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

Molecular Formula	C22H27N9O4
Molecular Weight	481.5077
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Distamycin A and derivatives as synergic drugs in cisplatin-sensitive and -resistant ovarian cancer cells.	2012-02	21814787
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.	2004-02-01	15037192
Antiviral activity of distamycin A against vaccinia virus is the result of inhibition of postreplicative mRNA synthesis.	2004-02	14747579
Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: the oligo-1,3-thiazolecarboxamide derivatives.	2000-11	11137227
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.	1999-12-16	10602698
Highly potent synthetic polyamides, bisdistamycins, and lexitropsins as inhibitors of human immunodeficiency virus type 1 integrase.	1998-08	9687569
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.	1996-12-03	8952492
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993-09-24	8402886
Inhibitors of human immunodeficiency virus integrase.	1993-03-15	8460151
Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin.	1986-07	3027326
Structure--activity relationships of pyrrole amidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain.	1979-11	230350
Congocidine and distamycin A, antipoxvirus antibiotics.	1972-06	4376908

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:51:44 GMT 2025` Edited by `admin` on `Wed Apr 02 06:51:44 GMT 2025`
Record UNII	80O63P88IS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STALLIMYCIN

Official Name

English

DISTAMYCIN A

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C2115