Camptothecin anticancer drugs Uses Production methods
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Topotecan

Camptothecin anticancer drugs Uses Production methods
Topotecan Structure
Topotecan
  • CAS No.123948-87-8
  • Chemical Name:Topotecan
  • CBNumber:CB1339804
  • Molecular Formula:C23H23N3O5
  • Formula Weight:421.45
  • MOL File:123948-87-8.mol
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.  :2-8°C
  • solubility  :H2O: soluble
  • pka :8.92±0.40(Predicted)
  • form  :liquid
  • color  :yellow
  • CAS DataBase Reference :123948-87-8(CAS DataBase Reference)
  • FDA UNII :7M7YKX2N15
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H341
  • Precautionary statements P281
Topotecan Price More Price(3)
  • Brand: Sigma-Aldrich
  • Product number: T2705
  • Product name : Topotecan hydrochloride hydrate
  • Purity: ≥98% (HPLC and enzymatic)
  • Packaging: 10mg
  • Price: $65.4
  • Updated: 2018/11/13
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: T2705
  • Product name : Topotecan hydrochloride hydrate
  • Purity: ≥98% (HPLC and enzymatic)
  • Packaging: 50mg
  • Price: $260
  • Updated: 2018/11/13
  • Buy: Buy
  • Brand: 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: 1003261000
  • Price: $132
  • Updated: 2019/12/02
  • Buy: Buy

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
  • 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
Topotecan Preparation Products And Raw materials
Raw materials
Preparation Products
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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