Dacarbazine
Dacarbazine is a triazene derivative with antineoplastic activity. Dacarbazine alkylates and cross-links DNA during all phases of the cell cycle, resulting in disruption of DNA function, cell cycle arrest, and apoptosis.
1: Maafi M, Lee LY. Determination of Dacarbazine Φ-Order Photokinetics, Quantum Yields, and Potential for Actinometry. J Pharm Sci. 2015 Jul 14. doi: 10.1002/jps.24568. [Epub ahead of print] PubMed PMID: 26173629.
2: Shih V, Ten Ham RM, Bui CT, Tran DN, Ting J, Wilson L. Targeted Therapies Compared to Dacarbazine for Treatment of BRAF(V600E) Metastatic Melanoma: A Cost-Effectiveness Analysis. J Skin Cancer. 2015;2015:505302. doi: 10.1155/2015/505302. Epub 2015 Jun 10. PubMed PMID: 26171248; PubMed Central PMCID: PMC4478371.
3: Carvajal RD, Schwartz GK, Mann H, Smith I, Nathan PD. Study design and rationale for a randomised, placebo-controlled, double-blind study to assess the efficacy of selumetinib (AZD6244; ARRY-142886) in combination with dacarbazine in patients with metastatic uveal melanoma (SUMIT). BMC Cancer. 2015 Jun 10;15:467. doi: 10.1186/s12885-015-1470-z. PubMed PMID: 26059332; PubMed Central PMCID: PMC4460965.
4: Latimer NR, Abrams KR, Amonkar MM, Stapelkamp C, Swann RS. Adjusting for the Confounding Effects of Treatment Switching-The BREAK-3 Trial: Dabrafenib Versus Dacarbazine. Oncologist. 2015 Jul;20(7):798-805. doi: 10.1634/theoncologist.2014-0429. Epub 2015 Jun 3. PubMed PMID: 26040620.
5: Urosevic-Maiwald M, Barysch MJ, Cheng PF, Karpova MB, Steinert H, Okoniewski MJ, Dummer R. In vivo profiling reveals immunomodulatory effects of sorafenib and dacarbazine on melanoma. Oncoimmunology. 2015 Jan 7;4(2):e988458. eCollection 2015 Feb. PubMed PMID: 25949886; PubMed Central PMCID: PMC4404845.
6: Ahmad I, Ahmad M. Dacarbazine as a minor groove binder of DNA: Spectroscopic, biophysical and molecular docking studies. Int J Biol Macromol. 2015 May 1;79:193-200. doi: 10.1016/j.ijbiomac.2015.04.055. [Epub ahead of print] PubMed PMID: 25940530.
7: Latosińska JN, Latosińska M, Seliger J, Žagar V, Burchardt DV, Derwich K. Unusual case of desmotropy. Combined spectroscopy (¹H-¹⁴N NQDR) and quantum chemistry (periodic hybrid DFT/QTAIM and Hirshfeld surface-based) study of solid dacarbazine (anti-neoplastic). Solid State Nucl Magn Reson. 2015 Jun-Jul;68-69:13-24. doi: 10.1016/j.ssnmr.2015.04.005. Epub 2015 Apr 23. PubMed PMID: 25936462.
8: Rozera C, Cappellini GA, D'Agostino G, Santodonato L, Castiello L, Urbani F, Macchia I, Aricò E, Casorelli I, Sestili P, Montefiore E, Monque D, Carlei D, Napolitano M, Rizza P, Moschella F, Buccione C, Belli R, Proietti E, Pavan A, Marchetti P, Belardelli F, Capone I. Intratumoral injection of IFN-alpha dendritic cells after dacarbazine activates anti-tumor immunity: results from a phase I trial in advanced melanoma. J Transl Med. 2015 May 2;13:139. doi: 10.1186/s12967-015-0473-5. PubMed PMID: 25933939; PubMed Central PMCID: PMC4438625.
9: Hardy KM, Strizzi L, Margaryan NV, Gupta K, Murphy GF, Scolyer RA, Hendrix MJ. Targeting nodal in conjunction with dacarbazine induces synergistic anticancer effects in metastatic melanoma. Mol Cancer Res. 2015 Apr;13(4):670-80. doi: 10.1158/1541-7786.MCR-14-0077. Epub 2015 Mar 12. PubMed PMID: 25767211; PubMed Central PMCID: PMC4398626.
10: Ferrucci PF, Minchella I, Mosconi M, Gandini S, Verrecchia F, Cocorocchio E, Passoni C, Pari C, Testori A, Coco P, Munzone E. Dacarbazine in combination with bevacizumab for the treatment of unresectable/metastatic melanoma: a phase II study. Melanoma Res. 2015 Jun;25(3):239-45. doi: 10.1097/CMR.0000000000000146. PubMed PMID: 25746039.
2: Shih V, Ten Ham RM, Bui CT, Tran DN, Ting J, Wilson L. Targeted Therapies Compared to Dacarbazine for Treatment of BRAF(V600E) Metastatic Melanoma: A Cost-Effectiveness Analysis. J Skin Cancer. 2015;2015:505302. doi: 10.1155/2015/505302. Epub 2015 Jun 10. PubMed PMID: 26171248; PubMed Central PMCID: PMC4478371.
3: Carvajal RD, Schwartz GK, Mann H, Smith I, Nathan PD. Study design and rationale for a randomised, placebo-controlled, double-blind study to assess the efficacy of selumetinib (AZD6244; ARRY-142886) in combination with dacarbazine in patients with metastatic uveal melanoma (SUMIT). BMC Cancer. 2015 Jun 10;15:467. doi: 10.1186/s12885-015-1470-z. PubMed PMID: 26059332; PubMed Central PMCID: PMC4460965.
4: Latimer NR, Abrams KR, Amonkar MM, Stapelkamp C, Swann RS. Adjusting for the Confounding Effects of Treatment Switching-The BREAK-3 Trial: Dabrafenib Versus Dacarbazine. Oncologist. 2015 Jul;20(7):798-805. doi: 10.1634/theoncologist.2014-0429. Epub 2015 Jun 3. PubMed PMID: 26040620.
5: Urosevic-Maiwald M, Barysch MJ, Cheng PF, Karpova MB, Steinert H, Okoniewski MJ, Dummer R. In vivo profiling reveals immunomodulatory effects of sorafenib and dacarbazine on melanoma. Oncoimmunology. 2015 Jan 7;4(2):e988458. eCollection 2015 Feb. PubMed PMID: 25949886; PubMed Central PMCID: PMC4404845.
6: Ahmad I, Ahmad M. Dacarbazine as a minor groove binder of DNA: Spectroscopic, biophysical and molecular docking studies. Int J Biol Macromol. 2015 May 1;79:193-200. doi: 10.1016/j.ijbiomac.2015.04.055. [Epub ahead of print] PubMed PMID: 25940530.
7: Latosińska JN, Latosińska M, Seliger J, Žagar V, Burchardt DV, Derwich K. Unusual case of desmotropy. Combined spectroscopy (¹H-¹⁴N NQDR) and quantum chemistry (periodic hybrid DFT/QTAIM and Hirshfeld surface-based) study of solid dacarbazine (anti-neoplastic). Solid State Nucl Magn Reson. 2015 Jun-Jul;68-69:13-24. doi: 10.1016/j.ssnmr.2015.04.005. Epub 2015 Apr 23. PubMed PMID: 25936462.
8: Rozera C, Cappellini GA, D'Agostino G, Santodonato L, Castiello L, Urbani F, Macchia I, Aricò E, Casorelli I, Sestili P, Montefiore E, Monque D, Carlei D, Napolitano M, Rizza P, Moschella F, Buccione C, Belli R, Proietti E, Pavan A, Marchetti P, Belardelli F, Capone I. Intratumoral injection of IFN-alpha dendritic cells after dacarbazine activates anti-tumor immunity: results from a phase I trial in advanced melanoma. J Transl Med. 2015 May 2;13:139. doi: 10.1186/s12967-015-0473-5. PubMed PMID: 25933939; PubMed Central PMCID: PMC4438625.
9: Hardy KM, Strizzi L, Margaryan NV, Gupta K, Murphy GF, Scolyer RA, Hendrix MJ. Targeting nodal in conjunction with dacarbazine induces synergistic anticancer effects in metastatic melanoma. Mol Cancer Res. 2015 Apr;13(4):670-80. doi: 10.1158/1541-7786.MCR-14-0077. Epub 2015 Mar 12. PubMed PMID: 25767211; PubMed Central PMCID: PMC4398626.
10: Ferrucci PF, Minchella I, Mosconi M, Gandini S, Verrecchia F, Cocorocchio E, Passoni C, Pari C, Testori A, Coco P, Munzone E. Dacarbazine in combination with bevacizumab for the treatment of unresectable/metastatic melanoma: a phase II study. Melanoma Res. 2015 Jun;25(3):239-45. doi: 10.1097/CMR.0000000000000146. PubMed PMID: 25746039.
| Chemical | |
|---|---|
| CAS Num | 4342-03-4 |
| Chemical Formula | C6H10N6O |
| Molecular Weight | 182.18 |
| IUPAC Chemical Name | (E)-5-(3,3-dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide |
| Exact Mass | 182.09161 |
| Elemental Analysis | C, 39.56; H, 5.53; N, 46.13; O, 8.78 |
| Synonym | Biocarbazine; Dacarbazina; Dacarbazina Almirall; Dacarbazine DTIC; Dakarbazin; Dimethyl (triazeno) imidazolecarboxamide; Dimethyl Triazeno Imidazol Carboxamide; Dimethyl Triazeno Imidazole Carboxamide; Imidazole Carboxamide |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C(C1=C(/N=N/N(C)C)NC=N1)N |
| Biological | |
| Targets and Effects | N/A |
| Pathways | alkylating agent AAA apoptosis |
| Physical | |
| Appearance | white solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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