Caspofungin

Caspofungin
Clinical data
Pronunciation	/ˌkæspoʊˈfʌndʒɪn/ KAS-poh-FUN-jin
Trade names	Cancidas
Other names	(4R,5S)-5-[(2-Aminoethyl)amino]-N2-(10,12-dimethyltetradecanoyl)-; 4-hydroxy-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-threo-3-hydroxy-L-ornithyl-trans-3-hydroxy-L-proline cyclic (6→1)-peptide; 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
AHFS/Drugs.com	Monograph
MedlinePlus	a615001
License data	US DailyMed: Caspofungin;
Pregnancy; category	AU: B3;
Routes of; administration	Intravenous
ATC code	J02AX04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% (intravenous use only)
Protein binding	~97%
Metabolism	Peptide hydrolysis, N-acetylation
Elimination half-life	9–11 hours
Excretion	Kidney (41%), feces (35%)
Identifiers
	IUPAC name (10R,12S)-N-{(2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-[(2-Aminoethyl)amino]-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l] [1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-10,12-dimethyltetradecanamide;
CAS Number	162808-62-0 ; as acetate: 179463-17-3;
PubChem CID	16119814; as acetate: 16119813;
DrugBank	DB00520 ; as acetate: DB00520;
ChemSpider	17277006; as acetate: 5254092;
UNII	F0XDI6ZL63; as acetate: VUW370O5QE ;
KEGG	D07626 ; as acetate: D02501;
ChEBI	CHEBI:474180 ;
ChEMBL	ChEMBL499808 ; as acetate: ChEMBL4297142;
CompTox Dashboard (EPA)	DTXSID30873204 ;
Chemical and physical data
Formula	C52H88N10O15
Molar mass	1093.331 g·mol−1
3D model (JSmol)	Interactive image; as acetate: Interactive image;
	SMILES [C@@]12(N(C[C@@H](C1)O)C([C@H]([C@@H](C)O)NC(=O)[C@](C[C@H]([C@@H](NCCN)NC([C@@H]3[C@H](CCN3C([C@H]([C@@H](CCN)O)NC(=O)[C@H]([C@@H]([C@H](C4=CC=C(C=C4)O)O)O)NC2=O)=O)O)=O)O)(NC(CCCCCCCC[C@H](C[C@H](CC)C)C)=O)[H])=O)[H]; ; as acetate: CC(O)=O.CC(O)=O.[H][C@@]12C[C@@H](O)CN1C(=O)[C@@H](NC(=O)[C@]([H])(C[C@@H](O)[C@@H](NCCN)NC(=O)[C@@H]1[C@@H](O)CCN1C(=O)[C@@H](NC(=O)[C@@H](NC2=O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@H](O)CCN)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@@H](C)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-/m0/s1 ; Key:JYIKNQVWKBUSNH-WVDDFWQHSA-N ; ; as acetate: InChI=1S/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;21-2(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);21H3,(H,3,4)/t28-,29+,30+,33+,34-,35-,36+,37-,38+,40-,41-,42-,43-,44-,45-,46-;;/m0../s1; Key:OGUJBRYAAJYXQP-IJFZAWIJSA-N;
	(what is this?)

Caspofungin (INN;^[1]^[5] brand name Cancidas) is a lipopeptide antifungal drug from Merck & Co., Inc.^[6] It is a member of a class of antifungals termed the echinocandins. It works by inhibiting the enzyme (1→3)-β-D-glucan synthase and thereby disturbing the integrity of the fungal cell wall.

Caspofungin was the first inhibitor of fungal (1→3)-β-D-glucan synthesis to be approved by the United States Food and Drug Administration.^[7] Caspofungin is administered intravenously.^[2] It is on the World Health Organization's List of Essential Medicines.^[8]

^ ^a ^b "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names (Rec.INN): List 42" (PDF). World Health Organization. 1999. Retrieved 11 November 2016.
^ ^a ^b ^c "Cancidas- caspofungin acetate injection, powder, lyophilized, for solution". DailyMed. 20 November 2023. Retrieved 20 March 2024.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ Gubbins PO, Anaissie EJ (January 2009). "CHAPTER 7 - Antifungal therapy". In Anaissie EJ, McGinnis MR, Pfaller MA (eds.). Clinical Mycology (Second ed.). Edinburgh: Churchill Livingstone. pp. 161–195. doi:10.1016/B978-1-4160-5680-5.00007-4. ISBN 978-1-4160-5680-5.
^ European Medicines Agency's list of authorised medicines for human use (C) Archived 17 October 2007 at the Wayback Machine
^ US 5378804, Balkovec JM, Black RM, Bouffard FA, "Aza cyclohexapeptide compounds", issued 3 January 1995, assigned to Merck Sharp and Dohme LLC
^ Deresinski SC, Stevens DA (June 2003). "Caspofungin". Clinical Infectious Diseases. 36 (11): 1445–57. doi:10.1086/375080. PMID 12766841.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[INN-1] "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names (Rec.INN): List 42" (PDF). World Health Organization. 1999. Retrieved 11 November 2016.

[Cancidas_FDA_label-2] "Cancidas- caspofungin acetate injection, powder, lyophilized, for solution". DailyMed. 20 November 2023. Retrieved 20 March 2024.

[3] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[4] Gubbins PO, Anaissie EJ (January 2009). "CHAPTER 7 - Antifungal therapy". In Anaissie EJ, McGinnis MR, Pfaller MA (eds.). Clinical Mycology (Second ed.). Edinburgh: Churchill Livingstone. pp. 161–195. doi:10.1016/B978-1-4160-5680-5.00007-4. ISBN 978-1-4160-5680-5.

[5] European Medicines Agency's list of authorised medicines for human use (C) Archived 17 October 2007 at the Wayback Machine

[US5378804-6] US 5378804, Balkovec JM, Black RM, Bouffard FA, "Aza cyclohexapeptide compounds", issued 3 January 1995, assigned to Merck Sharp and Dohme LLC

[Deresinski_2003-7] Deresinski SC, Stevens DA (June 2003). "Caspofungin". Clinical Infectious Diseases. 36 (11): 1445–57. doi:10.1086/375080. PMID 12766841.

[WHO23rd-8] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

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