127785-64-2

Basic information

• Product Name: Basifungin
• Synonyms: Basifungin;aureobasidin A;Cyclo[L-Phe-N-methyl-L-Phe-L-Pro-L-aIle-N-methyl-L-Val-L-Leu-N-methyl-β-hydroxy-L-Val-[(3R)-D-Hmp-]-N-methyl-L-Val-];LY-295337;Aureobasidin A (9CI);Aureobasidin A (AbA)
• CAS NO: 127785-64-2
• Molecular Formula: C60H92N8O11
• Molecular Weight: 1101.43
• Mol File: 127785-64-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 1229.1°C at 760 mmHg
• Flash Point: 697.1°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• PKA: 13.35±0.70(Predicted)
• CAS DataBase Reference: Basifungin(CAS DataBase Reference)
• NIST Chemistry Reference: Basifungin(127785-64-2)
• EPA Substance Registry System: Basifungin(127785-64-2)

Safety Data

• Hazardous Substances Data: 127785-64-2(Hazardous Substances Data)

Usage

Description

Basifungin, also known as aureuobacidin A, is a cyclodepsipeptide antibiotic derived from the filamentous fungus Aureobasidium pullulans R106. It exhibits fungicidal properties at low concentrations and is toxic to yeast at levels between 0.1-0.5 ug/ml. Basifungin functions by inhibiting inositol phosphorylceramide synthase, a crucial enzyme in fungal sphingolipid biosynthesis, which in turn may suppress fungal cell growth.

Uses

Used in Agricultural Industry:
Basifungin is used as a fungicide for controlling various fungal infections in crops due to its low concentration effectiveness and ability to inhibit fungal cell growth.
Used in Pharmaceutical Industry:
Basifungin is used as an orally available antibiotic for treating fungal infections in humans, as it can be ingested and still maintain its antimicrobial properties against yeast and other fungi.

Clinical Use

Aureobasidin A is a cyclic depsipeptide that is produced byfermentation in cultures of Aureobasidium pullulan.Aureobasidin A acts as a tight-binding noncompetitive inhibitorof the enzyme inositol phosphorylceramide synthase(IPC synthase), which is an essential enzyme for fungalsphingolipid biosynthesis. A unique structural feature of theaureobasidins is the N-methylation of four of seven amide nitrogenatoms. The lack of tautomerism dictated by N-methylationmay contribute to forming a stable solution conformerthat is shaped somewhat like an arrowhead, the presumed biologicallyactive conformation of aureobasidin-A.The pradimycins and benanomycins are naphthacenequinonesthat bind mannan in the presence of Ca2+ to disrupt the cell membrane in pathogenic fungi. Both demonstrate good in vitro and in vivo activity againstCandida spp. and C. neoformans clinical isolates.

InChI:InChI=1/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46-,47+,48+,49+,50-/m1/s1

Upstream product

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• 182205-65-8 (S)-2-{(S)-2-[((2S,3R)-2-Amino-3-methyl-pentanoyl)-methyl-amino]-3-methyl-butyrylamino}-4-methyl-pentanoic acid benzyl ester 
• 182205-76-1 (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester 
• 182205-77-2 (2R,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester 
• 174602-83-6 (S)-2-[((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-methyl-amino]-3-phenyl-propionic acid benzyl ester 
• 182205-78-3 (S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyric acid (1R,2R)-1-[((S)-1-benzyloxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-2-methyl-butyl ester 
• 174602-84-7 (S)-1-{(S)-2-[((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-methyl-amino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid benzyl ester 
• 182205-72-7 (S)-3-Hydroxy-3-methyl-2-methylamino-butyric acid (1R,2R)-1-[((S)-1-benzyloxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-2-methyl-butyl ester 
• 1738-69-8 L-Leucine benzyl ester 
• 13139-16-7 Boc-L-aIle-OH 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 102507-13-1 N-(tert-butoxycarbonyl)-3-hydroxy-L-valine 

Relevant articles and documents

Studies towards the synthesis of radiolabeled R106-1(LY295337)

A unique semisynthetic pathway has been used as a route to acquire radiolabeled material of a complex natural product, R106. The retro-aldol reaction of R106-1 gave a key intermediate R106-sarcosine that was used in a subsequent aldol reaction to incorporate acetone-[2-14C].

NOVEL POLYMORPHS OF SAQUINAVIR

The present invention provides novel polymorphs of saquinavir, processes for their preparation and pharmaceutical compositions comprising them. The present invention also provides a process for purification of saquinavir. The present invention further provides a novel process for preparation of known saquinavir crystalline form I.

Oral dosage forms of water insoluble drugs and methods of making the same

A method of making an oral dosage form of a water insoluble drug such as Saquinavir or Cyclosporine or Paclitaxel is carried out by: (a) providing a single phase working Solution comprising or consisting essentially of an active agent, water, a water-soluble polymer, and a solvent, said solvent selected from the group consisting of alcohol, acetone, and mixtures thereof; and may or may not contain a surfactant and pH of the said working solution may or may not be adjusted (b) providing particles formed from a pharmaceutically acceptable core material; (c) combining, preferably by spraying, said working solution with said particles to produce active agent-coated particles; such drug loaded particles may contain an external coat (d) drying said active agent-coated particles; and (e) forming said dried particles into an oral dosage form. Dried particles produced by the process, oral dosage forms containing such particles, and methods of treatment therewith are also described.