Dactinomycin

Title: Dactinomycin
CAS Registry Number: 50-76-0
CAS Name: Actinomycin D
Additional Names: actinomycin-[thr-val-pro-sar-meval]; meractinomycin; actinomycin AIV; actinomycin IV; actinomycin C1; actinomycin I1; actinomycin X1
Manufacturers' Codes: NSC-3053
Trademarks: Cosmegen (Merck & Co.)
Molecular Formula: C62H86N12O16
Molecular Weight: 1255.42
Percent Composition: C 59.32%, H 6.90%, N 13.39%, O 20.39%
Literature References: Antibiotic substance belonging to the actinomycin complex, produced by several Streptomyces spp. Historical background of actinomycins and chemistry, toxicology, pharmacology of actinomycin D: Ann. N.Y. Acad. Sci. 89, 285-485 (1960). Isoln from broth cultures of S. parvulus: Manaker et al., Antibiot. Ann. 1954/55, 853. Structure: Bullock, Johnson, J. Chem. Soc. 1957, 3280. Synthesis: Brockmann, Manegold, Naturwissenschaften 51, 383 (1964); Brockmann, Lackner, ibid. 384, 435 (1964); Brockmann et al., DE 1172680 (1964 to Bayer); eidem, Ber. 101, 1312 (1968); Meienhofer, J. Am. Chem. Soc. 92, 3771 (1970); T. Tanaka et al., Bull. Chem. Soc. Jpn. 53, 1352 (1980); K. Nakajima et al., Pept. Chem. 19, 143-148 (1981). Conformation from NMR: Conti, DeSantis, Nature 227, 1239 (1970); Lackner, Ber. 104, 3653 (1971). Toxicity data: F. S. Philips et al., Ann. N.Y. Acad. Sci. 89, 348 (1960). Review and evaluation of studies of carcinogenic action in laboratory animals: IARC Monographs 12, 29-41 (1976).
Derivative Type: Trihydrate
Properties: Bright red, rhomboid prisms from abs alc, dec 241.5-243°. [a]D28 -315° (c = 0.25 in methanol). Abs max (methanol): 244, 441 nm (A1%1cm 281, 206). Dil solns are very sensitive to light. Sol in alc, propylene glycol, water + glycol mixtures. LD50 orally in mice, rats: 13.0, 7.2 mg/kg (Philips).
Optical Rotation: [a]D28 -315° (c = 0.25 in methanol)
Absorption maximum: Abs max (methanol): 244, 441 nm (A1%1cm 281, 206)
Toxicity data: LD50 orally in mice, rats: 13.0, 7.2 mg/kg (Philips)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Actinomycins.
Dalapon Dalbavancin Dalfopristin D-Allose Dalteparin

Actinomycin D
Actinomycin D.png
Systematic (IUPAC) name
2-Amino-N,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
Clinical data
Trade names Cosmegen
AHFS/Drugs.com monograph
MedlinePlus a682224
Pregnancy cat. D (AU) D (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes IV
Pharmacokinetic data
Protein binding 5%
Half-life 36 hours
Identifiers
CAS number 50-76-0 YesY
ATC code L01DA01
PubChem CID 2019
DrugBank DB00970
ChemSpider 10482167 YesY
UNII 1CC1JFE158 YesY
KEGG C06770 N
ChEBI CHEBI:27666 YesY
ChEMBL CHEMBL1554 YesY
NIAID ChemDB 009885
Synonyms 2-Amino- 4,6-dimethyl- 3-oxo- 3H-phenoxazine- 1,9-dicarboxylic acid bis- [(5,12-diisopropyl- 9,13,16-trimethyl- 4,7,11,14,17-pentaoxo- hexadecahydro- 10-oxa- 3a,6,13,16-tetraaza- cyclopentacyclohexadecen- 8-yl)- amide]
Chemical data
Formula C62H86N12O16 
Mol. mass 1255.42 g/mol
 N (what is this?)  (verify)

Dactinomycin (INN, BAN, AAN and USAN also known generically as Actinomycin D), is the most significant member of actinomycines, which are a class of polypeptide antibiotics isolated from soil bacteria of the genus Streptomyces.[1] As one of the older chemotherapy drugs, it has been used for many years.