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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H45N3O7
Molecular Weight 571.7049
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 5
Charge 0

SHOW SMILES / InChI
Structure of PLOCABULIN

SMILES

COC1=CC[C@H](OC1=O)[C@@H](C)\C=C(C)\C=C/C=C\C(=O)N[C@H](C(=O)N\C=C/C[C@H](C\C=C/C)OC(N)=O)C(C)(C)C

InChI

InChIKey=IEKGSKLKBICCHQ-BDOJOPHNSA-N
InChI=1S/C31H45N3O7/c1-8-9-14-23(40-30(32)38)15-12-19-33-28(36)27(31(4,5)6)34-26(35)16-11-10-13-21(2)20-22(3)24-17-18-25(39-7)29(37)41-24/h8-13,16,18-20,22-24,27H,14-15,17H2,1-7H3,(H2,32,38)(H,33,36)(H,34,35)/b9-8-,13-10-,16-11-,19-12-,21-20+/t22-,23-,24-,27+/m0/s1

HIDE SMILES / InChI

Molecular Formula C31H45N3O7
Molecular Weight 571.7049
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 5
Optical Activity UNSPECIFIED

PM-060184 is a new type of marine polyketide isolated from the Madagascan sponge. PM060184 belongs to a new family of tubulin-binding agents. PM060184 is an inhibitor of tubulin polymerization that reduces microtubule dynamicity in cells by 59%. Interestingly, PM060184 suppresses microtubule shortening and growing at a similar extent. PM060184 is able to overcome P-gp mediated resistance in vivo, an effect that could be related to its high binding affinity for tubulin. PM-060184 demonstrated antimitotic properties in human tumor cells lines at subnanomolar concentrations and display a distinct inhibition mechanism on microtubules. An antivascular mechanism is contributing to the antitumor activities of plocabulin. PM-060184 I in phase II clinical trial for the treatment of breast and colorectal cancer.

Approval Year

PubMed

PubMed

TitleDatePubMed
Isolation and first total synthesis of PM050489 and PM060184, two new marine anticancer compounds.
2013 Jul 10
A previously undescribed tubulin binder.
2014 Sep 23
Molecular basis of resistance to the microtubule-depolymerizing antitumor compound plocabulin.
2018 Jun 5

Sample Use Guides

Dose range - from 1.3 mg/m2 to 14.5 mg/m2 Day (D) 1, D8 and D15 every four weeks
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:40:30 UTC 2023
Edited
by admin
on Sat Dec 16 10:40:30 UTC 2023
Record UNII
52Y8L60CR7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PLOCABULIN
INN  
Official Name English
plocabulin [INN]
Common Name English
PM060184
Code English
Plocabulin [WHO-DD]
Common Name English
J3.348.355D
Code English
PM-060184
Code English
2,4,6-NONATRIENAMIDE, N-((1S)-1-((((1Z,4S,6Z)-4-((AMINOCARBONYL)OXY)-1,6-OCTADIEN-1-YL)AMINO)CARBONYL)-2,2-DIMETHYLPROPYL)-8-((2S)-3,6-DIHYDRO-5-METHOXY-6-OXO-2H-PYRAN-2-YL)-6-METHYL-, (2Z,4Z,6E,8S)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2115
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
Code System Code Type Description
DRUG BANK
DB13137
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
INN
10618
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
SMS_ID
300000034328
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
PUBCHEM
57788271
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
NCI_THESAURUS
C95888
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
CAS
960210-99-5
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
FDA UNII
52Y8L60CR7
Created by admin on Sat Dec 16 10:40:30 UTC 2023 , Edited by admin on Sat Dec 16 10:40:30 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY