U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H10N6O.C6H8O7
Molecular Weight 374.3067
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DACARBAZINE CITRATE

SMILES

CN(C)\N=N\C1=C(N=CN1)C(N)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O

InChI

InChIKey=UKLSKIDEWQXQJZ-ASTDGNLGSA-N
InChI=1S/C6H10N6O.C6H8O7/c1-12(2)11-10-6-4(5(7)13)8-3-9-6;7-3(8)1-6(13,5(11)12)2-4(9)10/h3H,1-2H3,(H2,7,13)(H,8,9);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b11-10+;

HIDE SMILES / InChI
Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C6H10N6O
Molecular Weight 182.1832
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Dacarbazine (DTIC), also known as imidazole carboxamide, is an antineoplastic agent, which is used in the treatment of metastatic malignant melanoma. In addition, this drug also is indicated for Hodgkin’s disease as a second-line therapy when used in combination with other effective agents. 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. Dacarbazine is bioactivated in liver by demethylation to "MTIC" and then to diazomethane, which is an alkylating agent. Symptoms of anorexia, nausea, and vomiting are the most frequently noted of all toxic reactions. Over 90% of patients are affected with the initial few doses.

CNS Activity

Originator

Approval Year

1975
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
DNA
282
Target ID: CHEMBL2311221
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
DTIC-DOME

Approved Use

Dacarbazine for Injection USP is indicated in the treatment of metastatic malignant melanoma. In addition, Dacarbazine for Injection USP is also indicated for Hodgkin's disease as a secondary-line therapy when used in combination with other effective agents.

Launch Date

1975
Primary
Approved
8583
DTIC-DOME

Approved Use

Dacarbazine for Injection USP is indicated in the treatment of metastatic malignant melanoma. In addition, Dacarbazine for Injection USP is also indicated for Hodgkin's disease as a secondary-line therapy when used in combination with other effective agents.

Launch Date

1975
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.2 μg/mL
REVIEW
https://www.ncbi.nlm.nih.gov/pubmed/26940170
750 mg/m² single, intravenous
dose: 750 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DACARBAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14.8 μM × min
REVIEW
https://www.ncbi.nlm.nih.gov/pubmed/26940170
750 mg/m² single, intravenous
dose: 750 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DACARBAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
41.4 min
REVIEW
https://www.ncbi.nlm.nih.gov/pubmed/26940170
750 mg/m² single, intravenous
dose: 750 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DACARBAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
OTHER GOV
https://www.medicines.org.uk/emc/product/7747/smpc
DACARBAZINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1000 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
unhealthy, 34–79
Health Status: unhealthy
Age Group: 34–79
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
Disc. AE: Cerebral ischemia...
AEs leading to
discontinuation/dose reduction:
Cerebral ischemia (grade 4, 33%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
800 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 800 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
unhealthy, 34–79
Health Status: unhealthy
Age Group: 34–79
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
DLT: Thrombocytopenia...
Disc. AE: Thrombocytopenia...
Dose limiting toxicities:
Thrombocytopenia (grade 2, 6.25%)
AEs leading to
discontinuation/dose reduction:
Thrombocytopenia (grade 1, 6.25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
1000 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1000 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
unhealthy, 40–65
Health Status: unhealthy
Age Group: 40–65
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
Other AEs: Neutropenia, Fatigue...
Other AEs:
Neutropenia (grade 4, 2.2%)
Fatigue (grade 4, 2.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Disc. AE: Leukopenia, Thrombocytopenia...
AEs leading to
discontinuation/dose reduction:
Leukopenia (grade 3-5)
Thrombocytopenia (grade 3-5)
Anemia (sometimes)
Hematopoiesis impaired
Hepatotoxicity (grade 3-5, 0.01%)
Hepatic vein thrombosis (grade 3-5, 0.01%)
Necrosis hepatocellular (grade 3-5, 0.01%)
Anaphylaxis
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
850 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 850 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 850 mg/m2, 1 times / 3 weeks
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
Disc. AE: Anemia, Leukopenia...
AEs leading to
discontinuation/dose reduction:
Anemia (mild)
Leukopenia (grade 3-5)
Thrombocytopenia (grade 3-5)
Hepatotoxicity (grade 3-5)
Hepatic vein thrombosis (grade 3-5)
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
AEs

AEs

AESignificanceDosePopulation
Cerebral ischemia grade 4, 33%
Disc. AE
1000 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1000 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
unhealthy, 34–79
Health Status: unhealthy
Age Group: 34–79
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
Thrombocytopenia grade 1, 6.25%
Disc. AE
800 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 800 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
unhealthy, 34–79
Health Status: unhealthy
Age Group: 34–79
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
Thrombocytopenia grade 2, 6.25%
DLT
800 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 800 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
unhealthy, 34–79
Health Status: unhealthy
Age Group: 34–79
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20859231
Fatigue grade 4, 2.2%
1000 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1000 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
unhealthy, 40–65
Health Status: unhealthy
Age Group: 40–65
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
Neutropenia grade 4, 2.2%
1000 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1000 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
unhealthy, 40–65
Health Status: unhealthy
Age Group: 40–65
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/23735514
Anaphylaxis Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Hematopoiesis impaired Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Hepatic vein thrombosis grade 3-5, 0.01%
Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Hepatotoxicity grade 3-5, 0.01%
Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Necrosis hepatocellular grade 3-5, 0.01%
Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Leukopenia grade 3-5
Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Thrombocytopenia grade 3-5
Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Anemia sometimes
Disc. AE
250 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 250 mg/m2, 1 times / day
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
unhealthy
Health Status: unhealthy
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b6b97e41-5f15-498c-abfb-d8443ea4d216&type=display
Hepatic vein thrombosis grade 3-5
Disc. AE
850 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 850 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 850 mg/m2, 1 times / 3 weeks
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
Hepatotoxicity grade 3-5
Disc. AE
850 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 850 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 850 mg/m2, 1 times / 3 weeks
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
Leukopenia grade 3-5
Disc. AE
850 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 850 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 850 mg/m2, 1 times / 3 weeks
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
Thrombocytopenia grade 3-5
Disc. AE
850 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 850 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 850 mg/m2, 1 times / 3 weeks
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
Anemia mild
Disc. AE
850 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 850 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 850 mg/m2, 1 times / 3 weeks
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.ema.europa.eu/en/documents/referral/summary-information-referral-opinion-following-arbitration-pursuant-article-29-directive-2001/83/ec-formerly-article-10-paragraph-2-directive-75/319/eec-20-may-1975-amended-dacarbazine-fauld_en.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057
CYP1A2
1197

CYP1A1
389

CYP2E1
729
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
2141
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1193
 no
CYP3A4
1946
 no
CYP1A1
389
 yes
CYP1A2
1197
 yes
CYP2E1
729
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4305
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4305
eMolecules
37036088
https://www.emolecules.com/cgi-bin/more?vid=37036088
MolPort
MolPort-044-723-991
https://www.molport.com/shop/molecule-link/MolPort-044-723-991
ZINC
ZINC000254748682
http://zinc15.docking.org/substances/ZINC000254748682
PubMed

PubMed

TitleDatePubMed
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014-01
Glucocorticoid-dependent expression of O(6)-methylguanine-DNA methyltransferase gene modulates dacarbazine-induced hepatotoxicity in mice.
2010-06
Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites.
2009-06
Meta-analysis of ifosfamide-based combination chemotherapy in advanced soft tissue sarcoma.
2008-06
Cerebellar dysfunction caused by procarbazine and consumption of excessive amount of bananas.
2008-06
Unexpected clinical outcome in a patient with liver and brain metastasis from melanoma.
2008-05-29
Double-blind randomized phase II study of the combination of sorafenib and dacarbazine in patients with advanced melanoma: a report from the 11715 Study Group.
2008-05-01
Influence of therapy on the antioxidant status in patients with melanoma.
2008-04
The "old drug" dacarbazine as a second/third line chemotherapy in advanced soft tissue sarcomas.
2008-04
Plitidepsin has a dual effect inhibiting cell cycle and inducing apoptosis via Rac1/c-Jun NH2-terminal kinase activation in human melanoma cells.
2008-03
Glut-1 as a therapeutic target: increased chemoresistance and HIF-1-independent link with cell turnover is revealed through COMPARE analysis and metabolomic studies.
2008-03
Phase III comparison of vitespen, an autologous tumor-derived heat shock protein gp96 peptide complex vaccine, with physician's choice of treatment for stage IV melanoma: the C-100-21 Study Group.
2008-02-20
Hodgkin lymphoma presenting with various immunologic abnormalities, including autoimmune hepatitis, Hashimoto's thyroiditis, autoimmune hemolytic anemia, and immune thrombocytopenia.
2008-02
Multicenter phase II study of chemoimmunotherapy in the treatment of metastatic melanoma.
2008-02
The management of desmoids in patients with familial adenomatous polyposis (FAP).
2008
Adjuvant chemotherapy with doxorubicin and dacarbazine has no effect in recurrence-free survival of malignant phyllodes tumors of the breast.
2007-11-07
CD69 on CD56+ NK cells and response to chemoimmunotherapy in metastatic melanoma.
2007-11
Results of a multicenter randomized study to evaluate the safety and efficacy of combined immunotherapy with interleukin-2, interferon-{alpha}2b and histamine dihydrochloride versus dacarbazine in patients with stage IV melanoma.
2007-10
Comparison of a treatment strategy combining CCI-779 plus DTIC versus DTIC monotreatment in human melanoma in SCID mice.
2007-10
Biochemotherapy of metastatic melanoma in patients with or without recently diagnosed brain metastases.
2007-09-15
Durable complete responses with high-dose bolus interleukin-2 in patients with metastatic melanoma who have experienced progression after biochemotherapy.
2007-09-01
Chemoimmunotherapy for cutaneous melanoma with dacarbazine and epifocal contact sensitizers: results of a nationwide survey of the German Dermatologic Co-operative Oncology Group.
2007-07
Hemorrhagic cystitis in a patient receiving conventional doses of dacarbazine for metastatic malignant melanoma: case report and review of the literature.
2007-06
Combined treatment with Ad-hTRAIL and DTIC or SAHA is associated with increased mitochondrial-mediated apoptosis in human melanoma cell lines.
2007-06
Single-agent interleukin-2 in the treatment of metastatic melanoma.
2007-02
Resection in the popliteal fossa for metastatic melanoma.
2007-01-19
Interleukin-2-based biochemotherapy for patients with stage IV melanoma: long-term survivors outside a clinical trial setting.
2007
Serum VEGF-C is associated with metastatic site in patients with malignant melanoma.
2007
Alkylating benzamides with melanoma cytotoxicity: experimental chemotherapy in a mouse melanoma model.
2006-12
Chemoimmunotherapy with dacarbazine, cisplatin, interferon-alpha2b and interleukin-2 versus two cycles of dacarbazine followed by chemoimmunotherapy in patients with metastatic melanoma: a randomised phase II study of the European Organization for Research and Treatment of Cancer Melanoma Group.
2006-11
Bcl-2 antisense (oblimersen sodium) plus dacarbazine in patients with advanced melanoma: the Oblimersen Melanoma Study Group.
2006-10-10
Intralesional therapy of metastatic spreading melanoma with beta-interferon.
2006-09
Long-term survival in metastatic melanoma patients treated with sequential biochemotherapy: report of a Phase II study.
2006-08-31
Phase II multicenter study of neoadjuvant biochemotherapy for patients with stage III malignant melanoma.
2006-07-01
[Hypersensitivity to dacarbazine in patients with metastatic malignant melanoma].
2006-02
Long-term survival benefit after adjuvant treatment of cutaneous melanoma with dacarbazine and low dose natural interferon alpha: A controlled, randomised multicentre trial.
2006
Alterations in the expression of the apurinic/apyrimidinic endonuclease-1/redox factor-1 (APE/Ref-1) in human melanoma and identification of the therapeutic potential of resveratrol as an APE/Ref-1 inhibitor.
2005-12
Artesunate in the treatment of metastatic uveal melanoma--first experiences.
2005-12
Organ- and treatment-specific local response rates to systemic and local treatment modalities in stage IV melanoma.
2005-11
A retrospective study of biochemotherapy for metastatic melanoma: the importance of dose intensity.
2005-10
Dacarbazine, cisplatin, and interferon-alfa-2b with or without interleukin-2 in metastatic melanoma: a randomized phase III trial (18951) of the European Organisation for Research and Treatment of Cancer Melanoma Group.
2005-09-20
Sarcomatoid renal cell carcinoma with a chromophobe component producing beta-human chorionic gonadotropin.
2005-09
Thalidomide enhances the anti-tumor activity of standard chemotherapy in a human melanoma xenotransplatation model.
2005-08
Dana-Farber Cancer Institute studies in advanced sarcoma.
1990-02
[Hepatic veno-occlusive disease caused by Deticene: a cause of acute hypovolemic shock].
1990
Hepatic vascular toxicity of dacarbazine (DTIC): not a rare complication.
1989-05
Fatal hepatic vascular toxicity of DTIC. Is it really a rare event?
1988-05-15
Peripheral DTIC neurotoxicity: a case report.
1987
[DTIC: effect on fibrinolysis and thrombocyte function].
1986-10
Cardiomyopathy after widely separated courses of adriamycin exacerbated by actinomycin-D and mithramycin.
1975-11
Patents

Patents

US2004063677
3
US6573284
3
US6653331
3

Sample Use Guides

In Vivo Use Guide
Malignant Melanoma: the recommended dosage is 2 to 4.5 mg/kg/day for 10 days. Treatment may be repeated at 4 week intervals Hodgkin's Disease: The recommended dosage of Dacarbazine for Injection, USP in the treatment of Hodgkin’s disease is 150 mg/square meter body surface/day for 5 days, in combination with other effective drugs. Treatment may be repeated every 4 weeks.5 An alternative recommended dosage is 375 mg/square meter body surface on day 1, in combination with other effective drugs, to be repeated every 15 days
Route of Administration: Intravenous
In Vitro Use Guide
The effect of alkyating agent dacarbazine (DTIC) and imexon, alone and in combination, was evaluated for growth inhibition (MTT), radiolabeled drug uptake, cellular thiol content (HPLC), and DNA strand breaks (Comet assay). Growth inhibition in vitro was additive with the two drugs. There was no effect on drug uptake or on the number of DNA strand breaks. There was a >75% reduction in cellular glutathione and cysteine with imexon but not DTIC. Co-administration of the two drugs in mice caused an increase in the area under the curve of both drugs, but the combination was not effective in reducing human A375 melanoma tumors in vivo.
Substance Class Chemical
Created
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on Mon Mar 31 21:26:15 GMT 2025
Edited
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on Mon Mar 31 21:26:15 GMT 2025
Record UNII
9UYU348NIF
Record Status Validated (UNII)
Record Version
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Name Type Language
DACARBAZINE CITRATE
WHO-DD  
Common Name English
1H-IMIDAZOLE-4-CARBOXAMIDE, 5-(3,3-DIMETHYL-1-TRIAZEN-1-YL)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Preferred Name English
Dacarbazine citrate [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
100000092145
Created by admin on Mon Mar 31 21:26:15 GMT 2025 , Edited by admin on Mon Mar 31 21:26:15 GMT 2025
PRIMARY
EVMPD
SUB01547MIG
Created by admin on Mon Mar 31 21:26:15 GMT 2025 , Edited by admin on Mon Mar 31 21:26:15 GMT 2025
PRIMARY
FDA UNII
9UYU348NIF
Created by admin on Mon Mar 31 21:26:15 GMT 2025 , Edited by admin on Mon Mar 31 21:26:15 GMT 2025
PRIMARY
CAS
64038-56-8
Created by admin on Mon Mar 31 21:26:15 GMT 2025 , Edited by admin on Mon Mar 31 21:26:15 GMT 2025
PRIMARY
PUBCHEM
135565662
Created by admin on Mon Mar 31 21:26:15 GMT 2025 , Edited by admin on Mon Mar 31 21:26:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of DACARBAZINE
PARENT -> SALT/SOLVATE
Structure of Anhydrous citric acid
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DACARBAZINE
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