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Details

Stereochemistry ABSOLUTE
Molecular Formula C47H73NO17.C27H46O4S
Molecular Weight 1390.796
Optical Activity UNSPECIFIED
Defined Stereocenters 27 / 27
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPHOTERICIN B CHOLESTERYL SULFATE

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCCC(C)C.[H][C@]56C[C@@H](O[C@]7([H])O[C@H](C)[C@@H](O)[C@H](N)[C@@H]7O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]5C(O)=O)O6

InChI

InChIKey=PCTMTFRHKVHKIS-BMFZQQSSSA-N
InChI=1S/C47H73NO17.C27H46O4S/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56;1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60);9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+;/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+;19-,21+,22+,23-,24+,25+,26+,27-/m01/s1

HIDE SMILES / InChI

Molecular Formula C47H73NO17
Molecular Weight 924.079
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C27H46O4S
Molecular Weight 466.717
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

AMPHOTERICIN B CHOLESTERYL SULFATE COMPLEX (AMPHOTEC) is an antifungal medicine. AMPHOTEC® is a sterile, pyrogen-free, lyophilized powder for reconstitution and intravenous (IV) administration. AMPHOTEC consists of a 1:1 (molar ratio) complex of amphotericin B and cholesteryl sulfate. AMPHOTEC is indicated for the treatment of invasive aspergillosis in patients where renal impairment or unacceptable toxicity precludes the use of amphotericin B deoxycholate in effective doses, and in patients with invasive aspergillosis where prior amphotericin B deoxycholate therapy has failed. The active ingredient of AMPHOTEC, amphotericin B, is a polyene antibiotic that acts by binding to sterols (primarily ergosterol) in cell membranes of sensitive fungi, with subsequent leakage of intracellular contents and cell death due to changes in membrane permeability. Amphotericin B also binds to the sterols (primarily cholesterol) in mammalian cell membranes, which is believed to account for its toxicity in animals and humans. AMPHOTEC is active against Aspergillus spp (A. fumigatus, A. flavus), Candida spp (C. albicans, C. krusei, C. parapsilosis, C. tropicalis), Cryptococcus neoformans, and Blastomyces dermatitidis. Active against most fungi with the notable exceptions of Candida lusitaniae, Trichosporon beigelii, Aspergillus terreus (some isolates), Pseudallescheria boydii, Malassezia furfur and Fusarium spp. The lipid formulations are designed to reduce binding of amphotericin to mammalian cell membranes, therefore reducing toxicities.

Approval Year

PubMed

PubMed

TitleDatePubMed
Comparison of amphotericin B and N-D-ornithyl amphotericin B methyl ester in experimental cryptococcal meningitis and Candida albicans endocarditis with pyelonephritis.
1985 Dec
Serum pharmacology of amphotericin B applied in lipid emulsions.
1997 Apr
Comparative in vitro antifungal susceptibility activity of amphotericin B versus amphotericin B methyl ester against Candida albicans ocular isolates.
2012 Dec
In vitro efficacy of liposomal amphotericin B, micafungin and fluconazole against non-albicans Candida species biofilms.
2015 Sep
Patents

Sample Use Guides

The recommended dose for adults and pediatric patients is 3 - 4 mg/kg as required, once a day. AMPHOTEC, reconstituted in Sterile Water for Injection, is administered diluted in 5% Dextrose for Injection by intravenous infusion at a rate of 1 mg/kg/hour. A test dose immediately preceding the first dose is advisable when commencing all new courses of treatment. A small amount of drug (e.g., 10 mL of the final preparation containing between 1.6 to 8.3 mg) should be infused over 15 to 30 minutes and the patient carefully observed for the next 30 minutes.
Route of Administration: Intravenous
Amphotericin B cholesteryl sulfate (AMPHOTEC) is active in vitro against Aspergillus and Candida species. One hundred and twelve clinical isolates of four different Aspergillus species and 88 clinical isolates of five different Candida species were tested, with a majority of minimum inhibitory concentrations (MICs) < 1 ug/mL
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:57:24 GMT 2023
Edited
by admin
on Sat Dec 16 06:57:24 GMT 2023
Record UNII
774X4698X3
Record Status Validated (UNII)
Record Version
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Name Type Language
AMPHOTERICIN B CHOLESTERYL SULFATE
VANDF  
Common Name English
AMPHOTERICIN B COMPD WITH (3.BETA.)-CHOLEST-5-EN-3-YL HYDROGEN SULFATE (1:1
Common Name English
AMPHOTERICIN B COMPD WITH CHOLESTERYL SULFATE [MI]
Common Name English
Amphotericin b cholesteryl sulfate complex [WHO-DD]
Common Name English
AMPHOTERICIN B, COMPD. WITH (3.BETA.)-CHOLEST-5-EN-3-YL HYDROGEN SULFATE (1:1:1)
Common Name English
AMPHOTERICIN B CHOLESTERYL SULFATE COMPLEX
WHO-DD  
Common Name English
AMPHOTERICIN B CHOLESTERYL SULFATE [VANDF]
Common Name English
AMPHOCIL
Brand Name English
ABCD
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT000993
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY
EVMPD
SUB126972
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY
FDA UNII
774X4698X3
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY
MERCK INDEX
m1852
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID50153055
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY
PUBCHEM
9877168
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY
CAS
120895-52-5
Created by admin on Sat Dec 16 06:57:24 GMT 2023 , Edited by admin on Sat Dec 16 06:57:24 GMT 2023
PRIMARY