Camptothecin anticancer drugs Uses Production methods
ChemicalBook > CAS DataBase List > Topotecan

Topotecan

Camptothecin anticancer drugs Uses Production methods
Product Name
Topotecan
CAS No.
123948-87-8
Chemical Name
Topotecan
Synonyms
HYDROCHLORIDE;MURIATIC ACID;TOPOTECAN HCL;HYDROCHLORIC ACID, 6.000N;Topotecan hydrochloride hydrate;opotecan;TOPOTECAN;Hycamptin;nogitecan;NSC 609699
CBNumber
CB1339804
Molecular Formula
C23H23N3O5
Formula Weight
421.45
MOL File
123948-87-8.mol
More
Less

Topotecan Property

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)
More
Less

Safety

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
Hazardous Substances Data
123948-87-8(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H340May cause genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

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

Topotecan Chemical Properties,Usage,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.

Topotecan Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Topotecan Suppliers

Shanghai Zhen Li Biological Technology Co., Ltd
Tel
021-16621358918; 18516310516
Fax
13045646768
Email
zhenlipharma888@163.com
Country
China
ProdList
1996
Advantage
58
SiChuang NanBu Honesty Technology Co., Ltd.
Tel
0838-5675166 15883665058
Fax
0838-5675535
Email
nbcxkj@126.com
Country
China
ProdList
668
Advantage
55
Wuhan EnTai Technology Development Co,.Ltd
Tel
86-27-82330560
Fax
86-27-82330547
Email
2536851935@qq.com
Country
China
ProdList
347
Advantage
69
PharmaBlock Sciences (Nanjing),Inc.
Tel
025-86918202 4000255188
Fax
86-025-86918232
Email
sales@pharmablock.com
Country
China
ProdList
4986
Advantage
55
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12390
Advantage
60
Jia Xing Isenchem Co.,Ltd
Tel
0573-85285100 18627885956
Fax
0573-85285100
Email
isenchem@163.com
Country
China
ProdList
9513
Advantage
66
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
More
Less

View Lastest Price from Topotecan manufacturers

Baoji Guokang Healthchem co.,ltd
Product
Topotecan 123948-87-8
Price
US $65.00/G
Min. Order
1G
Purity
99%
Supply Ability
10kgs
Release date
2021-06-07
Zhuozhou Wenxi import and Export Co., Ltd
Product
Topotecan 123948-87-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Topotecan 123948-87-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-08

123948-87-8, TopotecanRelated Search:


  • 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, 6.000N
  • HYDROCHLORIC ACID, 6.00 N
  • HYDROCHLORIC ACID, 6.0N
  • HYDROCHLORIC ACID, 6.25 N
  • HYDROCHLORIC ACID, 6N
  • HYDROCHLORIC ACID, 6N IN IPA
  • HYDROCHLORIC ACID R1
  • HYDROCHLORIC ACID STANDARD
  • HYDROCHLORIDE
  • HYDROCHLORIC ACID DILUTE R
  • HYDROCHLORIC ACID FUMING
  • DEPURINATION SOLUTION
  • 9-[(DIMETHYLAMINO)METHYL]-10-HYDROXY-(20S)-CAMPTOTHECIN, HCL
  • 9-dimethylaminomethyl-10-hydroxycamptothecin hydrochloride salt
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-10-[(dimethylamino)methyl]-, hydrochloride, (S)
  • 9-Dimethylaminomethyl-10-hydroxycamptothecin, HCl salt
  • 9-[(Dimethylamino)methyl]-10-hydroxy-camptothecin
  • (s)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione monohydrochloride
  • SKF-104864A
  • SOLUTION, PH 0.50
  • MURIATIC ACID
  • NP F SOLUTION
  • NPW-150 HYDROCHLORIC ACID
  • TOPOTECAN
  • TOPOTECAN HCL
  • TOPOTECAN MONOHYDROCHLORIDE
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, (4S)-
  • TOPOTECAN HCL(P)
  • TOPOTECAN HCL(P)(CALL)
  • 10-Hydroxy-9-[(dimethylamino)methyl]-(20S)-camptothecin
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, (4S)- (9CI)
  • 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