Tanaproget
Identification
- Name
- Tanaproget
- Accession Number
- DB04787
- Type
- Small Molecule
- Groups
- Investigational
- Description
Tanaproget (NSP-989) is an investigational non-steroidal progestin. It is a high affinity, high efficacy, and very selective agonist of the progesterone receptor (PR). Due to its much more selective binding profile relative to most conventional, steroidal progestins, tanaproget may prove to produce fewer side effects in comparison. It is currently in the process of being developed for clinical use as a contraceptive by Ligand Pharmaceuticals. An analog of tanaproget, 4-fluoropropyltanaproget (18F), has been developed as a radiotracer for imaging of the PR in positron emission tomography.
- Structure
- Synonyms
- Not Available
- External IDs
- NSP-989
- Categories
- UNII
- W9F9H8GXWR
- CAS number
- 304853-42-7
- Weight
- Average: 297.375
Monoisotopic: 297.093582807 - Chemical Formula
- C16H15N3OS
- InChI Key
- PYVFWTPEBMRKSR-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H15N3OS/c1-16(2)12-8-10(4-6-13(12)18-15(21)20-16)14-7-5-11(9-17)19(14)3/h4-8H,1-3H3,(H,18,21)
- IUPAC Name
- 5-(4,4-dimethyl-2-sulfanylidene-2,4-dihydro-1H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile
- SMILES
- CN1C(=CC=C1C1=CC=C2NC(=S)OC(C)(C)C2=C1)C#N
Pharmacology
- Indication
- Not Available
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism AProgesterone receptor agonistHumans - 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
References
- Synthesis Reference
Arwinder Nagi, Ramarao Chatlapalli, Shamim Hasan, Mohamed Ghorab, Dhaval Gaglani, "Micronized tanaproget, compositions, and methods of preparing the same." U.S. Patent US20060246135, issued November 02, 2006.
US20060246135- General References
- Zhang Z, Olland AM, Zhu Y, Cohen J, Berrodin T, Chippari S, Appavu C, Li S, Wilhem J, Chopra R, Fensome A, Zhang P, Wrobel J, Unwalla RJ, Lyttle CR, Winneker RC: Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget. J Biol Chem. 2005 Aug 5;280(31):28468-75. Epub 2005 Jun 3. [PubMed:15937332]
- Bapst JL, Ermer JC, Ferron GM, Foss D, Orczyk GP: Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women. Contraception. 2006 Nov;74(5):414-8. Epub 2006 Sep 15. [PubMed:17046384]
- Bayes M, Rabasseda X, Prous JR: Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Sep;27(7):505-22. [PubMed:16258596]
- External Links
- PubChem Compound
- 4369524
- PubChem Substance
- 46509047
- ChemSpider
- 3572060
- BindingDB
- 50375821
- ChEMBL
- CHEMBL539163
- Therapeutic Targets Database
- DPR000116
- HET
- T98
- Wikipedia
- Tanaproget
- PDB Entries
- 1zuc
Clinical Trials
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
Property Value Source Water Solubility 0.0311 mg/mL ALOGPS logP 3.72 ALOGPS logP 3.82 ChemAxon logS -4 ALOGPS pKa (Strongest Acidic) 10.79 ChemAxon pKa (Strongest Basic) -2.1 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 49.98 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 88.42 m3·mol-1 ChemAxon Polarizability 32.33 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9867 Blood Brain Barrier + 0.8806 Caco-2 permeable + 0.5421 P-glycoprotein substrate Non-substrate 0.7957 P-glycoprotein inhibitor I Inhibitor 0.8716 P-glycoprotein inhibitor II Inhibitor 0.7057 Renal organic cation transporter Non-inhibitor 0.8453 CYP450 2C9 substrate Non-substrate 0.839 CYP450 2D6 substrate Non-substrate 0.7643 CYP450 3A4 substrate Substrate 0.6161 CYP450 1A2 substrate Inhibitor 0.7139 CYP450 2C9 inhibitor Inhibitor 0.7003 CYP450 2D6 inhibitor Non-inhibitor 0.8663 CYP450 2C19 inhibitor Inhibitor 0.708 CYP450 3A4 inhibitor Non-inhibitor 0.5155 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8987 Ames test Non AMES toxic 0.558 Carcinogenicity Non-carcinogens 0.8121 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4870 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9733 hERG inhibition (predictor II) Inhibitor 0.643
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzoxazines
- Sub Class
- Not Available
- Direct Parent
- Benzoxazines
- Alternative Parents
- N-methylpyrroles / Benzenoids / Thiocarbamic acid esters / Heteroaromatic compounds / Oxacyclic compounds / Nitriles / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- Benzoxazine / N-methylpyrrole / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Thiocarbamic acid ester / Thiocarbamic acid derivative / Oxacycle / Nitrile
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- 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
- 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. [PubMed:10592235]
- Zhang Z, Olland AM, Zhu Y, Cohen J, Berrodin T, Chippari S, Appavu C, Li S, Wilhem J, Chopra R, Fensome A, Zhang P, Wrobel J, Unwalla RJ, Lyttle CR, Winneker RC: Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget. J Biol Chem. 2005 Aug 5;280(31):28468-75. Epub 2005 Jun 3. [PubMed:15937332]
Drug created on September 11, 2007 11:49 / Updated on November 02, 2018 06:05