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Identification
NameTanaproget
Accession NumberDB04787
TypeSmall Molecule
GroupsInvestigational
DescriptionTanaproget (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
Thumb
SynonymsNot Available
External Identifiers
  • NSP-989
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIW9F9H8GXWR
CAS number304853-42-7
WeightAverage: 297.375
Monoisotopic: 297.093582807
Chemical FormulaC16H15N3OS
InChI KeyPYVFWTPEBMRKSR-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Progesterone receptorProteinyes
agonist
HumanP06401 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
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
  1. 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 ]
  2. 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 ]
  3. 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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9867
Blood Brain Barrier+0.8806
Caco-2 permeable+0.5421
P-glycoprotein substrateNon-substrate0.7957
P-glycoprotein inhibitor IInhibitor0.8716
P-glycoprotein inhibitor IIInhibitor0.7057
Renal organic cation transporterNon-inhibitor0.8453
CYP450 2C9 substrateNon-substrate0.839
CYP450 2D6 substrateNon-substrate0.7643
CYP450 3A4 substrateSubstrate0.6161
CYP450 1A2 substrateInhibitor0.7139
CYP450 2C9 inhibitorInhibitor0.7003
CYP450 2D6 inhibitorNon-inhibitor0.8663
CYP450 2C19 inhibitorInhibitor0.708
CYP450 3A4 inhibitorNon-inhibitor0.5155
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8987
Ames testNon AMES toxic0.558
CarcinogenicityNon-carcinogens0.8121
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4870 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9733
hERG inhibition (predictor II)Inhibitor0.643
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0311 mg/mLALOGPS
logP3.72ALOGPS
logP3.82ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.79ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.98 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.42 m3·mol-1ChemAxon
Polarizability32.33 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassNot Available
Direct ParentBenzoxazines
Alternative Parents
Substituents
  • Benzoxazine
  • Benzenoid
  • Substituted pyrrole
  • N-methylpyrrole
  • Heteroaromatic compound
  • Thiocarbamic acid ester
  • Pyrrole
  • Thiocarbamic acid derivative
  • Thiocarbonic acid derivative
  • Oxacycle
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
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 isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
References
  1. 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 ]
  2. 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 ]
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24