Details of the Drug

General Information of Drug (ID: DMC5TV6)

Drug Name

TPI-287

Synonyms

849213-15-6; (1S,2S,4S,7S,7aR,7a1S,10aS,11aR,13aS,13bR)-1-(benzoyloxy)-4-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-5-methylhexanoyl)oxy)-2-hydroxy-5,7a1,14,14-tetramethyl-9-vinyl-2,3,4,7,7a,7a1,10a,11,11a,13,13a,13b-dodecahydro-1H-8,10,12-trioxa-2,6-methanocyclobuta[b]cyclodeca[de]naphthalene-7,13a-diyl diacetate; TPI 287; SCHEMBL10000720; DTXSID50233967; Q27273546

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Phase 2	[1]
Glioblastoma multiforme	2A00.0	Phase 2	[2]
Alzheimer disease	8A20	Phase 1	[3]
Progressive supranuclear palsy	8A00.10	Phase 1	[4]
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Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

870

Logarithm of the Partition Coefficient (xlogp)

4.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C46H63NO15
IUPAC Name: [(1R,2S,5R,7S,11R,12S,15S,17S,18S,19S)-2,12-diacetyloxy-9-ethenyl-17-hydroxy-15-[(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]oxy-14,19,20,20-tetramethyl-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
Canonical SMILES: CC1=C2[C@@H]([C@H]3[C@@]4([C@H](C[C@@H]5[C@]([C@H]4[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](CC(C)C)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO5)OC(=O)C)OC(O3)C=C)C)OC(=O)C
InChI: InChI=1S/C46H63NO15/c1-13-32-58-30-20-31-45(22-55-31,61-26(6)49)36-38(60-39(51)27-17-15-14-16-18-27)46(54)21-29(57-40(52)34(50)28(19-23(2)3)47-41(53)62-42(7,8)9)24(4)33(43(46,10)11)35(56-25(5)48)37(59-32)44(30,36)12/h13-18,23,28-32,34-38,50,54H,1,19-22H2,2-12H3,(H,47,53)/t28-,29-,30-,31+,32?,34+,35-,36-,37-,38-,44+,45-,46+/m0/s1
InChIKey: FDTAUJJRHBRHIJ-FDJAAIFISA-N

Cross-matching ID

PubChem CID: 11564168
CAS Number: 849213-15-6
TTD ID: D3X2TH

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Microtubule (MicroTu)	TT1WDO0	NOUNIPROTAC	Stabilizer	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	ClinicalTrials.gov (NCT01332630) TPI 287 in Breast Cancer Metastatic to the Brain. U.S. National Institutes of Health.
2	ClinicalTrials.gov (NCT02047214) Safety & Efficacy Study of TPI 287 + Avastin in Adults With Glioblastoma That Progressed Following Prior Avastin Therapy. U.S. National Institutes of Health.
3	ClinicalTrials.gov (NCT01966666) A Safety, Tolerability, Pharmacokinetics, Pharmacodynamics and Preliminary Efficacy Study of TPI-287 in Alzheimer's Disease. U.S. National Institutes of Health.
4	ClinicalTrials.gov (NCT02133846) Safety Study of TPI-287 to Treat CBS and PSP (TPI-287-4RT). U.S. National Institutes of Health.
5	TPI-287, a new taxane family member, reduces the brain metastatic colonization of breast cancer cells. Mol Cancer Ther. 2012 Sep;11(9):1959-67.