Anidulafungin

Anidulafungin
Clinical data
Pronunciation	/eɪˌnɪdjʊləˈfʌndʒɪn/ ay-NID-yuu-lə-FUN-jin
Trade names	Eraxis, others
Other names	LY303366, (4R,5S)-4,5-Dihydroxy-N2-[[4''-(pentyloxy)-p-terphenyl-4-yl]carbonyl]-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline cyclic (6→1)-peptide; 1-[(4R,5R)-4,5-Dihydroxy-N2-[[4''-(pentyloxy)[1',1':4',1''-terphenyl]-4-yl]carbonyl]-L-ornithine]echinocandin B
AHFS/Drugs.com	Monograph
License data	US DailyMed: Anidulafungin;
Routes of; administration	Intravenous
ATC code	J02AX06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% (intravenous use only)
Protein binding	Extensive (>99%)
Metabolism	Hepatic metabolism not observed, CYP system not involved
Elimination half-life	27 hours; 40–50 hours (terminal)
Excretion	Feces (~30%), urine (<1%)
Identifiers
	IUPAC name N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2R)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.09,13]heptacosan-18-yl]- 4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide;
CAS Number	166663-25-8 ;
PubChem CID	166548;
DrugBank	DB00362 ;
ChemSpider	21106258 ;
UNII	9HLM53094I;
KEGG	D03211 ;
ChEBI	CHEBI:55346 ;
ChEMBL	ChEMBL1630215 ;
CompTox Dashboard (EPA)	DTXSID50873201 ;
ECHA InfoCard	100.184.856
Chemical and physical data
Formula	C58H73N7O17
Molar mass	1140.254 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCOc1ccc(cc1)c2ccc(cc2)c3ccc(cc3)C(=O)N[C@H]6C[C@@H](O)[C@@H](O)NC(=O)C4[C@@H](O)[C@@H](C)CN4C(=O)C(NC(=O)C(NC(=O)C5C[C@@H](O)CN5C(=O)C(NC6=O)[C@@H](C)O)[C@@H](O)[C@H](O)c7ccc(O)cc7)[C@@H](C)O;
	InChI InChI=1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42?,43+,44?,45?,46?,47?,48-,49+,50+,54+/m0/s1 ; Key:JHVAMHSQVVQIOT-QZNDWXLFSA-N ;
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Anidulafungin (INN)^: 42 (sold under the brand name Eraxis among others, is a semisynthetic echinocandin used as an antifungal medication. It may also have application in treating invasive Aspergillus infection when used in combination with voriconazole. It is a member of the class of antifungal drugs known as the echinocandins; its mechanism of action is by inhibition of (1→3)-β-D-glucan synthase, an enzyme important to the synthesis of the fungal cell wall.

It is on the World Health Organization's List of Essential Medicines.

Clinical data

Pronunciation	/eɪˌnɪdjʊləˈfʌndʒɪn/ ay-NID-yuu-lə-FUN-jin
Trade names	Eraxis, others
Other names	LY303366, (4R,5S)-4,5-Dihydroxy-N²-[[4''-(pentyloxy)-p-terphenyl-4-yl]carbonyl]-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline cyclic (6→1)-peptide 1-[(4R,5R)-4,5-Dihydroxy-N²-[[4''-(pentyloxy)[1',1':4',1''-terphenyl]-4-yl]carbonyl]-L-ornithine]echinocandin B
AHFS/Drugs.com	Monograph
License data	US DailyMed: Anidulafungin
Routes of administration	Intravenous
ATC code	J02AX06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	100% (intravenous use only)
Protein binding	Extensive (>99%)
Metabolism	Hepatic metabolism not observed, CYP system not involved
Elimination half-life	27 hours; 40–50 hours (terminal)
Excretion	Feces (~30%), urine (<1%)
Identifiers
IUPAC name N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2R)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^9,13]heptacosan-18-yl]- 4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide
CAS Number	166663-25-8^Y
PubChem CID	166548
DrugBank	DB00362^Y
ChemSpider	21106258^Y
UNII	9HLM53094I
KEGG	D03211^N
ChEBI	CHEBI:55346^N
ChEMBL	ChEMBL1630215^N
CompTox Dashboard (EPA)	DTXSID50873201
ECHA InfoCard	100.184.856
Chemical and physical data
Formula	C₅₈H₇₃N₇O₁₇
Molar mass	1140.254 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCOc1ccc(cc1)c2ccc(cc2)c3ccc(cc3)C(=O)N[C@H]6C[C@@H](O)[C@@H](O)NC(=O)C4[C@@H](O)[C@@H](C)CN4C(=O)C(NC(=O)C(NC(=O)C5C[C@@H](O)CN5C(=O)C(NC6=O)[C@@H](C)O)[C@@H](O)[C@H](O)c7ccc(O)cc7)[C@@H](C)O
InChI InChI=1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42?,43+,44?,45?,46?,47?,48-,49+,50+,54+/m0/s1^Y Key:JHVAMHSQVVQIOT-QZNDWXLFSA-N^Y
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