Topotecan supplier | CasNO.123948-87-8

Name
Topotecan
EINECS 231-595-7
CAS No. 123948-87-8
Article Data8
CAS DataBase
Density 1.49 g/cm³
Solubility soluble in water
Melting Point ?114 °C
Formula C₂₃H₂₃N₃O₅
Boiling Point 782.9 °C at 760 mmHg
Molecular Weight 421.453
Flash Point 427.3 °C
Transport Information UN 3286 3/PG 2
Appearance light yellow needle crystal or crystalline powder
Safety 26-45-36/37/39-37/39
Risk Codes 36/37/38-67-35-20-11-34
Molecular Structure
Hazard Symbols T,C,F,Xi
Synonyms 4-Ethyl-4,9-dihydroxy-10-[(dimethylamino)methyl]-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;9-Dimethylaminomethyl-10-hydroxycamptothecin;(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;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)-;
PSA 104.89000
LogP 1.84680

Synthetic route

: 50-00-0
formaldehyd

: 19685-09-7
(S)-10-hydroxycamptothecin

: 124-40-3
dimethyl amine

: 123948-87-8
topotecan

Conditions

Conditions	Yield
With acetic acid Mannich reaction;	65%
In acetic acid at 40 - 90℃; Mannich Aminomethylation;

...Expand

: 75-09-2
dichloromethane

: 19685-09-7
(S)-10-hydroxycamptothecin

: 124-40-3
dimethyl amine

: 123948-87-8
topotecan

Conditions

Conditions	Yield
With potassium carbonate at 20℃; for 5h; Mannich reaction;	65%

...Expand

: 7689-03-4
camptothecin

: 123948-87-8
topotecan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: H2; AcOH / PtO2 1.2: 51 percent / Pb(OAc)4; AcOH 2.1: 65 percent / aq. AcOH View Scheme

: 19685-09-7
(S)-10-hydroxycamptothecin

: 30354-18-8
N,N-dimethyl(methylene)ammonium chloride

: 123948-87-8
topotecan

Conditions

Conditions	Yield
With triethylamine In dichloromethane; isopropyl alcohol at 20 - 35℃; for 12h; Mannich Reaction;

: 994-30-9
triethylsilyl chloride

: 123948-87-8
topotecan

: 1004511-35-6
20-OTES topotecan

Conditions

Conditions	Yield
Stage #1: topotecan With 1H-imidazole In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: triethylsilyl chloride With dmap In N,N-dimethyl-formamide	94%
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 52.1667h;	94%

: 123948-87-8
topotecan

: 284049-22-5
tert-butyl (2-isocyanatoethyl)carbamate

: (S)-tert-butyl (10-((dimethylamino)methyl)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl) ethane-1,2-diyldicarbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 2h;	69%

: 123948-87-8
topotecan

: 113238-61-2
tert-butyl 2-isocyanatoacetate

: (S)-tert-butyl 2-((((10-((dimethylamino)methyl)-4-ethyl-4- hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl)oxy)carbonyl)amino)acetate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 2h;	68%

: 123948-87-8
topotecan

: 145577-00-0
[11C]methyl triflate

: 9-[([11C]trimethylammonium)methyl]-10-hydroxy-20(S)-camptothecin triflate

Conditions

Conditions	Yield
In acetonitrile	60%
In acetonitrile at -15 - 80℃;

: 123948-87-8
topotecan

: Topotecan hydroxyl acid

Conditions

Conditions	Yield
With phosphate buffer Ambient temperature; other camptothecin lactone; also in the presence of DNA oligonucleotides; rate of hydrolysis;
With poly(DL-lactide-co-glycolide); poly(vinyl alcohol) In various solvents at 37℃; for 192h; pH=7.4; Product distribution; Kinetics; Further Variations:; reaction times; Hydrolysis;
With water at 37℃;

: 123948-87-8
topotecan

: 119413-54-6, 123949-07-5
Topotecan hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 10 - 30℃; for 2h; Product distribution / selectivity;

: 123948-87-8
topotecan

: 333-27-7
methyl trifluoromethanesulfonate

A: 9-[(trimethylammonium)methyl]-10-hydroxy-20(S)-camptothecin triflate

B: 175613-38-4
C21H18N2O6

C: 1243272-93-6
CHF3O3S*C23H23N3O5

D: CF3O3S(1-)*C25H28N3O5(1+)

Conditions

Conditions	Yield
Stage #1: methyl trifluoromethanesulfonate With potassium carbonate In dichloromethane for 0.5h; Stage #2: topotecan In dichloromethane at 20℃; for 24h;

...Expand

: 66-27-3
Methyl methanesulfonate

: 123948-87-8
topotecan

A: 175613-38-4
C21H18N2O6

B: CH4O3S*C23H23N3O5

C: CH3O3S(1-)*C25H28N3O5(1+)

D: 123948-98-1
10-hydroxy-9-<(trimethylammonio)methyl>-(20S)-camptothecin methanosulfonate

Conditions

Conditions	Yield
Stage #1: Methyl methanesulfonate With potassium carbonate In dichloromethane for 0.5h; Stage #2: topotecan In dichloromethane at 20℃; for 24h;

...Expand

: 123948-87-8
topotecan

: 386768-13-4, 189397-70-4, 112269-92-8
25,26,27,28-terahydroxycalix[4]arene-5,11,7,23-tetrasulfonic acid

: C23H23N3O5*C28H24O16S4

Conditions

Conditions	Yield
In methanol; water at 20℃; for 48h;

: 123948-87-8
topotecan

: topotecan lactam

Conditions

Conditions	Yield
Stage #1: topotecan With isopropylamine Stage #2: With pyridine; acetic anhydride Stage #3: With ammonia In dichloromethane
Stage #1: topotecan With isopropylamine Stage #2: With pyridine; acetic anhydride Stage #3: With ammonia In dichloromethane

: 123948-87-8
topotecan

: C26H28N4O6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 66 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme

: 123948-87-8
topotecan

: (S)-7-((10-((dimethylamino)methyl)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl)oxy)heptanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Heating 2: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C View Scheme

: 123948-87-8
topotecan

: (S)-7-((10-((dimethylamino)methyl)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl)oxy)-N-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)heptanamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Heating 2: lithium hydroxide; water / tetrahydrofuran / 6 h / 20 °C 3: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere View Scheme

: 108-30-5
succinic acid anhydride

: 123948-87-8
topotecan

: 9-dimethylaminomethyl-hydroxycamptothecin-10-succinic acid

Conditions

Conditions	Yield
With pyridine at 50℃; for 48h;	0.35 g

: 123948-87-8
topotecan

: C62H70N7O20P

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 48 h / 50 °C 2: 1,1'-carbonyldiimidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 24 h / 20 °C View Scheme

Topotecan Specification

1. Introduction of Topotecan

The Topotecane with CAS registry number of 123948-87-8, has the systematic name is (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. It belongs to product categories of APIs. This chemical is a light yellow needle crystal or crystalline powder and it can be used as anti-cancer drugs.

2. Properties of Topotecan

Physical properties about Topotecane are: (1)ACD/LogP: 1.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.06; (4)ACD/LogD (pH 7.4): 0.45; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 21.36; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 81.2Å²; (13)Index of Refraction: 1.733; (14)Molar Refractivity: 112.73 cm³; (15)Molar Volume: 281.3 cm³; (16)Polarizability: 44.69×10^-24cm³; (17)Surface Tension: 82.8 dyne/cm; (18)Density: 1.49 g/cm³; (19)Flash Point: 427.3 °C; (20)Enthalpy of Vaporization: 119.49 kJ/mol; (21)Boiling Point: 782.9 °C at 760 mmHg; (22)Vapour Pressure: 8.13E-26 mmHg at 25 °C

3. Structure Descriptors of Topotecan

You could convert the following datas into the molecular structure:
1). Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=C(C5=C4)CN(C)C)O)O
2). Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=C(C5=C4)CN(C)C)O)O
3). InChI: InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
4). InChIKey: UCFGDBYHRUNTLO-QHCPKHFHSA-N

4. Preparation of Topotecan

Preparation of Topotecane: it is prepared by reaction of 37% formaldehyde with 40% dimethylamine. Besides, The reaction needs reagent acetic acid.

Topotecan hydrochloride is prepared by reaction of 37% formaldehyde with 40% dimethylamine.

5. Safety Information of Topotecan

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Besides, it has highly flammable and may causes severe burns. What's more, it is harmful by inhalation. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you feel unwell or accident happens seek medical advice immediately.

Product Name

Topotecan

Synthetic route

Topotecan Specification

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