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CHEMISTRY
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8 Drugs in Development

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Chemistry

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Also known as: Vi79rd8vnn, 236095-26-4, Gpx-150, Gpx150, Unii-vi79rd8vnn, Camsirubicin [inn]

Molecular Formula

C₂₇H₃₂N₂O₉

Molecular Weight

528.5 g/mol

InChI Key

GNCWGPLZJLZZPI-KUIJCEFOSA-N

FDA UNII

VI79RD8VNN

Camsirubicin is a synthetic non-cardiotoxic analogue of the anthracycline antibiotic doxorubicin with potential antineoplastic activity. Camsirubicin intercalates DNA and impedes the activity of topoisomerase II, inducing single and double-stranded breaks in DNA; inhibiting DNA replication and/or repair, transcription, and protein synthesis; and activating tumor cell apoptosis.

1 2D Structure

Camsirubicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,10S)-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one

2.1.2 InChI

InChI=1S/C27H32N2O9/c1-11-23(31)14(28)8-17(37-11)38-16-10-27(35,6-7-30)9-13-19(16)26(34)20-21(25(13)33)24(32)12-4-3-5-15(36-2)18(12)22(20)29/h3-5,11,14,16-17,23,29-31,33-35H,6-10,28H2,1-2H3/t11-,14-,16-,17-,23+,27-/m0/s1

2.1.3 InChI Key

GNCWGPLZJLZZPI-KUIJCEFOSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=N)C(=CC=C5)OC)O)(CCO)O)N)O

2.1.5 Isomeric SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=N)C(=CC=C5)OC)O)(CCO)O)N)O

2.2 Other Identifiers

2.2.1 UNII

VI79RD8VNN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-imino-13-deoxydoxorubicin

2. Gpx-150

2.3.2 Depositor-Supplied Synonyms

1. Vi79rd8vnn

2. 236095-26-4

3. Gpx-150

4. Gpx150

5. Unii-vi79rd8vnn

6. Camsirubicin [inn]

7. Camsirubicin [who-dd]

8. 5-imino-13-deoxydoxorubicin

9. (8r,10s)-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-5(8h)-naphthacenone

10. (8r,10s)-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxohexopyranosyl) Oxy)-6,8,11-trihydroxy-8-(2-hydroxyethyl)- 12-imino-1-methoxy-7,9,10,12-tetrahydrotetracen-5(8h)- One

11. 5(8h)-naphthacenone, 10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-, (8r,10s)-

12. 5(8h)-naphthacenone, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-, (8r,10s)-

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₂N₂O₉
Molecular Weight	528.5 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	5
Exact Mass	528.21078060 g/mol
Monoisotopic Mass	528.21078060 g/mol
Topological Polar Surface Area	196 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	906
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1