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Dacarbazine

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Revision as of 11:56, 2 November 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Dacarbazine
Clinical data
Trade namesDtic-dome
AHFS/Drugs.comMonograph
MedlinePlusa682750
Pregnancy
category
  • C
Routes of
administration
IV
ATC code
Legal status
Legal status
  • US: WARNING
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability?
Metabolism?
Elimination half-life5 hours
Excretion40% renal (unchanged)
Identifiers
IUPAC name
  • 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.022.179 Edit this at Wikidata
Chemical and physical data
FormulaC6H10N6O
Molar mass182.18 g·mol
3D model (JSmol)
SMILES
  • CN(C)/N=N/c1ncnc1C(N)=O
InChI
  • InChI=1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)/b11-10+
  • Key:FDKXTQMXEQVLRF-ZHACJKMWSA-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 injection (a shot) or 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

See also: History of cancer chemotherapy

Dacarbazine gained FDA approval in May 1975 as DTIC-Dome. The drug was initially marketed by Bayer.

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.

Common 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.

Experimental

Dacarbazine + Oblimersen. In clinical trials for malignant melanoma.

Suppliers

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

See also

Sources

  1. "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. http://www.fass.se/LIF/produktfakta/audit_page.jsp?_sourcePage=%2Fproduktfakta%2Fartikel_produkt.jsp&docType=7&nplId=19971212000080
Intracellular chemotherapeutic agents / antineoplastic agents (L01)
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