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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H53NO14
Molecular Weight 831.9023
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAROTAXEL

SMILES

CC1=C2[C@]([H])(C(=O)[C@@]34C[C@@]4([H])C[C@]5([H])[C@@](CO5)([C@@]3([H])[C@@]([H])([C@](C[C@]1([H])OC(=O)[C@@]([H])([C@]([H])(c6ccccc6)N=C(O)OC(C)(C)C)O)(C2(C)C)O)OC(=O)c7ccccc7)OC(=O)C)OC(=O)C

InChI

InChIKey=DXOJIXGRFSHVKA-BZVZGCBYSA-N
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

HIDE SMILES / InChI

Molecular Formula C45H53NO14
Molecular Weight 831.9023
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

LAROTAXEL is a taxoid with potential antineoplastic activity. It prevents microtubule depolymerization, thereby inhibiting cell proliferation. It displays a broad spectrum of antitumor activity in vitro and in vivo, including activity against P-glycoprotein expressing tumors. LAROTAXEL was in phase III clinical trials for the treatment of breast cancer, pancreatic cancer, and bladder cancer. However, its development was discontinued.

Approval Year

Targets
PubMed

PubMed

TitleDatePubMed
Preclinical evaluation of new taxoids.
2001 Sep
Phase II multicenter study of larotaxel (XRP9881), a novel taxoid, in patients with metastatic breast cancer who previously received taxane-based therapy.
2008 Jul
Larotaxel: broadening the road with new taxanes.
2009 Aug
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Jun 26 13:51:08 UTC 2021
Edited
by admin
on Sat Jun 26 13:51:08 UTC 2021
Record UNII
TWQ8K8A81Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAROTAXEL
INN   WHO-DD  
INN  
Official Name English
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)
Common Name English
LAROTAXEL [INN]
Common Name English
XRP-9881
Code English
XRP9881
Code English
LAROTAXEL [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1490
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
NCI_THESAURUS C67437
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
Code System Code Type Description
EVMPD
SUB36058
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
FDA UNII
TWQ8K8A81Y
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
PUBCHEM
6918260
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
CAS
156294-36-9
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
DRUG BANK
DB12984
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
INN
8671
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
MESH
C531079
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
NCI_THESAURUS
C48427
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
WIKIPEDIA
LAROTAXEL
Created by admin on Sat Jun 26 13:51:08 UTC 2021 , Edited by admin on Sat Jun 26 13:51:08 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY