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

• ChemBase ID: 402
• Molecular Formular: C52H88N10O15
• Molecular Mass: 1093.31312
• Monoisotopic Mass: 1092.64306217
• 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
• Canonical 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
• 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

NAMES AND DATABASE IDS

Names

• 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[22.3.0.0^{9,13}]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,^1^3]heptacosan-18-yl]-10,12-dimethyltetradecanamide
• IUPAC Traditional name: caspofungin
• Brand Name: Cancidas
• Synonyms: Caspofungin acetate; Capsofungin; Caspofungin; 1-[(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 Diacetate; Cancidas; Caspofungin Diacetate; L 743872; L 743873; MK 0991; 1-[(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; Caspofungin Acetate

Database IDs

• CAS Number: 179463-17-3
• PubChem SID: 46508288; 160963865
• PubChem CID: 2826718

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.752075
• H Acceptors: 18
• H Donor: 16
• LogD (pH = 5.5): -10.0807905
• LogD (pH = 7.4): -7.538204
• Log P: -4.8244286
• Molar Refractivity: 278.7797 cm^3
• Polarizability: 111.088356 Å^3
• Polar Surface Area: 412.03 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.17
• LOG S: -3.47
• Solubility (Water): 3.67e-01 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 204-206°C
• Hydrophobicity(logP): 0

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

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

Toronto Research Chemicals - 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.

REFERENCES

• 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
• 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
• Sandhu, P. et al.: Antimicrob. Agents Chemorther., 48, 1272 (2004)
• Bertsche, T. et al.: Pharamaz. Zeit., 148, 34 (2004)
• Hoang, A.: Am. J. Health-Sys. Pharm., 58, 1206 (2004)