Dactinomycin
DRACPC ID DRACPC0076
Active Ingredients Dactinomycin
Description A chromopeptide antineoplastic antibiotic isolated from the bacterium Streptomyces parvulus. This compound belongs to the class of organic compounds known as cyclic depsipeptides. Dactinomycin intercalates between adjacent guanine-cytosine base pairs, blocking the transcription of DNA by RNA polymerase; it also causes single-strand DNA breaks, possibly via a free-radical intermediate or an interaction with topoisomerase II.
Synonyms Actinomycin A IV; Actinomycin C1; ACTINOMYCIN D; Actinomycin I1; Actinomycin IV; Actinomycin X 1; Actinomycin-[thr-val-pro-sar-meval]; Cosmegen; Dactinomycine; Dactinomycin; DACT; Lyovac Cosmegen; Meractinomycin
Type Small Molecule
Disease Wilms' tumor, Childhood rhabdomyosarcoma, Ewing's sarcoma and metastatic, Nonseminomatous testicular cancer
Classification
Antibiotic Peptide and derivative Cyclic
Structure Information
Molecular Formula C62H86N12O16
Molecular Weight 1255.4
Active Sequence Not available
Sequence Length Not available
Modification Not available
IUPAC Name N1,N9-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
InChI InChI=1S/C66H94N12O16/c1-17-21-37-25-26-38(57(82)71-48-35(11)92-65(90)52(33(7)8)75(15)42(79)29-73(13)61(86)40-23-19-27-77(40)63(88)46(31(3)4)69-59(48)84)50-55(37)94-56-39(22-18-2)54(81)45(67)44(51(56)68-50)58(83)72-49-36(12)93-66(91)53(34(9)10)76(16)43(80)30-74(14)62(87)41-24-20-28-78(41)64(89)47(32(5)6)70-60(49)85/h25-26,31-36,40-41,46-49,52-53H,17-24,27-30,67H2,1-16H3,(H,69,84)(H,70,85)(H,71,82)(H,72,83)/t35-,36-,40+,41+,46-,47-,48+,49+,52+,53+/m1/s1
InChI_Key LJSAZAHIIMMOOW-PCHXSYTBSA-N
SMILES CC(C)[C@@H](NC([C@@H](NC(C1=C(N=C(C2=C3CCC)C(C(N[C@@H]([C@H](O4)C)C(N[C@@H](C(N5CCC[C@@]5([H])C(N(C)CC(N(C)[C@@H](C(C)C)C4=O)=O)=O)=O)C(C)C)=O)=O)=C(N)C3=O)C(O2)=C(CCC)C=C1)=O)[C@H](O6)C)=O)C(N7CCC[C@@]7([H])C(N(C)CC(N(C)[C@@H](C(C)C)C6=O)=O)=O)=O
External Codes
PubChem CID 457193
DrugBank Accession Number DB00970
NCI Thesaurus Code C412
UNII 1CC1JFE158 GSRS
CAS 50-76-0
Drug approval
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
| Drug Name | Strength | Dosage Form/Route | Company | Marketing Status | Drug ID | Approval year |
|---|---|---|---|---|---|---|
| Dactinomycin | 0.5mg/vial | Injectable; Injection | Hikma | Discontinued | ANDA: 090304 | 2010 |
| Dactinomycin | 0.5mg/vial | Injectable; Injection | Am Regent | Discontinued | ANDA: 202562 | 2013 |
| Dactinomycin | 0.5mg/vial | Injectable; Injection | Eugia Pharma | Prescription | ANDA: 203385 | 2017 |
| Dactinomycin | 0.5mg/vial | Injectable; Injection | Xgen Pharms | Prescription | ANDA: 203999 | 2019 |
| Dactinomycin | 0.5mg/vial | Injectable; Injection | Hisun Pharm Hangzhou | Prescription | ANDA: 207232 | 2019 |
| Dactinomycin | 0.5mg/vial | Injectable; Injection | Meitheal | Prescription | ANDA: 213463 | 2020 |
| Cosmegen | 0.5mg/vial | Injectable; Injection | Recordati Rare | Prescription | NDA: 213463 | 1964 |
| Cosmegen | 0.5 mg / vial | Powder For Solution | Recordati Rare Diseases Canada Inc | Prescription | DIN: 00213071 | 1963 |
| ClinicalTrials.gov Identifier | Title | Condition or disease | Phase | Purpose |
|---|---|---|---|---|
| NCT01323517 | A Phase II Trial of The Addition of Ipilimumab (MDX-010) To Isolated Limb Infusion (ILI) With Standard Melphalan and Dactinomycin In The Treatment of Advanced Unresectable Melanoma of The Extremity | Melanoma | Phase 2 | Treatment |
| NCT00003688 | Pulse Actinomycin-D as Salvage Therapy for Failed Low Risk Gestational Trophoblastic Neoplasia | Gestational Trophoblastic Tumor | Phase 2 | Treatment |
| NCT00075582 | Vincristine, Dactinomycin, and Lower Doses of Cyclophosphamide With or Without Radiation Therapy for Patients With Newly Diagnosed Low-Risk Embryonal/Botryoid/Spindle Cell Rhabdomyosarcoma | Adult Rhabdomyosarcoma; Embryonal Childhood Rhabdomyosarcoma; Embryonal-botryoid Childhood Rhabdomyosarcoma; Previously Untreated Childhood Rhabdomyosarcoma | Phase 3 | Treatment |
| NCT00245089 | Phase II Trial of VAC2.2/VA Therapy for Low-Risk B Group Patients With Rhabdomyosarcoma | Sarcoma | Phase 2 | Treatment |
| NCT00352534 | Treatment for Very Low and Standard Risk Favorable Histology Wilms Tumor | Stage I Wilms Tumor; Stage II Wilms Tumor; Stage III Wilms Tumor | Phase 3 | Treatment |
More clinical information is obtained from ClinicalTrials.gov.
