Dacarbazine

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Dacarbazine
Dacarbazine Formula V.1.svg
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
Pregnancy cat. C
Legal status Prescription only
Routes IV
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Half-life 5 hours
Excretion 40% renal (unchanged)
Identifiers
CAS number 4342-03-4 YesY
ATC code L01AX04
PubChem CID 2942
DrugBank DB00851
ChemSpider 10481959 YesY
UNII 7GR28W0FJI YesY
KEGG C06936 YesY
ChEBI CHEBI:4305 N
ChEMBL CHEMBL476 YesY
Chemical data
Formula C6H10N6O 
Mol. mass 182.18
 N (what is this?)  (verify)

Dacarbazine (da-KAR-ba-zeen) (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".

History[edit]

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

Side effects[edit]

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]

Common uses[edit]

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.

Experimental[edit]

Dacarbazine + Oblimersen. In clinical trials for malignant melanoma.

Suppliers[edit]

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

See also[edit]

Notes[edit]

References[edit]

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