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Dacarbazine

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Dacarbazine
File:Dacarbazine Formula V.1.svg
File:Dacarbazine ball-and-stick.png
Systematic (IUPAC) name
5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide
Clinical data
Trade names Dtic-dome
AHFS/Drugs.com monograph
MedlinePlus a682750
  • C
  • (Prescription only)
IV
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Half-life 5 hours
Excretion 40% renal (unchanged)
Identifiers
4342-03-4 7pxY
L01AX04
PubChem CID 2942
DrugBank DB00851 7pxY
ChemSpider 10481959 7pxY
UNII 7GR28W0FJI 7pxY
KEGG C06936 7pxY
ChEBI CHEBI:4305 7pxN
ChEMBL CHEMBL476 7pxY
Chemical data
Formula C6H10N6O
182.18
 14pxN (what is this?)  (verify)

Dacarbazine (/dəˈkɑrbəˌzn/) (brand names DTIC, DTIC-Dome; also known as DIC or Imidazole Carboxamide) is an antineoplastic chemotherapy drug used in the treatment of various cancers, among them malignant melanoma, Hodgkin lymphoma, sarcoma, and islet cell carcinoma of the pancreas.

Dacarbazine is a member of the class of alkylating agents, which destroy cancer cells by adding an alkyl group (CnH2n+1) to its DNA.

Dacarbazine is normally administered by intravenous infusion (IV) under the immediate supervision of a doctor or nurse. Dacarbazine is bioactivated in liver by demethylation to "MTIC" and then to diazomethane, which is an alkylating agent.

Medical uses

As of mid-2006, dacarbazine is commonly used as a single agent in the treatment of metastatic melanoma, and as part of the ABVD chemotherapy regimen to treat Hodgkin lymphoma, and in the MAID regimen for sarcoma. Dacarbazine was proven to be just as efficacious as procarbazine in the German trial for paediatric Hodgkin's Lymphoma, without the teratogenic effects. Thus COPDAC has replaced the former COPP regime in children for TG2 & 3 following OEPA.

Side effects

Like many chemotherapy drugs, dacarbazine may have numerous serious side effects, because it interferes with normal cell growth as well as cancer cell growth. Among the most serious possible side effects are birth defects to children conceived or carried during treatment; sterility, possibly permanent; or immune suppression (reduced ability to fight infection or disease). Dacarbazine is considered to be highly emetogenic, and most patients will be pre-medicated with antiemetic drugs like palonosetron or aprepitant. Other significant side effects include headache, fatigue and occasionally diarrhea.

The Swedish National Board of Health and Welfare has sent out a Black Box Warning and suggests avoiding Dacarbazine due to liver problems.[1]

History

Dacarbazine was developed by Y. Fulmer Shealy, Phd at Southern Research Institute in Birmingham, Alabama. Research was funded by a U.S. federal grant. Dacarbazine gained FDA approval in May 1975 as DTIC-Dome. The drug was initially marketed by Bayer.

Experimental

Dacarbazine + Oblimersen. In clinical trials for malignant melanoma.01

Suppliers

Bayer continues to supply DTIC-Dome. There are also generic versions of dacarbazine available from APP, Bedford, Mayne Pharma and Teva.

See also

Notes

References

  • MedLine, U.S. National Institutes of Health, National Library of Medicine,[1]
  • Cancerweb,[2]
  • OncoLink,[3]
  • Swedish National Board of Health and Welfare,[4]
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