CAS 104195-61-1 Rubitecan (HCID 472335)

Names & identifiers

Preferred name: Rubitecan
IUPAC: (19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
English name: Rubitecan
Molecular formula: C20H15N3O6
Molecular weight: 393.35

Names & synonyms

Rubitecan9-Nitrocamptothecin91421-42-09-nitro-20(S)-camptothecinOrathecinCamptogenRFS 2000RFS-2000NitrocamptothecinrubitecanumH19C446XXB9-nitro-20-(S)-camptothecin

Show more names

9-Nitrocellulose camptothecine9-NCOratheciRUBETICANRubitecane9-NITRO-CPT

DTXSID7046752CHEBI:90225RFS20009-nitro-(20S)-camptothecinDTXCID50267521H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-10-nitro-, (4S)-(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo(11.8.0.0^(2,11).0^(4,9).0^(15,20))henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

Database identifiers

CAS: 104195-61-1、91421-42-0
PubChem CID: 472335
DTXSID: DTXSID7046752
ChEMBL: CHEMBL77305
ChEBI: CHEBI:90225
UNII: H19C446XXB
EC Number: 995-853-7
Nikkaji: J448.357J

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 126 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 7
Rotatable bonds: 1
Heavy atoms: 29
Formal charge: 0
Complexity: 861

Physicochemical properties

Melting point: 182 · 182-186°C
alpha: 23 · D23 +27° (c = 0.2 in CH3OH-CHCl3, 1:4)
Boiling point: 816.3 · 816.3±65.0 °C(Predicted)
Density: 1.63 · 1.63
Flash point: 106 ℃ · 106℃
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO, Chloroform, Methanol
form: Solid
pka: 11.16 · 11.16±0.20(Predicted)
color: Yellow
biological source: synthetic (organic)
Merck: 14 · 14,8288
InChI: InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
InChIKey: VHXNKPBCCMUMSW-FQEVSTJZSA-N
SMILES: N1C2C(=C([N+]([O-])=O)C=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O
CAS DataBase Reference: 91421 · 91421-42-0(CAS DataBase Reference)
FDA UNII: 19 C446XXB · H19C446XXB
NCI Drug Dictionary: Orathecin
UNSPSC Code: 12352204 · 12352204
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
RTECS: 493300 · UQ0493300
HS Code: 29399990 · 29399990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity]；H350 (100%): May cause cancer [Danger Carcinogenicity]；H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Muta. 1B (100%)；Carc. 1B (100%)；STOT RE 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: UQ0493300
hs_code: 29399990
safety_code: 24/25
Storage Class: 11 - Combustible Solids

Chemistry & industry

Pharmacology

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

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Compounds that inhibit the activity of DNA TOPOISOMERASE I.

Applications · 3 items

DescriptionRubitecan, marketed by Supergen as Orathecin, is a promising oral treatment for solid melanoma, prostate, breast, ovarian, and other cancers, as well as leukemia. It is a derivative of camptothecin, a topoisomerase inhibitor known from Chinese Traditional Medicine. It selectively targets the critical S-stage of cellular reproduction – particularly in acidic environments, as in many cancer cells – relaxing DNA supercoiling and generating lethal breaks in the DNA. Due to insolubility, its biological delivery mechanism is not yet effective, and it has not been approved for clinical use.

DescriptionRubitecan is a DNA topoisomerase I inhibitor. It inhibits DNA topoisomerase I and increases the fraction of supercoiled DNA in a cell-free assay in a concentration-dependent manner. Rubitecan inhibits the growth of A121 ovarian and H460 lung cancer cells (IC50s = 4 and 2 nM, respectively). It also inhibits the growth of doxorubicin-susceptible and -resistant MCF-7 breast cancer cells (IC50s = 2 and 3 nM, respectively). Rubitecan (4 mg/kg twice per week) reduces tumor growth in a U937 leukemia mouse xenograft model.

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

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: 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.