Pirarubicin

Summary

Pirarubicin (CHEMBL2354444) is a phase-3 clinical-stage small-molecule antineoplastic agent (ATC L01DB08); indicated across 6 conditions including neoplasm and hepatocellular carcinoma.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• ATC class: L01DB08
• Indications: 6 conditions
• Clinical trials: 14
• Chemistry: 627.6 Da · C32H37NO12

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL2354444
Name	Pirarubicin
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	11296583
ChEBI	CHEBI:94770
ATC	L01DB08
Molecular formula	C32H37NO12
Molecular weight	627.6
InChIKey	KMSKQZKKOZQFFG-YXRRJAAWSA-N

SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6

IUPAC name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

ChEBI definition: An anthracycline that is doxorubicin in which the hydroxy group at position 4’ is replaced by a (2R)-tetrahydro-2H-pyran-2-yloxy group.

Pharmacological roles (ChEBI): antineoplastic agent, cardiotoxic agent.

Also known as: Adriamycin, tetrahydropyranyl, Pirarubicin, Pirarubicina, Pirarubicine, Theprubicin, Thp-adm, SID50113026, SID124893439, SID144206155, PIRARUBICINE, SID170465822

Parent form; salt/anhydrous children: CHEMBL6146655

Patent coverage: 12,165 distinct patent families (50,520 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 50,283 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Nuclear receptor ROR-gamma, RecQ-like DNA helicase BLM, Histone-lysine N-methyltransferase 2A, Protein deacetylase HDAC6, Menin/Histone-lysine N-methyltransferase MLL, Prostaglandin G/H synthase 1, MUS81-ECE1, Huntingtin.

Bioactivity

ChEMBL activities: 6 potent at pChembl ≥ 5 of 10 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGS1	6.3	AC50	500	nM	CHEMBL_ACT_25205070
ECE1	6.1	IC50	790	nM	CHEMBL_ACT_25482641
HDAC6	5.9	IC50	1257	nM	CHEMBL_ACT_23141059
PTGS1	5.8	AC50	1570	nM	CHEMBL_ACT_25206003
HTT	5.4	Potency	3981	nM	CHEMBL_ACT_3753915
MEN1	5.35	Potency	4467	nM	CHEMBL_ACT_3614475

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

6 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
neoplasm	3	MONDO:0005070	EFO:0000616
hepatocellular carcinoma	3	MONDO:0007256	EFO:0000182
breast neoplasm	3	MONDO:0021100	EFO:0003869
acute lymphoblastic leukemia	2	MONDO:0004967	EFO:0000220
lymphoma	2	MONDO:0005062	EFO:0000574
soft tissue sarcoma	2	MONDO:0018078	EFO:1001968

Clinical trials

Total trials: 14.

Phase distribution

Phase	Trials
PHASE2	5
PHASE4	4
PHASE2/PHASE3	2
PHASE3	1
PHASE1	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03892330	PHASE4	NOT_YET_RECRUITING	Combination Therapy of Anthracyclines for Children With Nephroblastoma
NCT01249690	PHASE4	UNKNOWN	Efficacy Study of PAD and TAD in Newly Diagnosed Multiple Myeloma
NCT01746992	PHASE4	UNKNOWN	CTOP/ITE/MTX Compared With CHOP as the First-line Therapy for Newly Diagnosed Young Patients With T Cell Lymphoma
NCT02903524	PHASE4	UNKNOWN	Doxorubicin Hydrochloride Liposome Injection Combination With Cyclophosphamide vs Pirarubicin Combination With Cyclophosphamide in Patients With Locally Advanced Breast Cancer
NCT02585479	PHASE2/PHASE3	WITHDRAWN	Systemic Chemotherapy Versus Transcatheter Arterial Chemoembolization(TACE) for Hepatocellular Carcinoma
NCT02613026	PHASE3	COMPLETED	Comparative Analysis of the Efficacies in Neoadjuvant Chemotherapy of Breast Cancer
NCT03342300	PHASE2/PHASE3	WITHDRAWN	Pegylated Liposomal Doxorubicin Versus Pirarubicin Plus Ifosfamide, Dacarbazine in Locally Advanced, Unresectable or Metastatic Soft-tissue Sarcoma
NCT06714383	PHASE2	RECRUITING	Trilaciclib Combing Chemotherapy in the Neoadjuvant Treatment of Osteosarcoma
NCT00131053	PHASE2	UNKNOWN	Applying Pediatric Regimens to Younger Adult Patients With Acute Lymphoblastic Leukemia (ALL)
NCT02740426	PHASE2	UNKNOWN	Prophylactic Intravesical Chemotherapy to Prevent Bladder Recurrence After Diagnostic Ureteroscopy for Primary Upper Tract Urothelial Carcinoma Patients
NCT02923557	PHASE2	UNKNOWN	Prophylactic Intravesical Chemotherapy to Prevent Bladder Recurrence After Nephroureterectomy for Primary Upper Tract Urothelial Carcinoma Patients
NCT04126811	PHASE2	UNKNOWN	Apatinib Combined With Chemotherapy in the Treatment of Soft Tissue Sarcoma
NCT07178171	PHASE1	RECRUITING	A Study of QL1706 Combined With Short-Cycle Anthracyclines or Taxanes for the Treatment of Early-Stage TNBC
NCT05287308	Not specified	NOT_YET_RECRUITING	Adjuvant Albumin-bound Paclitaxel Versus Taxanes in Breast Cancer: a Real-world Study

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).