Pirarubicin HCl

Synopsis, Chemistry

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Also known as: Therarubicin (tn), Pirarubicin hydrochloride, Pinorubin (tn), Dtxsid00915024, D08386, (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-[(2s)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

Molecular Formula

C₃₂H₃₈ClNO₁₂

Molecular Weight

664.1 g/mol

InChI Key

ZPHYPKKFSHAVOE-QXTSSQDCSA-N

Pirarubicin Hydrochloride is the hydrochloride salt form of pirarubicin, an analogue of the anthracycline antineoplastic antibiotic doxorubicin with antineoplastic activity. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair as well as RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.

1 2D Structure

Pirarubicin HCl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

ZPHYPKKFSHAVOE-QXTSSQDCSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OC6CCCCO6.Cl

2.1.5 Isomeric 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.Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 4'-o-tetrahydropyranyladriamycin

2. 4'-o-tetrahydropyranyldoxorubicin

3. 4'-o-tetrapyranyldoxorubicin

4. Pirarubicin

5. Pirarubicin Hydrochloride

6. Thprubicine

7. Thepirubicin

8. Theprubicin

9. Therarubicin

10. Thp-adm

11. Thp-adriamycin

12. Thp-dox

13. Thp-doxorubicin

2.2.2 Depositor-Supplied Synonyms

1. Therarubicin (tn)

2. Pirarubicin Hydrochloride

3. Pinorubin (tn)

4. Dtxsid00915024

5. D08386

6. (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-[(2s)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

7. 3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-o-oxan-2-ylhexopyranoside--hydrogen Chloride (1/1)

2.3 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₃₈ClNO₁₂
Molecular Weight	664.1 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Exact Mass	663.2082533 g/mol
Monoisotopic Mass	663.2082533 g/mol
Topological Polar Surface Area	204 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1120
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2