Daptomycin

Daptomycin
Daptomycin
	1. Daptomycin binds and inserts into the cell membrane. 2. It aggregates in the membrane. 3. It alters the shape of the membrane to form a hole, allowing ions in and out of the cell easily.
Identifiers
Symbol	N/A
TCDB	1.D.15
OPM superfamily	163
OPM protein	1t5n

Daptomycin
Clinical data
Trade names	Cubicin, Cubicin RF, Dapzura RT
Other names	LY 146032
AHFS/Drugs.com	Monograph
License data	US DailyMed: Daptomycin;
Pregnancy; category	AU: B1;
Routes of; administration	Intravenous
ATC code	J01XX09 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	n/a
Protein binding	90–95%
Elimination half-life	7–11 hours (up to 28 hours in renal impairment)
Excretion	Kidney (78%; primarily as unchanged drug); faeces (5.7%)
Identifiers
	IUPAC name N-Decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine[egr]1-lactone;
CAS Number	103060-53-3 ;
PubChem CID	16129629;
DrugBank	DB00080 ;
ChemSpider	10482098 ;
UNII	NWQ5N31VKK;
KEGG	D01080 ;
ChEBI	CHEBI:600103 ;
ChEMBL	ChEMBL508162 ;
CompTox Dashboard (EPA)	DTXSID1041009 ;
ECHA InfoCard	100.116.065
Chemical and physical data
Formula	C72H101N17O26
Molar mass	1620.693 g·mol−1
	InChI InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1 --> ; Key:DOAKLVKFURWEDJ-RWDRXURGSA-N ;
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Daptomycin, sold under the brand name Cubicin among others, is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms.^[4]

Daptomycin was removed from the World Health Organization's List of Essential Medicines in 2019.^[7]^[8] The World Health Organization classifies daptomycin as critically important for human medicine.^[9]

^ "Daptomycin Use During Pregnancy". Drugs.com. 3 December 2019. Retrieved 28 August 2020.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Cubicin 350 mg powder for solution for injection or infusion - Summary of Product Characteristics (SmPC)". (emc). 24 August 2018. Retrieved 28 August 2020.
^ ^a ^b "Cubicin- daptomycin injection, powder, lyophilized, for solution". DailyMed. 18 December 2018. Retrieved 28 August 2020.
^ "Cubicin RF- daptomycin injection, powder, lyophilized, for solution". DailyMed. 18 December 2018. Retrieved 28 August 2020.
^ "Cubicin". European Medicines Agency. 17 September 2018. Retrieved 28 August 2020.
^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.
^ World Health Organization (2019). The selection and use of essential medicines: report of the WHO Expert Committee on Selection and Use of Essential Medicines, 2019 (including the 21st WHO Model List of Essential Medicines and the 7th WHO Model List of Essential Medicines for Children). Geneva: World Health Organization. hdl:10665/330668. ISBN 9789241210300. ISSN 0512-3054. WHO technical report series;1021.
^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

[Drugs.com_pregnancy-1] "Daptomycin Use During Pregnancy". Drugs.com. 3 December 2019. Retrieved 28 August 2020.

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

[3] "Cubicin 350 mg powder for solution for injection or infusion - Summary of Product Characteristics (SmPC)". (emc). 24 August 2018. Retrieved 28 August 2020.

[Cubicin_FDA_label-4] "Cubicin- daptomycin injection, powder, lyophilized, for solution". DailyMed. 18 December 2018. Retrieved 28 August 2020.

[5] "Cubicin RF- daptomycin injection, powder, lyophilized, for solution". DailyMed. 18 December 2018. Retrieved 28 August 2020.

[6] "Cubicin". European Medicines Agency. 17 September 2018. Retrieved 28 August 2020.

[WHO21st-7] World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.

[8] World Health Organization (2019). The selection and use of essential medicines: report of the WHO Expert Committee on Selection and Use of Essential Medicines, 2019 (including the 21st WHO Model List of Essential Medicines and the 7th WHO Model List of Essential Medicines for Children). Geneva: World Health Organization. hdl:10665/330668. ISBN 9789241210300. ISSN 0512-3054. WHO technical report series;1021.

[9] World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

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