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idarubicin
idarubicin hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In chloroform; isopropyl alcohol | 95% |
With hydrogenchloride In methanol; dichloromethane pH=3; | 4.2 g |
With hydrogenchloride In methanol; ethanol; dichloromethane; water at 30 - 40℃; for 0.333333h; pH=Ca. 3; Inert atmosphere; | 4.2 g |
(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin
idarubicin hydrochloride
Conditions | Yield |
---|---|
Stage #1: (+)-N-Trifluoroacetyl-4-demethoxydaunorubicin With water; sodium hydroxide at 20℃; for 1h; Stage #2: With hydrogenchloride In water pH=8; | 80% |
With sodium hydroxide In water for 0.5h; Ambient temperature; | 77% |
Stage #1: (+)-N-Trifluoroacetyl-4-demethoxydaunorubicin With sodium hydroxide In water at 30℃; for 0.5h; Stage #2: With hydrogenchloride In chloroform; water; butan-1-ol pH=3.5; | |
Stage #1: (+)-N-Trifluoroacetyl-4-demethoxydaunorubicin With sodium hydroxide In water at 30℃; for 0.5h; Stage #2: With hydrogenchloride In water pH=7; |
idarubicin hydrochloride
Conditions | Yield |
---|---|
Stage #1: C34H35NO10 With palladium(II) hydroxide In tetrahydrofuran at 40℃; for 4h; Stage #2: With hydrogenchloride In methanol; diethyl ether pH=3; | 77% |
idarubicin hydrochloride
Conditions | Yield |
---|---|
Stage #1: C34H33NO11 With palladium(II) hydroxide In tetrahydrofuran at 40℃; for 4h; Stage #2: With hydrogenchloride In methanol; dichloromethane pH=3; | 74% |
2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose
idarubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Trimethylsilyl triflate, 4A mol. sieves / 1.) CH2Cl2-Et2O (3:1), -40 deg C than -3 - -5 deg C, 1h; 2.) -15 deg C, 2.5 hrs 2: 0.1 mol dm-3 NaOH / CH2Cl2; methanol / 0.5 h / 0 °C 3: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme |
(7S,9S)-idarubicinone
idarubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Trimethylsilyl triflate, 4A mol. sieves / 1.) CH2Cl2-Et2O (3:1), -40 deg C than -3 - -5 deg C, 1h; 2.) -15 deg C, 2.5 hrs 2: 0.1 mol dm-3 NaOH / CH2Cl2; methanol / 0.5 h / 0 °C 3: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 51 percent / Silver triflate 2: 0.1 mol dm-3 NaOH / CH2Cl2; methanol / 0.5 h / 0 °C 3: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 2: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme |
1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose
idarubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 51 percent / Silver triflate 2: 0.1 mol dm-3 NaOH / CH2Cl2; methanol / 0.5 h / 0 °C 3: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme |
2,3,6-Trideoxy-3-trifluoroacetamido-L-lixo-hexopyranose
idarubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 51 percent / diethyl ether 3: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme |
(-)-3-N-trifluoroacetyl-1,4-bis(O-trifluoroacetyl)-L-daunosamine
idarubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme |
(-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin
idarubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.1 mol dm-3 NaOH / CH2Cl2; methanol / 0.5 h / 0 °C 2: 77 percent / 0.1 mol dm-3 NaOH / H2O / 0.5 h / Ambient temperature View Scheme |
IUPAC Name: (7S,9S)-9-Acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione hydrochloride
Synonyms of 4-Demethoxydaunorubicin hydro-chloride (CAS NO.57852-57-0): (1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, hydrochloride ; (1S,3S)-3-Acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside hydrochloride ; (1S,3S)-3-Acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside hydrochloride (1:1) ; (7S,9S)-9-Acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracen-5,12-dionhydrochlorid ; (7S,9S)-9-Acétyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-6,9,11-trihydroxy-7,8,9,10-tétrahydrotétracène-5,12-dione chlorhydrate
Product Categories: API;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals
CAS NO: 57852-57-0
Molecular Formula: C26H28ClNO9
Molecular Weight: 533.95
Molecular Structure:
EINECS: 260-990-7
Mol File: 57852-57-0.mol
H bond acceptors: 10
H bond donors: 6
Freely Rotating Bonds: 8
Polar Surface Area: 109.83 Å2
Flash Point: 392.5 °C
Enthalpy of Vaporization: 111.2 kJ/mol
Boiling Point: 725.4 °C at 760 mmHg
Vapour Pressure: 4.34E-22 mmHg at 25°C
Melting point: 183-185°C
Storage temp: 2-8°C
SMILES: Cl.O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C[C@@](O)(C(=O)C)C[C@@H]5O[C@@H]4O[C@H]([C@@H](O)[C@@H](N)C4)C
InChI: InChI=1/C26H27NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10-,15-,16-,17-,21+,26-;/m0./s1
InChIKey: JVHPTYWUBOQMBP-RVFAQHLVBA
Std. InChI: InChI=1S/C26H27NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10-,15-,16-,17-,21+,26-;/m0./s1
Std. InChIKey: JVHPTYWUBOQMBP-RVFAQHLVSA-N
4-Demethoxydaunorubicin hydro-chloride (CAS NO.57852-57-0) is orally active anthracycline , analog of Daunorubicin and Antineoplastic.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD | intravenous | > 500ug/kg (0.5mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. | |
mouse | LD50 | intravenous | 4100ug/kg (4.1mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. | |
mouse | LD50 | oral | 13980ug/kg (13.98mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. | |
mouse | LD50 | subcutaneous | 4690ug/kg (4.69mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. | |
mouse | LDLo | intraperitoneal | 700ug/kg (0.7mg/kg) | Cancer Treatment Reports. Vol. 60, Pg. 829, 1976. | |
rat | LD50 | intravenous | 3080ug/kg (3.08mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. | |
rat | LD50 | oral | 5430ug/kg (5.43mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. | |
rat | LD50 | subcutaneous | 2930ug/kg (2.93mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 364, 1995. |
A poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic vapors of NOx, HCl, and Cl−.
Hazard Codes: T+Xn
Risk Statements: 60-61-28-40
R28: Very toxic if swallowed.
R40: Limited evidence of a carcinogenic effect.
R60: May impair fertility.
R61: May cause harm to the unborn child.
Safety Statements: 53-45-36-22
S22: Do not breathe dust.
S36: Wear suitable protective clothing.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S53: Avoid exposure - obtain special instructions before use.
RIDADR: UN2811
RTECS: HB7877000