U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO11
Molecular Weight 543.5203
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXORUBICIN

SMILES

C[C@@]1([H])[C@]([H])([C@]([H])(C[C@@]([H])(O1)O[C@@]2([H])C[C@@](Cc3c2c(c4c(C(=O)c5cccc(c5C4=O)OC)c3O)O)(C(=O)CO)O)N)O

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

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/dosage/doxorubicin.html

Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. Doxorubicin is used to produce regression in disseminated neoplastic conditions like acute lymphoblastic leukemia, acute myeloblastic leukemia, Wilms’ tumor, neuroblastoma, soft tissue and bone sarcomas, breast carcinoma, ovarian carcinoma, transitional cell bladder carcinoma, thyroid carcinoma, gastric carcinoma, Hodgkin’s disease, malignant lymphoma and bronchogenic carcinoma in which the small cell histologic type is the most responsive compared to other cell types. Doxorubicin is also indicated for use as a component of adjuvant therapy in women with evidence of axillary lymph node involvement following resection of primary breast cancer.

CNS Activity

Curator's Comment:: Doxorubicin did not have access to areas of the brain within the blood-brain barrier, passed from the blood into the nervous parenchyma in those areas of the brain located outside the blood-brain barrier in mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.67 µM [IC50]
Target ID: CHEMBL614517
200.0 nM [IC50]
24.68 µM [IC50]
0.074 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DOXIL

Approved Use

Indicated for: Ovarian cancer After failure of platinum-based chemotherapy. AIDS-related Kaposi’s Sarcoma After failure of prior systemic chemotherapy or intolerance to such therapy. Multiple Myeloma

Launch Date

8.1647999E11
Primary
DOXIL

Approved Use

Indicated for: Ovarian cancer After failure of platinum-based chemotherapy. AIDS-related Kaposi’s Sarcoma After failure of prior systemic chemotherapy or intolerance to such therapy. Multiple Myeloma

Launch Date

8.1647999E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2 μM
60 mg/m² 1 times / day steady-state, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
DOXORUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7.4 μM × h
60 mg/m² 1 times / day steady-state, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
DOXORUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
34.8 h
60 mg/m² 1 times / day steady-state, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
DOXORUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
DOXORUBICIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
150 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 150 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg/m2, 1 times / day
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Other AEs: Mucositis, Chills...
Other AEs:
Mucositis (severe, 1 patient)
Chills (1 patient)
Pyrexia (1 patient)
Sources:
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Other AEs: Sinus tachycardia, Neutropenia...
Other AEs:
Sinus tachycardia (1 patient)
Neutropenia (grade 4, 1 patient)
Thrombocytopenia (1 patient)
Mucositis (severe, 1 patient)
Sepsis (severe, 1 patient)
Sources:
60 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 60 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 60 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Disc. AE: Tissue injury...
Other AEs: Acute myeloid leukaemia, Myelodysplastic syndrome...
AEs leading to
discontinuation/dose reduction:
Tissue injury (severe)
Other AEs:
Acute myeloid leukaemia
Myelodysplastic syndrome
Myelosuppression (severe)
Sources:
300 mg/m2 1 times / 3 weeks multiple, intravenous (total)
Dose: 300 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Other AEs: Cardiomyopathy...
AEs

AEs

AESignificanceDosePopulation
Chills 1 patient
150 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 150 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg/m2, 1 times / day
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Pyrexia 1 patient
150 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 150 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg/m2, 1 times / day
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Mucositis severe, 1 patient
150 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 150 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg/m2, 1 times / day
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Sinus tachycardia 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Thrombocytopenia 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Neutropenia grade 4, 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Mucositis severe, 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Sepsis severe, 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Acute myeloid leukaemia
60 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 60 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 60 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Myelodysplastic syndrome
60 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 60 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 60 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Myelosuppression severe
60 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 60 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 60 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Tissue injury severe
Disc. AE
60 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 60 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 60 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Cardiomyopathy
300 mg/m2 1 times / 3 weeks multiple, intravenous (total)
Dose: 300 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / 3 weeks
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Km 5.2 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Experimental animal models of adriamycin cardiotoxicity.
1979 May
Protective effects of carvedilol against doxorubicin-induced cardiomyopathy in rats.
1999
Topical DMSO treatment for pegylated liposomal doxorubicin-induced palmar-plantar erythrodysesthesia.
1999
Potential inhibitors of HIV integrase.
1999 Apr-May
Sodium bicarbonate treatment reduces renal injury, renal production of transforming growth factor-beta, and urinary transforming growth factor-beta excretion in rats with doxorubicin-induced nephropathy.
1999 Aug
Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes.
1999 Aug 1
Doxorubicin-induced cardiomyopathy.
1999 Feb 25
Doxorubicin-induced cardiomyopathy.
1999 Feb 25
[Changes in left ventricular function during chemotherapy with doxorubicin].
1999 Jul
Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma.
1999 Jul
Effect of allopurinol in the course of adriamycin induced nephropathy.
1999 Mar
Role of thromboxane in the altered vascular reactivity of pregnant rats with adriamycin nephropathy.
1999 May
Low-dose vincristine-associated bilateral vocal cord paralysis.
1999 Oct
Renal protective effects of blocking the intrarenal renin-angiotensin system.
1999 Sep
Preclinical evaluation of the cardiac toxicity of HMR-1826, a novel prodrug of doxorubicin.
1999 Sep
Anthracyclines trigger apoptosis of both G0-G1 and cycling peripheral blood lymphocytes and induce massive deletion of mature T and B cells.
2000 Apr 1
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2.
2000 Aug
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance.
2000 Aug
Doxorubicin and paclitaxel in advanced breast carcinoma: importance of prior adjuvant anthracycline therapy.
2000 Dec 1
Curcumin prevents adriamycin nephrotoxicity in rats.
2000 Jan
Mechanism of doxorubicin-induced inhibition of sarcoplasmic reticulum Ca(2+)-ATPase gene transcription.
2000 Jan 7-21
Liposomal doxorubicin (Caelyx) in advanced pretreated soft tissue sarcomas: a phase II study of the Italian Sarcoma Group (ISG).
2000 Jan-Feb
Manic episode in an ifosfamide-treated patient.
2000 Jan-Feb
Doxorubicin-induced cardiomyopathy.
2000 Jul
Beta-blockade in adriamycin-induced cardiomyopathy.
2000 Jun
Evaluation of cardiac adrenergic neuronal damage in rats with doxorubicin-induced cardiomyopathy using iodine-131 MIBG autoradiography and PGP 9.5 immunohistochemistry.
2000 Jun
Deficiency of the stress kinase p38alpha results in embryonic lethality: characterization of the kinase dependence of stress responses of enzyme-deficient embryonic stem cells.
2000 Mar 6
Lovastatin potentiates antitumor activity and attenuates cardiotoxicity of doxorubicin in three tumor models in mice.
2000 May
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model.
2000 Oct
Progressive adriamycin nephropathy in mice: sequence of histologic and immunohistochemical events.
2000 Oct
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.
2000 Sep
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.
2000 Sep 15
Mobilization of hematopoietic progenitor cells with a combination of docetaxel, adriamycin, 5-fluorouracil and filgrastim in breast cancer patients.
2001 Jan
Reversal of LRP-associated drug resistance in colon carcinoma SW-620 cells.
2001 Jan 1
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.
2001 Jan 1
Patents

Sample Use Guides

When used in combination with other chemotherapy drugs, the most commonly used dosage of doxorubicin is 40 to 60 mg/m2 IV every 21 to 28 days. Alternatively, 60 to 75 mg/m2 IV once every 21 days.
Route of Administration: Intravenous
Alkalinization of extracellular pH by urease (2 U/ml) and urea (> or = 2 mM) was found to enhance the antitumor efficacy of doxorubicin (50 uM)
Name Type Language
DOXORUBICIN
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
DOXORUBICIN [HSDB]
Common Name English
DOXORUBICIN [VANDF]
Common Name English
ADRIABLASTIN
Common Name English
DOXORUBICIN [MART.]
Common Name English
DOXORUBICIN [MI]
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 C [EP]
Common Name English
DOXORUBICIN [WHO-DD]
Common Name English
EPIRUBICIN IMPURITY C
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY, DOXORUBICIN- [USP]
Common Name English
VALRUBICIN IMPURITY, DOXORUBICIN [USP]
Common Name English
EPIRUBICIN HYDROCHLORIDE SPECIFIED IMPURITY C [EP]
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
DOXORUBICIN [USAN]
Common Name English
HYDROXYDAUNORUBICIN
Common Name English
Classification Tree Code System Code
NDF-RT N0000007530
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 276009
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 553116
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 199904
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
NDF-RT N0000007530
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 248107
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 469215
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
WHO-VATC QL01DB01
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
NDF-RT N0000000176
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
NDF-RT N0000007530
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 139800
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 286109
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
NCI_THESAURUS C67502
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
NDF-RT N0000175414
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
FDA ORPHAN DRUG 117398
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
LIVERTOX 328
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
EU-Orphan Drug EU/3/15/1513
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
WHO-ATC L01DB01
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
Code System Code Type Description
EPA CompTox
23214-92-8
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
RXCUI
3639
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL53463
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
EVMPD
SUB35582
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
IUPHAR
7069
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
DRUG CENTRAL
960
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
LACTMED
Doxorubicin
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
CAS
23214-92-8
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-495-6
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
MESH
D004317
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
FDA UNII
80168379AG
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
DRUG BANK
DB00997
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
INN
3005
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
WIKIPEDIA
DOXORUBICIN
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
NCI_THESAURUS
C456
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
MERCK INDEX
M4757
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY Merck Index
EVMPD
SUB06391MIG
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
PUBCHEM
31703
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY
HSDB
3070
Created by admin on Fri Jun 25 22:01:59 UTC 2021 , Edited by admin on Fri Jun 25 22:01:59 UTC 2021
PRIMARY