2-amino-4,6-dimethyl-3-oxo-1-N,9-N-bis[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]-3H-phenoxazine-1,9-dicarboxamide

• ChemBase ID: 845
• Molecular Formular: C62H86N12O16
• Molecular Mass: 1255.41704
• Monoisotopic Mass: 1254.62847473
• SMILES: O=C1N2C(CCC2)C(=O)N(CC(=O)N(C(C(C)C)C(=O)OC(C(NC(=O)c2c3nc4c(C(=O)NC5C(=O)NC(C(=O)N6C(CCC6)C(=O)N(CC(=O)N(C(C(C)C)C(=O)OC5C)C)C)C(C)C)ccc(c4oc3c(c(=O)c2N)C)C)C(=O)NC1C(C)C)C)C)C
• Canonical SMILES: O=C1NC(C(C)C)C(=O)N2CCCC2C(=O)N(C)CC(=O)N(C(C(=O)OC(C1NC(=O)c1c2nc3c(ccc(c3oc2c(c(=O)c1N)C)C)C(=O)NC1C(C)OC(=O)C(C(C)C)N(C)C(=O)CN(C(=O)C2N(C(=O)C(NC1=O)C(C)C)CCC2)C)C)C(C)C)C
• 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)
• InChIKey: RJURFGZVJUQBHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4,6-dimethyl-3-oxo-1-N,9-N-bis[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]-3H-phenoxazine-1,9-dicarboxamide
• IUPAC Traditional name: actinomycin D
• Brand Name: ACT; ACT D; ACTINOMYCIN D; ACTO-D; Actactinomycin a Iv; Actinomycin 11 Cosmegen; Actinomycin 7; Actinomycin Aiv; Actinomycin C1; Actinomycin I; Actinomycin I1; Actinomycin Iv; Actinomycin X 1; Actinomycindioic D Acid, Dilactone; Chounghwamycin B; Cosmegen; Dactinomycin D; Dilactone Actinomycin D Acid; Dilactone Actinomycindioic D Acid; HBF 386 Meractinomycin; Lyovac Cosmegen; Meractinomycin; Oncostatin K; Oxamide
• Synonyms: Actinomycin IV; Dactinomycin; ACTINOMYCIN D; ACTINOMYCIN D AMP; AD; Antibiotic From Streptomyces Parvullus; Dactinomicina [INN-Spanish]; Dactinomycine [INN-French]; Dactinomycinum [INN-Latin]; Dactinomycin

Database IDs

• CAS Number: 50-76-0
• EC Number: 200-063-6
• PubChem SID: 160964308
• PubChem CID: 2019

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.516916
• H Acceptors: 16
• H Donor: 5
• LogD (pH = 5.5): -0.09688717
• LogD (pH = 7.4): -0.09717637
• Log P: -0.096882455
• Molar Refractivity: 326.1716 cm^3
• Polarizability: 124.87235 Å^3
• Polar Surface Area: 355.54 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.76
• LOG S: -4.8
• Solubility (Water): 2.00e-02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble at 10°C
• Melting Point: 87 °C
• Hydrophobicity(logP): 1.6

Safety Information

• Storage Condition: 2-8°C, Protect from light
• RTECS: AU1575000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: II
• Australian Hazchem: 2XE
• Risk Statements: R:28
• Safety Statements: S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

Product Information

• Purity: ~98%

DETAILS

MP Biomedicals - 02104658

Crystalline
Purity: ~98%
Potent apoptosis inducer.
Soluble in chloroform, acetone, methanol and decomposed by strong acids, light.

MP Biomedicals - 05224713

MP Biomedicals Rare Chemical collection

DrugBank - DB00970

• Drug Groups: approved
• Description: 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)
• 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
• 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.
• Toxicity: hepatoxicity
• Affected Organisms: Humans and other mammals
• Biotransformation: hepatic
• Absorption: poorly absorbed from gastrointestinal tract
• Half Life: 36 hours
• Protein Binding: 5%
• References: Sobell HM: Actinomycin and DNA transcription. Proc Natl Acad Sci U S A. 1985 Aug;82(16):5328-31. [Pubmed] ; Turan T, Karacay O, Tulunay G, Boran N, Koc S, Bozok S, Kose MF: Results with EMA/CO (etoposide, methotrexate, actinomycin D, cyclophosphamide, vincristine) chemotherapy in gestational trophoblastic neoplasia. Int J Gynecol Cancer. 2006 May-Jun;16(3):1432-8. [Pubmed] ; Abd El-Aal HH, Habib EE, Mishrif MM: Wilms' tumor: the experience of the pediatric unit of Kasr El-Aini center of radiation oncology and nuclear medicine (NEMROCK). J Egypt Natl Canc Inst. 2005 Dec;17(4):308-14. [Pubmed] ; Khatua S, Nair CN, Ghosh K: Immune-mediated thrombocytopenia following dactinomycin therapy in a child with alveolar rhabdomyosarcoma: the unresolved issues. J Pediatr Hematol Oncol. 2004 Nov;26(11):777-9. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Turan T, Karacay O, Tulunay G, Boran N, Koc S, Bozok S, Kose MF: Results with EMA/CO (etoposide, methotrexate, actinomycin D, cyclophosphamide, vincristine) chemotherapy in gestational trophoblastic neoplasia. Int J Gynecol Cancer. 2006 May-Jun;16(3):1432-8. Pubmed
• Abd El-Aal HH, Habib EE, Mishrif MM: Wilms' tumor: the experience of the pediatric unit of Kasr El-Aini center of radiation oncology and nuclear medicine (NEMROCK). J Egypt Natl Canc Inst. 2005 Dec;17(4):308-14. Pubmed
• Khatua S, Nair CN, Ghosh K: Immune-mediated thrombocytopenia following dactinomycin therapy in a child with alveolar rhabdomyosarcoma: the unresolved issues. J Pediatr Hematol Oncol. 2004 Nov;26(11):777-9. Pubmed
• Sobell HM: Actinomycin and DNA transcription. Proc Natl Acad Sci U S A. 1985 Aug;82(16):5328-31. Pubmed