Dacarbazine (DTIC)

Alias: DTIC-Dome; WR139007; Biocarbazine; Dacarbazine; DTIC; Dakarbazin; WR 139007; WR-139007; US trade name: DTICDome. Foreign trade names: Asercit; Dacatic; Deticene; Detimedac; Fauldetic.
Cat No.:V1458 Purity: ≥98%
Dacarbazine (formerly also known as DTIC, DTIC-Dome; WR-139007; Asercit; Dacatic; Deticene) is an antitumor chemotherapeutic drug approved by FDA in the 1970s for the treatment of various cancers, including advanced melanoma (major use), Hodgkin lymphoma, sarcoma, and islet cell carcinoma of the pancreas.
Dacarbazine (DTIC) Chemical Structure CAS No.: 4342-03-4
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Dacarbazine (formerly also known as DTIC, DTIC-Dome; WR-139007; Asercit; Dacatic; Deticene) is an antitumor chemotherapeutic drug approved by FDA in the 1970s for the treatment of various cancers, including advanced melanoma (major use), Hodgkin lymphoma, sarcoma, and islet cell carcinoma of the pancreas. Dacarbazine treatment activates a Fas-independent pathway that makes melanomas more susceptible to peptide-specific CTL lysis. Dacarbazine is a member of the class of agents known as DNA-alkylating agents, which alter the DNA of cancer cells by introducing an alkyl group.

Biological Activity I Assay Protocols (From Reference)
Targets
Nucleoside antimetabolite/analog
ln Vitro

Dacarbazine treatment causes melanomas to become more susceptible to peptide-specific CTL lysis, and this is mediated by a pathway that does not require Fas[2].

ln Vivo
In melanoma flank xenografts, treatment with a combination of axitinib and DTIC exhibits strong antitumor activity. It decreases tumor cell proliferation, shrinks the area of tumor necrosis, and boosts apoptosis. In mice, it also increases longevity and decreases factors linked to meta-tasis[3].
Cell Assay
Apotosis assay: UACC903 (UACC) cells treated with or without DTIC (20 μM) for 48 hours are incubated for 5 and 16 hours, respectively, with agonist anti-Fas Ab, CH-11 (500 ng/ml). In order to determine whether FasR mediates death or apoptosis, blocking anti-Fas Ab ZB4 (2 mg/ml) is added to the appropriate groups. Following the company's instructions, cells are harvested at the conclusion of the incubation period and stained with propidium iodide and FITC-annexin V (BD PharMingen) to identify apoptosis. Ten thousand cells are taken from each group, and CellQuest software is used to analyze dead and apoptotic cells without gating.
Animal Protocol
Dissolved in 0.9% sodium chloride; 80 mg/kg; i.p. injection
B16F1 melanoma xenograft model(C57BL/6 mice background)
References

[1]. J Exp Clin Cancer Res . 2000 Mar;19(1):21-34.

[2]. J Immunol . 2004 Apr 1;172(7):4599-608.

[3]. EOncol Lett . 2013 Jul;6(1):69-74.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H10N6O
Molecular Weight
182.18
Exact Mass
182.09
Elemental Analysis
C, 39.56; H, 5.53; N, 46.13; O, 8.78
CAS #
4342-03-4
Related CAS #
4342-03-4
Appearance
White solid powder
SMILES
CN(C)/N=N/C1=C(NC=N1)C(=O)N
InChi Key
FDKXTQMXEQVLRF-ZHACJKMWSA-N
InChi Code
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+
Chemical Name
4-[(E)-dimethylaminodiazenyl]-1H-imidazole-5-carboxamide
Synonyms
DTIC-Dome; WR139007; Biocarbazine; Dacarbazine; DTIC; Dakarbazin; WR 139007; WR-139007; US trade name: DTICDome. Foreign trade names: Asercit; Dacatic; Deticene; Detimedac; Fauldetic.
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 3~5 mg/mL (16.5~27.5 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 2 mg/mL (10.98 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

Solubility in Formulation 2: 5 mg/mL (27.45 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 3: 0.5% CMC Na : 30mg/mL


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.4891 mL 27.4454 mL 54.8908 mL
5 mM 1.0978 mL 5.4891 mL 10.9782 mL
10 mM 0.5489 mL 2.7445 mL 5.4891 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03016819 Active
Recruiting
Drug: AL3818
Drug: Dacarbazine
Leiomyosarcoma
Synovial Sarcoma
Advenchen Laboratories, LLC August 15, 2017 Phase 3
NCT05269355 Active
Recruiting
Drug: Dacarbazine
Other: Placebo
Leiomyosarcoma PTC Therapeutics May 23, 2022 Phase 2
Phase 3
NCT03233347 Active
Recruiting
Drug: Dacarbazine
Drug: Doxorubicin
Ann Arbor Stage I Hodgkin
Lymphoma
Classic Hodgkin Lymphoma
Academic and Community Cancer
Research United
October 13, 2017 Phase 2
NCT02076646 Active
Recruiting
Drug: L19IL2 - Ph I
Drug: L19IL2 at RD - Ph II
Metastatic Melanoma Stage IV Philogen S.p.A. July 31, 2013 Phase 1
Phase 2
NCT03023124 Recruiting Drug: Dacarbazine
Drug: Adriamycin
Solitary Fibrous Tumors Italian Sarcoma Group March 4, 2018 Phase 2
Biological Data
  • Phenotypic changes of UACC903 following exposure to 5-FU (25 μg/ml) or DTIC (20 μM) for 48 h, as determined by flow cytometer. J Immunol . 2004 Apr 1;172(7):4599-608.
  • Cytotoxic drugs, 5-FU and DTIC, sensitize melanoma cells to killing by gp100 peptide G209-specific CTL. J Immunol . 2004 Apr 1;172(7):4599-608.
  • Melanoma cells UACC903 treated with either 5-FU (25 μg/ml) or DTIC (20 μM) became sensitive to agonist anti-Fas Ab CH-11-mediated cytolysis. J Immunol . 2004 Apr 1;172(7):4599-608.
  • Hisptopathological changes induced by the vehicle, dacarbazine (DTIC), axitinib, or a simultaneous combination of DTIC and axitinib in mice inoculated with melanoma xenografts. Oncol Lett . 2013 Jul;6(1):69-74.
  • Axitinib, alone and in combination with dacarbazine (DTIC), affects metastasis-related factors and lifespan in mice inoculated with melanoma xeno-grafts. Oncol Lett . 2013 Jul;6(1):69-74.
  • Following the administration of axitinib, dacarbazine (DTIC), a combination of axitinib and dacarbazine, or vehicle, tumor tissue sections were obtained from mice that had previously been inoculated with melanoma xenografts. Oncol Lett . 2013 Jul;6(1):69-74.
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