamine-induced deficit in a novel rodent attention task. PF-04447943 enhances synaptic plasticity and cognitive function in rodents. PF-04447943 has completed Phase II clinical trials in subjects with mild to moderate AD in 2013 but this research was discontinued. Pfizer completes a phase I trial in Sickle cell anaemia.

CNS Activity

Originator

Pfizer
420
Curator's Comment: # Pfizer

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 8.3 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
45.8 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30597771
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PF-04447943 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1170 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30597771
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PF-04447943 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
242 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30597771
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PF-04447943 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
248.2 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30597771
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PF-04447943 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
HLM
31

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1819
 no
CYP2D6
1891
 no
CYP3A4
1925
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
HLM
31
 unlikely
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY34272
https://www.001chemical.com/chem/search?q=DY34272
1PlusChem LLC
1P008TZK
https://www.1pchem.com/search?query=1P008TZK
AChemBlock
L13959
http://www.achemblock.com/catalogsearch/result/?q=L13959
AK Scientific
3967AH
https://aksci.com/item_detail.php?cat=3967AH
Angene
AGN-PC-0WHEX1
http://www.angenechemical.com/productshow/AGN-PC-0WHEX1.html
AstaTech
42271
http://astatechinc.com/CPSResult.php?CRNO=42271
Axon MedChem
2148
https://www.axonmedchem.com/product/2148
Chem Scene
CS-0942
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0942
KeyOrganics
AS-35203
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35203
MedChem Express
HY-15441
https://www.medchemexpress.com/search.html?q=HY-15441&ft=&fa=&fp=
MolPort
MolPort-039-139-772
https://www.molport.com/shop/molecule-link/MolPort-039-139-772
MolPort
MolPort-046-426-413
https://www.molport.com/shop/molecule-link/MolPort-046-426-413
Molcore
MC34272
http://www.molcore.com/CatMC34272.html
Molnova
M10326
https://www.molnova.com/en/serch-list.html?keywords=M10326
Ryan Scientific
101-94118
https://ryansci.com/products?q=101-94118&list_q=&search_type=exact
eMolecules
271380522
https://orderbb.emolecules.com/search/#?query=271380522
eMolecules
300755989
https://orderbb.emolecules.com/search/#?query=300755989
eMolecules
313088314
https://orderbb.emolecules.com/search/#?query=313088314
eMolecules
44811342
https://orderbb.emolecules.com/search/#?query=44811342
mcule
MCULE-6189008811
https://mcule.com/MCULE-6189008811/
PubMed

PubMed

TitleDatePubMed
Patents

Patents

07964607
2
20090030003
2
7964607
2
WO2014024125A1
1

Sample Use Guides

In Vivo Use Guide
tablets, 25 mg every 12 hours for 12 wks
Route of Administration: Oral
In Vitro Use Guide
PF-04447943 inhibits human recombinant PDE9A expressed in Sf9 cells with IC50 8.3nM
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:39:06 GMT 2023
Edited
by admin
on Fri Dec 15 19:39:06 GMT 2023
Record UNII
7N969W8Y4O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Edelinontrine
INN  
Official Name English
CRD740
Code English
4H-PYRAZOLO(3,4-D)PYRIMIDIN-4-ONE, 1,5-DIHYDRO-6-((3S,4S)-4-METHYL-1-(2-PYRIMIDINYLMETHYL)-3-PYRROLIDINYL)-1-(TETRAHYDRO-2H-PYRAN-4-YL)-
Systematic Name English
PF04447943
Code English
CRD-740
Code English
6-{(3S,4S)-4-methyl-1-[(pyrimidin-2-yl)methyl]pyrrolidin-3-yl}-1-(oxan-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
Systematic Name English
PF-04447943
Code English
edelinontrine [INN]
Common Name English
PF-4447943
Code English
PF4447943
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 440514
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID801025596
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
DRUG BANK
DB11953
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
CAS
1082744-20-4
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
FDA UNII
7N969W8Y4O
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
PUBCHEM
135564558
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
SMS_ID
300000041326
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
INN
12731
Created by admin on Fri Dec 15 19:39:06 GMT 2023 , Edited by admin on Fri Dec 15 19:39:06 GMT 2023
PRIMARY
Related Record Type Details
HIGH AFFINITY CGMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE 9A
TARGET -> INHIBITOR
IC50
Related Record Type Details
Structure of Edelinontrine
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
BRAIN/PLASMA RATIO PHARMACOKINETIC Species
BIOLOGICAL
BRAIN/PLASMA RATIO PHARMACOKINETIC Species
BIOLOGICAL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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