Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Tanaproget
- DrugBank Accession Number
- DB04787
- Background
Tanaproget (NSP-989) is an investigational non-steroidal progestin. It is a high affinity, high efficacy agonist of the progesterone receptor (PR) with a much more selective binding profile relative to most conventional progestins. Because of this 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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Tanaproget (DB04787)
- Weight
- Average: 297.375
Monoisotopic: 297.093582807 - Chemical Formula
- C16H15N3OS
- Synonyms
- Tanaproget
- External IDs
- NSP-989
Pharmacology
- Indication
Not Available
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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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoxazine / Carbonitrile / Heteroaromatic compound / Hydrocarbon derivative / N-methylpyrrole / Nitrile / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- W9F9H8GXWR
- CAS number
- 304853-42-7
- 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
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. [Article]
- 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. [Article]
- Bayes M, Rabasseda X, Prous JR: Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Sep;27(7):505-22. [Article]
- External Links
- PubChem Compound
- 4369524
- PubChem Substance
- 46509047
- ChemSpider
- 3572060
- BindingDB
- 50375821
- ChEMBL
- CHEMBL539163
- ZINC
- ZINC000006245719
- Therapeutic Targets Database
- DPR000116
- PDBe Ligand
- T98
- Wikipedia
- Tanaproget
- PDB Entries
- 1zuc
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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) 3.51 Chemaxon pKa (Strongest Basic) -2.1 Chemaxon Physiological Charge -1 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 splash10-001i-2290000000-7330c4afb0dc8f7a8b3c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-8d7b91e2a90bca019b90 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-939bea383342fc887c89 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01p2-0090000000-be62d2f0c345b960a143 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05mt-0090000000-3f05da0d544a59c8cab2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ck9-0090000000-352a2f4ffe810874cdf5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ap1-0190000000-1c5e79c16f73ff45ede3 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.4863081 predictedDarkChem Lite v0.1.0 [M-H]- 160.28427 predictedDeepCCS 1.0 (2019) [M+H]+ 182.9725081 predictedDarkChem Lite v0.1.0 [M+H]+ 162.64226 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.7946081 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.73541 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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. Depending on the isoform, progesterone receptor functions as a transcriptional activator or repressor
- Specific Function
- Atpase binding
- 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. [Article]
- 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. [Article]
Drug created at September 11, 2007 17:49 / Updated at February 21, 2021 18:51