Dacarbazine

Dacarbazine: Dacarbazine

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^Y

ATC code L01AX04

PubChem CID 2942

DrugBank APRD00331

ChemSpider 10481959^Y

UNII 7GR28W0FJI^Y

KEGG C06936^Y

ChEMBL CHEMBL476^Y

Chemical data

Formula C₆H₁₀N₆O

Mol. mass 182.18

SMILES eMolecules & PubChem

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+^Y
Key:FDKXTQMXEQVLRF-ZHACJKMWSA-N^Y

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 (C_nH_2n+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".

Contents

1 History

2 Side effects

3 Common uses

4 Experimental

5 Suppliers

6 See also

7 Sources

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.^[1]

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

Melanoma

Hodgkin disease

ABVD

History of cancer chemotherapy

Alkylating antineoplastic agent

Sources

^ 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

v · d · eIntracellular chemotherapeutic agents/antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly

Vinca alkaloids (Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine)

Block microtubule disassembly

Taxanes (Cabazitaxel, Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel) • Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid

dihydrofolate reductase inhibitor (Aminopterin, Methotrexate, Pemetrexed, Pralatrexate) • thymidylate synthase inhibitor (Raltitrexed, Pemetrexed)

Purine

adenosine deaminase inhibitor (Pentostatin)

halogenated/ribonucleotide reductase inhibitors (Cladribine, Clofarabine, Fludarabine)
thiopurine (Thioguanine, Mercaptopurine)

Pyrimidine

thymidylate synthase inhibitor (Fluorouracil, Capecitabine, Tegafur, Carmofur, Floxuridine)

DNA polymerase inhibitor (Cytarabine)

ribonucleotide reductase inhibitor (Gemcitabine)
hypomethylating agent (Azacitidine, Decitabine)

Deoxyribonucleotide

ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I

Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan)

II

Podophyllum (Etoposide, Teniposide)

II+Intercalation

Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating

Nitrogen mustards: Mechlorethamine • Cyclophosphamide (Ifosfamide, Trofosfamide) • Chlorambucil (Melphalan, Prednimustine) • Bendamustine • Uramustine • Estramustine

Nitrosoureas: Carmustine • Lomustine (Semustine) • Fotemustine • Nimustine • Ranimustine • Streptozocin

Alkyl sulfonates: Busulfan (Mannosulfan, Treosulfan)
Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine

Alkylating-like

Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin)

Nonclassical

Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol

Intercalation

Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT
Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors

FI (Tipifarnib) • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)

Receptor antagonists

ERA (Atrasentan) • retinoid X receptor (Bexarotene) • sex steroid (Testolactone)

Other/ungrouped

Amsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

Categories:
Imidazoles
DNA replication inhibitors
IARC Group 2B carcinogens
Amides

Dacarbazine

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^Y
ATC code	L01AX04
PubChem	CID 2942
DrugBank	APRD00331
ChemSpider	10481959^Y
UNII	7GR28W0FJI^Y
KEGG	C06936^Y
ChEMBL	CHEMBL476^Y
Chemical data
Formula	C₆H₁₀N₆O
Mol. mass	182.18
SMILES	eMolecules & PubChem
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+^Y Key:FDKXTQMXEQVLRF-ZHACJKMWSA-N^Y
N(what is this?) (verify)

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Look at other dictionaries:

Dacarbazine — Général Nom IUPAC 5 (3,3 diméthyl 1 triazényl)imidazole 4 carboxamide No CAS … Wikipédia en Français
dacarbazine — /deuh kahr beuh zeen /, n. Pharm. a toxic, light sensitive powder, C6H10N6O, used in the treatment of Hodgkin s disease and metastatic malignant melanoma. [1960 65; contr. and rearrangement of the chemical name] * * * … Universalium
dacarbazine — noun An antineoplastic drug used in chemotherapy … Wiktionary
dacarbazine — An antineoplastic agent used in the treatment of malignant melanoma and sarcoma. * * * da·car·ba·zine də kär bə .zēn n an antineoplastic agent C6H10N6O used to treat esp. metastatic malignant melanoma, tumors of adult soft tissue, and Hodgkin s… … Medical dictionary
dacarbazine — n. a drug administered by injection in the treatment of melanoma and (in combination with other cytotoxic drugs) certain other cancers, including Hodgkin s disease. Side effects include severe vomiting. Trade names: DTIC Dome … The new mediacal dictionary
dacarbazine — An anticancer drug that is a type of alkylating agent … English dictionary of cancer terms
dacarbazine — /deuh kahr beuh zeen /, n. Pharm. a toxic, light sensitive powder, C6H10N6O, used in the treatment of Hodgkin s disease and metastatic malignant melanoma. [1960 65; contr. and rearrangement of the chemical name] … Useful english dictionary
4342-03-4 — Dacarbazine Dacarbazine Général Nom IUPAC 5 (3,3 diméthyl 1 triazényl)imidazole 4 carboxamide N … Wikipédia en Français
DTIC — • dacarbazine; • dimethyltriazenyl imidazole carboxamide … Dictionary of medical acronyms & abbreviations
Melanoma — Classification and external resources A melanoma ICD 10 C43 … Wikipedia

Academic Dictionaries and Encyclopedias

Dacarbazine

Contents

History

Side effects

Common uses

Experimental

Suppliers

See also

Sources

Look at other dictionaries:

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Academic Dictionaries and Encyclopedias

Wikipedia

Dacarbazine

Contents

History

Side effects

Common uses

Experimental

Suppliers

See also

Sources

Look at other dictionaries:

Share the article and excerpts

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