PLOCABULIN

Investigational

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29415678 | https://www.ncbi.nlm.nih.gov/pubmed/24486569 | https://www.ncbi.nlm.nih.gov/pubmed/23750450 | https://adisinsight.springer.com/drugs/800033610

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
First-in-human phase I study of the microtubule inhibitor plocabulin in patients with advanced solid tumors.	2019-08	30411218
Molecular basis of resistance to the microtubule-depolymerizing antitumor compound plocabulin.	2018-06-05	29872155
Plocabulin, a novel tubulin-binding agent, inhibits angiogenesis by modulation of microtubule dynamics in endothelial cells.	2018-02-07	29415678
A previously undescribed tubulin binder.	2014-09-23	25187564
A new tubulin-binding site and pharmacophore for microtubule-destabilizing anticancer drugs.	2014-09-23	25114240
PM060184, a new tubulin binding agent with potent antitumor activity including P-glycoprotein over-expressing tumors.	2014-04-01	24486569
New interfacial microtubule inhibitors of marine origin, PM050489/PM060184, with potent antitumor activity and a distinct mechanism.	2013-09-20	23859655
Isolation and first total synthesis of PM050489 and PM060184, two new marine anticancer compounds.	2013-07-10	23750450

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 23:23:00 GMT 2025` Edited by `admin` on `Mon Mar 31 23:23:00 GMT 2025`
Record UNII	52Y8L60CR7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

J3.348.355D

Preferred Name

English

PLOCABULIN

Official Name

English

plocabulin [INN]

Common Name

English

PM060184

Code

English

Plocabulin [WHO-DD]

Common Name

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