Betamethasone 17,21-Dipropionate - ≥97% , Glucocorticoid receptor agonist, CAS No.5593-20-4, Glucocorticoid receptor agonist

CAS: 5593-20-4 Cat. No.: B123297 Molecular Weight: 504.59 EC Number: 227-005-2

GRADE & PURITY ≥97%

Synonyms

Betamethasone (as dipropionate) | BETAMETHASONE DIPROPIONATE [GREEN BOOK] | KS-5303 | PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11-HYDROXY-16-METHYL-17,21-BIS(1-OXOPROPOXY)-, (11.BETA.,16.BETA.) | Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16-methyl-17,

Storage

Room temperature

Shipped In

Normal

Overview

Betamethasone 17,21-dipropionate is a glucocorticoid with anti-inflammatory and immunosuppressive activity.

Specifications

Synonyms

Betamethasone (as dipropionate) | BETAMETHASONE DIPROPIONATE [GREEN BOOK] | KS-5303 | PREGNA-1, 4-DIENE-3, 20-DIONE, 9-FLUORO-11-HYDROXY-16-METHYL-17, 21-BIS(1-OXOPROPOXY)-, (11.BETA., 16.BETA.) | Pregna-1, 4-diene-3, 20-dione, 9-fluoro-11-hydroxy-16-methyl-17,

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Action Type

AGONIST

Mechanism of action

Glucocorticoid receptor agonist

Purity

≥97%

Product Properties

• ALogP: 3.6

Names and Identifiers

• Pubchem Sid: 488182722
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488182722
• Canonical Smiles: CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)OC(=O)CC
• IUPAC Name: [2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
• InChIKey: CIWBQSYVNNPZIQ-XYWKZLDCSA-N
• INCHI: 1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
• Isomeric SMILES: CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)OC(=O)CC
• WGK Germany: 2
• RTECS: TU4058000
• Molecular Weight: 504.59
• Reaxy-Rn: 38002577
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38002577&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Pregnane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Gluco/mineralocorticoids, progestogins and derivatives
• Alternative Parents: Steroid esters 20-oxosteroids 11-beta-hydroxysteroids 3-oxo delta-1,4-steroids Halogenated steroids Delta-1,4-steroids Alpha-acyloxy ketones Dicarboxylic acids and derivatives Cyclic ketones Cyclic alcohols and derivatives Carboxylic acid esters Secondary alcohols Fluorohydrins Hydrocarbon derivatives Alkyl fluorides Organic oxides Organofluorides
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Progestogin-skeleton - Steroid ester - 20-oxosteroid - 3-oxo-delta-1,4-steroid - 3-oxosteroid - 11-hydroxysteroid - 11-beta-hydroxysteroid - Oxosteroid - 9-halo-steroid - Halo-steroid - Hydroxysteroid - Delta-1,4-steroid - Alpha-acyloxy ketone - Dicarboxylic acid or derivatives - Cyclic alcohol - Carboxylic acid ester - Cyclic ketone - Secondary alcohol - Fluorohydrin - Halohydrin - Ketone - Carboxylic acid derivative - Alcohol - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organofluoride - Organohalogen compound - Alkyl fluoride - Alkyl halide - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
• External Descriptors: propanoate ester - 11beta-hydroxy steroid - steroid ester - 20-oxo steroid - fluorinated steroid - 3-oxo-Delta(1),Delta(4)-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)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

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

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

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

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

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

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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

Discover Target: HTR1A

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

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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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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

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

MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 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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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

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

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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

Discover Target: ADRA1A

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 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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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

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MC3R Tchem Melanocortin receptor 3 (5659 Activities)

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Associated Targets(non-human)

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

Discover Target: Npy1r

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Cruzipain (33337 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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

Hdac6 Histone deacetylase 6 (222 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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FTL Ferritin light chain (43324 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: 50 mg/ml in chloroform
• Melt Point(°C): 175.0°C-179.0°C
• Molecular Weight: 504.600 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 504.252 Da
• Monoisotopic Mass: 504.252 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 1050.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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. Yangjie LI, Jiaying HUANG, Jihui FANG, Zhiye HUANG.  (2022)  [Fast screening and confirmation of 73 common prohibited compounds in cosmetics by ultra performance liquid chromatography-quadrupole-time-of-flight high resolution mass spectrometry]..  Chinese Journal of Chromatography,  40  (5): (433-442).  [PMID:35478002] [10.3724/sp.j.1123.2021.09010]