EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

dacarbazine
5-(3,3-dimethyltriazeno)imidazole-4-carboxamide

Supplier Sponsors

Name:(5E)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide
CAS Number: 4342-03-4Picture of molecule3D/inchi
Other(deleted CASRN):37626-23-6
ECHA EINECS - REACH Pre-Reg:224-396-1
FDA UNII: 7GR28W0FJI
MDL:MFCD00057167
XlogP3-AA:-0.30 (est)
Molecular Weight:182.18690000
Formula:C6 H10 N6 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystalline solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 205.00 °C. @ 760.00 mm Hg
Boiling Point: 302.60 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.001000 mmHg @ 25.00 °C. (est)
Flash Point: 278.00 °F. TCC ( 136.80 °C. ) (est)
logP (o/w): -0.240
Soluble in:
 water, 4219 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Dacarbazine >98%
Odor: characteristic
Use: Dacarbazine is an antineoplastic chemotherapy drug used in the treatment of various cancers.Dacarbazine is a member of the class of alkylating agents, which destroy cancer cells by adding an alkyl group (CnH2n+1) to its DNA.
George Uhe Company
Dacarbazine
Glentham Life Sciences
Dacarbazine
Sigma-Aldrich: Sigma
For experimental / research use only.
Dacarbazine antineoplastic purine analog
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
parenteral-hamster LD10 250 mg/kg
Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.

intravenous-human TDLo 3500 ug/kg
BLOOD: LEUKOPENIA GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 83, 1973.

intraperitoneal-mouse LD50 567 mg/kg
Cancer Treatment Reports. Vol. 62, Pg. 721, 1978.

intravenous-mouse LD50 466 mg/kg
BEHAVIORAL: ANTIPSYCHOTIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981.

oral-mouse LD50 2032 mg/kg
BEHAVIORAL: ANTIPSYCHOTIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981.

intraperitoneal-rat LD50 350 mg/kg
Archiv fuer Geschwulstforschung. Vol. 50, Pg. 306, 1980.

intravenous-rat LD50 411 mg/kg
BEHAVIORAL: ANTIPSYCHOTIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981.

oral-rat LD50 2147 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ANTIPSYCHOTIC
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for dacarbazine usage levels up to:
 not for fragrance use.
 
Recommendation for dacarbazine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5353562
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(5E)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide
Chemidplus:0004342034
EPA/NOAA CAMEO:hazardous materials
 
References:
 (5E)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5353562
Pubchem (sid):134985384
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C06936
HMDB (The Human Metabolome Database):HMDB14989
MedlinePlusSupp:View
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
dacarbazine is available as powder for preparing injections in vials containing 100 and 200 mg with mannitol and citric acid.
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 biocarbazine R
 dacarbazinum
4(5)-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide
5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide
4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide
4-(5)-(3,3-dimethyl-1-triazeno)imidazole-5(4)-carboxamide
4-(or 5)-(3,3-dimethyl-1-triazeno)imidazole-5(or 4)-carboxamide
(5E)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide
5-(dimethyltriazeno)imidazole-4-carboxamide
5-(3,3-dimethyltriazeno)imidazole-4-carboxamide
(dimethyltriazeno)imidazolecarboxamide
 imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazeno)-
 imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)-
1H-imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)-
 

Articles:

PubMed:Preclinical evaluation of IL2-based immunocytokines supports their use in combination with dacarbazine, paclitaxel and TNF-based immunotherapy.
PubMed:Immunotherapy in Melanoma: Recent Advances and Promising New Therapies.
PubMed:Insulin induces drug resistance in melanoma through activation of the PI3K/Akt pathway.
PubMed:Dabrafenib and trametinib, alone and in combination for BRAF-mutant metastatic melanoma.
PubMed:Brentuximab vedotin: first-line agent for advanced Hodgkin lymphoma.
PubMed:Triacetin-based acetate supplementation as a chemotherapeutic adjuvant therapy in glioma.
PubMed:Treatment with ipilimumab: a case report of complete response in a metastatic malignant melanoma patient.
PubMed:[Vemurafenib (Zelboraf) in the therapy of melanoma].
PubMed:Lycopene modulates growth and survival associated genes in prostate cancer.
PubMed:The European Medicines Agency review of vemurafenib (Zelboraf®) for the treatment of adult patients with BRAF V600 mutation-positive unresectable or metastatic melanoma: summary of the scientific assessment of the Committee for Medicinal Products for Human Use.
PubMed:[Antibody therapies for melanoma].
PubMed:Metastatic melanoma - a review of current and future drugs.
PubMed:New therapeutical strategies in the treatment of metastatic disease.
PubMed:Vemurafenib in patients with BRAF V600E mutation-positive advanced melanoma.
PubMed:Severe sustained cholestatic hepatitis following temozolomide in a patient with glioblastoma multiforme: case study and review of data from the FDA adverse event reporting system.
PubMed:Induction of brain tumor stem cell apoptosis by FTY720: a potential therapeutic agent for glioblastoma.
PubMed:Upcoming strategies for the treatment of metastatic melanoma.
PubMed:Combination of oncolytic adenovirus and dacarbazine attenuates antitumor ability against uveal melanoma cells via cell cycle block.
PubMed:Vemurafenib and BRAF inhibition: a new class of treatment for metastatic melanoma.
PubMed:Vemurafenib (PLX4032): an orally available inhibitor of mutated BRAF for the treatment of metastatic melanoma.
PubMed:New drugs in melanoma: it's a whole new world.
PubMed:Hematologic adverse events associated with temozolomide.
PubMed:FDA accelerated approval benefits glioblastoma.
PubMed:Sorafenib, a multikinase inhibitor, enhances the response of melanoma to regional chemotherapy.
PubMed:On assessing the presence of evaluation-time bias in progression-free survival in randomized trials.
PubMed:Malignant melanoma (metastatic).
PubMed:Combination of dacarbazine and dimethylfumarate efficiently reduces melanoma lymph node metastasis.
PubMed:Phase II clinical trial of a granulocyte-macrophage colony-stimulating factor-encoding, second-generation oncolytic herpesvirus in patients with unresectable metastatic melanoma.
PubMed:Prognostic factors in metastatic melanoma patients treated with biochemotherapy and maintenance immunotherapy.
PubMed:Neurological adverse effects caused by cytotoxic and targeted therapies.
PubMed:Adjuvant fermented wheat germ extract (Avemar) nutraceutical improves survival of high-risk skin melanoma patients: a randomized, pilot, phase II clinical study with a 7-year follow-up.
PubMed:Malignant melanoma (metastatic).
PubMed:Melanoma: immunotherapeutic approaches.
PubMed:Genasense: it ain't over till the fat lady sings.
PubMed:Cutaneous melanoma: available therapy for metastatic disease.
PubMed:Food and Drug Administration Drug approval summary: temozolomide plus radiation therapy for the treatment of newly diagnosed glioblastoma multiforme.
PubMed:Update on the systemic treatment of malignant melanoma.
PubMed:Dacarbazine-based chemotherapy for metastatic melanoma: thirty-year experience overview.
PubMed:Phase I dose-escalation and pharmacokinetic study of temozolomide (SCH 52365) for refractory or relapsing malignancies.
PubMed:A survey of treatments used in patients with metastatic melanoma: analysis of 189 patients referred to the National Cancer Institute.
PubMed:Intraindividual variations of DNA adduct levels in humans.
PubMed:Dose comparison of tropisetron (Navoban) 5 mg and 10 mg orally in the prophylaxis of dacarbazine-induced nausea and emesis.
 
Notes:
an antineoplastic agent. it has significant activity against melanomas. (from martindale, the extra pharmacopoeia, 31st ed, p564)
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