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Vincristine

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Identification
Molecular formula
C46H56N4O10
CAS number
57-22-7
IUPAC name
(6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(2R,3R)-2,3-dihydroxybutanedioic acid
State
State

At room temperature, vincristine is in a solid state, usually available as a lyophilized powder for injection after reconstitution.

Melting point (Celsius)
220.00
Melting point (Kelvin)
493.15
Boiling point (Celsius)
270.00
Boiling point (Kelvin)
543.15
General information
Molecular weight
824.99g/mol
Molar mass
824.9860g/mol
Density
1.2000g/cm3
Appearence

Vincristine is typically a white to off-white crystalline powder. It may appear as a lyophilized solid when used in its sulfate form for pharmaceutical preparations.

Comment on solubility

Solubility of the Compound

The compound (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide and (2R,3R)-2,3-dihydroxybutanedioic acid exhibit a unique solubility profile influenced by their intricate structures.

When examining solubility, consider the following factors:

  • Polarity: The presence of hydroxyl groups in the structure increases polarity, generally enhancing solubility in polar solvents like water.
  • Molecular Interactions: Hydrogen bonding capabilities due to hydroxyl groups may lead to interactions with water molecules.
  • Hydrophobic Regions: Certain portions of the molecule, such as the benzyl groups, may introduce hydrophobic characteristics, potentially limiting solubility in polar solvents.

As a general observation:

  • A compound with a high degree of functionalization, particularly with both polar and non-polar sections, can create a complex solubility behavior.
  • It’s often noted that "the more functional groups, the more nuanced the solubility."

In conclusion, understanding the solubility of such a compound is pivotal for applications in drug formulation and material science, as it can significantly affect bioavailability and performance in various environments.

Interesting facts

Interesting Facts About the Compound

This intriguing compound, which features a complex structure combining elements of both indole and quinoline moieties, is rich in potential applications and theoretical significance. Here are some fascinating aspects:

  • Structural Complexity: The compound showcases a unique arrangement of rings and functional groups, indicative of its intricate molecular architecture. The presence of a quinoline framework is known for its role in various biological activities.
  • Biological Relevance: Compounds like these are often investigated for their pharmacological properties. The indole unit, in particular, is prevalent in numerous natural products and biologically active molecules, contributing to mechanisms such as enzyme inhibition and receptor binding.
  • Natural Product Inspiration: Many components of this compound are inspired by naturally occurring systems. For instance, the interplay between the hydroxy groups and the dioxo functionalities may resemble naturally occurring metabolites, which often exhibit synergy in activity.
  • Synthesis Challenges: The total synthesis of such a compound is non-trivial and requires multiple synthetic steps, often incorporating strategies that involve protecting group chemistry and stereoselective reactions. The sophisticated synthesis process is a vibrant area of study in organic chemistry.
  • Potential Therapeutic Applications: Given its structural features, there may be prospects for this compound in drug discovery, particularly in the development of anticancer or antimicrobial agents. Various modifications can potentially enhance its efficacy and selectivity.

In the words of a chemist, “The beauty of chemistry lies not only in the elegance of the molecules but also in the stories they tell through their interactions.” Understanding compounds like this allows scientists to unlock new avenues for research, emphasizing the intricate relationship between structure and function.

As research unfolds, the significant potential of this compound may offer exciting new directions in both synthetic and medicinal chemistry!

Synonyms
ergotamine tartrate
Ergotamine D-tartrate
Wigrettes
Gotamine tartrate
Medihaler ergotamine
Ergostat
379-79-3
Ergotamine bitartrate
Femergin
Lingraine
Lingran
Secupan
Ergomar
Gynergen
MRU5XH3B48
Rigetamin
DTXSID3025253
Cornutamin
Migretamine
component of Cafergot
Exmigra
Secagyn
Avetol
Ergate
Ergam
Neo-ergotin
CAFERGOT COMPONENT ERGOTAMINE TARTRATE
MIGERGOT COMPONENT ERGOTAMINE TARTRATE
WIGRAINE COMPONENT ERGOTAMINE TARTRATE
Ergotamine, tartrate
NSC-41869
ETIN
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-, (R-(R*,R*))-2,3-dihydroxybutanedioate (2:1) (salt)
Ergotamine hemitartrate
DTXCID605253
Ergotartrate
ERGOTAMINE TARTRATE (MART.)
ERGOTAMINE TARTRATE [MART.]
ERGOTAMINE TARTRATE (USP-RS)
ERGOTAMINE TARTRATE [USP-RS]
Ergotamine, tartrate (2:1)
CAS-379-79-3
ERGOTAMINE TARTRATE (USP IMPURITY)
ERGOTAMINE TARTRATE [USP IMPURITY]
ERGOTAMINE TARTRATE (USP MONOGRAPH)
ERGOTAMINE TARTRATE [USP MONOGRAPH]
Ergotamine, tartrate (1:1) salt
NCGC00091935-01
Ergotamine tartrate (VAN)
UNII-MRU5XH3B48
CCRIS 487
ErgomarSublingual
Ergotamine tartrate [USP:JAN]
EINECS 206-835-9
Ergotamine tartrate (2:1) (salt)
NSC 41869
Tartrate, Ergotamine
GOTAMINE
NSC41869
Ergotamine, tartrate (2:1) (salt)
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) (salt)
Ergotamine Tartrate (2:1)
SCHEMBL134885
CHEMBL2131781
ERGOTAMINE TARTRATE [MI]
ERGOTAMINE TARTRATE [JAN]
CJMJLDQKTOJACI-BGQAIRJTSA-N
ERGOTAMINE TARTRATE [VANDF]
Tox21_111183
Tox21_201705
Tox21_303182
ERGOTAMINE TARTRATE [WHO-DD]
ERGOTAMINE TARTRATE [WHO-IP]
FE30656
ERGOTAMINE TARTRATE [ORANGE BOOK]
NCGC00257225-01
NCGC00259254-01
ERGOTAMINE, TARTRATE(2:1)(SALT)
ERGOTAMINI TARTRAS [WHO-IP LATIN]
ERGOTAMINE TARTRATE COMPONENT OF CAFERGOT
ERGOTAMINE TARTRATE COMPONENT OF MIGERGOT
ERGOTAMINE TARTRATE COMPONENT OF WIGRAINE
Q27284199
Ergotamine tartrate, European Pharmacopoeia (EP) Reference Standard
INDOLO(4,3-FG)QUINOLINE, ERGOTAMAN-3',6',18-TRIONE DERIV.
(5'S)-5'-Benzyl-12'-hydroxy-2'-methylergotaman-3',6',18-trione hemitartrate
8H-OXAZOLO(3,2-A)PYRROLO(2,1-C)PYRAZINE, ERGOTAMAN-3',6',18-TRIONE DERIV.
206-835-9
ERGOTAMAN-3',6',18-TRIONE, 12'-HYDROXY-2'-METHYL-5'-(PHENYLMETHYL)-, (5'.ALPHA.)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (2:1) (SALT)
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5alpha)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1)
Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-,(5'alpha)-,(2R,3R)-2,3-dihydroxybutanedioate(2:1)(salt)
ERGOTAMAN-3',6',18-TRIONE, 12'-HYDROXY-2'-METHYL-5'-(PHENYLMETHYL)-,(5'ALPHA)-,(R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE(2:1)(SALT)
Ergotamine tartrate, United States Pharmacopeia (USP) Reference Standard, monograph mol wt. 1313.41 ((C33H35N5O5)2 ?? C4H6O6)