NAV

Asoprisnil

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

Identification

Generic Name
Asoprisnil
DrugBank Accession Number
DB06680
Background

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

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 449.5818
Monoisotopic: 449.256608613
Chemical Formula
C28H35NO4
Synonyms
  • Asoprisnil
External IDs
  • BAY86-5294
  • J 867
  • J-867
  • J867
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Pharmacology

Indication

Investigated for use/treatment in uterine fibroids.

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Chemical TaxonomyProvided by Classyfire
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 / Aldoxime / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group / Cyclic ketone / Cyclohexenone / Dialkyl ether / Ether / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
72W09924WP
CAS number
199396-76-4
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
(1S,3aS,3bS,10R,11aS)-10-{4-[(E)-(hydroxyimino)methyl]phenyl}-1-methoxy-1-(methoxymethyl)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-7-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

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. [Article]
ChemSpider
7851660
ChEMBL
CHEMBL267431
ZINC
ZINC000003936191
PDBe Ligand
AS0
Wikipedia
Asoprisnil
PDB Entries
2ovh / 2ovm / 4a2j

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentFibroid Uterus / Hypermenorrhea / Metrorrhagia / Uterine Fibroids (Leiomyomas)3
3CompletedTreatmentHypermenorrhea / Metrorrhagia / Uterine Fibroids (Leiomyomas)3
2CompletedTreatmentAmenorrhea / Postmenopausal1
2CompletedTreatmentEndometriosis3
2CompletedTreatmentHypermenorrhea1

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)7.39Chemaxon
pKa (Strongest Basic)2.56Chemaxon
Physiological Charge-1Chemaxon
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/MSsplash10-0udi-0001900000-ba1885386565709852b9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000900000-9d880430084d086d744a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009200000-e3f5bbfca96269093a5a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-0009600000-140c35ac27a07ca558da
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1049500000-cbe7acef11fe1c9b347d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uyr-0645900000-daf6fda8ac6fb0c17b86
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]-207.26656
predicted
DeepCCS 1.0 (2019)
[M+H]+209.09145
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.69728
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Progesterone receptor
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. [Article]
  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. [Article]

Drug created at March 19, 2008 16:48 / Updated at February 21, 2021 18:52