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Substance Name: Dactinomycin [USAN:USP:INN:BAN]
RN: 50-76-0
UNII: 1CC1JFE158
InChIKey: RJURFGZVJUQBHK-IIXSONLDSA-N

Note

  • A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)

Molecular Formula

  • C62-H86-N12-O16

Molecular Weight

  • 1255.4294
 

Classification Codes

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
  • Protein Synthesis Inhibitors
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Dactinomycin
  • Dactinomycin [USAN:USP:INN:BAN]

MeSH Heading

  • Dactinomycin

Synonyms

  • 3H-Phenoxazine-1,9-dicarboxamide, 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-
  • ACT D
  • ACT [antibiotic]
  • Actinomycin 11 cosmegen
  • Actinomycin 7
  • Actinomycin A IV
  • Actinomycin Aiv
  • Actinomycin C(sub1)
  • Actinomycin C1
  • Actinomycin D
  • Actinomycin I
  • Actinomycin I(sub 1)
  • Actinomycin I1
  • Actinomycin IV
  • Actinomycin X 1
  • Actinomycin-(threo-val-pro-sar-meval)
  • Actinomycindioic D acid, dilactone
  • Acto-D
  • AD (VAN)
  • AI3-26374
  • Antibiotic from Streptomyces parvullus
  • CCRIS 9
  • Chounghwamycin B
  • Cosmegen
  • Cosmegen Lyovac
  • Dactinomicina
  • Dactinomicina [INN-Spanish]
  • Dactinomycin
  • Dactinomycin D
  • Dactinomycine
  • Dactinomycine [INN-French]
  • Dactinomycinum
  • Dactinomycinum [INN-Latin]
  • Dilactone actinomycin D acid
  • Dilactone actinomycindioic D acid
  • EINECS 200-063-6
  • HBF 386
  • HSDB 3220
  • Lyovac cosmegen
  • Lyovac-Cosmegen
  • Meractinomycin
  • NCI-C04682
  • NSC 3053
  • Oncostatin K
  • Specific stereoisomer of N,N'-((2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-diyl)-bis(carbonylimino(2-hydroxypropylidene)carbonyliminoisobutylidenecarbonyl-1,2-pyrrolidinediylcarbonyl(methylimino)methylenecarbonyl))bis(N-methyl-L-valine) dilactone
  • Stereoisomer of N,N'-((2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-diyl)bis(carbonylimino(2-(1-hydroxyethyl)-1-oxo-2,1-ethanediyl)imino(2-(1-methylethyl)-1-oxo-2,1-ethanediyl)-1,2-pyrrolidinediylcarbonyl(methylimino) (1-oxo-2,1-ethanediyl)))bis(N-methyl-L-valine)di-xi-lactone
  • UNII-1CC1JFE158
  • X 97

Systematic Names

  • Actinomycin D
  • Dactinomycin

Superlist Name

  • Actinomycin D

Registry Numbers

CAS Registry Number

  • 50-76-0

FDA UNII

  • 1CC1JFE158

System Generated Number

  • 0000050760

Structure Descriptors

InChI

1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1

InChIKey

RJURFGZVJUQBHK-IIXSONLDSA-N

Smiles

Cc1ccc(c2c1oc-3c(c(=O)c(c(c3n2)C(=O)N[C@H]4[C@H](OC(=O)[C@@H](N(C(=O)CN(C(=O)[C@@H]5CCCN5C(=O)[C@H](NC4=O)C(C)C)C)C)C(C)C)C)N)C)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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 1mg/kg (1mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LDLo intraperitoneal 75ug/kg (0.075mg/kg)   Antibiotiki. Vol. 16, Pg. 443, 1971.
cat LDLo intraperitoneal 75ug/kg (0.075mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotiki. Vol. 16, Pg. 443, 1971.
dog LDLo intravenous 160ug/kg (0.16mg/kg)   National Technical Information Service. Vol. PB225-594,
dog LDLo intravenous 160ug/kg (0.16mg/kg) BLOOD: LEUKOPENIA

GASTROINTESTINAL: NAUSEA OR VOMITING
National Technical Information Service. Vol. PB225-594,
guinea pig LD50 unreported 330ug/kg (0.33mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 236, 1980.
hamster LD50 unreported 600ug/kg (0.6mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 236, 1980.
human TDLo intravenous 40ug/kg/4D-I (0.04mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" New England Journal of Medicine. Vol. 281, Pg. 1094, 1969.
mouse LD50 intraperitoneal 750ug/kg (0.75mg/kg) IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Treatment Reports. Vol. 61, Pg. 103, 1977.
mouse LD50 intravenous 1025ug/kg (1.025mg/kg)   Antibiotiki. Vol. 16, Pg. 443, 1971.
mouse LD50 oral 13mg/kg (13mg/kg) BLOOD: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Annals of the New York Academy of Sciences. Vol. 89, Pg. 348, 1960.
mouse LD50 subcutaneous 500ug/kg (0.5mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1268, 1978.
mouse LDLo intratracheal 1mg/kg (1mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
rabbit LD50 unreported 150ug/kg (0.15mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 236, 1980.
rat LD50 intraperitoneal 100ug/kg (0.1mg/kg)   Acta Obstetrica et Gynaecologica Japonica, English Edition. Vol. 23, Pg. 219, 1976.
rat LD50 intravenous 460ug/kg (0.46mg/kg) BLOOD: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Annals of the New York Academy of Sciences. Vol. 89, Pg. 348, 1960.
rat LD50 oral 7200ug/kg (7.2mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: OTHER CHANGES
Annals of the New York Academy of Sciences. Vol. 89, Pg. 348, 1960.
rat LD50 subcutaneous 800ug/kg (0.8mg/kg) BLOOD: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Annals of the New York Academy of Sciences. Vol. 89, Pg. 348, 1960.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.910 (none)   EST
Atmospheric OH Rate Constant 2.83E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.