Therarubicin Tn

Synopsis, Chemistry

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Also known as: Pirarubicin, 72496-41-4, Pinorubicin, Pinorubin, Pirarubicin, >=95% (hplc), (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione

Molecular Formula

C₃₂H₃₇NO₁₂

Molecular Weight

627.6 g/mol

InChI Key

KMSKQZKKOZQFFG-NCXNULAVSA-N

Pirarubicin is 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. (NCI04)

1 2D Structure

Therarubicin Tn

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

KMSKQZKKOZQFFG-NCXNULAVSA-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

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)OC6CCCCO6

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. Thp-adm

10. Thp-adriamycin

11. Thp-dox

12. Thp-doxorubicin

2.2.2 Depositor-Supplied Synonyms

1. Pirarubicin

2. 72496-41-4

3. Pinorubicin

4. Pinorubin

5. Pirarubicin, >=95% (hplc)

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

7. Sr-01000944915

8. Sr-01000944915-1

2.3 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₃₇NO₁₂
Molecular Weight	627.6 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Exact Mass	627.23157562 g/mol
Monoisotopic Mass	627.23157562 g/mol
Topological Polar Surface Area	204 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	1120
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1