Product Name

  • Name

    Doxorubicin hydrochloride

  • EINECS 246-818-3
  • CAS No. 25316-40-9
  • Article Data13
  • CAS DataBase
  • Density
  • Solubility Soluble in water.
  • Melting Point 216 °C (dec.)(lit.)
  • Formula C27H30ClNO11
  • Boiling Point 810.3 °C at 760 mmHg
  • Molecular Weight 579.988
  • Flash Point 443.8 °C
  • Transport Information
  • Appearance orange-red crystalline solid
  • Safety 53-45-36/37/39-22-7/9
  • Risk Codes 45-22-40-26/27/28
  • Molecular Structure Molecular Structure of 25316-40-9 (Doxorubicin hydrochloride)
  • Hazard Symbols ToxicT,VeryT+
  • Synonyms 5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,hydrochloride, (8S,10S)- (9CI);5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,hydrochloride, (8S-cis)-;Adriamycin, hydrochloride (8CI);ADM hydrochloride;ADR;Adriablastina CS;Adriacin;Adriamycin;Adriblastin;Adriblastina;Adriblastina RD;DOX HCl;FI 106;FI 6804;Lipo-Dox;
  • PSA 206.07000
  • LogP 1.50360

Synthetic route

14-bromodaunorubicin hydrochloride
29742-67-4

14-bromodaunorubicin hydrochloride

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 80℃; for 2h;64%
C61H69N7O18*5.7HCl

C61H69N7O18*5.7HCl

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With human protease plasmin In various solvent(s) at 37℃; pH=7.3; Product distribution; Enzymatic reaction;
C63H70N8O18*7.5HCl

C63H70N8O18*7.5HCl

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With human protease plasmin In various solvent(s) at 37℃; pH=7.3; Product distribution; Enzymatic reaction;
C69H76N8O20*6.5HCl

C69H76N8O20*6.5HCl

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With human protease plasmin In various solvent(s) at 37℃; pH=7.3; Product distribution; Enzymatic reaction;
daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
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

doxorubicin hydrochloride

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
Purification / work up;
doxorubicin

doxorubicin

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
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;
N-((R)-1-((R)-2-(((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)isonicotinamide

N-((R)-1-((R)-2-(((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)isonicotinamide

A

N-(pyridin-4-carbonyl)-D-Ala-L-Proline

N-(pyridin-4-carbonyl)-D-Ala-L-Proline

B

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With fibroblast activating protein In water Kinetics; Reagent/catalyst; Enzymatic reaction;
C44H42F2N4O14

C44H42F2N4O14

A

C17H15F2N3O4

C17H15F2N3O4

B

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With fibroblast activating protein In water Enzymatic reaction;
C47H55N5O20S2

C47H55N5O20S2

A

C21H30N4O10S3

C21H30N4O10S3

B

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
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;
C63H88BNO17S2

C63H88BNO17S2

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With dihydrogen peroxide for 48h;
doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

doxorubicin
23214-92-8

doxorubicin

Conditions
ConditionsYield
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
120-18-3

naphthalene-2-sulfonate

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

doxorubicin naphthalene-2-sulfonate
1246449-86-4

doxorubicin naphthalene-2-sulfonate

Conditions
ConditionsYield
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%
Fmoc-Phe-Lys(MMT)-PABC-PNP

Fmoc-Phe-Lys(MMT)-PABC-PNP

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Fmoc-Phe-Lys(MMT)-PABC-Dox
847871-55-0

Fmoc-Phe-Lys(MMT)-PABC-Dox

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃;99.6%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

N-Fmoc doxorubicin

N-Fmoc doxorubicin

Conditions
ConditionsYield
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
1451073-54-3

carbonic acid 4-(2,5-dioxo-3,4-bis-phenylsulfanyl-2,5-dihydro-pyrrol-1-yl)-benzyl ester 4-nitro-phenyl ester

doxorubicin hydrochloride
25316-40-9

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
1451073-56-5

{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
ConditionsYield
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
25316-40-9

doxorubicin hydrochloride

biotinamidocaproate N-hydroxysuccinimide ester
89889-52-1

biotinamidocaproate N-hydroxysuccinimide ester

C43H54N4O14S
1401539-59-0

C43H54N4O14S

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 16h;98%
doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

adipic acid dihydrazide
1071-93-8

adipic acid dihydrazide

C33H41N5O12*2C2HF3O2

C33H41N5O12*2C2HF3O2

Conditions
ConditionsYield
In methanol at 20℃; for 5h;97%
doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

doxorubicin tosylate

doxorubicin tosylate

Conditions
ConditionsYield
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%
C47H51N7O11S2

C47H51N7O11S2

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C68H75N7O19S2

C68H75N7O19S2

Conditions
ConditionsYield
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
64987-85-5

4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

doxorubicin-succinimidyl 4-[N-maleimidomethyl]cyclohexane-1-carboxylate
400647-59-8

doxorubicin-succinimidyl 4-[N-maleimidomethyl]cyclohexane-1-carboxylate

Conditions
ConditionsYield
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
25316-40-9

doxorubicin hydrochloride

benzenesufonyl hydrazide
80-17-1

benzenesufonyl hydrazide

13-benzenesulfonylhydrazone-doxorubicin hydrochloride

13-benzenesulfonylhydrazone-doxorubicin hydrochloride

Conditions
ConditionsYield
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)

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
25316-40-9

doxorubicin hydrochloride

PHPMA-AH-NH-N=DOX-co-MA-AH-chol

PHPMA-AH-NH-N=DOX-co-MA-AH-chol

Conditions
ConditionsYield
acetic acid In methanol at 25℃; for 22h;96%
C21H20N2O6

C21H20N2O6

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C42H44N2O14

C42H44N2O14

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;96%
C19H14Cl2N2O6

C19H14Cl2N2O6

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C40H38Cl2N2O14

C40H38Cl2N2O14

Conditions
ConditionsYield
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
1350891-95-0

(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl) 4-nitrophenyl carbonate

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

N-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyloxycarbonyl)doxorubicin
1350892-00-0

N-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyloxycarbonyl)doxorubicin

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide94%
C59H106N2O30

C59H106N2O30

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C82H130N2O38

C82H130N2O38

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 14h; Inert atmosphere; Darkness;94%
doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-Trifluoroacetyladriamycin
26295-56-7

N-Trifluoroacetyladriamycin

Conditions
ConditionsYield
With pyridine In diethyl ether at -30 - 0℃; for 3h; Schlenk technique;94%
With pyridine In diethyl ether at -20℃; for 0.5h;91%
(9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-(((S)-4-amino- 1-((4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)amino)-1,4-dioxobutan-2-yl)amino)- 1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate

(9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-(((S)-4-amino- 1-((4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)amino)-1,4-dioxobutan-2-yl)amino)- 1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

Nα-Fmoc-Ala-Ala-Asn-PABC-doxorubicin

Nα-Fmoc-Ala-Ala-Asn-PABC-doxorubicin

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Darkness;94%
(E)-2,5-dioxopyrrolidin-1-yl 1-(cyclooct-4-en-1-yloxy)-1-oxo-5,8,11,14-tetraoxa-2-azaheptadecan-17-oate

(E)-2,5-dioxopyrrolidin-1-yl 1-(cyclooct-4-en-1-yloxy)-1-oxo-5,8,11,14-tetraoxa-2-azaheptadecan-17-oate

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C47H62N2O18

C47H62N2O18

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Darkness;94%
6-azidohexanoic hydrazide
1039044-92-2

6-azidohexanoic hydrazide

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C33H40N6O11*ClH

C33H40N6O11*ClH

Conditions
ConditionsYield
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
C27H25N3O14S2

C27H25N3O14S2

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C48H49N3O22S2

C48H49N3O22S2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h;93%
linolenyl hydrazide
1169394-01-7

linolenyl hydrazide

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C45H59N3O11*ClH

C45H59N3O11*ClH

Conditions
ConditionsYield
With trifluoroacetic acid In methanol at 20℃;92%
C17H15N5O8
1596412-91-7

C17H15N5O8

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

C38H39N5O16
1596412-92-8

C38H39N5O16

Conditions
ConditionsYield
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℃;
3,4-dithiophenoylmaleimide-N-hexanoic acid

3,4-dithiophenoylmaleimide-N-hexanoic acid

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

N-(hexanamide-N-doxorubicin)-3,4-dithiophenoylmaleimide

N-(hexanamide-N-doxorubicin)-3,4-dithiophenoylmaleimide

Conditions
ConditionsYield
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
25316-40-9

doxorubicin hydrochloride

diprop-2-enyl N-<(4-<<4-nitrophenoxycarbonyloxy>methyl>phenyl)carbamoyl>-L-glutamate
180839-15-0

diprop-2-enyl N-<(4-<<4-nitrophenoxycarbonyloxy>methyl>phenyl)carbamoyl>-L-glutamate

N-<4-(dipropen-2-yl-L-glutamylcarbonylamino)benzyloxycarbonyl>doxorubicin

N-<4-(dipropen-2-yl-L-glutamylcarbonylamino)benzyloxycarbonyl>doxorubicin

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 3.5h; Ambient temperature;91.1%
doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

N-(9-fluorenylmethoxycarbonyl)-β-alanyl-L-leucyl-L-alanyl-L-leucine

N-(9-fluorenylmethoxycarbonyl)-β-alanyl-L-leucyl-L-alanyl-L-leucine

N-[N-(9-fluorenylmethoxycarbonyl)-β-alanyl-L-leucyl-L-alanyl-L-leucyl]doxorubicin
274913-06-3

N-[N-(9-fluorenylmethoxycarbonyl)-β-alanyl-L-leucyl-L-alanyl-L-leucyl]doxorubicin

Conditions
ConditionsYield
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
25316-40-9

doxorubicin hydrochloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

4-(4-(N-maleimido)phenyl)butyric acid hydrazide hydrochloride

4-(4-(N-maleimido)phenyl)butyric acid hydrazide hydrochloride

C41H42N4O13*C2HF3O2

C41H42N4O13*C2HF3O2

Conditions
ConditionsYield
In methanol at 20℃; for 5h;90%
cis-aconitic anhydride
6318-55-4

cis-aconitic anhydride

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

cis-aconitic anhydride doxorubicin
1425615-40-2

cis-aconitic anhydride doxorubicin

Conditions
ConditionsYield
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
874302-76-8

4-nitrophenyl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

doxorubicin 2-(pyridy-2-yldithio)ethylcarbamate
1058725-05-5

doxorubicin 2-(pyridy-2-yldithio)ethylcarbamate

Conditions
ConditionsYield
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%
N-(p-benzoic acid)-3,4-dithiophenoylmaleimide

N-(p-benzoic acid)-3,4-dithiophenoylmaleimide

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

N-( p-benzamide-N-doxorubicin)-3,4-dithiophenoylmaleimide

N-( p-benzamide-N-doxorubicin)-3,4-dithiophenoylmaleimide

Conditions
ConditionsYield
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%

Doxorubicin hydrochloride Consensus Reports

NTP 10th Report on Carcinogens. EPA Genetic Toxicology Program.

Doxorubicin hydrochloride Specification

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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