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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Pinorubin
Primary
Pinorubin
Primary
Pinorubin
Primary
Pinorubin
Primary
Pinorubin
Primary
Pinorubin
Primary
Pinorubin
Primary
Pinorubin

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
The IC50 values of Pirarubicin in M5076 ovarian sarcoma cells was 0.366 uM.
Substance Class Chemical
Record UNII
D58G680W0G
Record Status Validated (UNII)
Record Version