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    Chemistry

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    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
    Daptomycin
    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

    API Reference Price

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    10-Feb-2021
    21-Oct-2024
    KGS
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