Pirarubicin

Pirarubicin (INN) is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.^[1]

Other names(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

AHFS/Drugs.comInternational Drug Names

ATC code

• L01DB08 (WHO)

Legal status

• In general: ℞ (Prescription only)

Quick facts Clinical data, Other names ...

Pirarubicin

Clinical data
Other names	(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
AHFS/Drugs.com	International Drug Names
ATC code	L01DB08 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside
CAS Number	72496-41-4 Y
PubChem CID	3033521
ChemSpider	2298189 N
UNII	D58G680W0G
KEGG	D01885 Y
ChEBI	CHEBI:94770
ChEMBL	ChEMBL1398373 N
CompTox Dashboard (EPA)	DTXSID2046755
Chemical and physical data
Formula	C32H37NO12
Molar mass	627.643 g·mol−1
3D model (JSmol)	Interactive image
Melting point	188 to 192 °C (370 to 378 °F) (decomposes)
SMILES C[C@H]1[C@H]([C@H](C[C@@H](O1)OC2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6
InChI 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 N Key:KMSKQZKKOZQFFG-YHKVCKOMSA-N N
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