Flumethasone - 10mM in DMSO , CAS No.2135-17-3

CAS: 2135-17-3 Cat. No.: F422579 Molecular Weight: 410.45 EC Number: 218-370-9 PubChem CID: 16490

GRADE & PURITY 10mM in DMSO

Synonyms

C22H28F2O5 | DB00663 | EINECS 218-370-9 | Flumethasone [USAN] | Cortexilar | Flumethasonum | A855571 | Flumetasone | NSC54702 | NSC-54702 | Pregna-1,4-diene-3,20-dione,6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6a,11b,16a)- | SMR000058690 | Flumetasonu

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Flumethasone is a glucocorticoid receptor agonist, this complex binds to the nucleus causing a variety of genetic activation and repressions.
A glucocorticoid. An anti-inflammatory.

Specifications

Synonyms

C22H28F2O5 | DB00663 | EINECS 218-370-9 | Flumethasone [USAN] | Cortexilar | Flumethasonum | A855571 | Flumetasone | NSC54702 | NSC-54702 | Pregna-1, 4-diene-3, 20-dione, 6, 9-difluoro-11, 17, 21-trihydroxy-16-methyl-, (6a, 11b, 16a)- | SMR000058690 | Flumetasonu

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Flumethasone is an anti-inflammatory glucocorticoid.Glucocorticoid receptor agonist. Inhibits platelet-activating factor-induced aggregation. Shows anti-inflammatory, antipruritic and vasoconstrictive effects in vivo.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C)F
• IUPAC Name: (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
• InChIKey: WXURHACBFYSXBI-GQKYHHCASA-N
• INCHI: 1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F
• WGK Germany: 3
• RTECS: TU3832000
• PubChem CID: 16490
• Molecular Weight: 410.45

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Hydroxysteroids
• Intermediate Tree Nodes: Not available
• Direct Parent: 21-hydroxysteroids
• Alternative Parents: Gluco/mineralocorticoids, progestogins and derivatives 20-oxosteroids 11-beta-hydroxysteroids 17-hydroxysteroids 3-oxo delta-1,4-steroids Halogenated steroids Delta-1,4-steroids Tertiary alcohols Alpha-hydroxy ketones Secondary alcohols Fluorohydrins Cyclic ketones Cyclic alcohols and derivatives Alkyl fluorides Hydrocarbon derivatives Organic oxides Organofluorides Primary alcohols
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Progestogin-skeleton - 21-hydroxysteroid - Pregnane-skeleton - 20-oxosteroid - 3-oxo-delta-1,4-steroid - 3-oxosteroid - 17-hydroxysteroid - 11-hydroxysteroid - 11-beta-hydroxysteroid - 9-halo-steroid - 6-halo-steroid - Halo-steroid - Oxosteroid - Delta-1,4-steroid - Alpha-hydroxy ketone - Cyclic alcohol - Tertiary alcohol - Ketone - Halohydrin - Fluorohydrin - Secondary alcohol - Cyclic ketone - Organofluoride - Alcohol - Primary alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Alkyl halide - Alkyl fluoride - Organooxygen compound - Organohalogen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
• External Descriptors: 11beta-hydroxy steroid - 17alpha-hydroxy steroid - glucocorticoid - 20-oxo steroid - fluorinated steroid - 3-oxo-Delta(1),Delta(4)-steroid - 21-hydroxy steroid

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(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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HIF1A Tchem Hypoxia-inducible factor 1 alpha (6027 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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GMNN Tbio Geminin (128009 Activities)

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RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)

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microRNA 21 (64692 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Rattus norvegicus (775804 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 410.500 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 410.19 Da
• Monoisotopic Mass: 410.19 Da
• Topological Polar Surface Area: 94.800 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 839.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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

References

1. Di Chen, Xinli Xu, Bin Wang, Xinmiao Bu, Manyu Zhang, Xia Xu, Nian Shi.  (2023)  Natural cotton fiber-supported liquid extraction for convenient protein-rich aqueous sample preparation: Determination of glucocorticoids in milk and plasma as a proof-of-concept study.  TALANTA,      [PMID:37156209] [10.1016/j.talanta.2023.124618]

2. Youfang Huang, Yanyun Li, Qing Luo, Xiaojia Huang.  (2020)  One-step preparation of functional groups-rich graphene oxide and carbon nanotubes nanocomposite for efficient magnetic solid phase extraction of glucocorticoids in environmental waters.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2020.126785]