CAS 179463-17-3|Caspofungin acetate|Capsofungin|Caspofungin|Cancidas|1-[(4R,5S)-5-[(2-Aminoethyl)amino]-N2-[(10R,12S)-10,12-dimethyl-1-oxotetradecyl]-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornit...

General Information

Structure

Molecular Formula

C₅₂H₈₈N₁₀O₁₅

Molecular Mass

1093.31312

Exact Mass

1092.64306217

Charge

InChI

InChI=1S/C52H88N10O15/c1-5-28(2)24-29(3)12-10-8-6-7-9-11-13-39(69)56-34-26-38(68)46(55-22-21-54)60-50(75)43-37(67)19-23-61(43)52(77)41(36(66)18-20-53)58-49(74)42(45(71)44(70)31-14-16-32(64)17-15-31)59-48(73)35-25-33(65)27-62(35)51(76)40(30(4)63)57-47(34)72/h14-17,28-30,33-38,40-46,55,63-68,70-71H,5-13,18-27,53-54H2,1-4H3,(H,56,69)(H,57,72)(H,58,74)(H,59,73)(H,60,75)/t28?,29?,30-,33-,34+,35+,36-,37+,38-,40+,41+,42+,43+,44+,45+,46+/m1/s1

InChIKey

JYIKNQVWKBUSNH-OGZDCFRISA-N

Canonic Smiles

NCCN[C@H]1NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@@H](C[C@H]1O)NC(=O)CCCCCCCCC(CC(CC)C)C)[C@H](O)C)C[C@@H](C2)O)[C@@H]([C@H](c1ccc(cc1)O)O)O)[C@@H](CCN)O

Isomeric Smiles

[C@@H]1([C@H](NC(=O)[C@@H]2[C@H](CCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](C1)NC(=O)CCCCCCCCC(CC(CC)C)C)C[C@@H](C2)O)[C@@H]([C@H](c1ccc(cc1)O)O)O)[C@@H](CCN)O)O)NCCN)O

Calculated Properties

JChem

Acid pKa

8.752075

H Acceptors

H Donor

LogD (pH = 5.5)

-10.0807905

LogD (pH = 7.4)

-7.538204

Log P

-4.8244286

Molar Refractivity

278.7797

Polarizability

111.088356

Polar Surface Area

412.03

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

0.17

LOG S

-3.47

Solubility (Water)

3.67e-01 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Caspofungin acetateCaspofunginCapsofunginCaspofungin AcetateL 7438721-[(4R,5S)-5-[(2-Aminoethyl)amino]-N2-[(10R,12S)-10,12-dimethyl-1-oxotetradecyl]-4-hydroxy-L-ornithine]-5-(threo-3-hydroxy-L-ornithine)pneumocandin B0 DiacetateCancidasL 743873Caspofungin DiacetateMK 09911-[(4R,5S)-5-[(2-Aminoethyl)amino]-N2-[(10R,12S)-10,12-dimethyl-1-oxotetradecyl]-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]pneumocandin B0 Diacetate

Brand Name

Cancidas

IUPAC name

N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-21-[(2-aminoethyl)amino]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0⁹,¹³]heptacosan-18-yl]-10,12-dimethyltetradecanamide N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-21-[(2-aminoethyl)amino]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^{9,13}]heptacosan-18-yl]-10,12-dimethyltetradecanamide

IUPAC Traditional name

caspofungin

Names and Identifiers

Registration numbers

PubChem CID

2826718

PubChem SID

16096386546508288

CAS Number

179463-17-3

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

Melting Point

204-206°C

Solubility

Methanol

Apperance

White Solid

Safety Information

MSDS Link

Download link

Storage Condition

-20°C Freezer, Under Inert Atmosphere

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00520

Drug Groups

approved

Description

Caspofungin (brand name Cancidas worldwide) is an antifungal drug, the first of a new class termed the echinocandins from Merck & Co., Inc. It shows activity against infections with Aspergillus and Candida, and works by inhibiting β(1,3)-D-Glucan of the fungal cell wall. Caspofungin is administered intravenously.

Indication

For the treatment of esophageal candidiasis and invasive aspergillosis in patients who are refractory to or intolerant of other therapies.

Pharmacology

Caspofungin is an antifungal drug, and belongs to a new class termed the echinocandins. It is used to treat Aspergillus and Candida infection, and works by inhibiting cell wall synthesis. Antifungals in the echinocandin class inhibit the synthesis of glucan in the cell wall, probably via the enzyme 1,3-beta glucan synthase. There is a potential for resistance development to occur, however in vitro resistance development to Caspofungin by Aspergillus species has not been studied.

Toxicity

Side effects include rash, swelling, and nausea (rare)

Affected Organisms

Aspergillis, Candida and other fungi

Biotransformation

Metabolized slowly by hydrolysis and N-acetylation

Absorption

92% tissue distribution within 36-48 hours after intravenous infusion

Half Life

9-11 hours

Protein Binding

97%

Elimination

After single intravenous administration of [3H] caspofungin acetate, excretion of caspofungin and its metabolites in humans was 35% of dose in feces and 41% of dose in urine.

Clearance

* 12 mL/min [After single IV administration]

References

• Letscher-Bru, Valérie, and Raoul Herbrecht. 2003. Caspofungin: the first representative of a new antifungal class. Journal of Antimicrobial Chemotherapy 51, no. 3 (March 1): 513 -521. "doi:10.1093/jac/dkg117":http://dx.doi.org/10.1093/jac/dkg117.

• Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. [Pubmed]

• Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [Pubmed]

• McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [Pubmed]

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. [Pubmed]

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

TRC

C184900

An echinocandin that inhibits the synthesis of β (1,3)-D-glucan, an integral component of the fungal cell wall. An antifungal drug used in the treatment of invasive fungal infections.

Molecule Details

References

PubChem Literature

From Data Sources

• McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. Pubmed

• Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. Pubmed

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. Pubmed

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. Pubmed

• Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. Pubmed

• Bertsche, T. et al.: Pharamaz. Zeit., 148, 34 (2004)

• Sandhu, P. et al.: Antimicrob. Agents Chemorther., 48, 1272 (2004)

• Hoang, A.: Am. J. Health-Sys. Pharm., 58, 1206 (2004)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• Synonyms

• Brand Name

• IUPAC name

• IUPAC Traditional name

Registration numbers

• PubChem CID

• PubChem SID

• CAS Number

Properties

• Physical Property

• Safety Information

• Product Information

Related Proteins

Molecular Spectra

Molecule Details

• DrugBank

• TRC

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Commercial Catalog

TRC

C184900

Synonyms

IUPAC name

IUPAC Traditional name

caspofungin

PubChem SID

16096386546508288

CAS Number

179463-17-3

Physical Property

Hydrophobicity(logP)

Melting Point

204-206°C

Solubility

Methanol

Apperance

White Solid

Safety Information

MSDS Link

Download link

Storage Condition

-20°C Freezer, Under Inert Atmosphere

Product Information

Certificate of Analysis

Download link

From Data Sources

• McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. Pubmed

• Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. Pubmed

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. Pubmed

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. Pubmed

• Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. Pubmed

• Bertsche, T. et al.: Pharamaz. Zeit., 148, 34 (2004)

• Sandhu, P. et al.: Antimicrob. Agents Chemorther., 48, 1272 (2004)

• Hoang, A.: Am. J. Health-Sys. Pharm., 58, 1206 (2004)

DrugBank

DB00520

Drug Groups

approved

Description

Indication

For the treatment of esophageal candidiasis and invasive aspergillosis in patients who are refractory to or intolerant of other therapies.

Pharmacology

Toxicity

Side effects include rash, swelling, and nausea (rare)

Affected Organisms

Aspergillis, Candida and other fungi

Biotransformation

Metabolized slowly by hydrolysis and N-acetylation

Absorption

92% tissue distribution within 36-48 hours after intravenous infusion

Half Life

9-11 hours

Protein Binding

97%

Elimination

After single intravenous administration of [3H] caspofungin acetate, excretion of caspofungin and its metabolites in humans was 35% of dose in feces and 41% of dose in urine.

Clearance

* 12 mL/min [After single IV administration]

References

• Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. [Pubmed]

• Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [Pubmed]

• McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [Pubmed]

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. [Pubmed]

• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

TRC

C184900

An echinocandin that inhibits the synthesis of β (1,3)-D-glucan, an integral component of the fungal cell wall. An antifungal drug used in the treatment of invasive fungal infections.

Molecule

ID:402