 Home > Encyclopedia > 9-Nitrocamptothecin

9-Nitrocamptothecin

9-Nitrocamptothecin structure

CAS No:
91421-42-0
Formula:
C20H15N3O6
Chemical Name:
9-Nitrocamptothecin
Synonyms:
1H-Pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-ethyl-4-hydroxy-10-nitro-,(4S)-;1H-Pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-ethyl-4-hydroxy-10-nitro-,(S)-;(4S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;9-Nitrocamptothecin;9-Nitro-20(S)-camptothecin;RFS 2000;Rubitecan;Orathecin;2050741-77-8
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Rubitecan (RFS 2000), a camptothecin derivative, is an orally active topoisomerase I inhibitor with broad antitumor activity, and induces protein-linked DNA single-strand breaks, thereby blocking DNA and RNA synthesis in dividing cells[1][2][3].

Rubitecan is a pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin. It has a role as an antineoplastic agent, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and a prodrug. It is a pyranoindolizinoquinoline, a C-nitro compound, a semisynthetic derivative, a tertiary alcohol and a delta-lactone.|Rubitecan is a semisynthetic agent related to camptothecin with potent antitumor and antiviral properties. Rubitecan binds to and inhibits the enzyme topoisomerase I and induces protein-linked DNA single-strand breaks, thereby blocking DNA and RNA synthesis in dividing cells; this agent also prevents repair of reversible single-strand DNA breaks. (NCI04)

9-Nitrocamptothecin Basic Attributes

Molecular Weight：

393.35

Exact Mass：

393.35

UNII：

H19C446XXB

DSSTox ID：

DTXSID7046752

NCI Thesaurus Code：

C1485

HScode：

29399990

Characteristics

PSA：

127.24000

XLogP3：

1.38

Appearance：

Yellow amorphous powder

Density：

1.6±0.1 g/cm3

Melting Point：

182-186 °C

Boiling Point：

816.3±65.0 °C at 760 mmHg

Flash Point：

106℃

Refractive Index：

1.762

Storage Conditions：

room temp

Vapor Pressure：

3.53E-28mmHg at 25°C

Specific rotation：

D23 +27° (c = 0.2 in CH3OH-CHCl3, 1:4)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

24/25

RTECS Number：

UQ0493300

Drug Information

Drug Indication：

Investigated for use/treatment in pancreatic cancer, leukemia (unspecified), melanoma, ovarian cancer, and cancer/tumors (unspecified).

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)

Mechanism of Action：

Rubitecan prevents DNA from unwinding during replication via DNA topoisomerase 1, therefore interfering with tumor growth.

MeSH Entry Terms：

9-nitro-20(S)-camptothecin

9-Nitrocamptothecin Use and Manufacturing

Uses

Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin. Antineoplastic

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:393.3
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:393.09608521
Monoisotopic Mass:393.09608521
Topological Polar Surface Area:126
Heavy Atom Count:29
Complexity:861
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of 9-Nitrocamptothecin

HANGZHOU LEAP CHEM CO., LTD. Contact Supplier

CN
5 YRS

Business licensed

Trader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives

Rubitecan

CAS No.: 91421-42-0

Content: 99.00%

Inquiry
Shaanxi Dideu Medichem Co. Ltd Contact Supplier

CN
4 YRS

Business licensed Certified factory

Manufactory Supplier of Chemical Pesticides,Food Additives,Agrochemicals,Active Pharm Ingredients,Flavors and Fragrances,Chemical Catalyst,Chemical Materials,Chem&Pharm Intermediates,Organic Intermediates,Feed Additive

Rubitecan

CAS No.: 91421-42-0

Grade: Pharmaceutical Grade

Content: 95%

Inquiry