[(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methyl carbamate

• ChemBase编号: 190
• 分子式: C15H18N4O5
• 平均质量: 334.32722
• 单一同位素质量: 334.1277197
• SMILES: O([C@@]12N(C[C@@H]3N[C@H]13)C1=C([C@H]2COC(=O)N)C(=O)C(=C(C1=O)C)N)C
• Canonical SMILES: CO[C@@]12[C@H]3N[C@H]3CN2C2=C([C@H]1COC(=O)N)C(=O)C(=C(C2=O)C)N
• InChI: InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1
• InChIKey: NWIBSHFKIJFRCO-WUDYKRTCSA-N

名称和登记号

名称

• IUPAC标准名: [(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methyl carbamate; [(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^2,^7.0^4,^6]trideca-1(9),11-dien-8-yl]methyl carbamate
• IUPAC系统名: {11-Amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^2,7.0^4,6]trideca-1(9),11-dien-8-yl}methyl carbamate
• IUPAC传统名: mitomycin-C; mitamycin
• 商标名: Ametycin; Ametycine; Mit-C; Mito-C; Mitocin-C; Mitomycin (TN); Mitomycin C; Mitomycin-C; Mitomycinum; Mitomycinum C; Mitomycyna C [Polish]; Mitozytrex; Muamycin; Mutamycin; Mytomycin; Mytozytrex
• 别名: 丝裂霉素 C 来源于头状链霉菌; Mitomycin C from Streptomyces caespitosus; [1aS-(1aα,8β,8aα,8bα)-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2,’3’:3,4]pyrrolo[1,2-a]indole-4,7-dione; Ametycine; Mutamycin; Mitonco; Mitoplus; NSC 26980; Mitocin C; Mitomycin C; 7-Amino-9α -methoxymitosane; Mitamycin; MMC; Mitomycin; Mitomycin C

登记号

• CAS号: 50-07-7
• EC号: 200-008-6
• MDL号: MFCD00078109
• Beilstein号: 7231816; 3570056
• PubChem SID: 46508353; 160963653; 24896554
• PubChem CID: 5746
• CHEBI ID: 27504
• ATC码: L01DC03
• CHEMBL: 105
• Chemspider ID: 5544
• DrugBank ID: DB00305
• KEGG ID: C06681
• 美国药典/FDA物质标识码: 50SG953SK6
• 维基百科标题: Mitomycin

理论计算性质

JChem

• Acid pKa: -0.3018127
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -2.9682753
• LogD (pH = 7.4): -3.2154355
• Log P: -2.9575114
• 摩尔折射率: 83.2689 cm^3
• 极化性: 31.659235 Å^3
• 极化表面积: 146.89 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.55
• LOG S: -1.52
• 溶解度: 1.01e+01 g/l

分子性质

理化性质

• 溶解度: 8.43 g L^-1 in water; Acetone; Methanol; Soluble (8430 mg/L); Water
• 外观: Blue-Violet Crystals; White or colourless solid
• 熔点: >300°C; 360°C (low of range)
• 分配系数: -1.6
• 疏水性(logP): -1.6
• 等电点: 10.9

安全信息

• 保存条件: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• RTECS编号: CN0700000
• 欧盟危险性物质标志: 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 22-40; 25-40
• 安全公开号: 28-36/37-45; 36/37
• GHS危险品标识: GHS06; GHS07; GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H300-H351; H302-H351
• GHS警示性声明: P264-P281-P301 + P310; P281
• 个人保护装置: 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
• RID/ADR: UN 3462 6.1/PG 2
• 保存温度: 2-8°C

药理学性质

• 给药途径: Eye drops Intravenous
• 半衰期: 8–48 min
• 代谢: Hepatic
• 法定药品分级: POM (UK); Rx (US)
• 妊娠期药物分类: D (Australia); D (US)

产品相关信息

• 纯度: ≥970 μg/mg (USP XXIV)
• Empirical Formula (Hill Notation): C15H18N4O5

详细说明

DrugBank - DB00305

• Drug Groups: approved
• Description: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional alkylating agents causing cross-linking of DNA and inhibition of DNA synthesis. [PubChem]
• Indication: For treatment of malignant neoplasm of lip, oral cavity, pharynx, digestive organs, peritoneum, female breast, and urinary bladder. Also used as an adjunct to ab externo glaucoma surgery.
• Pharmacology: Mitomycin is one of the older chemotherapy drugs, which has been around and in use for decades. It is an antibiotic which has been shown to have antitumor activity. Mitomycin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of mitomycin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. Mitomycin has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2.
• Toxicity: Oral, mouse: LD₅₀ = 23 mg/kg; Oral, rat: LD₅₀ = 30 mg/kg. Symptoms of overdose include nausea and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, some in various other tissues.
• Absorption: Erratic.
• Half Life: 8-48 min
• Elimination: Approximately 10% of a dose of mitomycin is excreted unchanged in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M0440

Application
Used as a sequence specific (5′-CpG-3′) DNA crosslinking (alkylation) agent.
Biochem/physiol Actions
DNA 合成、细胞核分裂和癌细胞的抑制剂。对革兰氏阳性菌、革兰氏阴性菌、抗酸杆菌有抗菌性。
Other Notes
无 NaCl
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 69824

Biochem/physiol Actions
DNA 合成、细胞核分裂和癌细胞的抑制剂。对革兰氏阳性菌、革兰氏阴性菌、抗酸杆菌有抗菌性。
Other Notes
Vial contains 2 mg mitomycin C and 48 mg NaCl (increases solubility).

Toronto Research Chemicals - M371900

An antitumor antibiotic. It is used as antineoplastic.

参考文献

• Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971)
• Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 16, 361 (1971)