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Chlormadinone acetate

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Identification
Molecular formula
C23H29ClO4
CAS number
302-22-7
IUPAC name
[(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
State
State

In its pure form, chlormadinone acetate is a solid at room temperature. As a crystalline powder, it is normally stable and is used in various pharmaceutical formulations.

Melting point (Celsius)
201.00
Melting point (Kelvin)
474.00
Boiling point (Celsius)
485.20
Boiling point (Kelvin)
758.35
General information
Molecular weight
479.01g/mol
Molar mass
479.0070g/mol
Density
1.3100g/cm3
Appearence

Chlormadinone acetate appears as a white to off-white crystalline powder. It may vary slightly in color, but it typically maintains a bright appearance under normal conditions.

Comment on solubility

Solubility of the Compound

The solubility of [(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate is influenced by various factors due to its complex structure. Understanding its solubility characteristics is essential for applications in pharmaceuticals and related fields.

Factors Affecting Solubility

The solubility of this compound can be analyzed through several critical aspects:

  • Polarity: Due to the presence of both polar (acetyl and chloro groups) and non-polar (hydrocarbon rings) components, the compound may exhibit a moderate level of solubility in polar solvents.
  • Temperature: Solubility is often temperature-dependent. As temperature increases, it can enhance solubility, particularly in organic solvents.
  • pH levels: The ionization state of the functional groups may vary with pH, thereby affecting solubility. Changes in acidity can lead to increased solubility in aqueous solutions.
  • Solvents: This compound may be more soluble in organic solvents such as ethanol or DMSO, while being poorly soluble in water.

General Comments

Based on the structural complexity and the presence of multiple functional groups, one might expect the solubility to vary significantly. As experts often say, “like dissolves like,” which infers that selecting the appropriate solvent is crucial for maximizing solubility. In summary, when working with [(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate, a systematic approach considering these factors will yield the best results in terms of solubility.

Interesting facts

Interesting Facts about [8R,9S,10R,13S,14S,17R]-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

This compound is a fascinating member of the steroid class, showcasing the intricate nature of organic chemistry. Here are some of its intriguing aspects:

  • Cyclic Structure: The compound features a complex cyclic structure, which is a hallmark of many steroids. The presence of multiple rings contributes to its unique chemical properties and biological activities.
  • Stereochemistry: The specific stereochemical configuration (indicated by the R and S designations) of the compound plays a critical role in how it interacts with biological systems. Different configurations can lead to vastly different effects in a biological context.
  • Biological Significance: Compounds similar to this one are often studied for their potential pharmacological properties. Many steroids possess significant biological activities, including anti-inflammatory and anabolic effects.
  • Chlorine Atom: The presence of a chlorine substituent can enhance the reactivity and stability of the molecule, influencing its biological activity and potential applications in medicinal chemistry.
  • Acetyl Group: The acetylation of the molecule can increase lipophilicity, which may affect the compound's absorption, distribution, metabolism, and excretion in biological systems.

As a chemist or student of chemistry, appreciating the nuanced relationships between structure, function, and biological activity in compounds like this not only deepens your understanding of organic molecules but also opens the door to innovative therapeutic applications. As you delve into the world of steroids and their derivatives, remember the profound impact that small changes in molecular structure can have on the behavior of these compounds in dynamic biological environments.

Synonyms
chlormadinone acetate
302-22-7
Menstridyl
Matrol
Chlormadinon acetate
Cero
Gestafortin
Bovisynchron
Fertiletten
Chlordion
Clordion
Lutinyl
Minipill
Skedule
Traslan
Retex
Synchrosyn P
Skedule TM
Lutoral (Syntex)
Normenon
Synchrosyn
Chloramdinone acetate
Chloromadinone acetate
Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-chloro-
Chlormadinonu
NSC-92338
Chlormadinonu [Polish]
Luteran
Lormin
CCRIS 129
Chlormadinone (acetate)
Ay 13390-6
HSDB 3591
EINECS 206-118-0
17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione
17alpha-Acetoxy-6-chloro-6-dehydroprogesterone
6-Chloro-delta6-17-acetoxyprogesterone
DTXSID6020274
0SY050L61N
6-Chloro-17-hydroxypregna-4,6-diene-3,20-dione acetate
6-Chloro-delta6-(17alpha)acetoxyprogesterone
6-Chloro-delta(sup 6)-17-acetoxyprogesterone
6-Chloro-17alpha-hydroxypregna-4,6-diene-3,20-dione acetate
6-Chloro-6-dehydro-17alpha-acetoxyprogesterone
Chloromadinone 17-acetate
[(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
17-alpha-Acetoxy-6-chloro-6-dehydroprogesterone
6-Chloro-6-dehydro-17-alpha-acetoxyprogesterone
6-Dehydro-6-chloro-17-alpha-acetoxyprogesterone
Chlormadinone acetate [USAN:JAN:NF]
17-alpha-Acetoxy-6-chloro-6,7-dehydroprogesterone
delta(sup 6)-6-Chloro-17alpha-acetoxyprogesterone
RS-1280
delta(sup 6)-6-Chloro-17-alpha-acetoxyprogesterone
6-Chloro-delta-6-17alpha-hydroxyprogesterone acetate
6-Chloro-6-dehydro-17alpha-hydroxyprogesterone acetate
6-Chloro-delta(sup 6)-dehydro-17-acetoxyprogesterone
DTXCID80274
17-alpha-Acetoxy-6-chloro-4,6-pregnadiene-3,20-dione
6-Chloro-17-alpha-acetoxy-4,6-pregnadiene-3,20-dione
6-Chloro-6-dehydro-17-alpha-hydroxyprogesterone acetate
Progesterone, 6-chloro-6-dehydro-17-hydroxy-, acetate
MLS000028451
MLS001148653
6-Chloro-pregna-4,6-dien-17alpha-ol-3,20-dione acetate
Pregna-4,6-diene-3,20-dione, 17-(acetoxy)-6-chloro-
6-Chloro-17-alpha-hydroxy-delta(sup 6)-progesterone acetate
6-Chloro-pregna-4,6-dien-17-alpha-ol-3,20-dione acetate
CHEBI:31394
CHLORMADINONE ACETATE [MI]
CHLORMADINONE ACETATE [JAN]
6-Chloro-6-dehydro-17.alpha.-acetoxyprogesterone
6-Chloro-delta(sup 4,6)-pregnadiene-17-alpha-ol-3,20-dione 17-acetate
NSC92338
CHLORMADINONE ACETATE [HSDB]
CHLORMADINONE ACETATE [USAN]
CHLORMADINONE ACETATE [MART.]
CHLORMADINONE ACETATE [WHO-DD]
6-Chloro-6-dehydro-17.alpha.-hydroxyprogesterone acetate
NCGC00022680-04
SMR000058325
Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-, acetate
17-Acetoxy-6-chloro-6-dehydroprogesterone
CHLORMADINONE ACETATE [EP MONOGRAPH]
Chronosyn
Cyclonorm
Prostal
17.ALPHA.-ACETOXY-6-CHLORO-6,7-DEHYDROPROGESTERONE
6-Chloro-3,20-dioxopregna-4,6-dien-17-yl acetate
CHLORMADINONE ACETATE (MART.)
CAS-302-22-7
CHLORMADINONE ACETATE (EP MONOGRAPH)
Fertileen
UNII-0SY050L61N
Chlormadinone acetate [Progestins]
((8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta(a)phenanthren-17-yl) acetate
Clormadinone acetate
6-Chloro-.delta.6-17-acetoxyprogesterone
chlormadinone-acetate
Lutoral (TN)
MFCD00056471
Opera_ID_343
17.alpha.-Acetoxy-6-chloro-6-dehydroprogesterone
6-Chloro-.delta.6-[17.alpha.]acetoxyprogesterone
Chlormadinon-17-acetate
.delta.(sup 6)-6-Chloro-17.alpha.-acetoxyprogesterone
SCHEMBL15046
CHEMBL110691
Chlormadinone acetate, >=98%
HMS2231J04
HMS3715E19
BCP28307
HY-B1095
Chlormadinone acetate (JP18/USAN)
Tox21_110881
Tox21_200665
s4593
6-Chloro-pregna-4,20-dione acetate
AKOS015955610
Tox21_110881_1
CCG-220989
CS-4683
FC19935
KS-5157
Ay-13390-6
NCGC00022680-05
NCGC00258219-01
(1S,11S,15S,2R,10R,14R)-14-acetyl-8-chloro-2,15-dimethyl-5-oxotetracyclo[8.7.0 .0<2,7>.0<11,15>]heptadeca-6,8-dien-14-yl acetate
(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
17.alpha.-Acetoxy-6-chloro-4,20-dione
6-Chloro-17.alpha.-acetoxy-4,20-dione
Chlormadinone Acetate for system suitability
C3116
NS00004056
17.alpha.-Acetoxy-6-chloropregna-4,20-dione
6-Chloro-.delta.(sup 4,20-dione 17-acetate
6-Chloro-17-hydroxypregna-4,20-dione acetate
C74552
D01299
6-Chloro-.delta.(sup 6)-17-acetoxyprogesterone
Pregna-4,20-dione, 17-(acetyloxy)-6-chloro-
SR-01000003040
Pregna-4,20-dione, 6-chloro-17-hydroxy-, acetate
Q5102980
SR-01000003040-2
6-Chloro-17.alpha.-hydroxypregna-4,20-dione acetate
17alpha-Acetoxy-6-chloro-4,6-pregnadiene-3,20-dione
17ALPHA-ACETOXY-6-CHLORO-6,7-DEHYDROPROGESTERONE
17alpha-Acetoxy-6-chloropregna-4,6-diene-3,20-dione
6-Chloro-.delta.(sup 6)-dehydro-17-acetoxyprogesterone
6-Chloro-.delta.-6-17.alpha.-hydroxyprogesterone acetate
6-Chloro-17-hydroxypregna-4,6-diene-3,20-dione, acetate
WLN: L E5 B666 OV KU MUTJ A1 E1 FV1 FOV1 LG
6-Chloro-17.alpha.-hydroxy-.delta.(sup 6)-progesterone acetate
Chlormadinone acetate, European Pharmacopoeia (EP) Reference Standard
(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylacetate
17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione;17-Acetoxy-6-chloro-6-dehydroprogesterone;6-Chloro-17-acetoxy-4,6-pregnadiene-3,2 0-dione
206-118-0