TALISOMYCIN

Details

Stereochemistry	UNKNOWN
Molecular Formula	C68H110N22O27S2
Molecular Weight	1731.862
Optical Activity	UNSPECIFIED
Defined Stereocenters	23 / 26
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](O)[C@H](NC(=O)C[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)C1=NC(=NC(N)=C1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]3O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]3O)C4=CNC=N4)C(=O)NC(O[C@@H]5O[C@@H](C)[C@@H](N)[C@@H](O)[C@H]5O)C(O)C6=NC(=CS6)C7=NC(=CS7)C(=O)NCCCC(N)CC(=O)NCCCNCCCCN

InChI

InChIKey=VUPBDWQPEOWRQP-RIJHKAIISA-N

InChI=1S/C68H110N22O27S2/c1-25-42(87-57(89-55(25)74)31(16-38(72)95)81-18-30(71)56(75)105)59(107)88-44(52(32-19-78-24-82-32)114-67-54(48(101)45(98)36(20-91)113-67)115-66-50(103)53(116-68(76)110)46(99)37(21-92)112-66)61(109)83-26(2)35(94)17-40(97)86-43(27(3)93)60(108)90-62(117-65-49(102)47(100)41(73)28(4)111-65)51(104)64-85-34(23-119-64)63-84-33(22-118-63)58(106)80-13-7-9-29(70)15-39(96)79-14-8-12-77-11-6-5-10-69/h19,22-24,26-31,35-37,41,43-54,62,65-67,77,81,91-94,98-104H,5-18,20-21,69-71,73H2,1-4H3,(H2,72,95)(H2,75,105)(H2,76,110)(H,78,82)(H,79,96)(H,80,106)(H,83,109)(H,86,97)(H,88,107)(H,90,108)(H2,74,87,89)/t26-,27-,28+,29?,30+,31+,35+,36+,37-,41-,43+,44+,45-,46-,47-,48+,49-,50+,51?,52+,53+,54+,62?,65+,66-,67+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6174223 | https://adisinsight.springer.com/drugs/800000802

Talisomycin (former trivial name: tallysomycin A), a third generation bleomycin analog that was studied as an antitumor antibiotic. The drug cleaved DNA preferentially at G-C and G-T sequences and produced specific cleavages at G-A sequences. Talisomycin participated in phase II clinical trial for the treatment of cancer; however, the further development of the drug was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Comparison of the sequences at specific sites on DNA cleaved by the antitumor antibiotics talisomycin and bleomycin.	1982-04	6174223
Pulmonary toxicity studies of bleomycin and talisomycin.	1981-03-01	6165468
Preliminary studies of the pharmacokinetics of talisomycin in the rhesus monkey.	1981-03	6166971
Tallysomycin, a third generation bleomycin analog.	1981	6165058

Name

Type

Language

TALLYSOMYCIN A

Preferred Name

English

TALISOMYCIN

Official Name

English

talisomycin [INN]

Common Name

English

NSC-279496

Code

English

BU-2231A

Code

English

BLEOMYCINAMIDE, N1-(4-AMINO-6-((3-((4-AMINOBUTYL)AMINO)PROPYL)AMINO)-6-OXOHEXYL)-13-((4-AMINO-4,6-DIDEOXY-A-L-TALOPYRANOSYL)OXY)-19-DEMETHYL-12-HYDROXY-

Systematic Name

English

TALISOMYCIN [USAN]

Common Name

English

TALISOMYCIN A

Common Name

English

TALLYSOMYCIN A [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2311