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Chemistry

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Also known as: Ar-67, 220913-32-6, Db-67, Ar67, Db 67; silatecan, Db 67

Molecular Formula

C₂₆H₃₀N₂O₅Si

Molecular Weight

478.6 g/mol

InChI Key

XUSKJHCMMWAAHV-SANMLTNESA-N

FDA UNII

3YEA04NV6H

Silatecan AR-67 is a synthetic, highly lipophilic derivative of camptothecin, with potential antineoplastic and radiosensitizing activities. 7-tert-butyldimethylsilyl-10-hydroxycamptothecin binds to and stabilizes the topoisomerase I-DNA covalent complex. This inhibits the religation of topoisomerase I-mediated single-stranded DNA breaks and produces lethal double-stranded DNA breaks when encountered by the DNA replication machinery, thereby inhibiting DNA replication and inducing apoptosis. Camptothecin readily undergoes hydrolysis at physiological pH, changing its conformation from the active lactone structure to an inactive carboxylate form. Modifications on the E ring of camptothecin prevent binding of human serum albumin, which prefers the inactive carboxylate form, thereby enhancing the stability of the active lactone structure and resulting in prolonged agent activity. In addition, this agent sensitizes tumor cells toward radiation treatment.

1 2D Structure

Silatecan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(19S)-10-[tert-butyl(dimethyl)silyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

2.1.2 InChI

InChI=1S/C26H30N2O5Si/c1-7-26(32)18-11-20-21-16(12-28(20)23(30)17(18)13-33-24(26)31)22(34(5,6)25(2,3)4)15-10-14(29)8-9-19(15)27-21/h8-11,29,32H,7,12-13H2,1-6H3/t26-/m0/s1

2.1.3 InChI Key

XUSKJHCMMWAAHV-SANMLTNESA-N

2.1.4 Canonical SMILES

CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=C(C=CC(=C5)O)N=C4C3=C2)[Si](C)(C)C(C)(C)C)O

2.1.5 Isomeric SMILES

CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=C(C=CC(=C5)O)N=C4C3=C2)[Si](C)(C)C(C)(C)C)O

2.2 Other Identifiers

2.2.1 UNII

3YEA04NV6H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)- Dione, 11-((1,1-dimethylethyl)dimethylsilyl)-4-ethyl-4,9- Dihydroxy-, (4s)-

2. 7-t-butyldimethylsilyl-10-hydroxycamptothecin

3. 7-tert-butyldimethylsilyl-10-hydroxycamptothecin

4. Ar 67 Cpd

5. Ar-67 Cpd

6. Db 67

7. Db-67

2.3.2 Depositor-Supplied Synonyms

1. Ar-67

2. 220913-32-6

3. Db-67

4. Ar67

5. Db 67; Silatecan

6. Db 67

7. Nsc-708298

8. 3yea04nv6h

9. Db67

10. (s)-11-(tert-butyldimethylsilyl)-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

11. (20s)-7-t-butyldimethylsilyl-10-hydroxycamptothecin

12. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 11-((1,1-dimethylethyl)dimethylsilyl)-4-ethyl-4,9-dihydroxy-, (4s)-

13. Nci60_038363

14. Ar 67 Cpd

15. Ar-67 Cpd

16. Unii-3yea04nv6h

17. Chembl412309

18. Gtpl8919

19. Schembl1266162

20. Dtxsid00176592

21. Ar 67

22. Nsc708298

23. Zinc170020689

24. Compound 14 [pmid:11052802]

25. Db12384

26. Nsc 708298

27. Q27074492

28. (20s)-7-tert-butyldimethysilyl-10-hydroxycamptothecin

29. (19s)-10-[tert-butyl(dimethyl)silyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

30. 1h-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione, 11-[(1,1-dimethylethyl)dimethylsilyl]-4-ethyl-4,9-dihydroxy-, (4s)-

2.4 Create Date

2006-06-05

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₀N₂O₅Si
Molecular Weight	478.6 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	478.19239860 g/mol
Monoisotopic Mass	478.19239860 g/mol
Topological Polar Surface Area	100 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	982
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1