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Doxorubicin hydrochloride

  CAS No.: 25316-40-9   Cat No.: BADC-00038   Purity: >98% COA HNMR MS 4.5  

Doxorubicin is an anthracycline antibiotic with antineoplastic activity produced by the bacterium Streptomyces peucetius var. Doxorubicin is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.

Doxorubicin hydrochloride

Structure of 25316-40-9

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Category
ADC Cytotoxin
Molecular Formula
C27H30ClNO11
Molecular Weight
579.98
Target
DNA Topoisomerase II
Shipping
-20°C (International: -20°C)
Storage
Store at -20 °C

* For research and manufacturing use only. We do not sell to patients.

Size Price Stock Quantity
1 g $398 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
Daunorubicin EP Impurity D hydrochloride; (8S,10S)-10-[(3-Aamino-2,3,6-trideoxy-α-L-lyxohexopyranosyl)oxy]-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride; Doxorubicine hydrochloride; Adriblastina hydrochloride; 14-Hydroxydaunomycin hydrochloride; 14-Hydroxydaunorubicine hydrochloride; Hydroxydaunorubicin hydrochloride; (1S,3S)-3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride; Epirubicin EP Impurity C hydrochloride
IUPAC Name
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O.Cl
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
InChIKey
MWWSFMDVAYGXBV-RUELKSSGSA-N
Solubility
Soluble ethanol, methanol, DMF, DMSO
Melting Point
>168°C
Flash Point
443.8°C
PSA
206.07000
Vapor Pressure
9.64E-28mmHg at 25°C
Source
Streptomyces peucetius
Appearance
Orange Crystal Powder
Quantity
Milligrams-Grams
Quality Standard
USP
Shelf Life
≥360 days if stored properly
Shipping
-20°C (International: -20°C)
Storage
Store at -20 °C
Pictograms
Irritant; Health Hazard
Signal Word
Danger
Boiling Point
810.3°C at 760 mmHg
In Vitro
MTT assay in MCF7 cells showed significantly higher (p<0.0001) cytotoxicity for doxorubicin hydrochloride in SPIONs than doxorubicin hydrochloride solution (IC50 values 6.294±0.4169 and 11.316±0.1102μgmL(-1), respectively).
In Vivo
When CVA21 was combined with doxorubicin hydrochloride, synergistically enhanced cell death was observed when CVA21 was administered both simultaneously or 24 h prior to doxorubicin hydrochloride exposure. Doxorubicin hydrochloride had no effect on CVA21 replication. Through the use of an orthotopic (MDA-MB-231-luc) xenograft SCID mouse model of human breast cancer we showed that a single intravenous injection of CVA21 in combination with an intraperitoneal injection of doxorubicin hydrochloride resulted in significantly greater tumor reduction compared to either agent alone.
NCT NumberTitleCondition Or DiseasePhaseStart DateSponsorStatus
NCT00000626Phase II Study of Filgrastim (G-CSF) Plus ABVD in the Treatment of HIV-Associated Hodgkin's DiseaseHIV InfectionsPhase 2National Institute of Allergy and Infectious Diseases (NIAID)Completed
NCT00000658A Phase III Randomized Trial of Low-Dose Versus Standard-Dose mBACOD Chemotherapy With rGM-CSF for Treatment of AIDS-Associated Non-Hodgkin's LymphomaLymphoma, Non-HodgkinPhase 3National Institute of Allergy and Infectious Diseases (NIAID)Completed
NCT00000681A Phase I Study of the Combination of Recombinant GM-CSF, AZT, and Chemotherapy (ABV) (Adriamycin, Bleomycin, Vincristine) in AIDS and Kaposi's SarcomaSarcoma, KaposiPhase 1National Institute of Allergy and Infectious Diseases (NIAID)Completed
NCT00000689Phase I Trial of mBACOD and Granulocyte-Macrophage Colony-Stimulating Factor (GM-CSF) in AIDS-Associated Large Cell, Immunoblastic, and Small Non-cleaved LymphomaLymphoma, Non-HodgkinPhase 1National Institute of Allergy and Infectious Diseases (NIAID)Completed
NCT00000703Chemotherapy and Azidothymidine, With or Without Radiotherapy, for High Grade Lymphoma in AIDS-Risk Group MembersLymphoma, Non-HodgkinNational Institute of Allergy and Infectious Diseases (NIAID)Completed

Doxorubicin hydrochloride is an anthracycline antibiotic and a potent ADC cytotoxin widely utilized as an ADC payload in antibody-drug conjugates. Its cytotoxic mechanism involves intercalation into DNA, inhibition of topoisomerase II, and generation of reactive oxygen species (ROS), leading to DNA strand breaks, cell cycle arrest, and induction of apoptosis in proliferating tumor cells. The hydrochloride form enhances solubility and chemical stability, facilitating conjugation to monoclonal antibodies via cleavable or non-cleavable linker chemistries, enabling precise intracellular delivery in ADC applications.

Within antibody-drug conjugates, Doxorubicin hydrochloride is covalently attached to antibodies using linker systems designed to maintain systemic stability and prevent premature payload release. The ADC remains inactive in circulation, reducing off-target cytotoxicity. Upon internalization into antigen-expressing tumor cells via receptor-mediated endocytosis, enzymatic or chemical cleavage releases the active doxorubicin payload. Once liberated, it intercalates into nuclear DNA, inhibits topoisomerase II, and generates ROS, leading to apoptosis. This targeted delivery ensures cytotoxic activity is confined to tumor cells, enhancing the specificity of tumor-targeted therapy.

Applications of Doxorubicin hydrochloride include incorporation into ADCs targeting both hematologic malignancies and solid tumors with defined antigen expression. Its compatibility with various linker chemistries allows optimization of conjugation efficiency, intracellular release kinetics, and pharmacokinetic profiles. Doxorubicin hydrochloride demonstrates reproducible cytotoxic activity in target-expressing tumor cells, supporting the development of ADCs with defined DNA-damaging mechanisms and controlled induction of apoptosis, providing a mechanistically precise approach for antibody-drug conjugate design in targeted cancer therapy.

1.Electrochemical Behavior and Square Wave Voltammetric Determination of Doxorubicin Hydrochloride
Younghee Hahn and Ho Young Lee. Arch Pharm Res Vol 27, No 1, 31-34, 2004
The detecting system connected to CE was a carbon disk working electrode with an applied potential of 0.95 V vs. a Ag/AgCI (3 M KCI), which measured anodic currents due to the oxidation of two phenolic hydroxyls in the aglycone of daunorubicin (Hu et aL, 2000). Meanwhile, reductive detecting system measured at -0.30 V was preferred to oxidation in which the chromatographic profile suffered severe interference from substances that result from the biological matrix (Ricciarello et aL, 1998). Electrochemical assay often offers selectivity and sensitivity due to the selective detection of electroactive species among the complex samples. The chemical structure of doxorubicin contains a electrochemically a reducible quinone moiety in the aglycone which prompted us to study its electro-chemical behavior by using mercury electrodes, followed by developing the fast and sensitive square wave voltammetric (SWV) procedure for the determination of doxorubicin hydrochloride in the present study.
2.Facile fabrication of thermally responsive Pluronic F127-based nanocapsules for controlled release of doxorubicin hydrochloride
Zhipeng Zeng & Zhiping Peng & Lei Chen & Yiwang Chen. Colloid Polym Sci (2014) 292:1521–1530
The short cross-linking reaction time led to the formation of nanocapsules with thin and low-cross-linked PL shell because the cross-linking reaction between the –NPC groups and –NH2 groups was slow. The difference of the contrast between the PL shell and the hollow core resulted in the typical empty core–shell structure which can be found in the TEM images. After reacting for 20 h, the diameter of the nanocapsules increased to about 200 nm as shown in Fig. 2b. Assuming that the size change of the inner cavity was negligible, the thickness of the PL shell can be estimated to be more than 60 nm. The denser and tighter (with high cross-linking density for long reaction time) PL shell resulted in the empty core–shell structure invisible in the TEM image even though the hollow inner cavity was still there. For the Pluronic F127/HA nanocapsules as shown in Fig. 2d, the smaller and instable nanocapsules were formed because of the slower reaction rate between –COOH groups and –NH2 groups. After reacting for 20 h, the diameter of the Pluronic F127/HA nanocapsules was determined to be about 220 nm. The size of the Pluronic F127/HA nanocapsules was larger than the Pluronic F127/PL nanocapsules because the content of HA was more than PL taken up by the nanocapsules. The average size was consistent with those determined from DLS results.
3.A Method for Evaluation of Therapeutic Dose of Doxorubicin Hydrochloride Using Breast Tumor Cell Culture MCF-7
Ya. D. Shanskij, Yu. A. Ershov*, and V. M. Pechennikov*. Bulletin of Experimental Biology and Medicine, Vol. 148, No. 3, 2009
Statistical data suggest that the use of anticancer drug does not signifi cantly increase the total survival of patient. This is largely associated with difficulties in rational regimen of drug usage. The choice of the dose of anticancer drugs is mainly empirical. This is also true for doxorubicin hydrochloride, antitumor antibiotic of the anthracycline family used for breast cancer management.

What is Doxorubicin hydrochloride?

Doxorubicin hydrochloride is an anthracycline cytotoxic agent widely used as an ADC payload. It intercalates into DNA, inhibiting topoisomerase II activity, leading to DNA damage and apoptosis in targeted cancer cells when delivered via antibodies.

19/8/2020

Could you explain how Doxorubicin hydrochloride functions in ADCs?

In ADCs, Doxorubicin hydrochloride is delivered selectively to antigen-expressing cells. Once internalized, it intercalates into DNA and inhibits topoisomerase II, inducing cell death while minimizing systemic toxicity.

22/10/2022

We would like to know which linkers are appropriate for Doxorubicin hydrochloride.

Doxorubicin hydrochloride can be conjugated with cleavable linkers responsive to intracellular conditions such as pH or enzymes. This ensures controlled release inside target cells while maintaining stability in circulation.

3/10/2021

What precautions should be taken when handling Doxorubicin hydrochloride?

Handling Doxorubicin hydrochloride requires standard cytotoxic safety measures including protective gloves, lab coats, and containment. These precautions prevent accidental exposure during synthesis, conjugation, and laboratory testing.

6/12/2021

Good afternoon! Is Doxorubicin hydrochloride used in preclinical ADC research?

Yes, Doxorubicin hydrochloride is frequently employed in preclinical ADC studies to assess DNA-targeted cytotoxicity, evaluate linker stability, and determine the selective delivery efficiency of antibody conjugates.

16/9/2022

— Dr. Jason Carter, Senior Scientist (USA)

Doxorubicin hydrochloride delivered by BOC Sciences had excellent purity, critical for our conjugation protocols.

3/10/2021

— Dr. Andrew Scott, Oncology Researcher (USA)

Doxorubicin hydrochloride from BOC Sciences was delivered with high purity and proper documentation, essential for ADC development.

16/9/2022

— Ms. Sophie Wagner, Senior Scientist (Germany)

Batch consistency and excellent analytical data for Doxorubicin hydrochloride enabled seamless conjugation studies.

6/12/2021

— Dr. Richard Evans, Biopharmaceutical Scientist (UK)

We achieved reproducible results in all assays using Doxorubicin hydrochloride, reflecting its high-quality manufacture.

19/8/2020

— Mr. Marc Lefevre, ADC Development Specialist (France)

BOC Sciences provided responsive support and timely delivery for Doxorubicin hydrochloride, helping meet project deadlines.

— Dr. Emma Larsen, Laboratory Head (Denmark)

Reliable sourcing and quality of Doxorubicin hydrochloride allowed us to accelerate our ADC research programs.

22/10/2022

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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