Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H10N6O |
Molecular Weight | 182.1832 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)\N=N\C1=C(N=CN1)C(N)=O
InChI
InChIKey=FDKXTQMXEQVLRF-ZHACJKMWSA-N
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+
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 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24284332 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DTIC-DOME Approved UseDacarbazine 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 Date1975 |
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Primary | DTIC-DOME Approved UseDacarbazine 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 Date1975 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.2 μg/mL |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.8 μM × min |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
41.4 min |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95% |
DACARBAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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: |
unhealthy, 34–79 |
Disc. AE: Cerebral ischemia... AEs leading to discontinuation/dose reduction: Cerebral ischemia (grade 4, 33%) Sources: |
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: |
unhealthy, 34–79 |
DLT: Thrombocytopenia... Disc. AE: Thrombocytopenia... Dose limiting toxicities: Thrombocytopenia (grade 2, 6.25%) AEs leading todiscontinuation/dose reduction: Thrombocytopenia (grade 1, 6.25%) Sources: |
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: |
unhealthy, 40–65 |
Other AEs: Neutropenia, Fatigue... Other AEs: Neutropenia (grade 4, 2.2%) Sources: Fatigue (grade 4, 2.2%) |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Leukopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Leukopenia (grade 3-5) Sources: 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 |
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: |
unhealthy |
Disc. AE: Anemia, Leukopenia... AEs leading to discontinuation/dose reduction: Anemia (mild) Sources: Leukopenia (grade 3-5) Thrombocytopenia (grade 3-5) Hepatotoxicity (grade 3-5) Hepatic vein thrombosis (grade 3-5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
unhealthy, 34–79 |
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: |
unhealthy, 34–79 |
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: |
unhealthy, 34–79 |
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: |
unhealthy, 40–65 |
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: |
unhealthy, 40–65 |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy |
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: |
unhealthy |
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: |
unhealthy |
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: |
unhealthy |
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: |
unhealthy |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 208.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 2195.0 |
no | |||
Page: 2195.0 |
no | |||
Page: abstract |
yes | |||
Page: abstract |
yes | |||
Page: abstract |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Cardiomyopathy after widely separated courses of adriamycin exacerbated by actinomycin-D and mithramycin. | 1975 Nov |
|
[DTIC: effect on fibrinolysis and thrombocyte function]. | 1986 Oct |
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Peripheral DTIC neurotoxicity: a case report. | 1987 |
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Fatal hepatic vascular toxicity of DTIC. Is it really a rare event? | 1988 May 15 |
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Hepatic vascular toxicity of dacarbazine (DTIC): not a rare complication. | 1989 May |
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[Hepatic veno-occlusive disease caused by Deticene: a cause of acute hypovolemic shock]. | 1990 |
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Dana-Farber Cancer Institute studies in advanced sarcoma. | 1990 Feb |
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Cisplatin, dacarbazine, and fotemustine plus interferon alpha in patients with advanced malignant melanoma. A multicenter phase II study of the Italian Cooperative Oncology Group. | 2000 Dec 15 |
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Increased susceptibility to chemotherapeutic alkylating agents of mice deficient in DNA repair methyltransferase. | 2000 Oct |
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Dacarbazine-induced carotid artery and deep venous thrombosis in a patient with leiomyosarcoma: case report. | 2001 Apr |
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Dacarbazine DTIC and carboplatin as an outpatient treatment for disseminated malignant melanoma. | 2001 Jul-Aug |
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Analysis of O(6)-methylguanine-DNA methyltransferase in melanoma tumours in patients treated with dacarbazine-based chemotherapy. | 2002 Aug |
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The role of glucocorticoids in the treatment of fulminant hepatitis induced by dacarbazine. | 2002 Feb |
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Dacarbazine causes transcriptional up-regulation of interleukin 8 and vascular endothelial growth factor in melanoma cells: a possible escape mechanism from chemotherapy. | 2003 Aug |
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Second-line chemotherapy with dacarbazine and fotemustine in nitrosourea-pretreated patients with recurrent glioblastoma multiforme. | 2003 Jul |
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Mcl-1 antisense therapy chemosensitizes human melanoma in a SCID mouse xenotransplantation model. | 2003 Jun |
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O6-methylguanine-DNA-methyltransferase expression and gene polymorphisms in relation to chemotherapeutic response in metastatic melanoma. | 2003 Oct 20 |
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[Chemoimmunotherapy with dacarbazine and aranose combined with interferon-alpha in disseminated cutaneous melanoma]. | 2004 |
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Biochemotherapy in patients with advanced vulvovaginal mucosal melanoma. | 2004 Dec |
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The prognostic role of CD4+ and CD8+ lymphocytes during chemoimmunotherapy in metastatic melanoma. | 2004 Dec |
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Exposure of melanoma cells to dacarbazine results in enhanced tumor growth and metastasis in vivo. | 2004 Jun 1 |
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Correspondence re: DC Lev et al., Dacarbazine causes transcriptional up-regulation of interleukin 8 and vascular endothelial growth factor in melanoma cells: a possible escape mechanism from chemotherapy. Mol Cancer Ther, 2003;2(8):753-63. | 2004 Mar |
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Randomized trial of dacarbazine versus bleomycin, vincristine, lomustine and dacarbazine (BOLD) chemotherapy combined with natural or recombinant interferon-alpha in patients with advanced melanoma. | 2005 Aug |
|
Artesunate in the treatment of metastatic uveal melanoma--first experiences. | 2005 Dec |
|
Combined chemoimmunotherapy of metastatic melanoma: a single institution experience. | 2005 Jun |
|
Functional erythropoietin autocrine loop in melanoma. | 2005 Mar |
|
Organ- and treatment-specific local response rates to systemic and local treatment modalities in stage IV melanoma. | 2005 Nov |
|
Long-term survival in metastatic melanoma patients treated with sequential biochemotherapy: report of a Phase II study. | 2006 Aug-Sep |
|
Alkylating benzamides with melanoma cytotoxicity: experimental chemotherapy in a mouse melanoma model. | 2006 Dec |
|
[Hypersensitivity to dacarbazine in patients with metastatic malignant melanoma]. | 2006 Feb |
|
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 Nov |
|
Bcl-2 antisense (oblimersen sodium) plus dacarbazine in patients with advanced melanoma: the Oblimersen Melanoma Study Group. | 2006 Oct 10 |
|
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 |
|
Single-agent interleukin-2 in the treatment of metastatic melanoma. | 2007 Feb |
|
Resection in the popliteal fossa for metastatic melanoma. | 2007 Jan 19 |
|
Chemoimmunotherapy for cutaneous melanoma with dacarbazine and epifocal contact sensitizers: results of a nationwide survey of the German Dermatologic Co-operative Oncology Group. | 2007 Jul |
|
Hemorrhagic cystitis in a patient receiving conventional doses of dacarbazine for metastatic malignant melanoma: case report and review of the literature. | 2007 Jun |
|
Combined treatment with Ad-hTRAIL and DTIC or SAHA is associated with increased mitochondrial-mediated apoptosis in human melanoma cell lines. | 2007 Jun |
|
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 Oct |
|
Comparison of a treatment strategy combining CCI-779 plus DTIC versus DTIC monotreatment in human melanoma in SCID mice. | 2007 Oct |
|
Biochemotherapy of metastatic melanoma in patients with or without recently diagnosed brain metastases. | 2007 Sep 15 |
|
The management of desmoids in patients with familial adenomatous polyposis (FAP). | 2008 |
|
Hodgkin lymphoma presenting with various immunologic abnormalities, including autoimmune hepatitis, Hashimoto's thyroiditis, autoimmune hemolytic anemia, and immune thrombocytopenia. | 2008 Feb |
|
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 Mar |
|
Unexpected clinical outcome in a patient with liver and brain metastasis from melanoma. | 2008 Mar-Apr |
|
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 May 1 |
|
Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites. | 2009 Jun |
|
Glucocorticoid-dependent expression of O(6)-methylguanine-DNA methyltransferase gene modulates dacarbazine-induced hepatotoxicity in mice. | 2010 Jun |
|
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 Jan |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21868520
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
by
admin
on
Edited
Mon Mar 31 18:20:31 GMT 2025
by
admin
on
Mon Mar 31 18:20:31 GMT 2025
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Record UNII |
7GR28W0FJI
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C902
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LIVERTOX |
NBK548913
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WHO-ATC |
L01AX04
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NDF-RT |
N0000175558
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WHO-VATC |
QL01AX04
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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1162308
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7GR28W0FJI
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100000088395
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3232
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7GR28W0FJI
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DB00851
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45388
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Dacarbazine
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DACARBAZINE
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3219
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4342-03-4
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C411
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DTXSID0020369
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135398738
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224-396-1
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CHEMBL476
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DACARBAZINE
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PRIMARY | Description: A colourless or pale yellow, crystalline powder.Solubility: Slightly soluble in water and ethanol (~750 g/l) TS.Category: Cytotoxic drug.Storage: Dacarbazine should be kept in a tightly closed container, protected from light, and stored at a temperature notexceeding 8 ?C.Additional information: CAUTION: Dacarbazine must be handled with care, avoiding contact with the skin and inhalation ofairborne particles. | ||
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m4065
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PRIMARY | Merck Index | ||
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4305
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SUB06882MIG
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D003606
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773
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3098
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PRIMARY | RxNorm |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE INACTIVE -> PARENT |
Plasma exposure to AIC was equivalent to that of DTIC, whereas urinary recovery of DTIC and AIC was low and highly variable.
MAJOR
PLASMA
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE ACTIVE -> PRODRUG |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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