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Chemistry

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Also known as: Actinomycin d, Actinomycin c1, Actinomycin iv, Cosmegen, Meractinomycin, 50-76-0
Molecular Formula
C62H86N12O16
Molecular Weight
1255.4  g/mol
InChI Key
RJURFGZVJUQBHK-IIXSONLDSA-N
FDA UNII
1CC1JFE158

Dactinomycin
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)
Dactinomycin is an Actinomycin. The mechanism of action of dactinomycin is as a Nucleic Acid Synthesis Inhibitor, and Protein Synthesis Inhibitor.
1 2D Structure

Dactinomycin

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 InChI
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
2.1.3 InChI Key
RJURFGZVJUQBHK-IIXSONLDSA-N
2.1.4 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
2.1.5 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
2.2 Other Identifiers
2.2.1 UNII
1CC1JFE158
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Actinomycin

2. Actinomycin D

3. Cosmegen

4. Cosmegen Lyovac

5. Lyovac Cosmegen

6. Lyovac, Cosmegen

7. Lyovac-cosmegen

8. Lyovaccosmegen

9. Meractinomycin

2.3.2 Depositor-Supplied Synonyms

1. Actinomycin D

2. Actinomycin C1

3. Actinomycin Iv

4. Cosmegen

5. Meractinomycin

6. 50-76-0

7. Actinomycin I1

8. Dactinomycinum

9. Dilactone Actinomycin D Acid

10. Actd

11. Actinomycin X1

12. Oncostatin K

13. Actinomycin-d

14. Act D

15. Nci-c04682

16. Dactinomycine [inn-french]

17. Dactinomycinum [inn-latin]

18. Dactinomicina [inn-spanish]

19. Lyovac Cosmegen

20. Gnf-pf-2290

21. Dactinomycin D

22. Chounghwamycin B

23. Actinomycin 7

24. Actinomycin Aiv

25. Actinomycin I

26. Mls001424196

27. 1cc1jfe158

28. Chebi:27666

29. Actinomycin X 1

30. Actinomycin A Iv

31. Acto-d

32. Nsc-3053

33. Actinomycin C(sub1)

34. Dilactone Actinomycindioic D Acid

35. Ncgc00161622-02

36. Actinomycin I(sub 1)

37. Smr000469227

38. Dsstox_cid_31

39. Actinomycin 11 Cosmegen

40. Cosmegen Lyovac

41. Lyovac-cosmegen

42. Ccris 9

43. Dsstox_rid_75330

44. Dsstox_gsid_20031

45. 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

46. Hsdb 3220

47. Dactinomicina

48. Dactinomycine

49. Actinomycindioic D Acid, Dilactone

50. Antibiotic From Streptomyces Parvullus

51. Actinomycin-(threo-val-pro-sar-meval)

52. Cas-50-76-0

53. Act [antibiotic]

54. X 97

55. 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

56. Mfcd00005033

57. Ad (van)

58. Gnf-pf-1977

59. Nsc3053

60. Unii-1cc1jfe158

61. Dtxsid9020031

62. Glycopeptide, 4a

63. 2-amino-4,6-dimethyl-3-oxo-n,n'-bis[(6s,9r,10s,13r,18as)-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxohexadecahydro-1h-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-3h-phenoxazine-1,9-dicarboxamide

64. Nsc 3053

65. Dactinomycin [usan:usp:inn:ban]

66. Einecs 200-063-6

67. Ai3-26374

68. Dactinomycin [mi]

69. Dactinomycin [inn]

70. Upcmld-dp055

71. Dactinomycin [hsdb]

72. Dactinomycin [usan]

73. Schembl3844

74. Actinomycin D [jan]

75. Chembl1554

76. Dactinomycin [vandf]

77. Actinomycin D [iarc]

78. Dactinomycin [mart.]

79. Dactinomycin [usp-rs]

80. Dactinomycin [who-dd]

81. Dactinomycin [who-ip]

82. Cid_457193

83. Actinomycin D [who-ip]

84. Upcmld-dp055:001

85. Upcmld-dp055:002

86. Bdbm43866

87. Dactinomycin [orange Book]

88. Hms2052o17

89. Dactinomycin [usp Monograph]

90. Tox21_111997

91. Tox21_202482

92. Bdbm50089528

93. S8964

94. Dactinomycinum [who-ip Latin]

95. Akos030228553

96. Tox21_111997_1

97. Ccg-101134

98. Db00970

99. Nc00384

100. Ncgc00090796-01

101. Ncgc00161622-01

102. Ncgc00260031-01

103. Ncgc00271789-02

104. 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-

105. Bp-25384

106. 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

107. 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

108. Ab00514445-05

109. 050a760

110. Q186127

111. Sr-01000763161

112. Sr-01000763161-4

113. Actinomycin D, From Streptomyces Sp., >=95% (hplc)

114. Actinomycin D, From Streptomyces Sp., ~98% (hplc)

115. Brd-k70578146-001-01-8

116. Brd-k70578146-001-04-2

117. Dactinomycin, United States Pharmacopeia (usp) Reference Standard

118. Actinomycin D, For Fluorescence, >=90% (hplc), From Streptomyces Sp.

119. Actinomycin D, From Streptomyces Sp., Suitable For Cell Culture, >=95%

120. 1-n,9-n-bis[(6s,9r,10s,13r,18as)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-bis(propan-2-yl)-hexadecahydro-1h-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxo-3h-phenoxazine-1,9-dicarboxamide

121. 2-amino-4,6-dimethyl-3-oxo-1-n,9-n-bis-[(18as)-10c,14,17-trimethyl-5,8,12,15,18-pentaoxo-6c,13t-di(propan-2-yl)-18ar-hexadecahydro-1h-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-9c-yl]-3h-phenoxazine-1,9-dicarboxamide

122. 2-amino-4,6-dimethyl-3-oxo-n1,n9-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

123. 2-amino-n,n''''''''-bis[(3r,6s,7r,10s,16s)-3,10-diisopropyl-2,5,9,12,15-pentaketo-7,11,14-trimethyl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-3-keto-4,6-dimethyl-phenoxazine-1,9-dicarboxamide

124. 2-amino-n,n''''-bis[(3r,6s,7r,10s,16s)-3,10-diisopropyl-2,5,9,12,15-pentaketo-7,11,14-trimethyl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-3-keto-4,6-dimethyl-phenoxazine-1,9-dicarboxamide

125. 2-amino-n,n''-bis[(3r,6s,7r,10s,16s)-3,10-diisopropyl-2,5,9,12,15-pentaketo-7,11,14-trimethyl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-3-keto-4,6-dimethyl-phenoxazine-1,9-dicarboxamide

126. 2-amino-n1,n9-bis[(3r,6s,7r,10s,16s)-3,10-diisopropyl-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-4,6-dimethyl-3-oxo-phenoxazine-1,9-dicarboxamide

127. 2-azanyl-4,6-dimethyl-3-oxidanylidene-n1,n9-bis[(3r,6s,7r,10s,16s)-7,11,14-trimethyl-2,5,9,12,15-pentakis(oxidanylidene)-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]phenoxazine-1,9-dicarboxamide

128. 3h-phenoxazine-1,9-dicarboxamide, 2-amino-n,n'-bis(hexadecahydro-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-1h-pyrrolo(2,1-i)(1,4,7,10,13)oxatetraazacyclohexadecin-10-yl)-4,6-dimethyl-3-oxo-

129. 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

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 1255.4 g/mol
Molecular Formula C62H86N12O16
XLogP33.8
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count18
Rotatable Bond Count8
Exact Mass1254.62847470 g/mol
Monoisotopic Mass1254.62847470 g/mol
Topological Polar Surface Area356 Ų
Heavy Atom Count90
Formal Charge0
Complexity3030
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCosmegen
PubMed HealthDactinomycin (Injection)
Drug ClassesAntibiotic
Drug LabelDactinomycin is one of the actinomycins, a group of antibiotics produced by various species of Streptomyces. Dactinomycin is the principal component of the mixture of actinomycins produced by Streptomyces parvullus. Unlike other species of Streptomyc...
Active IngredientDactinomycin
Dosage FormInjectable
RouteInjection
Strength0.5mg/vial
Market StatusPrescription
CompanyRecordati Rare

2 of 4  
Drug NameDactinomycin
PubMed HealthDactinomycin (Injection)
Drug ClassesAntibiotic
Drug LabelDactinomycin is one of the actinomycins, a group of antibiotics produced by various species of Streptomyces. Dactinomycin is the principal component of the mixture of actinomycins produced by Streptomyces parvullus. Unlike other species of Streptomyc...
Active IngredientDactinomycin
Dosage FormInjectable
RouteInjection
Strength0.5mg/vial
Market StatusPrescription
CompanyLuitpold; Eurohlth Intl

3 of 4  
Drug NameCosmegen
PubMed HealthDactinomycin (Injection)
Drug ClassesAntibiotic
Drug LabelDactinomycin is one of the actinomycins, a group of antibiotics produced by various species of Streptomyces. Dactinomycin is the principal component of the mixture of actinomycins produced by Streptomyces parvullus. Unlike other species of Streptomyc...
Active IngredientDactinomycin
Dosage FormInjectable
RouteInjection
Strength0.5mg/vial
Market StatusPrescription
CompanyRecordati Rare

4 of 4  
Drug NameDactinomycin
PubMed HealthDactinomycin (Injection)
Drug ClassesAntibiotic
Drug LabelDactinomycin is one of the actinomycins, a group of antibiotics produced by various species of Streptomyces. Dactinomycin is the principal component of the mixture of actinomycins produced by Streptomyces parvullus. Unlike other species of Streptomyc...
Active IngredientDactinomycin
Dosage FormInjectable
RouteInjection
Strength0.5mg/vial
Market StatusPrescription
CompanyLuitpold; Eurohlth Intl

4.2 Therapeutic Uses

Antineoplastic; Anti-Bacterial Agents; Nucleic Acid Synthesis Inhibitors; Protein Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Dactinomycin, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms' tumor, childhood rhabdomyosarcoma, Ewing's sarcoma and metastatic, nonseminomatous testicular cancer. /Included in US Product label/

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (March 2009). Available from, as of October 14, 2009 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10007


Dactinomycin is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. /Included in US Product label/

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (March 2009). Available from, as of October 14, 2009 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10007


Dactinomycin, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. /Included in US Product label/

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (March 2009). Available from, as of October 14, 2009 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10007


For more Therapeutic Uses (Complete) data for DACTINOMYCIN (7 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ COSMEGEN (Dactinomycin for Injection) should be administered only under the supervision of a physician who is experienced in the use of cancer chemotherapeutic agents.

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (Updated: February 2013). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9914e793-a49c-eb00-1ab7-f606c786fe25


/BOXED WARNING/ This drug is HIGHLY TOXIC and both powder and solution must be handled and administered with care. Inhalation of dust or vapors and contact with skin or mucous membranes, especially those of the eyes, must be avoided. Avoid exposure during pregnancy. Due to the toxic properties of dactinomycin (eg, corrosivity, carcinogenicity, mutagenicity, teratogenicity), special handling procedures should be reviewed prior to handling and followed diligently. Dactinomycin is extremely corrosive to soft tissue. If extravasation occurs during intravenous use, severe damage to soft tissues will occur. In at least one instance, this has led to contracture of the arms.

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (Updated: February 2013). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9914e793-a49c-eb00-1ab7-f606c786fe25


COSMEGEN is a toxic drug and very careful and frequent observation of the patient for adverse reactions is necessary. These reactions may involve any tissue of the body, most commonly the hematopoietic system resulting in myelosuppression. As such, live virus vaccines should not be administered during therapy with COSMEGEN. The possibility of an anaphylactoid reaction should be borne in mind.

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (March 2009). Available from, as of October 14, 2009 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10007


Pt may ... become more susceptible to infections due to suppression of normal immune mechanisms. If dactinomycin is given at or about time of infection with chickenpox, severe generalized disease, which is sometimes fatal, may occur.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1130


For more Drug Warnings (Complete) data for DACTINOMYCIN (24 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of Wilms' tumor, childhood rhabdomyosarcoma, Ewing's sarcoma and metastatic, nonseminomatous testicular cancer as part of a combination chemotherapy and/or multi-modality treatment regimen


5 Pharmacology and Biochemistry
5.1 Pharmacology

Generally, the actinomycins exert an inhibitory effect on gram-positive and gram-negative bacteria and on some fungi. However, the toxic properties of the actinomycins (including dactinomycin) in relation to antibacterial activity are such as to preclude their use as antibiotics in the treatment of infectious diseases. Because the actinomycins are cytotoxic, they have an antineoplastic effect which has been demonstrated in experimental animals with various types of tumor implant. This cytotoxic action is the basis for their use in the treatment of certain types of cancer. Dactinomycin is believed to produce its cytotoxic effects by binding DNA and inhibiting RNA synthesis.


5.2 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)


Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)


Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)


Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DACTINOMYCIN
5.3.2 FDA UNII
1CC1JFE158
5.3.3 Pharmacological Classes
Nucleic Acid Synthesis Inhibitors [MoA]; Protein Synthesis Inhibitors [MoA]; Actinomycin [EPC]
5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01D - Cytotoxic antibiotics and related substances

L01DA - Actinomycines

L01DA01 - Dactinomycin


5.5 Absorption, Distribution and Excretion

Absorption

poorly absorbed from gastrointestinal tract


Dactinomycin is poorly absorbed from the GI tract. The drug is extremely irritating to tissues and, therefore, must be administered iv.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1025


Dactinomycin is rapidly distributed into tissues, with high concentrations in bone marrow and nucleated cells, including granulocytes and lymphocytes. The drug appears to cross the blood-brain barrier poorly, if at all.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1025


Plasma protein binding /of dactinomycin/ is 5%.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 494


Dactinomycin apparently crosses the placenta. It is not known if dactinomycin is distributed into milk.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1025


For more Absorption, Distribution and Excretion (Complete) data for DACTINOMYCIN (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

hepatic


Dactinomycin appears to be only slightly metabolized; small amounts of monolactones of the drug have been detected in the urine.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1025


5.7 Biological Half-Life

36 hours


The terminal plasma half-life for radioactivity was approximately 36 hours.

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (March 2009). Available from, as of October 14, 2009 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10007


The terminal elimination half life of actinomycin D is 36 to 48 hours.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 494


5.8 Mechanism of Action

Good evidence exists that this drug bind strongly, but reversibly, to DNA, interfering with synthesis of RNA (prevention of RNA polymerase elongation) and, consequently, with protein synthesis.


The capacity of actinomycins to bind with double-helical DNA is responsible for their biological activity and cytotoxicity. X-ray studies of a crystalline complex between dactinomycin and deoxyguanosine permitted formulation of a model that appears to explain the binding of the drug to DNA. The planar phenoxazone ring intercalates between adjacent guanine-cytosine base pairs of DNA, while the polypeptide chains extend along the minor groove of the helix. The summation of these interactions provides great stability to the dactinomycin-DNA complex, and as a result of the binding of dactinomycin, the transcription of DNA by RNA polymerase is blocked. The DNA-dependent RNA polymerases are much more sensitive to the effects of dactinomycin than are the DNA polymerases. In addition, dactinomycin causes single-strand breaks in DNA, possibly through a free-radical intermediate or as a result of the action of topoisomerase II

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 1357


Dactinomycin is an antineoplastic antibiotic. The drug has bacteriostatic activity, particularly against gram-positive organisms, but its cytotoxicity precludes its use as an anti-infective agent. Although the exact mechanism(s) of action has not been fully elucidated, the drug appears to inhibit DNA-dependent RNA synthesis by forming a complex with DNA by intercalating with guanine residues and impairing the template activity of DNA. Protein and DNA synthesis are also inhibited but less extensively and at higher concentrations of dactinomycin than are needed to inhibit RNA synthesis. Dactinomycin is immunosuppressive and also possesses some hypocalcemic activity similar to plicamycin.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1025


Generally, the actinomycins exert an inhibitory effect on gram-positive and gram-negative bacteria and on some fungi. However, the toxic properties of the actinomycins (including dactinomycin) in relation to antibacterial activity are such as to preclude their use as antibiotics in the treatment of infectious diseases.

US Natl Inst Health; DailyMed. Current Medication Information for COSMEGEN (dactinomycin) injection, powder, lyophilized, for solution (March 2009). Available from, as of October 14, 2009 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10007


Dactinomycin acts by forming stable complexes with double-helical DNA that inhibit DNA-directed RNA synthesis (interfere with RNA polymerase) more than DNA synthesis. The drug is cell-cycle active.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 793


The effect of dactinomycin on cellular respiration and accompanying ATP formation was investigated in Jurkat and HL-60 cells. Cellular mitochondrial oxygen consumption (measured by a homemade phosphorescence analyzer) and ATP content (measured by the luciferin-luciferase bioluminescence system) were determined as functions of time t during continuous exposure to the drug. The rate of respiration, k, was the negative of the slope of [O2] versus t. Oxygen consumption and ATP content were diminished by cyanide, confirming that both processes involved oxidations in the mitochondrial respiratory chain. In the presence of dactinomycin, k decreased gradually with t, the decrease being more pronounced at higher drug concentrations. Cellular ATP remained constant for 5 h in untreated cells, but in the presence of 20 microM dactinomycin it decreased gradually (to one-tenth the value at 5 h for untreated cells). The drug-induced inhibition of respiration and decrease in ATP were blocked by the pancaspase inhibitor benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethyl ketone (zVAD-fmk). A rapid but temporary decrease in cellular ATP observed on the addition of zVAD-fmk was shown to be due to DMSO (added with zVAD-fmk). The effect of dactinomycin on respiration differed from that of doxorubicin. Plots of [O2] versus t were curved for dactinomycin so that k decreased gradually with t. The corresponding plots for doxorubicin were well fit by two straight lines; so k was constant for approximately 150 min, at which time k decreased, remaining constant at a lower level thereafter. The results for cells treated with mixtures of the two drugs indicated that the drugs acted synergistically. These results show the onset and severity of mitochondrial dysfunction in cells undergoing apoptosis induced by dactinomycin.

PMID:17140264 Tao Z et al; Mol Pharm 3 (6): 762-72 (2006).


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