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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H37NO12.ClH
Molecular Weight 664.097
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRARUBICIN HYDROCHLORIDE

SMILES

Cl.[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=ZPHYPKKFSHAVOE-YZIXBPQXSA-N
InChI=1S/C32H37NO12.ClH/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;1H/t14-,17-,19-,21+,22-,31+,32-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Fri Dec 15 14:57:50 GMT 2023
Edited
by admin
on Fri Dec 15 14:57:50 GMT 2023
Record UNII
E7V83174BE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRARUBICIN HYDROCHLORIDE
MI   WHO-DD  
Common Name English
PIRARUBICIN HYDROCHLORIDE [MI]
Common Name English
THEPRUBICIN HYDROCHLORIDE
Common Name English
Pirarubicin hydrochloride [WHO-DD]
Common Name English
THERARUBICIN
Brand Name English
PINORUBIN
Brand Name English
NSC-333054
Code English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
Code System Code Type Description
EVMPD
SUB20711
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
PUBCHEM
20846247
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
CAS
95343-20-7
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
MERCK INDEX
m8871
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY Merck Index
SMS_ID
100000086477
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
DRUG BANK
DBSALT001933
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
FDA UNII
E7V83174BE
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID00915024
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
NCI_THESAURUS
C95319
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
MESH
C027260
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
NSC
333054
Created by admin on Fri Dec 15 14:57:50 GMT 2023 , Edited by admin on Fri Dec 15 14:57:50 GMT 2023
PRIMARY
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