14-bromodaunorubicin hydrochloride
doxorubicin hydrochloride
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 80℃; for 2h; | 64% |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With human protease plasmin In various solvent(s) at 37℃; pH=7.3; Product distribution; Enzymatic reaction; |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With human protease plasmin In various solvent(s) at 37℃; pH=7.3; Product distribution; Enzymatic reaction; |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With human protease plasmin In various solvent(s) at 37℃; pH=7.3; Product distribution; Enzymatic reaction; |
daunomycin hydrochloride
doxorubicin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54 percent / bromine / methanol; dioxane; CHCl3 / 144 h / 0 - 5 °C 2: 64 percent / dimethylsulfoxide; H2O / 2 h / 80 °C View Scheme |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
Purification / work up; |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With 3,6-dimethyl-1,2,4,5-tetrazine In acetonitrile Reagent/catalyst; | |
With 3,6-dimethyl-1,2,4,5-tetrazine In acetonitrile Reagent/catalyst; |
B
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With fibroblast activating protein In water Kinetics; Reagent/catalyst; Enzymatic reaction; |
Conditions | Yield |
---|---|
With fibroblast activating protein In water Enzymatic reaction; |
Conditions | Yield |
---|---|
Stage #1: C47H55N5O20S2 With triethyl ammonium acetate; triethylamine In aq. buffer at 20℃; for 2h; pH=9.5 - 9.9; Darkness; Stage #2: With acetic acid In aq. buffer pH=8.2; Darkness; Stage #3: In aq. buffer pH=6-7; Darkness; |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With dihydrogen peroxide for 48h; |
doxorubicin hydrochloride
doxorubicin
Conditions | Yield |
---|---|
With triethylamine In chloroform at 25℃; for 24h; Darkness; | 100% |
With 4 Å molecular sieves Aqueous carbonate buffer; | 73% |
With triethylamine In dimethyl sulfoxide for 1h; |
naphthalene-2-sulfonate
doxorubicin hydrochloride
doxorubicin naphthalene-2-sulfonate
Conditions | Yield |
---|---|
Stage #1: doxorubicin hydrochloride With potassium tert-butylate In tetrahydrofuran at 20.2 - 21.4℃; for 1.41667h; Inert atmosphere; Stage #2: naphthalene-2-sulfonate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
doxorubicin hydrochloride
Fmoc-Phe-Lys(MMT)-PABC-Dox
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; | 99.6% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Darkness; | 99% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 80% |
With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; | 80% |
carbonic acid 4-(2,5-dioxo-3,4-bis-phenylsulfanyl-2,5-dihydro-pyrrol-1-yl)-benzyl ester 4-nitro-phenyl ester
doxorubicin hydrochloride
{3-hydroxy-2-methyl-6-[3,5,12-trihydroxy-3-(2-hydroxy-acetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyran-4-yl}-carbamic acid 4-(2,5-dioxo-3,4-bis-phenylsulfanyl-2,5-dihydro-pyrrol-1-yl)-benzyl ester
Conditions | Yield |
---|---|
With triethylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 72h; | 99% |
With triethylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 72h; Darkness; | 99% |
doxorubicin hydrochloride
biotinamidocaproate N-hydroxysuccinimide ester
C43H54N4O14S
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 16h; | 98% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 5h; | 97% |
Conditions | Yield |
---|---|
Stage #1: doxorubicin hydrochloride With potassium tert-butylate In tetrahydrofuran at 19 - 22.4℃; for 1.91667h; Inert atmosphere; Stage #2: toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 0.5h; | 97% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 16h; Inert atmosphere; | 97% |
4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester
doxorubicin hydrochloride
doxorubicin-succinimidyl 4-[N-maleimidomethyl]cyclohexane-1-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; | 96% |
With triethylamine In N,N-dimethyl-formamide at 20℃; | |
With triethylamine In N,N-dimethyl-formamide | |
With triethylamine In N,N-dimethyl-formamide at 20℃; pH=Ca. 8; Darkness; |
doxorubicin hydrochloride
benzenesufonyl hydrazide
Conditions | Yield |
---|---|
In methanol at 0 - 45℃; for 16 - 240h; | 96% |
poly(17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester of 6-(2-methacryloylamino)hexanoic acid-co-N1-(6-hydrazino-6-oxohexyl)-2-methylacrylamide-co-N-(2-hydroxypropyl)methacrylamide)
doxorubicin hydrochloride
Conditions | Yield |
---|---|
acetic acid In methanol at 25℃; for 22h; | 96% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 95% |
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 95% |
(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl) 4-nitrophenyl carbonate
doxorubicin hydrochloride
N-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyloxycarbonyl)doxorubicin
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide | 94% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 14h; Inert atmosphere; Darkness; | 94% |
doxorubicin hydrochloride
trifluoroacetic anhydride
N-Trifluoroacetyladriamycin
Conditions | Yield |
---|---|
With pyridine In diethyl ether at -30 - 0℃; for 3h; Schlenk technique; | 94% |
With pyridine In diethyl ether at -20℃; for 0.5h; | 91% |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Darkness; | 94% |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Darkness; | 94% |
Conditions | Yield |
---|---|
With acetic acid; sodium sulfate In methanol at 20℃; for 12h; Darkness; | 93% |
With acetic acid; sodium sulfate In methanol at 65℃; for 24h; Darkness; | 62.4% |
With acetic acid; sodium sulfate In methanol at 65℃; for 24h; | 62.4% |
With acetic acid In methanol |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; | 93% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In methanol at 20℃; | 92% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 92% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
Stage #1: 3,4-dithiophenoylmaleimide-N-hexanoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 0.05h; Inert atmosphere; Stage #2: doxorubicin hydrochloride In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 6h; Inert atmosphere; | 92% |
doxorubicin hydrochloride
diprop-2-enyl N-<(4-<<4-nitrophenoxycarbonyloxy>methyl>phenyl)carbamoyl>-L-glutamate
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 3.5h; Ambient temperature; | 91.1% |
doxorubicin hydrochloride
N-[N-(9-fluorenylmethoxycarbonyl)-β-alanyl-L-leucyl-L-alanyl-L-leucyl]doxorubicin
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 90% |
doxorubicin hydrochloride
trifluoroacetic acid
Conditions | Yield |
---|---|
In methanol at 20℃; for 5h; | 90% |
cis-aconitic anhydride
doxorubicin hydrochloride
cis-aconitic anhydride doxorubicin
Conditions | Yield |
---|---|
Stage #1: doxorubicin hydrochloride With sodium hydrogencarbonate In water at 0℃; Stage #2: cis-aconitic anhydride In 1,4-dioxane; water at 0 - 20℃; for 0.666667h; pH=8.5; Stage #3: With hydrogenchloride In 1,4-dioxane; water | 90% |
With triethylamine In N,N-dimethyl-formamide at 25℃; for 24h; | |
With triethylamine In N,N-dimethyl-formamide |
4-nitrophenyl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate
doxorubicin hydrochloride
doxorubicin 2-(pyridy-2-yldithio)ethylcarbamate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 90% |
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 12h; Darkness; | 87% |
With triethylamine In dichloromethane; N,N-dimethyl-d6-formamide at 20℃; for 12h; Darkness; | 87% |
doxorubicin hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-(p-benzoic acid)-3,4-dithiophenoylmaleimide With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 0.05h; Inert atmosphere; Stage #2: doxorubicin hydrochloride In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 6h; Inert atmosphere; | 90% |
NTP 10th Report on Carcinogens. EPA Genetic Toxicology Program.
The Doxorubicin hydrochloride, with the CAS registry number 25316-40-9,is also known as (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride. It belongs to the product categories of Pharmaceuticals;Antitumour. This chemical's molecular formula is C27H29NO11.HCl and molecular weight is 579.99.Its EINECS number is 246-818-3. What's more,Its systematic name is Adriamycin hydrochloride. It is a Orange-Red Crystalline Solid which is Used as an antineoplastic.Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of daunorubicin.
Physical properties about Doxorubicin hydrochloride are:
(1)ACD/LogP: 2.821; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 0.02; (4)ACD/LogD (pH 7.4): 1.12; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.62; (7)ACD/KOC (pH 5.5): 1.29; (8)ACD/KOC (pH 7.4): 16.07; (9)#H bond acceptors: 12; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 11; (12)Flash Point: 443.8 °C; (13)Enthalpy of Vaporization: 123.51 kJ/mol; (14)Boiling Point: 810.3 °C at 760 mmHg; (15)Vapour Pressure: 9.64E-28 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:Cl.O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)C[C@@](O)(C(=O)CO)C[C@@H]5O[C@@H]4O[C@H]([C@@H](O)[C@@H](N)C4)C;
(2)Std. InChI:InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1;
(3)Std. InChIKey:MWWSFMDVAYGXBV-RUELKSSGSA-N.
Safety Information of Doxorubicin hydrochloride:
The Doxorubicin hydrochloride is harmful if swallowed and very toxic by inhalation, in contact with skin and if swallowed. It may cause cancer. But there is limited evidence of a carcinogenic effect. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .Avoid exposure - obtain special instructions before use. When you use it ,wear suitable protective clothing, gloves and eye/face protection ,and do not breathe dust. After you use it ,keep container tightly closed, and keep container in a well-ventilated place.
The toxicity data of Doxorubicin hydrochloride are as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | LDLo | intravenous | 2571ug/kg/3W- (2.571mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Archives of Internal Medicine. Vol. 137, Pg. 385, 1977. |
man | TDLo | intravenous | 12mg/kg/26W-I (12mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | Annals of Internal Medicine. Vol. 106, Pg. 814, 1987. |
mouse | LD50 | intramuscular | 13700ug/kg (13.7mg/kg) | Drugs in Japan Vol. 6, Pg. 506, 1982. | |
mouse | LD50 | intraperitoneal | 11160ug/kg (11.16mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | intravenous | 1245ug/kg (1.245mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | oral | 698mg/kg (698mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: MUSCLE WEAKNESS | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973. |
mouse | LD50 | subcutaneous | 7678ug/kg (7.678mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
rabbit | LD50 | intravenous | 5980ug/kg (5.98mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: FOOD INTAKE (ANIMAL) | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973. |
rat | LD50 | intramuscular | 16mg/kg (16mg/kg) | Drugs in Japan Vol. 6, Pg. 506, 1982. | |
rat | LD50 | intraperitoneal | 16030ug/kg (16.03mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER TOPICAL EXPOSURE" | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973. |
rat | LD50 | intravenous | 12510ug/kg (12.51mg/kg) | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973. | |
rat | LD50 | intravenous | 12510ug/kg (12.51mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER TOPICAL EXPOSURE" | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973. |
rat | LD50 | subcutaneous | 21840ug/kg (21.84mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER TOPICAL EXPOSURE" GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973. |
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