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Camptothecin

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Identification
Molecular formula
C20H16N2O4
CAS number
7689-03-4
IUPAC name
methyl (1R,9R,10S,11R,12R,19R)-11-acetoxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
State
State

At room temperature, Camptothecin is a solid. It is typically found in crystalline form and is stable under standard conditions.

Melting point (Celsius)
268.00
Melting point (Kelvin)
541.15
Boiling point (Celsius)
245.00
Boiling point (Kelvin)
518.15
General information
Molecular weight
349.36g/mol
Molar mass
349.3640g/mol
Density
1.2800g/cm3
Appearence

Camptothecin is a colorless crystalline compound. Its appearance may vary slightly depending on purity and form, but it generally presents as a solid with a pale hue ranging from colorless to a very faint yellow.

Comment on solubility

Solubility Characteristics

The compound methyl (1R,9R,10S,11R,12R,19R)-11-acetoxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate presents a unique set of solubility challenges due to its complex structure and functional groups. Here are several key points related to its solubility:

  • Polarity: The presence of multiple hydroxyl (-OH) and acetate (-OCOCH3) groups suggests that the compound may exhibit some degree of polarity, which can enhance solubility in polar solvents, such as water and alcohols.
  • Hydrophobic Regions: However, its extensive nonpolar hydrocarbon backbone might limit its overall solubility in polar solvents, leading to potential solubility issues. Compounds with bulky and complex structures often exhibit reduced solubility in aqueous environments.
  • Solvent Compatibility: This compound may demonstrate soluble behavior in organic solvents like dichloromethane or ethyl acetate where nonpolar interactions can prevail.
  • Temperature Influence: Generally, an increase in temperature can lead to enhanced solubility, particularly for solids, by providing the necessary energy to overcome intermolecular forces.
  • pH Sensitivity: The solubility can also be affected by the pH of the solution, particularly due to the presence of acidic and basic functional groups, which may ionize at certain pH levels, improving solubility.

In conclusion, while components such as acetoxy and hydroxyl groups may improve solubility in appropriate solvents, the overall structural complexity and hydrophobic characteristics could hinder its solubility in aqueous environments. Therefore, careful consideration of solvent selection and potential modifications may be necessary for achieving desired solubility levels.

Interesting facts

Interesting Facts about Methyl (1R,9R,10S,11R,12R,19R)-11-acetoxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

Methyl (1R,9R,10S,11R,12R,19R)-11-acetoxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate is a remarkable compound that joins the ranks of complex organic molecules. Here are some intriguing aspects to consider:

  • Structural Complexity: This compound possesses intricate bicyclic and tetracyclic frameworks, showcasing the vast diversity possible in organic chemistry.
  • Biological Significance: Compounds with similar structural features have been investigated for their potential pharmacological properties, including anti-inflammatory and anticancer activities.
  • Chirality: With multiple chiral centers, this compound highlights the importance of stereochemistry in determining the biological activity of organic molecules.
  • Natural Inspirations: Many such complex compounds are often derived from natural products, suggesting evolutionary adaptations in biochemical pathways.

As a student of chemistry, one can't help but be fascinated by the possibilities of synthesizing and characterizing such compounds. The ability to alter even a single aspect of the structure can have profound effects on the compound's reactivity and interaction with biological systems. As discussed in some academic circles, "Understanding the structure-function relationship of complex molecules unlocks the potential for medicinal advancements."

This compound serves as a prime example of the intersection of chemical research and practical applications, motivating further exploration into synthetic strategies and the quest for novel therapeutic agents.

Synonyms
vinblastine
865-21-4
Vinblastin
Vincaleucoblastin
Vinblastina
Vincaleukoblastine
Vincoblastine
Rozevin
Nincaluicolflastine
Vinblastinum
VR-8
Vinblastinum [INN-Latin]
CCRIS 9002
HSDB 3263
NCI-C04842
UNII-5V9KLZ54CY
EINECS 212-734-0
5V9KLZ54CY
NSC 47842
NDC 0002-1452-01
NSC-47842
(2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
DTXSID8021430
(3aR-(3aalpha,4beta,5beta,5abeta,9(3R*,5S*,7R*,9S*),10bR*,13aalpha))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino(8,1-cd)carbazole-5-carboxylate
1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, (3aR-(3aalpha,4beta,5beta,5abeta,9(3R*,5S*,7R*,9S*),10bR*,13aalpha))-
Vinblastinum (INN-Latin)
VLB
DTXCID801430
L01CA01
212-734-0
(3ar-(3aalpha,4beta,5beta,5abeta,9(3r*,5s*,7r*,9s*),10br*,13aalpha))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2h-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1h-indolizino (8,1-cd)carbazole-5-carboxylate
vbl
vincaleucoblastine
Velban
CHEMBL159
methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Vinblastina [DCIT]
Vinblastine [INN:BAN]
VINBLASTINE [INN]
cid_5388983
[3H]-Vinblastine
1z2b
VINBLASTINE [MI]
VINBLASTINE [HSDB]
VINBLASTINE [VANDF]
SCHEMBL3628
BIDD:PXR0201
BSPBio_001228
VINBLASTINE [WHO-DD]
GTPL6851
132142-72-4
MSK15295
BDBM50012278
NSC816570
AKOS015965500
CS-1336
DB00570
NSC-816570
NCGC00022585-04
NCGC00022585-05
NCGC00485975-02
AC-24191
AS-15821
BP-43221
HY-17418
VinblastineVincaleukoblastine; Vinblastina
EN300-19874057
VINDESINE SULFATE IMPURITY B [EP IMPURITY]
VINCRISTINE SULFATE IMPURITY H [EP IMPURITY]
BRD-K01188359-001-02-0
BRD-K01188359-001-03-8
BRD-K01188359-065-02-5
BRD-K01188359-065-23-1
(2alpha,2'beta,3alpha,5beta,19beta)-vincaleukoblastine
(2ALPHA,2''''BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
(3AR-(3AALPHA,4BETA,5BETA,5ABETA,9(3R*,5S*,7R*,9S*),10BR*,13AALPHA))-METHYL 4-(ACETYLOXY)-3A-ETHYL-9-(5-ETHYL-1,4,5,6,7,8,9,10-OCTAHYDRO-5-HYDROXY-9- (METHOXYCARBONYL)-2H-3,7-METHANOAZACYCLOUNDECINO(5,4-B)INDOL-9-YL)- 3A,4,5,5A,6,11,12,13A-OCTAHYDRO-5-HYDROXY-8-METHOXY-6-METHYL-1H-INDOLIZINO (8,1-CD)CARBAZOLE-5-CARBOXYLATE
methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate
methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate