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Estramustine

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Identification
Molecular formula
C23H31Cl2NO3
CAS number
2998-57-4
IUPAC name
[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate
State
State

Estramustine is a solid under standard conditions (room temperature and pressure).

Melting point (Celsius)
154.00
Melting point (Kelvin)
427.15
Boiling point (Celsius)
691.50
Boiling point (Kelvin)
964.65
General information
Molecular weight
540.45g/mol
Molar mass
540.4520g/mol
Density
1.3120g/cm3
Appearence

Estramustine is typically found as a white or off-white crystalline powder. It is used in its hydrochloride form for medical purposes, specifically in cancer treatment.

Comment on solubility

Solubility of 2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate

The solubility of this compound is notably complex due to its intricate structure. Several factors can influence its solubility, including:

  • Molecular Weight: With a high molecular weight, solubility can be limited in polar solvents.
  • Functional Groups: The presence of multiple hydroxyl (–OH) groups may enhance solubility in water; however, the bulky hydrocarbon components might hinder it.
  • Steric Hindrance: The large and complex three-dimensional configuration may obstruct solvation process, reducing solubility.
  • Hydrophobic and Hydrophilic Balance: The balance between hydrophilic hydroxyl groups and hydrophobic phenanthrene sections plays a critical role.

In practice, this compound's solubility can be assessed using solvents with varying polarities. For instance:

  1. Water: Likely limited solubility due to hydrophobic regions.
  2. Organic Solvents: Better solubility might be expected in non-polar organic solvents like chloroform or dichloromethane.
  3. Mixed Solvents: Some success may be found in mixed solvent systems, exploiting the polar and non-polar characteristics effectively.

Ultimately, the solubility of this compound is expected to be moderate to low, requiring careful consideration when selecting solvents for dissolution or formulation in various applications. Understanding these properties is crucial for optimizing its use in scientific and pharmaceutical contexts.

Interesting facts

Interesting Facts about 2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate

This fascinating compound is a notable example of an anti-cancer agent, which combines the structural attributes of steroid-like compounds with potent alkylating capabilities commonly found in certain chemotherapeutics. Here are some intriguing aspects:

  • Dual Mechanism of Action: The compound features both steroidal and non-steroidal elements that may inhibit tumor growth through different pathways, offering a multifaceted approach to combating cancer.
  • Steroidal Backbone: Its cyclopenta[a]phenanthren core structure, commonly associated with certain hormones, lends the compound properties akin to corticosteroids, which play significant roles in metabolism and immune response.
  • Chloroethyl Moiety: The bis(2-chloroethyl)amino group is crucial for the compound’s capacity to alkylate DNA, a mechanism that can effectively induce apoptosis in rapidly dividing cancer cells.
  • Potential Synergy: When used in combination with other chemotherapeutic agents, this compound could enhance treatment efficacy by targeting cancer cells that have developed resistance to more conventional therapies.

Furthermore, compounds like this one serve as a great example of how medicinal chemistry intertwines with pharmacology to develop novel therapeutic agents. Researchers are continually investigating its potential, aiming to unlock new treatment modalities that could significantly improve patient outcomes.

As expressed by a prominent chemist in the field: "The beauty of synthetic compounds lies in their potential to challenge the status quo of treatment paradigms."

This compound’s intricate design not only represents a leap forward in cancer treatment but also encapsulates the innovative spirit of modern chemistry.

Synonyms
PREDNIMUSTINE
Sterecyt
29069-24-7
Stereocyt
Prednimustina
LEO 1031
Prednimustinum
Leo-1031
prednisolone chlorambucil ester
Chlorambucil prednisolone ester
NSC 134087
NSC-134087
DTXSID4021183
9403SIO2S8
NSC-171345
Pregna-1,4-diene-3,20-dione, 21-(4-(4-(bis(2-chloroethyl)amino)phenyl)-1-oxobutoxy)-11,17-dihydroxy-, (11beta)-
NSC134087
Pregna-1,4-diene-3,20-dione, 21-[4-[4-[bis(2-chloroethyl)amino]phenyl]-1-oxobutoxy]-11,17-dihydroxy-, (11beta)-
Leo1031
NSC171345
RefChem:389234
DTXCID901183
L01AA08
11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-(4-(p-(bis(3-chloroethyl)amino)phenyl)butyrate)
11beta-21-(4-(4-(bis(2-chloroethyl)amino)phenyl)-1-oxobutoxy)-11,17-dihydroxypregna-1,4-diene-3,20-dione
2-((1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo(8.7.0.02,?.011,1?)heptadeca-3,6-dien-14-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
249-410-3
Pregna-1,4-diene-3,20-dione, 11-beta,17,21-trihydroxy-,21-(4-(p-(bis(2-chloroethyl)amino)phenyl)butyrate)
CHEBI:82524
[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate
Prednimustine [USAN:INN]
Prednimustinum [INN-Latin]
Prednimustina [INN-Spanish]
(11beta)-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl 4-{4-[bis(2-chloroethyl)amino]phenyl}butanoate
C35H45Cl2NO6
CCRIS 6741
HSDB 6882
Chlorambucil ester of prednisolone
EINECS 249-410-3
BRN 2826967
UNII-9403SIO2S8
Prednisolone 21-(4-(p-(bis(2-chloroethyl)amino)phenyl)butyrate)
PREDNIMUSTINE [MI]
PREDNIMUSTINE [INN]
Prednimustine (USAN/INN)
SCHEMBL8246
PREDNIMUSTINE [HSDB]
PREDNIMUSTINE [IARC]
PREDNIMUSTINE [USAN]
11beta,17,21-Trihydroxypregna-1,4-diene-3,20-dione 21-(4-(p-(bis(2-chloroethyl)amino)phenyl)butyrate)
PREDNIMUSTINE [MART.]
PREDNIMUSTINE [WHO-DD]
orb1983213
CHEMBL2103751
Leo 1031; NSC 134087; NSC 171345;Prednisolone chlorambucil ester; Sterecyt; Stereocyt
DB12832
DA-59733
HY-13732
Pregna-1,4-diene-3,20-dione, 11-beta,17,21-trihydroxy-, 21-(4-(p-(bis(2-chloroethyl)amino)phenyl)butyrate)
Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-, 21-(4-(p-(bis(2-chloroethyl)amino)phenyl)butyrate)
CS-0007761
NS00028621
C19512
D05602
Q7239694
[2-(11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate
11.BETA.,17,21-TRIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE 21-(4-(P-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRATE)
PREGNA-1,4-DIENE-3,20-DIONE, 21-(4-(4-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-1-OXOBUTOXY)-11,17-DIHYDROXY-, (11.BETA.)-