Dacarbazine 达卡巴嗪三嗪咪唑胺

CAS 4342-03-4 MFCD00057167

化学结构图

4342-03-4
SMILES: CN(C)N=Nc1[nH]cnc1C(N)=O

化学属性

Mol. FormulaC6H10N6O
Mol. Weight182
Melting Point210-212°
TSCANo
SolubilityDMSO 3 mg/mL Water <1 mg/mL Ethanol <1 mg/mL
Appearance 微黄色结晶或粉末。熔点205℃，也有报道250-255℃（分解）。易溶于酸，微溶于甲醇，乙醇，不溶于水。遇热分解，对酸和光不稳定。

别名和识别编码

Chemical NameDacarbazine
CAS Number4342-03-4
Synonym (Dimethyltriazeno)imidazolecarboxamide (dimethyltriazeno)imidazolecarboxamide 1H-Imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)- 4-(3,3-Dimethyl-1-triazeno)imidazole-5-carboxamide 4-(3,3-dimethyltriazeno)imidazole-5-carboxamide 4-(5)-(3,3-Dimethyl-1-triazeno)imidazole-5(4)-carboxamide 4-(5)-(3,3-dimethyl-1-triazeno)imidazole-5(4)-carboxamide 4-(Dimethyltriazeno)imidazole-5-carboxamide 4-(dimethyltriazeno)imidazole-5-carboxamide 5-(3,3-DIMETHYL-1-TRIAZENYL)-1H-IMIDAZOLE-4-CARBOXAMIDE 5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide DTIC 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide; 4-(3,3-Dimethyltriazeno)imidazole-5-carboxamide; 4-(Dimethyltriazeno)imidazole-5-carboxamide 5-(3,3-Dimethyltriazeno)imidazole-4-carboxamide 5-(3,3-dimethyl-1-triazeno)-imidazole-4-carboxamid 5-(3,3-dimethyl-1-triazeno1-imidazole-4-carboxamid 5-(3,3-二甲基-1-三氮烯)-咪唑-4-酰胺 5-(3,3-二甲基-1-三氮烯)咪唑-4-羧酰胺 5-(Dimethyltriazeno)imidazole-4-carboxa 5-(dimethyltriazeno)imidazole-4-carboxamide 5-[3,3-DIMETHYL-1-TRIAZENYL]IMIDAZOLE-4-CARBOXAMIDE Biocarbazine R DACARBAZINE DIC DTIC Dacarbazine Dacatic Deticene NCI-C04717 NSC-45388 biocarbaziner deticene {} {Ch {} {Che {} {Chemicalbook} 三嗪咪唑胺 三嗪唑胺 三氮烯咪唑胺 抗黑瘤 氮烯咪胺 氮烯唑胺 甲嗪咪唑胺 达卡巴嗪
MDL NumberMFCD00057167
PubChem Substance ID135398738
EC Number224-396-1
Merck Number2798
Reaxys-RN521487
Chemical Name Translation达卡巴嗪三嗪咪唑胺
Wiswesser Line NotationT5M CNJ DVZ ENUNN1&1
InChIInChI=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+
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分类

  • Bases & Related Reagents
  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antitumor Agents, Cancer Research, DNA Modification / Repair, Interferes with DNA Synthesis, Mechanism of Action
  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antitumor Agents, Biochemicals and Reagents, Cancer Research, Cell Biology, DNA Modification / Repair, Interferes with DNA Synthesis, Mechanism of Action
  • Nucleotides
  • Heterocycles
  • {SNA} Antibiotics A to Z, Antibiotics A-F,
  • {SNA} Antibiotics A to Z,

产品应用

  • Dacarbazine is used as an antineoplastic for treatment of malignant melanoma and sarcomas.

相关文献及参考

  • Shealy, et al.: Biochem. Pharmacol., 11, 674 (1962),
  • Carter, et al.: Eur. J. Cancer, 8, 85 (1972),

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P308+P313
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H332 Harmful if inhaled 吸入有害
  • H315 Causes skin irritation 会刺激皮肤
  • H312 Harmful in contact with skin 皮肤接触有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H350 May cause cancer 可能致癌
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H340 May cause genetic defects 可能导致遗传性缺陷
  • H302+H312+H332
  • H303 May be harmfully swallowed 吞食可能有害
RTECSNI3950000
Signal word Danger
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Hazard Codes T
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
Risk Statements
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R45 May cause cancer 可能致癌
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
Storage condition 0-10 储存温度-20°C 2-8°C 0-10°C 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 25 mg/kg
                          female 20 day(s) after conception
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Reproductive - Tumorigenic effects - transplacental tumorigenesis
   Brain and Coverings - tumors
REFERENCE :
   ARGEAR Archiv fuer Geschwulstforschung.  (VEB Verlag Volk und Gesundheit
   Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.)  V.1-    1949-
   Volume(issue)/page/year: 50,306,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 3900 mg/kg/26W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Blood - lymphoma, including Hodgkin's disease
   Skin and Appendages - tumors
REFERENCE :
   RRCRBU Recent Results in Cancer Research.  (Springer-Verlag New York, Inc.,
   Service Center, 44 Hartz Way, Secaucus, NJ 07094)  V.1-    1965-
   Volume(issue)/page/year: 52,1,1975

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1950 mg/kg/26W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Blood - lymphoma, including Hodgkin's disease
REFERENCE :
   RRCRBU Recent Results in Cancer Research.  (Springer-Verlag New York, Inc.,
   Service Center, 44 Hartz Way, Secaucus, NJ 07094)  V.1-    1965-
   Volume(issue)/page/year: 52,1,1975

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 3700 mg/kg/14W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by R

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 411 mg/kg
TOXIC EFFECTS :
   Behavioral - changes in motor activity (specific assay)
   Behavioral - antipsychotic
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 9,3105,1981

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 466 mg/kg
TOXIC EFFECTS :
   Behavioral - changes in motor activity (specific assay)
   Behavioral - antipsychotic
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 9,3105,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human
DOSE/DURATION           : 3500 ug/kg
TOXIC EFFECTS :
   Gastrointestinal - nausea or vomiting
   Blood - leukopenia
   Biochemical - Enzyme inhibition, induction, or change in blood or tissue
   levels - dehydrogenases
REFERENCE :
   CCROBU Cancer Chemotherapy Reports, Part 1.  (Washington, DC)  V.52(6)-59,
   1968-75.  For publisher information, see CTRRDO.  Volume(issue)/page/year:
   57,83,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 350 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ARGEAR Archiv fuer Geschwulstforschung.  (VEB Verlag Volk und Gesundheit
   Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.)

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - rat Cells - not otherwise specified
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   36,2827,1976

TYPE OF TEST            : DNA repair
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 600 pg/plate
REFERENCE :
   NULSAK Nucleus (Calcutta).  (Dr. A.K. Sharma, Centre of Advanced Studies in
   Cell and Chromosome Research, Calcutta, 35 Baliygunge Circular Rd., Calcutta
   700 019, India)  V.1-    1958-  Volume(issue)/page/year: 28,159,1985

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - rat Cells - not otherwise specifi

TYPE OF TEST            : Sex chromosome loss and nondisjunction
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 500 umol/L/3D
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 202,251,1988

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 9 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 223,259,1989

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Fibroblast
DOSE/DURATION           : 100 umol/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   24,615,1975

{haza

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 400 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   33,2231,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 50 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   33,2231,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 200 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
   ANREAK Anatomical Record.  (Alan R. Liss, Inc., 41 E. 11th St., New York, NY
   10003)  V.1-    1906/08-  Volume(issue)/page/year: 186,461,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 100 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Sp

其他信息

  • 下游产品:氯磺隆
  • 上游原料:氰乙酸乙酯 --> 乙酰胺 --> Β乙氧基丙酸乙酯 --> 氨基咪唑
  • TCI Shanghai:达卡巴嗪 Dacarbazine,>;98.0%(LC)(T)(4342-03-4)
  • 用途一:抗肿瘤药，主要用于黑色素瘤，亦用于软组织肉瘤和恶性淋巴瘤等
  • 达卡巴嗪价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D3634 达卡巴嗪 Dacarbazine 5G 1960元 2014/06/02 D3634 达卡巴嗪 Dacarbazine 1G 660元
  • MOL 文件:4342-03-4.mol
  • MSDS 信息:4-(Dimethyltriazeno)imidazole-5-carboxamide(4342-03-4).msds
  • 用途二:抗肿瘤药。临床上用于恶性黑色素瘤，约20-30%有效，与长春醛碱和卡氮芥合并应用，可提高疗效。此外对肺鳞癌、肉瘤、平滑肌肉瘤、纤维肉瘤亦有一定疗效。对消化道癌的疗效不佳。
  • Sigma Aldrich:4342-03-4(sigmaaldrich)
  • 方法一:以氰乙酸乙酯为原料，经加成、胺化、重氮化、偶合、还原、甲酰化、环合、中和、重氮化、缩合，经过中间体β-亚胺基-β-乙氧基丙酸乙酯盐酸盐，α-脒基乙酰胺盐酸盐，α-脒基-α-苯偶氮基乙酰胺盐酸盐，5-氨基咪唑-4-羧酰胺盐酸盐而得。

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics A-F - Antibiotics A to Z
  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Mechanism of Action - Antibiotics
  4. Interferes with DNA Synthesis - Mechanism of Action

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