Asoprisnil

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

Identification

Name
Asoprisnil
Accession Number
DB06680
Type
Small Molecule
Groups
Investigational
Description

Asoprisnil (J867) is a selective progesterone receptor modulator. It can be used to treat progesterone sensitive myomata.

Structure
Thumb
Synonyms
Not Available
External IDs
BAY86-5294 / J 867 / J-867 / J867
Categories
UNII
72W09924WP
CAS number
199396-76-4
Weight
Average: 449.5818
Monoisotopic: 449.256608613
Chemical Formula
C28H35NO4
InChI Key
GJMNAFGEUJBOCE-MEQIQULJSA-N
InChI
InChI=1S/C28H35NO4/c1-27-15-24(19-6-4-18(5-7-19)16-29-31)26-22-11-9-21(30)14-20(22)8-10-23(26)25(27)12-13-28(27,33-3)17-32-2/h4-7,14,16,23-25,31H,8-13,15,17H2,1-3H3/b29-16+/t23-,24+,25-,27-,28+/m0/s1
IUPAC Name
(10S,11S,14S,15S,17R)-17-{4-[(1E)-(hydroxyimino)methyl]phenyl}-14-methoxy-14-(methoxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6-dien-5-one
SMILES
[H]\C(=N/O)C1=CC=C(C=C1)[C@@]1([H])C[C@@]2(C)[C@@]([H])(CC[C@]2(COC)OC)[C@]2([H])CCC3=CC(=O)CCC3=C12

Pharmacology

Indication

Investigated for use/treatment in uterine fibroids.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProgesterone receptorNot 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
Toxicity
Not Available
Affected organisms
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

References

General References
  1. DeManno D, Elger W, Garg R, Lee R, Schneider B, Hess-Stumpp H, Schubert G, Chwalisz K: Asoprisnil (J867): a selective progesterone receptor modulator for gynecological therapy. Steroids. 2003 Nov;68(10-13):1019-32. [PubMed:14667995]
External Links
ChemSpider
7851660
ChEMBL
CHEMBL267431
ZINC
ZINC000003936191
PDBe Ligand
AS0
Wikipedia
Asoprisnil
PDB Entries
2ovh / 2ovm / 4a2j

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAmenorrhea / One to five years postmenopausal1
2CompletedTreatmentEndometriosis3
2CompletedTreatmentHypermenorrhea1
2CompletedTreatmentLeiomyomas2
2CompletedTreatmentLeiomyomas / Uterine Leiomyomas1
2CompletedTreatmentOne to five years postmenopausal1
3CompletedTreatmentFibroid Uterus / Hypermenorrhea / Leiomyomas / Metrorrhagia / Uterine Leiomyomas3
3CompletedTreatmentHypermenorrhea / Leiomyomas / Metrorrhagia3

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 Solubility0.00211 mg/mLALOGPS
logP4.28ALOGPS
logP4.28ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)8.34ChemAxon
pKa (Strongest Basic)2.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.12 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.27 m3·mol-1ChemAxon
Polarizability51.46 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
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 oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
Oxosteroids
Alternative Parents
3-oxosteroids / Cyclohexenones / Benzene and substituted derivatives / Aldoximes / Dialkyl ethers / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxosteroid / Oxosteroid / Cyclohexenone / Monocyclic benzene moiety / Benzenoid / Ketone / Aldoxime / Cyclic ketone / Dialkyl ether / Ether
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Chwalisz K, Perez MC, Demanno D, Winkel C, Schubert G, Elger W: Selective progesterone receptor modulator development and use in the treatment of leiomyomata and endometriosis. Endocr Rev. 2005 May;26(3):423-38. Epub 2005 Apr 27. [PubMed:15857972]
  2. Schubert G, Elger W, Kaufmann G, Schneider B, Reddersen G, Chwalisz K: Discovery, chemistry, and reproductive pharmacology of asoprisnil and related 11beta-benzaldoxime substituted selective progesterone receptor modulators (SPRMs). Semin Reprod Med. 2005 Feb;23(1):58-73. [PubMed:15714390]

Drug created on March 19, 2008 10:48 / Updated on March 01, 2020 19:43

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