STALLIMYCIN

Possibly Marketed Outside US

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

Structure Search

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)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14754456 | https://www.ncbi.nlm.nih.gov/pubmed/23507040 | https://www.drugfuture.com/chemdata/stallimycin.html

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
		16650070
Congocidine and distamycin A, antipoxvirus antibiotics.	1972 Jun	4376908
Structure--activity relationships of pyrrole amidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain.	1979 Nov	230350
Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin.	1986 Jul	3027326
Inhibitors of human immunodeficiency virus integrase.	1993 Mar 15	8460151
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
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	8952492
Highly potent synthetic polyamides, bisdistamycins, and lexitropsins as inhibitors of human immunodeficiency virus type 1 integrase.	1998 Aug	9687569
Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1, 4]benzodiazepine and minor-groove-binding oligopyrrole carriers.	1999 Dec 16	10602698
Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: the oligo-1,3-thiazolecarboxamide derivatives.	2000 Nov	11137227
Antiviral activity of distamycin A against vaccinia virus is the result of inhibition of postreplicative mRNA synthesis.	2004 Feb	14747579
Binding of hybrid molecules containing pyrrolo [2,1-c][1,4]benzodiazepine (PBD) and oligopyrrole carriers to the human immunodeficiency type 1 virus TAR-RNA.	2004 Feb 1	15037192
Distamycin A and derivatives as synergic drugs in cisplatin-sensitive and -resistant ovarian cancer cells.	2012 Feb	21814787

Patents

Name

Type

Language

STALLIMYCIN

Official Name

English

N''-(2-AMIDINOETHYL)-4-FORMAMIDO-1,1',1''-TRIMETHYL-N,4':N',4''-TER(PYRROLE-2-CARBOXAMIDE)

Systematic Name

English

DISTAMYCIN A [MI]

Common Name

English

stallimycin [INN]

Common Name

English

1H-PYRROLE-2-CARBOXAMIDE, N-(5-(((3-AMINO-3-IMINOPROPYL)AMINO)CARBONYL)-1-METHYL-1H-PYRROL-3-YL)-4-(((4-(FORMYLAMINO)-1-METHYL-1H-PYRROL-2-YL)CARBONYL)AMINO)-1-METHYL-

Systematic Name

English

NSC-82150

Code

English

DISTAMYCIN A

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2115