DOXORUBICIN

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H29NO11
Molecular Weight	543.5193
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DOXORUBICIN

Structure Search

SMILES

[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(=O)CO

InChI

InChIKey=AOJJSUZBOXZQNB-TZSSRYMLSA-N

InChI=1S/C27H29NO11/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/t10-,13-,15-,17-,22+,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H29NO11
Molecular Weight	543.5193
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:21:26 UTC 2023` Edited by `admin` on `Fri Dec 15 17:21:26 UTC 2023`
Record UNII	80168379AG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DOXORUBICIN

Official Name

English

DOXORUBICIN [HSDB]

Common Name

English

DOXORUBICIN [VANDF]

Common Name

English

ADRIABLASTIN

Common Name

English

DAUNORUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]

Common Name

English

DOXORUBICIN [MART.]

Common Name

English

DOXORUBICIN [MI]

Common Name

English

Doxorubicin [WHO-DD]

Common Name

English

NSC-123127

Code

English

5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-

Common Name

English

EPIRUBICIN HYDROCHLORIDE IMPURITY, DOXORUBICIN- [USP IMPURITY]

Common Name

English

NSC-759155

Code

English

doxorubicin [INN]

Common Name

English

ADRIBLASTINA

Brand Name

English

(8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE

Common Name

English

VALRUBICIN IMPURITY, DOXORUBICIN [USP IMPURITY]

Common Name

English

EPIRUBICIN HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

DOXORUBICIN [USAN]

Common Name

English

HYDROXYDAUNORUBICIN

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007530

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

199904

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

276009

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

553116

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

820821

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

NDF-RT

N0000007530

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

WHO-ESSENTIAL MEDICINES LIST

8.2

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

248107

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

469215

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

844921

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

808521

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

WHO-VATC

QL01DB01

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

NDF-RT

N0000000176

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

NDF-RT

N0000007530

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

139800

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

286109

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

NCI_THESAURUS

C67502

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

NDF-RT

N0000175414

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

FDA ORPHAN DRUG

117398

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

LIVERTOX

NBK548622

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

EU-Orphan Drug

EU/3/15/1513

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

WHO-ATC

L01DB01

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

Code System Code Type Description

EPA CompTox

DTXSID8021480

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

RXCUI

3639

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

RxNorm

ChEMBL

CHEMBL53463

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

EVMPD

SUB35582

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

IUPHAR

7069

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

DRUG CENTRAL

960

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

LACTMED

Doxorubicin

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

CAS

23214-92-8

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

ECHA (EC/EINECS)

245-495-6

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

NSC

123127

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

MESH

D004317

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

DAILYMED

80168379AG

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

NSC

759155

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

FDA UNII

80168379AG

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

DRUG BANK

DB00997

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

SMS_ID

100000085265

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

CHEBI

28748

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

INN

3005

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

WIKIPEDIA

DOXORUBICIN

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

NCI_THESAURUS

C456

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

CHEBI

64816

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

MERCK INDEX

m4757

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

Merck Index

EVMPD

SUB06391MIG

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

PUBCHEM

31703

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

HSDB

3070

Created by admin on Fri Dec 15 17:21:26 UTC 2023 , Edited by admin on Fri Dec 15 17:21:26 UTC 2023

PRIMARY

Related Record Type Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> SUBSTRATE


					XBG3W2GCL2

ATP-dependent translocase ABCB1 [Canis lupus familiaris]

TRANSPORTER -> SUBSTRATE

Comments:

Dogs homozygous or heterozygous for the ABCB1-1Δ mutation are significantly more likely than normal dogs to develop haematological and gastrointestinal toxicity.

Amount:


					L5GTM43M4I

DNA TOPOISOMERASE 2-ALPHA

TARGET -> INHIBITOR

Interaction Type:

BINDING


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					Y49M64GZ4Q

MRP-1

TRANSPORTER -> SUBSTRATE

Amount:


					82F2G7BL4E

DOXORUBICIN HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:


					GX4RN38YCG

ATP-BINDING CASSETTE SUB-FAMILY B MEMBER 5

TRANSPORTER -> SUBSTRATE

Comments:

Responsible for the resistance to doxorubicin of a subset of malignant melanomas.

Amount:

Related Record Type Details


					X023T6C35L

METABOLITE -> PARENT

Interaction Type:

MAJOR

Amount:


					C28MV4IM0B

PRODRUG -> METABOLITE ACTIVE

Comments:

Reacts with the Cys-34 of albumin gets transported to tumor microenvironment and released in acidic environment.

Amount:


					HUH05KI4CF

METABOLITE -> PARENT


					VB2YU5128G

7-DEOXYDOXORUBICINONE

METABOLITE -> PARENT

Amount:

Related Record Type Details


					2C6NUM6878

PARENT -> IMPURITY

Amount:


					UD984I04LZ

DAUNORUBICIN HYDROCHLORIDE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					22966TX7J5

EPIRUBICIN HYDROCHLORIDE

PARENT -> IMPURITY

Related Record Type Details


					80168379AG

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC