CAS 154-93-8|Carmubris|Gliadel Wafer|Carmustin|Nitrumon|BiCNU|Bi CNU|Bischlorethylnitrosurea|1,3-bis(2-chloroethyl)-1-nitrosourea|Becenun|Bischlorethylnitrosourea|1,3-bis(2-chloroethyl)-1-nitrosoure...

基本信息

化学结构

分子式

C₅H₉Cl₂N₃O₂

分子量

214.04986

精确质量

213.0071819

电荷

InChI

InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

InChIKey

DLGOEMSEDOSKAD-UHFFFAOYSA-N

Canonic Smiles

ClCCNC(=O)N(CCCl)N=O

Isomeric Smiles

ClCCN(N=O)C(=O)NCCCl

计算属性

JChem

Acid pKa

11.963143

质子受体

质子供体

LogD (pH = 5.5)

1.0226562

LogD (pH = 7.4)

1.0226457

Log P

1.0226563

摩尔折射率

46.9797

极化性

17.322094

极化表面积

61.77

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

1.24

LOG S

-2.15

溶解度

1.53e+00 g/l

数据来源

名称和标识

商标名

CarmubrisGliadel WaferNitrumonBiCNUBi CNUBecenunGliadel

别名

CarmustinBischlorethylnitrosureaBischlorethylnitrosoureaBCNUCarmustine1,3-Bis(2-chloroethyl)-1-nitrosoureaCarmustineCarmubrisNitrumonBecenumBCNU, N,N’-Bis(2-chloroethyl)-N-nitrosourea, NSC-409962, Becenun, Bicnu,

IUPAC标准名

1,3-bis(2-chloroethyl)-1-nitrosourea 1,3-bis(2-chloroethyl)-3-nitrosourea

IUPAC传统名

1,3-bis(2-chloroethyl)-1-nitrosourea carmustine

名称和标识

数据登录号

CAS号

154-93-8

PubChem CID

2578

PubChem SID

1609636102427828946506980

EC号

205-838-2

MDL号

MFCD00057706

数据登录号

化合物性质

产品相关信息

纯度

≥98%

Empirical Formula (Hill Notation)

C5H9Cl2N3O2

质检报告

下载链接

应用领域

Antineoplastic agent

Used to treat gliomas, glioblastoma multiforme, medulloblastoma and astrocytoma, multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin).

药理学性质

相关基因信息

human ... GSR(2936)

生物活性机理

Alkylating agent in cancer chemotherapy

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

DrugBank

DB00262

Drug Groups

approved

Description

A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed)

Indication

For the treatment of brain tumors, multiple myeloma, Hodgkin's disease and Non-Hodgkin's lymphomas.

Pharmacology

Carmustine is one of the nitrosoureas indicated as palliative therapy as a single agent or in established combination therapy with other approved chemotherapeutic agents in treatment of brain tumors, multiple myeloma, Hodgkin's disease, and non-Hodgkin's lymphomas. Although it is generally agreed that carmustine alkylates DNA and RNA, it is not cross resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins.

Toxicity

The oral LD₅₀s in rat and mouse are 20 mg/kg and 45 mg/kg, respectively. Side effects include leukopenia, thrombocytopenia, nausea. Toxic effects include pulmonary fibrosis (20-0%) and bone marrow toxicity.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic and rapid with active metabolites. Metabolites may persist in the plasma for several days.

Absorption

5 to 28% bioavailability

Half Life

15-30 minutes

Protein Binding

80%

Elimination

Approximately 60% to 70% of a total dose is excreted in the urine in 96 hours and about 10% as respiratory CO2.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

C0400

Biochem/physiol Actions
Carmustine is a DNA alkylating agent causing DNA interstrand crosslinks.1 Effective against glioma and other solid tumors.

TRC

C183875

An alkylating and carbamoylating nitrosourea compound. It interacts with DNA, RNA and proteins causing DNA interstrand cross linking which is cytotoxic and leads to apoptotic cell death.

描述信息

参考文献

PubChem文献

数据源提供

• Kokkinakis, D.M., et al.: Clin. Cancer Res., 5(1992)

• 3676 (1992)

• Hickman, M.J., et al.: Proc. Natl. Acad. Sci. USA, 96(1992)

• Stahl, et al.: Chem. Res. Toxicol., 5, 106 (1992)

• 10764 (1992)

• IARC Monog., 1981, 26, 79; Suppl. 6, 116; Suppl. 7, 150, (rev, tox)

• Lien, E.J. et al., Spectrosc. Lett., 1972, 5, 293, (pmr)

• Reed, D.J. et al., Anticancer Drugs: Reactive Metabolism and Drug Interactions, (Ed. Powis, G.) Pergamon Press, 1994, 187, (rev)

• Kaba, S.E. et al., Drugs, 1997, 53, 235, (use, rev)

• Lown, J.W. et al., J.O.C., 1981, 46, 5309, (synth, cmr, N-15 nmr)

• Paoletti, R. et al., Am. J. Cardiol., 1983, 52, 21, (rev)

• Wiencke, J.K. et al., Mutat. Res., 1995, 339, 91, (rev, genotox)

• Loo, T.L. et al., J. Pharm. Sci., 1966, 55, 492, (pharmacol)

• Gombar, C.T. et al., Diss. Abstr. Int., B, 1980, 40, 5223; 5686, (props)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 550

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BIF750

• Johnston, T.P. et al., J. Med. Chem., 1963, 6, 669, (synth)

• Thompson, G.R. et al., Toxicol. Appl. Pharmacol., 1972, 21, 405, (tox)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

CarmubrisGliadel WaferNitrumonBiCNUBi CNUBecenunGliadel

别名

IUPAC标准名

1,3-bis(2-chloroethyl)-1-nitrosourea 1,3-bis(2-chloroethyl)-3-nitrosourea

IUPAC传统名

1,3-bis(2-chloroethyl)-1-nitrosourea carmustine

数据登录号

CAS号

154-93-8

PubChem CID

2578

PubChem SID

1609636102427828946506980

EC号

205-838-2

MDL号

MFCD00057706

描述信息

DrugBank

DB00262

Drug Groups

approved

Description

Indication

For the treatment of brain tumors, multiple myeloma, Hodgkin's disease and Non-Hodgkin's lymphomas.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic and rapid with active metabolites. Metabolites may persist in the plasma for several days.

Absorption

5 to 28% bioavailability

Half Life

15-30 minutes

Protein Binding

80%

Elimination

Approximately 60% to 70% of a total dose is excreted in the urine in 96 hours and about 10% as respiratory CO2.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

C0400

Biochem/physiol Actions
Carmustine is a DNA alkylating agent causing DNA interstrand crosslinks.1 Effective against glioma and other solid tumors.

TRC

C183875

An alkylating and carbamoylating nitrosourea compound. It interacts with DNA, RNA and proteins causing DNA interstrand cross linking which is cytotoxic and leads to apoptotic cell death.

参考文献

PubChem文献

数据源提供

• Kokkinakis, D.M., et al.: Clin. Cancer Res., 5(1992)

• 3676 (1992)

• Hickman, M.J., et al.: Proc. Natl. Acad. Sci. USA, 96(1992)

• Stahl, et al.: Chem. Res. Toxicol., 5, 106 (1992)

• 10764 (1992)

• IARC Monog., 1981, 26, 79; Suppl. 6, 116; Suppl. 7, 150, (rev, tox)

• Lien, E.J. et al., Spectrosc. Lett., 1972, 5, 293, (pmr)

• Reed, D.J. et al., Anticancer Drugs: Reactive Metabolism and Drug Interactions, (Ed. Powis, G.) Pergamon Press, 1994, 187, (rev)

• Kaba, S.E. et al., Drugs, 1997, 53, 235, (use, rev)

• Lown, J.W. et al., J.O.C., 1981, 46, 5309, (synth, cmr, N-15 nmr)

• Paoletti, R. et al., Am. J. Cardiol., 1983, 52, 21, (rev)

• Wiencke, J.K. et al., Mutat. Res., 1995, 339, 91, (rev, genotox)

• Loo, T.L. et al., J. Pharm. Sci., 1966, 55, 492, (pharmacol)

• Gombar, C.T. et al., Diss. Abstr. Int., B, 1980, 40, 5223; 5686, (props)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 550

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BIF750

• Johnston, T.P. et al., J. Med. Chem., 1963, 6, 669, (synth)

• Thompson, G.R. et al., Toxicol. Appl. Pharmacol., 1972, 21, 405, (tox)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

纯度

≥98%

Empirical Formula (Hill Notation)

C5H9Cl2N3O2

质检报告

下载链接

应用领域

Antineoplastic agent

Used to treat gliomas, glioblastoma multiforme, medulloblastoma and astrocytoma, multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin).

药理学性质

化合物信息

ID:147