5758-63-4

Basic information

• Product Name: 17-hydroxy-21-iodopregn-4-ene-3,11,20-trione
• CAS NO: 5758-63-4
• Molecular Formula: C₂₁H₂₇IO₄
• Molecular Weight: 470.3412
• Mol File: 5758-63-4.mol

Chemical Properties

• Boiling Point: 574.3°C at 760 mmHg
• Flash Point: 301.1°C
• Density: 1.55g/cm³
• Vapor Pressure: 1.4E-15mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 17-hydroxy-21-iodopregn-4-ene-3,11,20-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 17-hydroxy-21-iodopregn-4-ene-3,11,20-trione(5758-63-4)
• EPA Substance Registry System: 17-hydroxy-21-iodopregn-4-ene-3,11,20-trione(5758-63-4)

Safety Data

• Hazardous Substances Data: 5758-63-4(Hazardous Substances Data)

Usage

Type of Compound

Organic compound

Molecular Weight

522.4 g/mol

Appearance

White crystalline powder

Solubility

Soluble in water, slightly soluble in ethanol, and practically insoluble in nonpolar solvents

Medical Applications

a. Radiocontrast agent for X-rays and CT scans
b. Visualization of gallbladder, bile ducts, and urinary system
c. Treatment of hyperthyroidism by blocking thyroid hormone production

Mechanism of Action

Absorbs X-rays to provide contrast in medical imaging

Additional Studies

Potential use in cancer treatment and as a contrast agent for brain and spinal cord imaging

Safety Precautions

May cause allergic reactions, gastrointestinal disturbances, and other side effects; contraindicated in patients with a history of iodine allergy or hypersensitivity

Regulatory Status

Approved by the FDA for use as a radiocontrast agent and in the treatment of hyperthyroidism

Storage

Store in a tightly closed container, protected from light, and at room temperature

Stability

Stable under normal conditions, but may degrade upon exposure to heat, light, or moisture

Environmental Impact

Classified as a hazardous substance due to its potential environmental and health risks; proper disposal and handling are required

Synonyms

Telepaque, Iopamidol, Iopamiron

Chemical Structure

A steroidal compound with a 21-iodo substituent, a 17-hydroxy group, and a 3,11,20-trione functionality

Synthesis

Typically synthesized through a series of chemical reactions starting from a steroidal precursor, such as pregnenolone or progesterone

Upstream product

• 53-06-5 Cortisone 
• 106496-86-0 21-p-toluenesulfonate of 17α,21-dihydroxy-4-pregnene-3,11,20-trione 
• 5783-48-2 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl methanesulfonate 
• 53-06-5 17,21-dihydroxy-pregn-4-ene-3,11,20-trione 

Downstream Products

• 96971-36-7 17β-(2-anilino-thiazol-4-yl)-17α-hydroxy-androst-4-ene-3,11-dione 
• 123885-40-5 21-(benzyloxy-hydroxy-phosphoryloxy)-17-hydroxy-pregn-4-ene-3,11,20-trione 
• 93644-70-3 C₃₀H₄₁N₃O₁₅P₂ 
• 5739-00-4 21-(bis-benzyloxy-phosphoryloxy)-17-hydroxy-pregn-4-ene-3,11,20-trione 
• 1882-82-2 17-hydroxy-pregn-4-ene-3,11,20-trione 
• 96262-20-3 17α-hydroxy-17β-(2-methylamino-thiazol-4-yl)-androst-4-ene-3,11-dione 
• 96310-85-9 17α-hydroxy-17β-[2-(N-methyl-anilino)-thiazol-4-yl]-androst-4-ene-3,11-dione 
• 508-95-2 17-hydroxy-21-phosphonooxy-pregn-4-ene-3,11,20-trione 

Relevant articles and documents

Nucleoside conjugates. 6. Synthesis and comparison of antitumor activity of 1-β-D-arabinofuranosylcytosine conjugates of corticosteroids and selected lipophilic alcohols

Five new P1-(steroid-21-yl)-P2-(1-β-D-arabinofuranosylcytosin-5'-yl)pyrophosphat es (ara-CDP-steroids), five 1-β-D-arabinofuranosylcytosine 5'-O-(alkyl)phosphates (ara-CMP-alkyl esters), and two P1-(alkyl)-P2-(1-β-D-arabinofuranosylcytosin-5'-yl)pyrophosphate (ara-CDP-alkyl esters) have been prepared and evaluated against L1210 lymphoid leukemia in culture and in mice (C3D2F1/J). These include ara-CDP-11-deoxycorticosterone, ara-CDP-cortisone, ara-CDP-corticosterone, ara-CDP-cortexolone, and ara-CDP-prednisone, ara-CMP hexadecyl ester, ara-CMP 1-cyclohexylmethyl ester, ara-CMP 1-adamantylmethyl ester, ara-CMP 2-(1-adamanthyl)ethyl ester, ara-CMP 2-chloroethyl ester, ara-CDP hexadecyl ester, and ara-CDP 1-cyclohexylmethyl ester. The in vitro antitumor results indicated that ara-CDP-steroids were as active as the previously reported ara-CMP-steroids and that ara-CMP and ara-CDP-alkyl esters were less growth inhibiting than ara-CDP-steroids and ara-C. However, the in vivo antitumor results indicated that ara-CDP-steroids were generally less effective than the previous monophosphate derivatives. Among them ara-CDP-corticosterone and the known ara-CDP-cortisol showed greater efficacy than ara-C with ILS value of 152% and 209%, respectively, at the optimal dose of 40 and 80 (mg/kg)/day for 9 days, while that of ara-C was 138% at the optimum dose of 9.2 (mg/kg)/day. Generally, ara-CMP alkyl esters, given ip to the L1210 leukemic mice, were found to be toxic and ineffective. However, ara-CDP hexadecyl ester showed marginal activity (ILS, 38%). These preliminary results support the thesis that the ara-C conjugates of this type may require a lipophilic and naturally occurring moiety for improved efficacy.