dactinomycin

Also known as Cosmegen, ActD, Actinomycin D, 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

Dactinomycin, also known as actinomycin D, is a chemotherapy medication used to treat a number of types of cancer. This includes Wilms tumor, rhabdomyosarcoma, Ewing's sarcoma, trophoblastic neoplasm, testicular cancer, and certain types of ovarian cancer. It is given by injection into a vein.

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

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

Mass: 1254.628

Show 5 more facts

chemical formula: C₆₂H₈₆N₁₂O₁₆
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

~5 min read

Article

8 sections

Contents

Medical use
Side effects
Mechanism
History
Research use
Biosynthesis
References
External links

Most people develop side effects. Common side effects include bone marrow suppression, vomiting, mouth ulcers, hair loss, liver problems, infections, and muscle pains. Other serious side effects include future cancers, allergic reactions, and tissue death if extravasation occurs. Use in pregnancy may harm the baby. Dactinomycin is in the cytotoxic antibiotic family of medications. It is believed to work by blocking the creation of RNA.