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Dacarbazine

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Title: Dacarbazine  
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Subject: Temozolomide, Hodgkin's lymphoma, Melanoma, History of cancer chemotherapy, List of drugs: D-Dd
Collection: Amides, Dna Replication Inhibitors, Iarc Group 2B Carcinogens, Imidazoles, Teratogens
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Dacarbazine

Dacarbazine
Systematic (IUPAC) name
5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide
Clinical data
Trade names Dtic-dome
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • C
Legal status
  • (Prescription only)
Routes of
administration
IV
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Biological half-life 5 hours
Excretion 40% renal (unchanged)
Identifiers
CAS Registry Number  Y
ATC code L01
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  N
ChEMBL  Y
Chemical data
Formula C6H10N6O
Molecular mass 182.18
 N   

Dacarbazine () (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.

Contents

  • Medical uses 1
  • Side effects 2
  • Mechanism of Action 3
  • History 4
  • Experimental 5
  • Suppliers 6
  • See also 7
  • Notes 8
  • References 9

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]

Mechanism of Action

Dacarbazine works by methylating guanine at the O-6 and N-7 positions. Guanine is one of the four nucleotides that makes up DNA. The alkylated DNA strands stick together such that cell division becomes impossible. This affects cancer cells more than healthy cells because cancer cells divide faster. Unfortunately however, some of the healthy cells will still be damaged.

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

  1. ^ http://www.fass.se/LIF/produktfakta/audit_page.jsp?_sourcePage=%2Fproduktfakta%2Fartikel_produkt.jsp&docType=7&nplId=19971212000080

References

  • MedLine, U.S. National Institutes of Health, National Library of Medicine,[5]
  • Cancerweb,[6]
  • OncoLink,[7]
  • Swedish National Board of Health and Welfare,[8]
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