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25316-40-9

Basic Information
CAS No.: 25316-40-9
Name: Doxorubicin hydrochloride
Article Data: 13
Molecular Structure:
Molecular Structure of 25316-40-9 (Doxorubicin hydrochloride)
Formula: C27H30ClNO11
Molecular Weight: 579.988
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;
EINECS: 246-818-3
Melting Point: 216 °C (dec.)(lit.)
Boiling Point: 810.3 °C at 760 mmHg
Flash Point: 443.8 °C
Solubility: Soluble in water.
Appearance: orange-red crystalline solid
Hazard Symbols: ToxicT,VeryT+
Risk Codes: 45-22-40-26/27/28
Safety: 53-45-36/37/39-22-7/9
PSA: 206.07000
LogP: 1.50360
Synthetic route
29742-67-4

14-bromodaunorubicin hydrochloride

25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 80℃; for 2h;64%

C61H69N7O18*5.7HCl

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

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

25316-40-9

doxorubicin hydrochloride

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

daunomycin 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

25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
Purification / work up;

doxorubicin

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

A

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

B

25316-40-9

doxorubicin hydrochloride

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

C44H42F2N4O14

A

C17H15F2N3O4

B

25316-40-9

doxorubicin hydrochloride

Conditions
ConditionsYield
With fibroblast activating protein In water Enzymatic reaction;

C47H55N5O20S2

A

C21H30N4O10S3

B

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;
Raw Materials
23541-50-6
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    Chemical Name (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 CAS

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Consensus Reports

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

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.