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

Details

Stereochemistry ABSOLUTE
Molecular Formula C32H37NO12
Molecular Weight 627.6357
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRARUBICIN

SMILES

[H][C@]1(CCCCO1)O[C@H]2[C@@H](N)C[C@H](O[C@@]3([H])C[C@@](O)(CC4=C(O)C5=C(C(=O)C6=C(C=CC=C6OC)C5=O)C(O)=C34)C(=O)CO)O[C@H]2C

InChI

InChIKey=KMSKQZKKOZQFFG-YXRRJAAWSA-N
InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1

HIDE SMILES / InChI

Molecular Formula C32H37NO12
Molecular Weight 627.6357
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://newdrugapprovals.org/2015/06/01/pirarubicin-hydrochloride/ | http://www.kegg.jp/medicus-bin/japic_med_product?id=00053425-001#00053425-001

Pirarubicin is a new kind of anthracene nucleus broad-spectrum antitumor antibiotic. This compound was rapidly incorporated into tumor cells, inhibiting DNA polymerase alpha, DNA topoisomerase II and subsequently DNA synthesis. Inhibition of RNA synthesis was also noted. It is indicated as an antineoplastic agent for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer, ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma. Among the side effects, cardiac toxicity, alopecia and disturbance of the digestive organs were mild.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
Primary
Pinorubin

Approved Use

It is indicated for the treatment of the following diseases: head and neck cancer, breast cancer, gastric cancer, urothelial cancer (bladder, renal, ureter neoplasms), ovarian cancer, uterine cancer, acute leukemia, malignant lymphoma.
PubMed

PubMed

TitleDatePubMed
[Pirarubicin (THP-adriamycin)].
1988 Sep
Patents

Sample Use Guides

25-50 mg/m2 BSA every 3-4 wk, to be given as injection over 5-10 minutes into a rapidly-flowing infusion of glucose 5%
Route of Administration: Intravenous
The IC50 values of Pirarubicin in M5076 ovarian sarcoma cells was 0.366 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:10:55 GMT 2023
Edited
by admin
on Sat Dec 16 05:10:55 GMT 2023
Record UNII
D58G680W0G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRARUBICIN
INN   MART.   MI   WHO-DD  
INN  
Official Name English
(8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-4-O-(2R-TETRAHYDRO-2H-PYRAN-2-YL)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE
Common Name English
THEPRUBICIN
Common Name English
THP-ADM
Common Name English
PIRARUBICIN [MART.]
Common Name English
ADRIAMYCIN, TETRAHYDROPYRANYL
Common Name English
PIRARUBICIN [MI]
Common Name English
pirarubicin [INN]
Common Name English
Pirarubicin [WHO-DD]
Common Name English
PIRARUBICIN [JAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QL01DB08
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
FDA ORPHAN DRUG 778820
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
WHO-ATC L01DB08
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
NCI_THESAURUS C1594
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
Code System Code Type Description
EVMPD
SUB09894MIG
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
PUBCHEM
11296583
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
NCI_THESAURUS
C1197
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
SMS_ID
100000081658
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
FDA UNII
D58G680W0G
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
MERCK INDEX
m8871
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB11616
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID2046755
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
INN
5877
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL1398373
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
CAS
72496-41-4
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
WIKIPEDIA
PIRARUBICIN
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
DRUG CENTRAL
2198
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY
RXCUI
33764
Created by admin on Sat Dec 16 05:10:56 GMT 2023 , Edited by admin on Sat Dec 16 05:10:56 GMT 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY