37927-01-8

Basic information

• Product Name: 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid
• Synonyms: (-)-Dexamethasone Acid;(11,16a,17a)-9-Fluoro-11,17-dihydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid;9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid;(11β,16α,17α)-9-Fluoro-11,17-dihydroxy-16-Methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid;9-Fluoro-11β,17-dihydroxy-16α-Methyl-3-oxoandrosta -1,4-diene-17β-carboxylic Acid;DexaMethasone SodiuM phosphate IMpurity G;DexaMethasone SodiuM phosphate IMpurity G ((-)-DexaMethasone Acid);(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid
• CAS NO: 37927-01-8
• Molecular Formula: C₂₁H₂₇FO₅
• Molecular Weight: 378.43
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 37927-01-8.mol

Chemical Properties

• Melting Point: 274-2770C
• Boiling Point: 566.865°C at 760 mmHg
• Flash Point: 296.63°C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 3.58±0.70(Predicted)
• CAS DataBase Reference: 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid(37927-01-8)
• EPA Substance Registry System: 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid(37927-01-8)

Safety Data

• Hazardous Substances Data: 37927-01-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid is used as a glucocorticoid receptor agonist for the treatment of various inflammatory and immune-mediated conditions. Its potent anti-inflammatory and immunosuppressive effects make it an effective treatment for conditions such as rheumatoid arthritis, asthma, allergies, and certain skin disorders.
Used in Oncology:
In the field of oncology, 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid is used as an inhibitor of angiogenesis and tumor growth. Its ability to suppress the growth of new blood vessels that supply tumors with nutrients and oxygen makes it a valuable tool in the fight against cancer.
Used in Ophthalmology:
9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid is used as a treatment for ocular hypertension, a condition characterized by increased pressure within the eye. Its anti-inflammatory properties help to reduce intraocular pressure, thereby decreasing the risk of developing glaucoma and other vision-threatening conditions.
Chemical Properties:
9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid is a white solid with a molecular formula of C22H29FO5. It is derived from the androstane class of steroids and exhibits potent anti-inflammatory and immunosuppressive activities. The presence of a fluorine atom at the 9th position enhances its activity and reduces its mineralocorticoid effects, making it a preferred choice for various medical applications.

InChI:InChI=1/C21H27FO5/c1-11-8-15-14-5-4-12-9-13(23)6-7-18(12,2)20(14,22)16(24)10-19(15,3)21(11,27)17(25)26/h6-7,9,11,14-16,24,27H,4-5,8,10H2,1-3H3,(H,25,26)/t11-,14+,15+,16+,18+,19+,20+,21+/m1/s1

Upstream product

• 50-02-2 dexamethasone 
• 2964-79-6 dexamethasone glyoxal 

Downstream Products

• 473273-04-0 17α-formyloxy-11β-hydroxy-9α-fluoro-16α-methyl-3-oxo-1,4-androstadien-17β-carboxylic acid 
• 218782-88-8 Carbonic acid 11-[((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-undecyl ester 4-nitro-phenyl ester 
• 71878-79-0 N-benzyl 9α-fluoro-16α-methyl-11β,17α-dihydroxy-3-oxo-1,4-androstadiene-17β-carboxamide 
• 74997-40-3 N-phenylethyl 9α-fluoro-16α-methyl-11β,17α-dihydroxy-3-oxo-1,4-androstadiene-17β-carboxamide 
• 1140535-14-3 9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid [2-(2-{[(2-(4-methyl-benzyl)-3-(2-hydroxy-ethyl)-3-isobutyl-isoxazolidin-5-ylmethyl)-carbamoyl]-methoxy}-ethoxy)-ethyl]-amide 
• 1140535-16-5 N-(2-(2-(2-((2-(biphenyl-4-ylmethyl)-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl)methylamino)-2-oxoethoxy)ethoxy)ethyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxamide 
• 1140535-12-1 9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid [2-(2-{[4-benzylamino-2-hydroxy-4-(2-hydroxy-ethyl)-6-methyl-heptylcarbamoyl]-methoxy}-ethoxy)-ethyl]-amide 
• 1140535-17-6 9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid [2-(2-{[(2-benzyl-3-(2,3-dihydroxy-propyl)-3-isobutyl-isoxazolidin-5-ylmethyl)-carbamoyl]-methoxy}-ethoxy)-ethyl]-amide 
• 1140535-20-1 N-(2-(2-(2-((2-(biphenyl-4-ylmethyl)-3-(2,3-dihydroxypropyl)-3-isobutylisoxazolidin-5-yl)methylamino)-2-oxoethoxy)ethoxy)ethyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxamide 
• 282092-89-1 C₄₇H₆₂FN₃O₇S₂ 

Relevant articles and documents

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Abstract: Glucocorticoid, such as dexamethasone (Dex) is often used along with chemotherapy to antagonize side effects of chemotherapy. However, sustained use of Dex frequently develops drug resistance in patients. As a strategy to re-induce drug sensitivity, we planned to modify Dex by chemically conjugating it with twin ten carbon aliphatic chain containing cationic lipid. The resultant molecule, DX10, inhibited STAT3 activation through lowering the production of IL-6. To enhance the STAT3 inhibitory effect of DX10, we used WP (a commercially available STAT3 inhibitor) along with DX10. Combination treatment of both significantly inhibited STAT3 activation when compared to either of the individual treatment. The effect of DX10, either in combination or alone, was mediated through glucocorticoid receptor (GR), thereby repurposing the role of GR in the context of p-STAT3 inhibition-mediated cancer treatment. Cellular viability study proved the synergistic effect of WP and DX10. Further, combination treatment led to induction of early stage of apoptosis and cell cycle arrest. In vivo melanoma tumor regression study confirmed the enhanced anti-tumor activity of co-treatment over individual treatment of DX10 or WP. Thus, together our result demonstrates that DX10 may be used in combination therapy with STAT3 inhibitor like WP for combating cancer with constitutively active STAT3. Graphical abstract: [Figure not available: see fulltext.].

Design, Synthesis, and Biological Evaluation of Dexamethasone-Salvianolic Acid B Conjugates and Nanodrug Delivery against Cisplatin-Induced Hearing Loss

Cisplatin (CDDP) is an extensively used chemotherapeutic agent but has a high incidence of severe ototoxicity. Although a few molecules have entered clinical trials, none have been approved to prevent or treat CDDP-induced hearing loss by the Food and Drug Administration. In this study, an amphiphilic drug-drug conjugate was synthesized by covalently linking dexamethasone (DEX) and salvianolic acid B (SAL) through an ester or amide bond. The conjugates could self-assemble into nanoparticles (NPs) with ultrahigh drug loading capacity and favorable stability. Compared with DEX, SAL, or their physical mixture at the same concentrations, both conjugates and NPs showed enhanced otoprotection in vitro and in vivo. More importantly, the conjugates and NPs almost completely restored hearing in a guinea pig model with good biocompatibility. Immunohistochemical analyses suggested that conjugates and NPs activated the glucocorticoid receptor, which may work as one of the major mechanisms for their protective effects.

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