Dienogest - Moligand™, ≥99% , CAS No.65928-58-7

CAS: 65928-58-7 Cat. No.: D129393 Formula: C₂₀H₂₅NO₂ Molecular Weight: 311.42 EC Number: 639-448-2 PubChem CID: 68861

GRADE & PURITY Moligand™, ≥99%

Synonyms

STS557|Dienogest for system suitability|17-alpha-Cyanomethyl-17-beta-hydroxy-estra-4,9(10)-dien-3-one|17alpha-Cyanomethyl-17beta-hydroxyestra-4,9(10)-dien-3-one|DIENOGEST [WHO-DD]|MJR-35|2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile|[(17beta)-17-hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile|STS 557|Visanne|17-Hydroxy-3-oxo-19-nor-17alpha-pregna-4,9-diene-21-nitrile|17alpha-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile|DIENOGEST [MART.]|2-[(1R,3aS,3bS,11aS)-1-hydroxy-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]acetonitrile|DIENOGEST [ORANGE BOOK]|DIENOGEST [MI]|DIENOGEST [USAN]|17-cyanomethyl-17-hydroxy-estra-4,9-dien-3-one|17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile|BAY 86-5258|Dienogest (JAN/USAN/INN)|19-NORPREGNA-4,9-DIENE-21-NITRILE, 17-HYDROXY-3-OXO-, (17.ALPHA.)-|2-((8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)acetonitrile|DIENOGEST [VANDF]|STS-557|Dienogest [INN]|Dienogest [USAN:INN:BAN]|M-18575|(17-hydroxy-3-oxoestra-4,9-dien-17beta-yl)acetonitrile|Endometrion (TN)|Dienogestrel|M 18575|Dienogest|DIENOGEST [JAN]|Dienogest; Dienogestril; Dinagest; STS 557; (17alpha)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile; 17alpha-Cyanomethyl-17beta-hydroxyestra-4,9-dien-3-one|Dienogestum [Latin]|Dinagest|DIENOGEST [EP MONOGRAPH]|Dienogestril|19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17-alpha)-|19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17alpha)-|Natazia|Dienogestum|BAY86-5258|ZK 37659

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Dienogest is an orally active synthetic progesterone, used for contraception and the treatment of endometriosis.
A progesterone 19-nortestosterone derivative

Specifications

Synonyms

STS557 | Dienogest for system suitability | 17-alpha-Cyanomethyl-17-beta-hydroxy-estra-4,9(10)-dien-3-one | 17alpha-Cyanomethyl-17beta-hydroxyestra-4,9(10)-dien-3-one | DIENOGEST [WHO-DD] | MJR-35 | 2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile | [(17beta)-17-h Show more

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

A derivative of 19-Nortestosterone.Steroidal progesterone. Non-ethinylated progestin structurally related to testosterone. Anti-androgenic and antiproliferative effects in vitro .

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Product Properties

ALogP

1.8

Names and Identifiers

Pubchem Sid

504754310

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504754310

Canonical Smiles

CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(CC#N)O

IUPAC Name

2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile

InChIKey

AZFLJNIPTRTECV-FUMNGEBKSA-N

INCHI

1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1

Isomeric SMILES

C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(CC#N)O

Alternate CAS

65928-58-7

PubChem CID

68861

MeSH Entry Terms

17 alpha-cyanomethyl-17 beta-hydroxy-13 beta-methylgona-4,9-dien-3-one;17 alpha-cyanomethyl-17 beta-hydroxyestra-4,9(10)-diene-3-one;19-norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17alpha)-;dienogest;STS 557;STS-557

Molecular Weight

311.42

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Oxosteroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Oxosteroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxosteroids
• Alternative Parents: 3-oxosteroids 17-hydroxysteroids Cyclohexenones Tertiary alcohols Cyclic alcohols and derivatives Nitriles Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: 3-oxosteroid - Hydroxysteroid - 17-hydroxysteroid - Oxosteroid - Cyclohexenone - Cyclic alcohol - Tertiary alcohol - Ketone - Cyclic ketone - Carbonitrile - Nitrile - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Alcohol - Aliphatic homopolycyclic compound
• 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.
• External Descriptors: aliphatic nitrile - 3-oxo Delta(4)-steroid - 17beta-hydroxy steroid - steroid hormone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in Pyridine DMSO 62 mg/mL Water <1 mg/mL Ethanol <1 mg/mL
• Sensitivity: Heat Sensitive
• Specific Rotation[α]: -307° (C=1,CHCl3)
• Melt Point(°C): 215 °C
• Molecular Weight: 311.400 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 311.189 Da
• Monoisotopic Mass: 311.189 Da
• Topological Polar Surface Area: 61.100 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 679.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1