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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 compoundClinical data | |
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Trade names | Dtic-dome |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682750 |
Pregnancy category |
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Routes of administration | IV |
ATC code | |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | ? |
Metabolism | ? |
Elimination half-life | 5 hours |
Excretion | 40% renal (unchanged) |
Identifiers | |
IUPAC name
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CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.022.179 |
Chemical and physical data | |
Formula | C6H10N6O |
Molar mass | 182.18 g·mol |
3D model (JSmol) | |
SMILES
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InChI
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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 chemotherapyDacarbazine 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
- "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.
- http://www.fass.se/LIF/produktfakta/audit_page.jsp?_sourcePage=%2Fproduktfakta%2Fartikel_produkt.jsp&docType=7&nplId=19971212000080
- MedLine, U.S. National Institutes of Health, National Library of Medicine, http://www.nlm.nih.gov/medline/
- Cancerweb, http://cancerweb.ncl.ac.uk/cancerweb/
- OncoLink, http://oncolink.upenn.edu/
- Swedish National Board of Health and Welfare, http://www.fass.se/LIF/produktfakta/audit_page.jsp?_sourcePage=%2Fproduktfakta%2Fartikel_produkt.jsp&docType=7&nplId=19971212000080