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ACTIVE PHARMA INGREDIENTS

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Also known as: Larotaxel [inn], 156294-36-9, Xrp-9881, Xrp9881, Twq8k8a81y, Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-alpha-hydroxy-, (1s,2s,4s,7r,8ar,9as,10ar,12as,12br)-7,12a-bis(acetyloxy)-1-(benzoyloxy)-1,3,4,7,8,9,9a,10,10a,12,12a,12b-dodecahydro-2-hydroxy-5,13,13-trimethyl-8-oxo-2,6-methano-2h-cyclodeca[3,4]cyclopropa[4,5]benz[1,2-b]oxet-4-yl ester, (alphar,betas)-

Molecular Formula

C₄₅H₅₃NO₁₄

Molecular Weight

831.9 g/mol

InChI Key

DXOJIXGRFSHVKA-BZVZGCBYSA-N

FDA UNII

TWQ8K8A81Y

Larotaxel is a semi-synthetic derivative of the taxane 10-deacetylbaccatin III with potential antineoplastic activities. Larotaxel binds to tubulin, promoting microtubule assembly and stabilization and preventing microtubule depolymerization, thereby inhibiting cell proliferation. As it represents poor substrate for P-glycoprotein-related drug resistance mechanisms, this agent may be useful for treating multi-drug resistant tumors. Larotaxel penetrates the blood brain barrier.

1 2D Structure

Larotaxel

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-diacetyloxy-1-hydroxy-16-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-2-yl] benzoate

2.1.2 InChI

InChI=1S/C45H53NO14/c1-23-29(57-39(52)33(49)32(26-15-11-9-12-16-26)46-40(53)60-41(4,5)6)21-45(54)37(58-38(51)27-17-13-10-14-18-27)35-43(36(50)34(56-24(2)47)31(23)42(45,7)8)20-28(43)19-30-44(35,22-55-30)59-25(3)48/h9-18,28-30,32-35,37,49,54H,19-22H2,1-8H3,(H,46,53)/t28-,29+,30-,32+,33-,34-,35+,37+,43-,44+,45-/m1/s1

2.1.3 InChI Key

DXOJIXGRFSHVKA-BZVZGCBYSA-N

2.1.4 Canonical SMILES

CC1=C2C(C(=O)C34CC3CC5C(C4C(C(C2(C)C)(CC1OC(=O)C(C(C6=CC=CC=C6)NC(=O)OC(C)(C)C)O)O)OC(=O)C7=CC=CC=C7)(CO5)OC(=O)C)OC(=O)C

2.1.5 Isomeric SMILES

CC1=C2[C@H](C(=O)[C@]34C[C@H]3C[C@@H]5[C@]([C@H]4[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C6=CC=CC=C6)NC(=O)OC(C)(C)C)O)O)OC(=O)C7=CC=CC=C7)(CO5)OC(=O)C)OC(=O)C

2.2 Other Identifiers

2.2.1 UNII

TWQ8K8A81Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Xrp 9881

2. Xrp-9881

3. Xrp9881

2.3.2 Depositor-Supplied Synonyms

1. Larotaxel [inn]

2. 156294-36-9

3. Xrp-9881

4. Xrp9881

5. Twq8k8a81y

6. Benzenepropanoic Acid, Beta-[[(1,1-dimethylethoxy)carbonyl]amino]-alpha-hydroxy-, (1s,2s,4s,7r,8ar,9as,10ar,12as,12br)-7,12a-bis(acetyloxy)-1-(benzoyloxy)-1,3,4,7,8,9,9a,10,10a,12,12a,12b-dodecahydro-2-hydroxy-5,13,13-trimethyl-8-oxo-2,6-methano-2h-cyclodeca[3,4]cyclopropa[4,5]benz[1,2-b]oxet-4-yl Ester, (alphar,betas)-

7. (1s,2s,4s,7r,8ar,9as,10ar,12as,12br)-1-(benzoyloxy)-4-(((2r,3s)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-2-hydroxy-5,13,13-trimethyl-8-oxo-1,3,4,7,8,9,9a,10,10a,12b-decahydro-2h-2,6-methanocyclodeca[3,4]cyclopropa[4,5]benzo[1,2-b]oxete-7,12a(12h)-diyl Diacetate

8. Xrp 9881

9. Unii-twq8k8a81y

10. Pnu 100940

11. Benzenepropanoic Acid, Beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, (1s,2s,4s,7r,8ar,9as,10ar,12as,12br)-7,12a-bis(acetyloxy)-1-(benzoyloxy)-1,3,4,7,8,9,9a,10,10a,12,12a,12b-dodecahydro-2-hydroxy-5,13,13-trimethyl-8-oxo-2,6-methano-2h-cyclodeca(3,4)cyclopropa(4,5)benz(1,2-b)oxet-4-yl Ester, (alphar,betas)-

12. Larotaxel [who-dd]

13. Schembl125697

14. Chembl4279455

15. Zinc95627892

16. Db12984

17. Pnu-100940

18. Hy-125374

19. Cs-0091011

20. Q6489757

21. [(1s,2s,3r,4s,7r,9s,11r,13r,16s)-4,13-diacetyloxy-1-hydroxy-16-[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-2-yl] Benzoate

22. 1-hydroxy-9-oxo-5.beta.,20-epoxy-7.beta.,19-cyclotax-11-ene-2.alpha.,4,10.beta.,13.alpha.-tetrayl 4,10-diacetate 2-benzoate 13-((2r,3s)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoate)

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₄₅H₅₃NO₁₄
Molecular Weight	831.9 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	15
Exact Mass	831.34660536 g/mol
Monoisotopic Mass	831.34660536 g/mol
Topological Polar Surface Area	210 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1790
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1