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Caspofungin

Caspofungin

Synopsis, Chemistry

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Also known as: Cancidas, Caspofungin diacetate, 179463-17-3, Mk 0991, L 743872, Cancidas (tn)

Molecular Formula

C₅₆H₉₆N₁₀O₁₉

Molecular Weight

1213.4 g/mol

InChI Key

OGUJBRYAAJYXQP-LLXMLGLCSA-N

A cyclic lipopeptide echinocandin and beta-(1,3)-D-glucan synthase inhibitor that is used to treat internal or systemic MYCOSES.

1 2D Structure

Caspofungin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

acetic acid;N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-aminoethylamino)-3-[(1R)-3-amino-1-hydroxypropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamide

2.1.2 InChI

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;2*1-2(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);2*1H3,(H,3,4)/t28?,29?,30-,33-,34+,35+,36-,37+,38-,40+,41+,42+,43+,44+,45+,46+;;/m1../s1

2.1.3 InChI Key

OGUJBRYAAJYXQP-LLXMLGLCSA-N

2.1.4 Canonical SMILES

CCC(C)CC(C)CCCCCCCCC(=O)NC1CC(C(NC(=O)C2C(CCN2C(=O)C(NC(=O)C(NC(=O)C3CC(CN3C(=O)C(NC1=O)C(C)O)O)C(C(C4=CC=C(C=C4)O)O)O)C(CCN)O)O)NCCN)O.CC(=O)O.CC(=O)O

2.1.5 Isomeric SMILES

CCC(C)CC(C)CCCCCCCCC(=O)N[C@H]1C[C@H]([C@H](NC(=O)[C@@H]2[C@H](CCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)O)[C@@H]([C@H](C4=CC=C(C=C4)O)O)O)[C@@H](CCN)O)O)NCCN)O.CC(=O)O.CC(=O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Cancidas

2. Caspofungin

3. Caspofungin Msd

4. L 743,872

5. L 743872

6. L-743,872

7. L-743872

8. L743,872

9. L743872

10. Mk 0991

11. Mk-0991

12. Mk0991

2.2.2 Depositor-Supplied Synonyms

1. Cancidas

2. Caspofungin Diacetate

3. 179463-17-3

4. Mk 0991

5. L 743872

6. Cancidas (tn)

7. Mk-0991

8. Caspofungin Acetate- Bio-x

9. Schembl149293

10. L 743873

11. Chembl4297142

12. Caspofungin Acetate (jan/usan)

13. Mfcd08141839

14. Akos025401982

15. Ac-27763

16. Bc164293

17. D02501

18. F20901

19. 463c173

2.3 Create Date

2006-06-06

3 Chemical and Physical Properties

Molecular Formula	C₅₆H₉₆N₁₀O₁₉
Molecular Weight	1213.4 g/mol
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	22
Rotatable Bond Count	23
Exact Mass	1212.68532087 g/mol
Monoisotopic Mass	1212.68532087 g/mol
Topological Polar Surface Area	487 Å²
Heavy Atom Count	85
Formal Charge	0
Complexity	1930
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Caspofungin acetate
Active Ingredient	Caspofungin acetate
Dosage Form	Injectable
Route	injection
Strength	70mg/vial; 50mg/vial
Market Status	Tentative Approval
Company	Sandoz

2 of 2
Drug Name	Caspofungin acetate
Active Ingredient	Caspofungin acetate
Dosage Form	Injectable
Route	injection
Strength	70mg/vial; 50mg/vial
Market Status	Tentative Approval
Company	Sandoz

4.2 Drug Indication

- Treatment of invasive candidiasis in adult or paediatric patients.

- Treatment of invasive aspergillosis in adult or paediatric patients who are refractory to or intolerant of amphotericin B, lipid formulations of amphotericin B and/or itraconazole. Refractoriness is defined as progression of infection or failure to improve after a minimum of 7 days of prior therapeutic doses of effective antifungal therapy.

- Empirical therapy for presumed fungal infections (such as Candida or Aspergillus) in febrile, neutropaenic adult or paediatric patients.

Fungal infections

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Lipopeptides [CS]; Echinocandin Antifungal [EPC]

5.3 ATC Code

J02AX04