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| CAS No.: | 25316-40-9 |
|---|---|
| Name: | Doxorubicin hydrochloride |
| Molecular Structure: | |
|
|
|
| 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: |
 T, T+
|
| Risk Codes: | 45-22-40-26/27/28 |
| Safety: | 53-45-36/37/39-22-7/9 |
| PSA: | 206.07000 |
| LogP: | 1.50360 |
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; |
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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. |
