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Daptomycin
Also known as: 103060-53-3, Cubicin, Deptomycin, Cidecin, Daptomycine [french], Daptomycinum [latin]
Molecular Formula
C72H101N17O26
Molecular Weight
1620.7  g/mol
InChI Key
DOAKLVKFURWEDJ-OFNKPWESSA-N

A cyclic lipopeptide antibiotic that inhibits GRAM-POSITIVE BACTERIA.
1 2D Structure

Daptomycin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-3-[[(2S)-4-amino-2-[[(2S)-2-(decanoylamino)-3-(1H-indol-3-yl)propanoyl]amino]-4-oxobutanoyl]amino]-4-[[(3S,6S,9R,15S,18R,21S,24S)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-(1-carboxypropan-2-yl)-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacont-30-yl]amino]-4-oxobutanoic acid
2.1.2 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
2.1.3 InChI Key
DOAKLVKFURWEDJ-OFNKPWESSA-N
2.1.4 Canonical SMILES
CCCCCCCCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C
2.1.5 Isomeric SMILES
CCCCCCCCCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)NC3C(OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Cubicin

2. Daptomycin, 9 L Beta Aspartic Acid

3. Daptomycin, 9-l Beta-aspartic Acid

4. Deptomycin

5. Ly 146032

6. Ly-146032

7. Ly146032

2.2.2 Depositor-Supplied Synonyms

1. 103060-53-3

2. Cubicin

3. Deptomycin

4. Cidecin

5. Daptomycine [french]

6. Daptomycinum [latin]

7. Daptomicina [spanish]

8. Schembl1650768

9. Akos026750170

2.3 Create Date
2007-07-03
3 Chemical and Physical Properties
Molecular Weight 1620.7 g/mol
Molecular Formula C72H101N17O26
XLogP3-5.1
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count28
Rotatable Bond Count35
Exact Mass1619.71036639 g/mol
Monoisotopic Mass1619.71036639 g/mol
Topological Polar Surface Area702 Ų
Heavy Atom Count115
Formal Charge0
Complexity3480
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCubicin
PubMed HealthDaptomycin (Injection)
Drug ClassesAntibiotic
Drug LabelCUBICIN contains daptomycin, a cyclic lipopeptide antibacterial agent derived from the fermentation of Streptomyces roseosporus. The chemical name is N-decanoyl-L-tryptophyl-D-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L...
Active IngredientDaptomycin
Dosage FormInjectable
RouteIv (infusion)
Strength500mg/vial
Market StatusPrescription
CompanyCubist

2 of 4  
Drug NameDaptomycin
PubMed HealthDaptomycin (Injection)
Drug ClassesAntibiotic
Drug LabelCUBICIN contains daptomycin, a cyclic lipopeptide antibacterial agent derived from the fermentation of Streptomyces roseosporus. The chemical name is N-decanoyl-L-tryptophyl-D-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L...
Active IngredientDaptomycin
Dosage FormInjectable
Routeinjection; Iv (infusion)
Strength500mg/vial; 350mg
Market StatusTentative Approval; Prescription
CompanyHospira

3 of 4  
Drug NameCubicin
PubMed HealthDaptomycin (Injection)
Drug ClassesAntibiotic
Drug LabelCUBICIN contains daptomycin, a cyclic lipopeptide antibacterial agent derived from the fermentation of Streptomyces roseosporus. The chemical name is N-decanoyl-L-tryptophyl-D-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L...
Active IngredientDaptomycin
Dosage FormInjectable
RouteIv (infusion)
Strength500mg/vial
Market StatusPrescription
CompanyCubist

4 of 4  
Drug NameDaptomycin
PubMed HealthDaptomycin (Injection)
Drug ClassesAntibiotic
Drug LabelCUBICIN contains daptomycin, a cyclic lipopeptide antibacterial agent derived from the fermentation of Streptomyces roseosporus. The chemical name is N-decanoyl-L-tryptophyl-D-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L...
Active IngredientDaptomycin
Dosage FormInjectable
Routeinjection; Iv (infusion)
Strength500mg/vial; 350mg
Market StatusTentative Approval; Prescription
CompanyHospira

4.2 Drug Indication

Cubicin is indicated for the treatment of the following infections.

- Adult and paediatric (1 to 17 years of age) patients with complicated skin and soft-tissue infections (cSSTI).

- Adult patients with right-sided infective endocarditis (RIE) due to Staphylococcus aureus.

It is recommended that the decision to use daptomycin should take into account the antibacterial susceptibility of the organism and should be based on expert advice.

- Adult and paediatric (1 to 17 years of age) patients with Staphylococcus aureus bacteraemia (SAB). In adults, use in bacteraemia should be associated with RIE or with cSSTI, while in paediatric patients, use in bacteraemia should be associated with cSSTI.

Daptomycin is active against Gram positive bacteria only. In mixed infections where Gram negative and/or certain types of anaerobic bacteria are suspected, Cubicin should be co-administered with appropriate antibacterial agent(s). Consideration should be given to official guidance on the appropriate use of antibacterial agents.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Lipopeptides [CS]; Lipopeptide Antibacterial [EPC]
5.3 ATC Code

J01XX09


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XX - Other antibacterials

J01XX09 - Daptomycin


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  • POWDER;INTRAVENOUS - 350MG/VIAL
  • POWDER;INTRAVENOUS - 500MG/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
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