Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H27N9O4 |
| Molecular Weight | 481.5077 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=C(NC=O)C=C1C(=O)NC2=CN(C)C(=C2)C(=O)NC3=CN(C)C(=C3)C(=O)NCCC(N)=N
InChI
InChIKey=UPBAOYRENQEPJO-UHFFFAOYSA-N
InChI=1S/C22H27N9O4/c1-29-9-13(26-12-32)6-17(29)21(34)28-15-8-18(31(3)11-15)22(35)27-14-7-16(30(2)10-14)20(33)25-5-4-19(23)24/h6-12H,4-5H2,1-3H3,(H3,23,24)(H,25,33)(H,26,32)(H,27,35)(H,28,34)
Stallimycin also known as distamycin A is an antibacterial and antitumor compound. It is able to bind to the minor groove of double-stranded B-DNA in a non intercalative manner, where it forms strong reversible complex preferentially at the nucleotide sequences consisting of 4-5 adjacent AT base pairs. The pyrrole-amide skeleton of distamycin A has been also used as DNA sequence selective vehicles for the delivery of alkylating functions to DNA targets, leading to a sharp increase of its cytotoxicity, in comparison to that, very weak, of distamycin itself.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Congocidine and distamycin A, antipoxvirus antibiotics. | 1972 Jun |
|
| Structure--activity relationships of pyrrole amidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain. | 1979 Nov |
|
| Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin. | 1986 Jul |
|
| Inhibitors of human immunodeficiency virus integrase. | 1993 Mar 15 |
|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
|
| Linked lexitropsins and the in vitro inhibition of HIV-1 reverse transcriptase RNA-directed DNA polymerization: a novel induced-fit of 3,5 m-pyridyl bisdistamycin to enzyme-associated template-primer. | 1996 Dec 3 |
|
| Highly potent synthetic polyamides, bisdistamycins, and lexitropsins as inhibitors of human immunodeficiency virus type 1 integrase. | 1998 Aug |
|
| Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: the oligo-1,3-thiazolecarboxamide derivatives. | 2000 Nov |
|
| Antiviral activity of distamycin A against vaccinia virus is the result of inhibition of postreplicative mRNA synthesis. | 2004 Feb |
|
| Distamycin A and derivatives as synergic drugs in cisplatin-sensitive and -resistant ovarian cancer cells. | 2012 Feb |
Patents
| Name | Type | Language | ||
|---|---|---|---|---|
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Official Name | English | ||
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Systematic Name | English | ||
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Code | English | ||
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C2115
Created by
admin on Sat Dec 16 15:46:50 UTC 2023 , Edited by admin on Sat Dec 16 15:46:50 UTC 2023
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NCI_THESAURUS |
C446
Created by
admin on Sat Dec 16 15:46:50 UTC 2023 , Edited by admin on Sat Dec 16 15:46:50 UTC 2023
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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100000083833
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PRIMARY | |||
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80O63P88IS
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636-47-5
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PRIMARY | |||
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82150
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PRIMARY | |||
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DTXSID9045637
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PRIMARY | |||
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SUB10640MIG
Created by
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PRIMARY | |||
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C1517
Created by
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PRIMARY | |||
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3346
Created by
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PRIMARY | |||
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3553
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PRIMARY | |||
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CHEMBL11252
Created by
admin on Sat Dec 16 15:46:50 UTC 2023 , Edited by admin on Sat Dec 16 15:46:50 UTC 2023
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PRIMARY | |||
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m4674
Created by
admin on Sat Dec 16 15:46:50 UTC 2023 , Edited by admin on Sat Dec 16 15:46:50 UTC 2023
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PRIMARY | Merck Index | ||
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C030000
Created by
admin on Sat Dec 16 15:46:50 UTC 2023 , Edited by admin on Sat Dec 16 15:46:50 UTC 2023
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PRIMARY | |||
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3115
Created by
admin on Sat Dec 16 15:46:50 UTC 2023 , Edited by admin on Sat Dec 16 15:46:50 UTC 2023
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PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
