179463-17-3

Basic information

• Product Name: Cancidas
• Synonyms: Caspofungin acetate;(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-Aminoethylamino)-3-[3-amino-1(R)-hydroxypropyl]-6-[1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl]-18-(10,12-dimethyltetradecanamido)-11,20,25-trihydroxy-15-[1(R)-hydroxyethyl]-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0(9,13)]heptacosane-2,5,8,14,17,23-hexaone diacetate;Cancidas;L 743,872;L 743872;L-743,872;L-743872;Mk 0991
• CAS NO: 179463-17-3
• Molecular Formula: C52H88N10O15.2(C2H4O2)
• Molecular Weight: 1213.42
• EINECS: 1592732-453-0
• Product Categories: Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API
• Mol File: 179463-17-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 1501.4 °C at 760 mmHg
• Flash Point: 861.8 °C
• Appearance: white to beige/
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: ?20°C
• Solubility: H2O: soluble15mg/mL (clear solution)
• CAS DataBase Reference: Cancidas(CAS DataBase Reference)
• NIST Chemistry Reference: Cancidas(179463-17-3)
• EPA Substance Registry System: Cancidas(179463-17-3)

Safety Data

• WGK Germany: 3
• RTECS: TP8046500
• Hazardous Substances Data: 179463-17-3(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 179463-17-3 differently. You can refer to the following data:
1. Caspofungin is the first in a new class of antifungal agents named echinocandin to be launched in the US for the parenteral treatment of invasive aspergillosis in patients refractory to, or intolerant of other antifungal therapies such as amphotericin-B1 lipid formulation of amphotericin-B and/or itraconazole. Caspofungin is a water soluble, stable, aza-substituted semisynthetic derivative of pneumocandin B, a fermentation product of the fungus Zalerion arboricola. Since fungi and humans are both eukaryotes, new antifungal agents must focus on fungus-specific targets in order to minimize potential toxicity in the human host. In this respect, the lipopeptide caspofungin, inhibits the synthesis of 1,3-beta- D-glucans present only in the fungal cell wall, which leads to the specific lysis of the pathogenic cells. The compound is fungicidal rather than fungistatic, an unusual feature among antifungal agents. Caspofungin has activity in vitro and in vivo against a range of Candida species (including azole and amphotericin B resistant Candida) and also against Aspergillus, an important pathogen which is not susceptible to fluconazole. Caspofungin was generally more active than amphotericin B, flucytosine, fluconazole and itraconazole against Candida species. Cryptococcus is not susceptible to caspofungin. Caspofungin has a half-life in human beings around 10 hours. Unlike the azoles, caspofungin does not inhibit cytochrome P450. The drug has been given intravenously with loading dose of 70 rag, followed by 50 mg daily to be effective in invasive aspergillosis refractory to prior antifungal therapy. Most of the side effects were mild and comprised fever, thrombophlebitis, headache, nausea, rash and flushing.
2. Caspofungin is an antifungal compound that is classified as an echinocandin, as it acts by noncompetititvely inhibiting the enzyme 1,3-β glucan synthase and preventing the synthesis of glucan in the fungal cell wall. It is effective against disseminated or invasive aspergillosis and candidiasis in mice. Caspofungin has a 50% minimum effective concentration against Aspergillus spp. of 0.015 μg/ml. It does not antagonize other antifungal compounds, like amphotericin B, and, in some cases, may show additive or synergistic activity.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 179463-17-3 differently. You can refer to the following data:
1. 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.
2. Caspofungin acetate is a semi-synthetic analogue of pneumocandin B0 with improved water solubility, a significant limitation in the development of the echinocandin class as pharmaceuticals. Caspofungin acetate acts by inhibiting the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi.
3. Calcium antagonist, coronary vasodilator, anti-inflammatory, analgesic
4. Caspofungin Diacetate is an impurity of Caspofungin Acetate(C184900) which is 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.

Definition

ChEBI: The diacetate salt of caspofungin. It is used for the treatment of invasive candidiasis, and of aspergillosis in patients who are refractory to, or intolerant of, other therapy.

Brand name

Cancidas (Merck).

Biochem/physiol Actions

Caspofungin is an echinocandin antifungal that inhibits 1,3-β-D-glucan synthase, which is required for cell wall synthesis, thereby disturbing the integrity of the fungal cell wall.

Veterinary Drugs and Treatments

Caspofungin has potential for treating invasive aspergillosis or disseminated candidal infections in companion animals although little, if any, information on its use in dogs or cats is available.

InChI:InChI=1/C52H88N10O15.2C2H4O2/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;2*1-2(3)4/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);2*1H3,(H,3,4)/t28?,29?,30-,33-,34-,35+,36-,37+,38-,40+,41+,42+,43?,44+,45+,46+;;/m1../s1

Upstream product

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• 107-15-3 ethylenediamine 
• 75-36-5 acetyl chloride 
• 57260-73-8 N-BOC-1,2-diaminoethane 
• 935732-69-7 C₅₆H₈₃BN₈O₁₇ 
• 936000-60-1 C₅₆H₈₄N₈O₁₆S 
• 150283-04-8 10,12-dimethyl-tetradecanoic acid [3-(3-amino-1-hydroxy-propyl)-6-[1,2-dihydroxy-2-(4-hydroxy-phenyl)-ethyl]-11,20,21,25-tetrahydroxy-15-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.0^9,13]heptacos-18-yl]-amide 
• 1230487-11-2 C₅₇H₈₈N₈O₁₅S 

Relevant articles and documents

CASPOFUNGIN ANALOG AND APPLICATIONS THEREOF

Disclosed are a caspofungin analog and applications thereof. Said caspofungin analog is a compound having a structure as indicated in Formula (4), or pharmaceutically acceptable slats thereof. R1 can be chosen from hydroxyl, benzyloxy, phenoxy, substituted phenoxy, or substituted benzyloxy. R 2 , R 3 , R 4 , R 5 can be chosen from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, hydroxyl, benzyloxyphenyl, substituted benzyloxyphenyl, nitro, fluorine, chlorine, bromine, or iodine. Also disclosed are a preparation method for and applications of said compound.

PROCESS FOR PREPARING CASPOFUNGIN AND NOVEL INTERMEDIATES THEREOF

The present invention relates to a novel process for preparing the aza cyclohexapeptide compound 1-[(4R,5S)-5-[(2-aminoethyl)amino]-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]-pneumocandin B0 (caspofungin), which can improve the problem due to a pungent odor and toxicity during the process and can prepare caspofungin as a final product at high yield compared to conventional processes, and to novel intermediates which are used in the preparation process.

Caspofungin free of caspofungin Co

The present invention provides Caspofungin and salts thereof substantially free of Caspofungin C0 and salts thereof. The present invention also provides processes for the preparation of said Caspofungin and salts thereof and processes for the d