Carmustine 卡莫司汀

CAS 154-93-8 MFCD00057706

化学结构图

154-93-8
SMILES: O=NN(CCCl)C(=O)NCCCl

化学属性

Mol. FormulaC5H9Cl2N3O2
Mol. Weight214
Melting Point30
SolubilitySoluble in water (4 mg/ml), and 50% ethanol (150 mg/ml).
Appearance (Oily liquid to amorphous solid) 微黄色结晶性粉末。熔点30-32℃，熔化后为油状液体。溶于甲醇、乙醇，在50%乙醇中溶解度为150mg/ml，在水中溶解度为4mg/ml。在石油醚和pH4的水溶液中最稳定。
Stability对热敏感

别名和识别编码

Chemical NameCarmustine
CAS Number154-93-8
Synonym NSC-409962 CARMUSTINE Carmubris 卡莫司汀;卡氮芥;双氯乙亚硝脲;1,3-双(2-氯乙基)-1-亚硝基脲 SK 27702 carmustine N,N'-BIS(2-CHLOROETHYL)-N-NITROSOUREA 双氯乙亚硝脲 NCI-C04773 BiCnu 卡氮芥、双氯乙亚硝脲 bischlorethylnitrosurea bis(2-chloroethyl)nitrosourea fda0345 Urea, N,N'-bis(2-chloroethyl)-N-nitroso- CARMUSTIN FDA 0345 1,3-Bis(2-chloroethyl)-1-nitrosourea; Bis(2-chloroethyl)nitrosourea; N,N-Bis (2-chloroethyl)-N-nitrosourea; BCNU 卡氮芥 氯乙亚硝脲 1,3-BIS(2-CHLOROETHYL)-1-NITROSOUREA BCNU, N,N?-Bis(2-chloroethyl)-N-nitrosourea, NSC-409962, Becenun, Bicnu, N,N'-Bis(2-chloroethyl)-N-nitrosourea nci-c04773 1,3-双(2-氯乙基)-1-亚硝基脲 BCNU Bis(2-chloroethyl)nitrosourea BECENUN 1,3-bis(2-chloroethyl)-1-nitroso-ure 1,3-BIS(2-CHLOROETHYL)NITROSOUREA 1,3-bis(beta-chloroethyl)-1-nitrosourea BICNU carmubris 1,3-Bis(2-chloroethyl)-1-nitrosourea BCNU 1,3-Bis-(2-chloroethyl)-1-nitrosourea SRI 1720 nitrumon 1,3-Bis(beta-chloroethyl)-1-nitrosourea Nitrumon Bischloroethylnitrosourea Carmustine 卡莫司汀 亚硝基脲氮芥 bischloroethylnitrosourea Urea, N,N'-bis(2-chloroethyl)-N-nitroso- 1,3-Bis(2-chloroethyl)-1-nitrosourea sk27702 氯化亚硝脲 n,n’-bis(2-chloroethyl)-n-nitroso-ure
PubChem Substance ID2578
EC Number205-838-2
MDL NumberMFCD00057706
Chemical Name Translation卡莫司汀
Reaxys-RN2049744
Merck Number1845
Wiswesser Line NotationONN2GVM2G
Beilstein Registry Number2049744
InChIInChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
LabNetwork Molecule IDLN00191648
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分类

  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Biochemicals and
  • Antitumor Agents, Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Biochemicals and Reagents, Bristol-Myers Squibb, C-CH, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, D to K, DNA Intercalators and Crosslinkers, DNA Modification / Repair, DNA metabolism, Diaphorase, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Glutathione Reductase
  • {SNA} Apoptosis and Cell Cycle,
  • {SNA} Apoptosis and Cell Cycle,

产品应用

  • A DNA alkylating and cross-linking agent used in the treatment of brain tumors and various other malignant neoplasmsv

相关文献及参考

  • Stahl, et al.: Chem. Res. Toxicol., 5, 106 (1992),
  • Kokkinakis, D.M., et al.: Clin. Cancer Res., 5(11), 3676 (1999),
  • Hickman, M.J., et al.: Proc. Natl. Acad. Sci. USA, 96(19), 10764 (1999),
  • 1. Stahl, et al. Chem. Res. Toxicol. 5 , 106, (1992) 摘要
  • Becker, K. and H.R. Schirmer Meth. Enzymol. 251 , 173, (1995) 摘要
  • Arredondo, S.A., et al., Role Of Dimerization In The Catalytic Properties Of The Escherichia Coli Disulfide Isomerase DsbC. J. Thorac. Cardiovasc. Surg. 284 , 23972-9, (2009)
  • Skretas, G., and Georgiou, G., Simple Genetic Selection Protocol For Isolation Of Overexpressed Genes That Enhance Accumulation Of Membrane-integrated Human G Protein-coupled Receptors In Escherichia Coli. Appl. Environ. Microbiol. 76 , 5852-9, (2010) 摘要
  • Blazeck, J., and Alper, H., Systems Metabolic Engineering: Genome-scale Models And Beyond. Biotechnol. J. 5 , 647-59, (2010) 摘要
  • Merck 14 ,1845
  • Short: III/35B Title: Nuclear Magnetic Resonance (NMR) Data: Chemical Shifts and Coupling Constants for Fluorine-19 and Nitrogen-15 Author: Balasubramanian, M.; Gupta, R.R.; Jain, M.; Perumal, S. Editor: Gupta, R.R.; Lechner, M.D. Source: Landolt-Börnstein, New Series Volume: III/35B Year: 1998 ISBN: 3-540-63275-1 ISBN: 978-3-540-63275-7 Internet Resource: DOI:10.1007/b55685 RefComment: VII, 242 pages. With CD-ROM. Hardcover Abstract: This volume provides a comprehensive and evaluated compilation of nuclear magnetic resonance data. Chemical shifts and coupling constants of boron-11 and phosphorus-31 (subvol. A), fluorine-19 and nitrogen-15 (subvol. B), hydrogen-1 (subvol. C), and carbon-13 (subvol. D) compounds are tabulated together with the gross- and structure formulas and the most readily available solvents. Due to the large amount of the data merely chemical shifts are presented in the printed versions, and al

安全信息

GHS Symbol
WGK Germany3
Hazard Codes T+ 6.1
Hazard statements
  • H350 May cause cancer 可能致癌
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H300 Fatal if swallowed 吞食致命
  • H302 Harmful if swallowed 吞食有害
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSYS2625000
Precautionary statements
  • P301+P310+P330
  • 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。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P308+P313
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P405 Store locked up. 上锁保管。
  • P301+P312+P330
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P308+P311
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P310
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
Signal word
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • 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；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
  • 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）；
Risk Statements
  • R45 May cause cancer 可能致癌
  • R28 Very toxic if swallowed 吞咽极毒
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
  • R60 May impair fertility 可能降低生殖能力
Packing GroupII
UN Number 3249 2811
Storage condition -20°C 储存温度-20°C，充氩储存 储存温度-20°C -20
Hazard Class6.1 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 15 mg/kg/7W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Gastrointestinal - tumors
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Lippincott/Harper, Journal Fulfillment
   Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1948-
   Volume(issue)/page/year: 40,1935,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 98 mg/kg/26W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Gastrointestinal - tumors
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Lippincott/Harper, Journal Fulfillment
   Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1948-
   Volume(issue)/page/year: 40,1935,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 276 mg/kg/23W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Skin and Appendages - hair
   Skin and Appendages - tumors
REFERENCE :
   EXPEAM Experientia.  (Birkhaeuser Verlag, POB 133, CH-4010 Basel,
   Switzerland)  V.1-    1945-  Volume(issue)/page/year: 36,1211,1980

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 51 mg/kg/24W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Gastrointestinal - tumors
REFERENCE :
   DTESD7 52 Van

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 13800 ug/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - chronic pulmonary edema
   Gastrointestinal - ulceration or bleeding from stomach
   Blood - changes in bone marrow (not otherwise specified)
REFERENCE :
   ONCOBS Oncology.  (S. Karger AG, Postfach CH-4009 Basel, Switzerland) V.21- 
     1967-  Volume(issue)/page/year: 37,177,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human
DOSE/DURATION           : 6 mg/kg
TOXIC EFFECTS :
   Gastrointestinal - nausea or vomiting
   Blood - leukopenia
   Blood - thrombocytopenia
REFERENCE :
   CTRRDO Cancer Treatment Reports.  (Washington, DC)  V.60-71, 1976-87.  For
   publisher information,  see JNCIEQ.  Volume(issue)/page/year: 60,709,1976

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 19 mg/kg
TOXIC EFFECTS :
   Gastrointestinal - hypermotility, diarrhea
   Liver - jaundice, other or unclassified
   Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   21,405,1972

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 17420 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCISP* National Cancer Institute Screeni

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE

TYPE OF TEST

{hazard_co

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 5 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   49,1899,1989

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Leukocyte
DOSE/DURATION           : 1 umol/L
REFERENCE :
   BBACAQ Biochimica et Biophysica Acta.  (Elsevier Science Pub. B.V., POB 211,
   1000 AE Amsterdam, Netherlands)  V.1-    1947- Volume(issue)/page/year:
   425,463,1976

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 10 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   40,2719,1980

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 100 gm/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 106,85,1982

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Hum

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 25 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000

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

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 4 mg/kg
SEX/DURATION            : female 6-9 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   30,422,1974

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 40 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - live birth index (measured after birth)
   Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4
   per # born alive)
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
REFERENCE :
   TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis.  (Alan R. Liss, Inc.,
   41 E. 11th St., New York, NY 10003)  V.1-    1980- Volume(issue)/page/year:
   7,7,1987

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 11 mg/kg
SEX/DURATION            : male 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/p

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE

其他信息

  • 用途一:该品为广谱抗癌药。对何杰金氏病和急性白血病有较好的疗效，对乳腺癌、肺癌、脑瘤和癌的骨转移等也有一定疗效。小鼠口服LD50为19-25mg/kg，腹腔注射26mg/kg，皮下注射24mg/kg；大鼠口服30-40mg/kg。
  • 毒性分级:高毒
  • 毒性反应:1，骨髓抑制：是限制剂量的毒性反应，可表现为白细胞减少及有严重的血小板减少，通常在给药后3～5周发生，连续1～3周，抑制的最低点在3～5周出现，缓解较其他烷化剂慢。 2，胃肠道反应：严重的恶心、呕吐通常在用药后2小时开始，持续4～6小时，在用药前给予止吐剂可预防。 3，其他反应：注射部位及肢体立即出现烧灼感。罕见毒性反应包括肝肾功能障碍，一般发生在大剂量给药时，有报告可发生无痛性黄疸及肝昏迷、肺纤维化等。
  • 周期非特异性抗肿瘤药:无色或微黄或微黄绿色结晶，或结晶性粉末，无臭。不溶于水，溶于甲醇或乙醇。其水溶液pH4时稳定，其pH7以上溶液迅速分解。 卡莫司汀又称双氯乙亚硝脲、亚硝基脲氮芥、卡氮芥，和洛莫司汀，福莫司汀，司莫司汀都是目前使用最广泛的周期非特异性抗肿瘤药，为亚硝脲类烷化剂，虽具有烷化剂作用，但与一般烷化剂无交叉耐药性，具有脂溶性高、抗瘤谱广、见效快、易透过血脑屏障等特点。在体内分解为两种活性成分，一种具有氨甲酰化活性，一种为烷化剂，能与DNA聚合酶作用，抑制RNA和DNA的合成，对增殖细胞各期都有作用，而对非增殖期细胞不敏感。口服易吸收，静注给药后1小时即进入脑中，6小时后脑中药物浓度为血浆中浓度的60% ～70%，体内分布以肝、胆汁、肾、脾最多。本品半衰期短，不到15分钟。但其代谢产物半衰期长，且仍有抗癌作用，与血浆蛋白结合后缓慢释放，故作用持久，并产生延缓性毒性。本品吸收后在血液中迅速代谢，代谢产物排泄缓慢，48小时后仍有较高的血药浓度。60%以代谢物形式经尿排泄。 常用于治疗原发和继发脑部恶性肿瘤、霍奇金病、脑膜白血病。也可治疗多发性骨髓瘤、淋巴瘤、乳腺癌、恶性淋巴瘤、黑色素瘤、肺癌；与氟尿
  • 储
  • MOL 文件:154-93-8.mol
  • Carmustine is a cell-cycle phase nonspecific alkylating antineoplastic agent
  • 卡氮芥:卡氮芥为亚硝脲类烷化剂，又称卡莫司汀、双氯乙亚硝脲、氯乙亚硝脲、亚硝基脲氮芥，一方面通过烷化作用与DNA结合，另一方面通过氨甲酰基化作用于蛋白质，可抑制DNA聚合酶作用，从而阻止DNA和RNA合成，对G1-S过渡期作用最强，对S期有阻滞作用，对G2期作用又增强，对G0期也有作用，为细胞周期非特异性药。本品脂溶性好，解离度低，能透过血-脑脊液屏障，其代谢产物仍有抗癌作用，与蛋白质结合后缓慢释放，故作用持久。抗瘤谱广，对脑膜性白血病、恶性肿瘤的脑及脊髓转移、霍奇金病、急性白血病疗效好，对乳腺癌、肺癌、癌的骨转移、淋巴肉瘤、黑色素瘤和睾丸肿瘤有一定疗效，对原发与继发性脑肿瘤有效。局部外用对淋巴瘤性丘疹有良效。该药与氟尿嘧啶、长春新碱、甲氮咪胺组成FIVB方案治疗结肠癌; 与氟尿嘧啶及阿霉素组成FAB方案用于胃癌; 与长春新碱和甲氮咪胺联用，治疗黑色素瘤; 与雄激素联用治疗乳腺癌。
  • 方法一:该品有三条合成路线：（1）以乙烯亚胺为原料，经与光气缩合生成双（β-氯乙基）脲，再经亚硝化制得卡氮芥；（2）以脲为原料，经缩合、开环、氯化、亚硝化而得；（3）以乙醇胺为原料，经与方法（2）相似的步骤得到卡氮芥。第一种方法只需两步操作就可得到产品，但使用的原料乙烯亚胺及光气均为极毒品，劳动保护和生产设备要求很高。第二种方法原料易得，操作也较方便。
  • 周期非特异性抗肿瘤药:无色或微黄或微黄绿色结晶，或结晶性粉末，无臭。不溶于水，溶于甲醇或乙醇。其水溶液pH4时稳定，其pH7以上溶液迅速分解。 卡莫司汀又称双氯乙亚硝脲、亚硝基脲氮芥、卡氮芥，和洛莫司汀，福莫司汀，司莫司汀都是目前使用最广泛的周期非特异性抗肿瘤药，为亚硝脲类烷化剂，虽具有烷化剂作用，但与一般烷化剂无交叉耐药性，具有脂溶性高、抗瘤谱广、见效快、易透过血脑屏障等特点。在体内分解为两种活性成分，一种具有氨甲酰化活性，一种为烷化剂，能与DNA聚合酶作用，抑制RNA和DNA的合成，对增殖细胞各期都有作用，而对非增殖期细胞不敏感。口服易吸收，静注给药后1小时即进入脑
  • 急性毒性:口服-大鼠 LD50:

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Enzyme - Enzyme Inhibitors
  6. D to K - Enzyme Inhibitors by Enzyme
  7. Diaphorase - D to K
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. DNA metabolism - Apoptosis and Cell Cycle
  6. DNA Intercalators and Crosslinkers - DNA metabolism

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