Actinomycin D

Also known as Cosmegen, ActD, 2-amino-N,N'-bis(hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo(2,1-I)(1,4,7,10,13)oxatetra-azacyclohexadecin-10-yl)-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide, Actinomycin iv, Meractinomycin, Actinomycin C1, GNF-Pf-1977

chemische Verbindung

In the Vinony graph

Vinony's link graph records 348 inbound references to Actinomycin D, and connects out to chemotherapy, intravenous infusion and defusion and nephroblastoma.

It is catalogued under topics including Cyclic peptides, Depsipeptides and DNA intercalaters.

Vinony links it to 27 Wikipedia language editions.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 477241639
Drug.IUPAC_name: 2-Amino-N,''- bis[(6S,9R,10S,13R,18aS)-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,11,14-pentaoxohexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-4,6-dimethyl-3-oxo-3H''-phenoxazine-1,9-dicarboxamide
Drug.image: Actinomycin C1.svg
Drug.image_class: skin-invert-image
Drug.image2: Actinomycin D sticks.png
Drug.image_class2: bg-transparent
Drug.tradename: Cosmegen
Drug.MedlinePlus: a682224
Drug.pregnancy_AU: D
Drug.pregnancy_US: D
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.routes_of_administration: IV
Drug.protein_bound: 5%

via Wikipedia infobox

Chemical data

Formula: C62H86N12O16
Molecular weight: 1255.4 g/mol
IUPAC name: 2-amino-4,6-dimethyl-3-oxo-1-N,9-N-bis[(3R,6S,7R,10S,16S)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]phenoxazine-1,9-dicarboxamide
SMILES: C[C@@H]1[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N(CC(=O)N([C@H](C(=O)O1)C(C)C)C)C)C(C)C)NC(=O)C3=C4C(=C(C=C3)C)OC5=C(C(=O)C(=C(C5=N4)C(=O)N[C@H]6[C@H](OC(=O)[C@@H](N(C(=O)CN(C(=O)[C@@H]7CCCN7C(=O)[C@H](NC6=O)C(C)C)C)C)C(C)C)C)N)C
InChIKey: RJURFGZVJUQBHK-IIXSONLDSA-N
XLogP: 3.8
Polar surface area: 356 Å²
H-bond donors: 5
H-bond acceptors: 18
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 1964
Admin. routes: parenteral
Indications: Ewing sarcoma, alveolar rhabdomyosarcoma, embryonal rhabdomyosarcoma, leukemia

via ChEMBL · EBI

Research

19,514 papers

Dactinomycin potentiation of radiation pneumonitis: a forgotten interaction.Pediatric hematology and oncology · 1991
Dactinomycin in acute myeloid leukemia with NPM1 mutations.European journal of haematology · 2020
Dactinomycin.The Medical letter on drugs and therapeutics · 1965
Correction: Dactinomycin dose.Annals of internal medicine · 1983
[Importance of dactinomycin in the current therapy of tumors].Antibiotiki i meditsinskaia biotekhnologiia = Antibiotics and medical biotechnology · 1985

via PubMed

Wikidata facts

Has part: nitrogen
Mass: 1254.628
Has use: medication

Show 7 more facts

chemical formula: C₆₂H₈₆N₁₂O₁₆
medical condition treated: Ewing sarcoma
subject has role: essential medicine
isomeric SMILES: C[C@@H]1[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N(CC(=O)N([C@H](C(=O)O1)C(C)C)C)C)C(C)C)NC(=O)C3=C4C(=C(C=C3)C)OC5=C(C(=O)C(=C(C5=N4)C(=O)N[C@H]6[C@H](OC(=O)[C@@H](N(C(=O)CN(C(=O)[C@@H]7CCCN7C(=O)[C@H](NC6=O)C(C)C)C)C)C(C)C)C)N)C
canonical SMILES: CC1C(C(=O)NC(C(=O)N2CCCC2C(=O)N(CC(=O)N(C(C(=O)O1)C(C)C)C)C)C(C)C)NC(=O)C3=C4C(=C(C=C3)C)OC5=C(C(=O)C(=C(C5=N4)C(=O)NC6C(OC(=O)C(N(C(=O)CN(C(=O)C7CCCN7C(=O)C(NC6=O)C(C)C)C)C)C(C)C)C)N)C
Commons category: Dactinomycin
stylized name: DACTINomycin

Sources (9)

via Wikidata · CC0

Article · Deutsch

Actinomycin D oder Dactinomycin (Handelsnamen Lyovac-Cosmegen, Cosmegen (EU); Hersteller: MSD) ist ein Zytostatikum zur Behandlung von Krebserkrankungen. Es gehört zur Gruppe der zytotoxischen Antibiotika (genannt auch Tumorantibiotika). Seine antineoplastische Wirkung wird durch die Bindung an DNA vermittelt, wo Actinomycin D die RNA-Synthese hemmt.

Abstract from DBpedia / Wikipedia · CC BY-SA