(19S)-8-[(Dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-13-aza-3-azoniapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;chloride

Base Information

• Chemical Name: (19S)-8-[(Dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-13-aza-3-azoniapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;chloride
• CAS No.: 119413-54-6
• Molecular Formula: C₂₃H₂₃N₃O₅*ClH
• Molecular Weight: 457.914
• Hs Code.: 29420000
• Mol file: 119413-54-6.mol

Synonyms:9 Dimethylaminomethyl 10 hydroxycamptothecin;9-Dimethylaminomethyl-10-hydroxycamptothecin;Hycamtamine;Hycamtin;Hydrochloride, Nogitecan;Hydrochloride, Topotecan;Nogitecan Hydrochloride;NSC 609699;NSC-609699;NSC609699;SK and F 104864 A;SK and F-104864-A;SK and F104864A;SKF 104864 A;SKF-104864-A;SKF104864A;Topotecan;Topotecan Hydrochloride;Topotecan Monohydrochloride, (S)-Isomer

Chemical Property of (19S)-8-[(Dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-13-aza-3-azoniapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;chloride

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Vapor Pressure: 8.13E-26mmHg at 25°C
• Melting Point: 213-218 °C
• Refractive Index: 1.733
• Boiling Point: 782.9 °C at 760 mmHg
• Flash Point: 427.3 °C
• PSA: 104.89000
• Density: 1.49 g/cm³
• LogP: 2.64880
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 457.1404486
• Heavy Atom Count: 32
• Complexity: 867

Purity/Quality:

99%, ^*data from raw suppliers

Topotecan, Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38-46
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)[NH+]=C4C3=C2)O.[Cl-]
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)[NH+]=C4C3=C2)O.[Cl-]
• Uses: It is used as antineoplastic agent. Naturally occurring amino acid; precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme. Antineoplastic (photosensitizer) antineoplastic; topoisomerase I inhibitor A DNA topoisomerase I inhibitor; semisynthetic analog of Camptothecin. Antineoplastic. Topotecan hydrochloride is a chemotherapy agent that is a topoisomerase 1 inhibitor.
• Description: Topotecan is a chemotherapeutic agent medication and acts as a topoisomerase inhibitor. Topotecan is asynthetic, water-soluble analog of camptothecin. It is used in the form of its hydrochloride salt to treat ovarian cancer, lung cancer and other cancer types.
• Therapeutic Function: Antineoplastic
• Clinical Use: This active camptothecin analogue is used by the IV route in the treatment of ovarian and small cell lung cancer that has not responded to first-line therapy.

Technology Process of (19S)-8-[(Dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-13-aza-3-azoniapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;chloride

There total 23 articles about (19S)-8-[(Dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-13-aza-3-azoniapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

bis-(dimethylamino)methane (51-80-9) + (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) → Topotecan hydrochloride (119413-54-6,123949-07-5)

Guidance literature:

In propan-1-ol; dichloromethane;

DOI:10.1016/0040-4039(96)01205-1

Reference yield: 69.0%

diiodomethane (75-11-6) + (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) + dimethyl amine (124-40-3) → Topotecan hydrochloride (119413-54-6,123949-07-5)

Guidance literature:

diiodomethane; (S)-10-hydroxycamptothecin; dimethyl amine; potassium carbonate; In water; at 20 ℃; for 5h;

With hydrogenchloride; In water;

Reference yield: 67.0%

(S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) + dimethyl amine (124-40-3) + 1,1-dibromomethane (74-95-3) → Topotecan hydrochloride (119413-54-6,123949-07-5)

Guidance literature:

(S)-10-hydroxycamptothecin; dimethyl amine; 1,1-dibromomethane; potassium carbonate; In water; at 20 ℃; for 5h;

With hydrogenchloride; In water;

upstream raw materials:

bis-(dimethylamino)methane

(S)-10-hydroxycamptothecin

10-methoxycamptothecin

2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

Refernces

• 1、 -. "Crystalline polymorphs of topotecan hydrochloride and methods for the preparation thereof". Page/Page column 4-5. . Retrieved 2009/07/10.
• 2、 -. "Crystalline forms of topotecan hydrochloride and processes for making the same". Page/Page column 3. . Retrieved 2008/12/04.