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Topotecan

CAS No.
123948-87-8
Chemical Name:
Topotecan
Synonyms
HYDROCHLORIDE;MURIATIC ACID;TOPOTECAN HCL;HYDROCHLORIC ACID, 6.000N;Topotecan hydrochloride hydrate;opotecan;nogitecan;Hycamptin;TOPOTECAN;SKF 104864
CBNumber:
CB1339804
Molecular Formula:
C23H23N3O5
Molecular Weight:
421.45
MDL Number:
MFCD00870670
MOL File:
123948-87-8.mol
MSDS File:
SDS
Last updated:2024-02-04 22:50:33

Topotecan Properties

Melting point −114 °C(lit.)
Boiling point >100 °C(lit.)
Density 1.2 g/mL at 25 °C(lit.)
vapor density 1.3 (vs air)
vapor pressure 613 psi ( 21.1 °C)
Flash point 12 °C
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility H2O: soluble
form liquid
pka 8.92±0.40(Predicted)
color yellow
CAS DataBase Reference 123948-87-8(CAS DataBase Reference)
FDA UNII 7M7YKX2N15
ATC code L01CE01

Pharmacokinetic data

Protein binding 35%
Excreted unchanged in urine 51%
Volume of distribution 132 Litres +/- 57(L/kg)
Biological half-life 2-3 / 4.9 (in moderate renal failure)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H340-H361d
Precautionary statements  P201-P202-P280-P308+P313-P405-P501
Hazard Codes  T,C,F,Xi
Risk Statements  36/37/38-67-35-20-11-34-48-46-36
Safety Statements  26-45-36/37/39-37/39-36-22-24/25-16-7
RIDADR  UN 3286 3/PG 2
WGK Germany  2
RTECS  MW4025000
3
HazardClass  8
PackingGroup  II

Topotecan price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T2705 Topotecan hydrochloride hydrate ≥98% (HPLC and enzymatic) 123948-87-8 10mg $84.1 2024-03-01 Buy
Sigma-Aldrich T2705 Topotecan hydrochloride hydrate ≥98% (HPLC and enzymatic) 123948-87-8 50mg $335 2024-03-01 Buy
Sigma-Aldrich 1.00326 Hydrochloric acid in 2-propanol acc. to DIN 51558 part 1 c(HCl) = 0.1 mol/l (0,1 N), Titripur? 123948-87-8 1003261003 $83 2022-05-15 Buy
Sigma-Aldrich 1.00326 Hydrochloric acid in 2-propanol acc. to DIN 51558 part 1 c(HCl) = 0.1 mol/l (0,1 N) Titripur? Reag. USP 123948-87-8 1L $150 2022-05-15 Buy
Sigma-Aldrich 1.00326 Hydrochloric acid in 2-propanol acc. to DIN 51558 part 1 c(HCl) = 0.1 mol/l (0,1 N) Titripur? Reag. USP 123948-87-8 1003 $72.24 2021-12-16 Buy
Product number Packaging Price Buy
T2705 10mg $84.1 Buy
T2705 50mg $335 Buy
1.00326 1003261003 $83 Buy
1.00326 1L $150 Buy
1.00326 1003 $72.24 Buy

Topotecan Chemical Properties,Uses,Production

Camptothecin anticancer drugs

Camptothecin anticancer drugs are alkaloids or derivatives of them after the structure transformation raised from deciduous plant Davidia involucrata Camptotheca acuminate seed or root bark. Clinical application of them mainly includes camptothecin,hydroxycamptothecin, topotecan and irinotecan.
Topotecan is a water-soluble semi-synthetic derivative of camptothecin,it is a topoisomerase I inhibitor, inhibiting DNA single strand DNA scission reconnect to damage DNA, its cytotoxicity occurs in cancer cell division S phase, it is an s phase cell cycle specific drug . In vivo it is a two-compartment model,it can be quickly distributed to the liver, kidneys and other parts , of a single intravenous infusion 1.5mg/m2 every 30 minutes , t1/2αis 4.1 to 8.1 minutes, plasma protein binding rate is 6.6%~21.3%,it can go into the cerebrospinal fluid. Most of it is excreted by the kidneys, a small part of it is excreted by the bile, within 12 hours, 90% of it is excreted.Clearance rate of renal dysfunction decreases.it is clinically used for the treatment of small cell lung cancer (SCLC), and advanced ovarian cancer, because it can penetrate the blood-brain barrier ,it has a certain effect on the central nervous system cancer and brain metastases. Usage: every single drug dose 1.2mg/m2 intravenous infusion once a day, once every 5 days, 21 days is 1 cycle, there is the need to reduce the dose when in combination with other anticancer drugs. The main adverse events are hematologic toxicity, white blood cells, platelets and hemoglobin decrease; non-hematologic toxicity adverse events are loss of appetite, nausea, vomiting, hair loss, stomatitis, diarrhea, headache, fever, constipation, transient elevated transaminase; occasionally breathing difficulties, hematuria, andelectrocardiogram abnormalities.
Severe bone marrow suppression are hanged. Monitor the blood and adjust the dose in accordance with changes in blood during the treatment , if necessary, granulocyte colony stimulating factor (G-CSF), and transfusion of blood components may be given .
The above information is edited by the chemicalbook of Tian Ye.

Uses

Anti-cancer drugs.It can be used alone for the treatment of initially or continuously ineffective chemotherapy metastatic ovarian cancer.

Production methods

Compound (I) with 37% formaldehyde and 40% dimethylamine,after aminomethylation in acetic acid, produces the product.

Description

Topotecan was launched in the US for the second-line treatment of ovarian cancer. It can be prepared in four steps from camptothecin and is a water soluble derivative of the natural product with decreased toxicity. Unlike its chemical relative irinotecan, topotecacan in not a prodrug and does not require bioactivation. It is an inhibitor of topoisomerase I. Specifically, it inhibits the release of topoisomerase I from DNA, where it relaxes supercoiled DNA, giving rise to single-strand breaks. When the replication fork reaches this complex, double-stand breaks can occur. This signals apoptosis and eventually gives rise to cell death. Evidence indicates hycamtin is safe for people with impaired hepatic function.

Chemical Properties

Off-white Cryst

Originator

SmithKline Beecham (UK)

Uses

antineoplastic;DNA topoisomerase type 1 inhibitor

Uses

(S)-Topotecan is a DNA topoisomerase I inhibitor; semisynthetic analog of Camptothecin. Antineoplastic. Topotecan hydrochloride is a chemotherapy agent that is a topoisomerase 1 inhibitor.

Uses

Topotecan has been used as a positive control for the identification and analysis of HIF-1α and VEGF inhibitors in human glioma cells under hypoxic conditions1. It has also been used for in vitro apoptosis assays in PA317 cells2.

Definition

ChEBI: A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.

Manufacturing Process

Camptothecin (CPT) - a compound isolated from the bark, leaves and fruit of Camptotheca acuminate (Wall M. E. et al., J. Am. Chem. Soc. 88, 3888, 1966).
10-Hydroxycamptothecin (10-HCPT) was prepared by subjecting CPT (3.2 g 0.0092 mol), 0.8 g of Pt0 (prepared by pre-reduction of 8 g of amorphous PtO2 in 80 ml of acetic acid for 1.5 h under 1 atm hydrogen pressure) and acetic acid to 1 atm of H2 for 8.5 h after which theoretical amount of H2 absorbed (slightly more than 0.4 L) and uptake of H2 gets slowed down. The reaction mixture was degassed under steam of helium and filtered through celite and washed with acetic acid (20 ml). The resulting solution was treated immediately with Pb(OAc)4 (6.4 g 0.014 mol) in portions and reaction mixture, stirred vigorously under helium for 30 min. Gumy residue was obtained on evaporation of solvent which was triturated with cold water (100 ml) to produce light brown solid. The solid was collected, washed with cold water and air dried overnight when a mixture of 10-HCPT (44%), acetyl 10- hydroxycamptothecin (10-AcHCPT, 26%) and unreacted CPT (32%) on HPLC basis was obtained. This crude mixture was combined with 150 ml of 50% acetic acid and heated under reflux conditions overnight. The reaction mixture was cooled, concentrated to 20 ml and treated with cold water (100 ml) to produce precipitate, which is filtered, washed with more cold water and dried to afford 2.1 g of solid containing 10-HCPT (70%), 10-AcCPT (1.2%) and CPT (21.3%) on the basis HPLC. Mixture was triturating with 0.5% aq HCl to dissolve the water-soluble. When insoluble CPT was removed by filtration. Water-soluble was extracted with chloroform and crystallized from boiling solution of 20% of MeOH in CHCl3 by adding EtOAC dropwise until turbidity appeared to obtain pure yellow 10-(HCPT), melting point 268°-270°C. 10-HCPT (0.364 g 0.01 mmol) and 40% aqueous dimethylamine (12 ml) was added in dichloromethane (50 ml) in which anhydrous potassium carbonate (2.17 g, 15 mmol) has been suspended. The reaction mixture was stirred at room temperature for 5 h, then filtered and solid extracted with ethylacetate (20 ml). The solvent is evaporated in vacuo giving a residue. The residue was triturated with 0.5% aq HCl (50 ml) to dissolve the water-soluble adduct. Water-soluble were partitioned with petroleum ether (3 times 50 ml) and followed by ethylacetate (3 times 50 ml). The aqueous layer was lyophilized as an off white hydrochloride salt of 9-[(dimethylamino)methyl]10- hydroxy(20S)-camptothecin (topotecan hydrochloride) yield 0.236 g (65%).

brand name

Hycamtin

Therapeutic Function

Antineoplastic

Biochem/physiol Actions

Topotecan is a topoisomerase I inhibitor and an apoptosis inducer. It is a potent antineoplastic agent.

Clinical Use

Antineoplastic agent:
Treatment of metastatic ovarian, cervical and small cell lung cancer

Metabolism

Topotecan undergoes reversible, pH-dependent hydrolysis of the active lactone moiety to the inactive hydroxyacid (carboxylate) form. A relatively small amount of topotecan is metabolised by hepatic microsomal enzymes to an active metabolite, N-demethyltopotecan; the clinical significance of this metabolite is not known. Excretion is via biliary and renal routes with 20-60
% excreted in the urine as topotecan or the open ring form.

References

[1] creemers gj1, lund b, verweij j. topoisomerase i inhibitors: topotecan and irenotecan. cancer treat rev. 1994 jan;20(1):73-96.

7689-03-4
123948-87-8
Synthesis of Topotecan from (+)-Camptothecin

Topotecan Preparation Products And Raw materials

Global( 354)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Lingding Biotechnology Co., Ltd.
+86-18031140164 +86-19933155420 erin@hbldbiotech.com China 881 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3424 58
Nanjing Dolon Biotechnology Co.,Ltd.
18905173768 sales@dolonchem.com CHINA 2972 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
Alchem Pharmtech,Inc.
8485655694 sales@alchempharmtech.com United States 63711 58

View Lastest Price from Topotecan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Topotecan pictures 2024-02-03 Topotecan
123948-87-8
US $50.00-50.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
	Topotecan pictures 2021-11-02 Topotecan
123948-87-8
US $65.00 / G 1G 99% 10kgs Baoji Guokang Healthchem co.,ltd
Topotecan pictures 2021-10-20 Topotecan
123948-87-8
US $50.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
  • Topotecan pictures
  • Topotecan
    123948-87-8
  • US $50.00-50.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.
  • 	Topotecan pictures
  • Topotecan
    123948-87-8
  • US $65.00 / G
  • 99%
  • Baoji Guokang Healthchem co.,ltd
  • Topotecan pictures
  • Topotecan
    123948-87-8
  • US $50.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.

Topotecan Spectrum

1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, (S)- Hycamptin nogitecan NSC 609699 SKF 104864 SKF-S 104864 Topotecan lactone Hydrochloric Acid Solution, 0.02N (N/50) Hydrogen chloride, 2N solution in diethyl ether Hydrochloric Acid Solution, 0.2N (N/5) Hydrochloric Acid Solution, 0.1N, In isopropanol Hydrochloric Acid Solution, 0.5N (N/2) Hydrochloric acid, ca. 37% Solution in Water Hydrochloric Acid Solution, 0.1N (N/10) Hydrogen chloride, 0.5M solution in methanol Hydrochloric Acid Solution, 1N Hydrochloric Acid Concentrate, 10N Hydrochloric Acid Solution, 0.01N (N/100) Hydrochloric Acid Concentrate, 1N Hydrogen chloride, 1N Solution in Diethyl Ether ACIDUM HYDROCHLORICUM 4-ethyl-4,9-dihydroxy-10-[(dimethylamino)methyl]-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione hydrochloride (4S)-10-[(DIMETHYLAMINO)METHYL]-4-ETHYL-4,9-DIHYDROXY-1H-PYRANO[3',4',6-7]INDOLIZINO[1,2-B]QUINOLINE-3,14(4H,12H)-DIONE 4 N HCL CONSTANT BOILING Hydrochloric acid in 2-Propanol Hydrogen chloride - 2-propanol solution 4-Ethyl-4,9-dihydroxy-10-[(dimethylamino)methyl]-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Hydride chlorine/methanol,(1:x) (4S)-4α-Ethyl-10-dimethylaminomethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (4S)-4α-Ethyl-4,12-dihydro-4,9-dihydroxy-10-dimethylaminomethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione (19S)-8-[(diMethylaMino)Methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione hydrochloride 9-[(dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin hydrochloride hydrate hycamptamine hydrochloride hydrate NSC-609669 hydrochloride hydrate SKF-104864A hydrochloride hydrate Hydrochloric acid, 0.05N Hydrochloric acid, 0.01N Hydrochloric Acid Solution, 6N Hydrochloric Acid, 25% (v/v) (1+3) hycamptamine HYDROGEN CHLORIDE, BUTANOL REAGENT HYDROGEN CHLORIDE GAS HYDROGEN CHLORIDE, METHANOL REAGENT HYDROGEN CHLORIDE, METHANOL REAGENT 10 HYDROGEN CHLORIDE, METHANOL REAGENT 5 HYDROCHLORIC ACID,1.1M HYDROCHLORIC ACID, 1N HYDROCHLORIC ACID, 2.00 N HYDROCHLORIC ACID, 20 DEG BAUME HYDROCHLORIC ACID, 2.50 N HYDROCHLORIC ACID, 3.00 N HYDROCHLORIC ACID, 5.00 N HYDROCHLORIC ACID, 5N HYDROCHLORIC ACID, 6.00 N HYDROCHLORIC ACID, 6.0N HYDROCHLORIC ACID, 6.25 N HYDROCHLORIC ACID, 6N HYDROCHLORIC ACID, 6N IN IPA