OBATOCLAX MESYLATE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H19N3O.CH4O3S
Molecular Weight	413.49
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.COC1=CC(=N\C1=C/C2=C(C)C=C(C)N2)C3=CC4=C(N3)C=CC=C4

InChI

InChIKey=ZFKXDVMHNXPEIY-PEZBNFGJSA-N

InChI=1S/C20H19N3O.CH4O3S/c1-12-8-13(2)21-16(12)10-19-20(24-3)11-18(23-19)17-9-14-6-4-5-7-15(14)22-17;1-5(2,3)4/h4-11,21-22H,1-3H3;1H3,(H,2,3,4)/b19-10-;

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H19N3O
Molecular Weight	317.3844
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22324354 | https://www.ncbi.nlm.nih.gov/pubmed/18040043
Curator's Comment: Description was created based on several sources, including http://en.pharmacodia.com/web/drug/1_2376.html | http://adisinsight.springer.com/drugs/800013657

Obatoclax (GX15-070) is a novel BH3 mimetic pan Bcl- 2 inhibitor. The clinically studied formulation is as obatoclax mesylate (Box 1), a salt. It is only under study as an intravenous preparation. It functions to block BH3-mediated binding of Bcl-2, Bcl-XL, Mcl-1 and A1 to Bax and Bak. Bax and Bak thus are unopposed and able to dimerize to allow initiation of intrinsic apoptosis. Preclinically, obatoclax has been shown to reverse inhibition of Bax or Bak by Bcl-2, Bcl-XL, Bcl-w and Mcl-1. Obatoclax was discovered by Gemin X, which was acquired by Cephalon, which has since been acquired by Teva Pharmaceuticals. Obatoclax had been in phase III clinical trials by Gemin X Biotechnologies (subsidiary of Teva) for the treatment of non-small lung cancer (NSCLC). The compound received orphan drug designation in the U.S. in 2004 for the treatment of chronic lymphocytic leukemia (CLL). However, Teva discontinued the development of obatoclax in 2013.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis regulator Bcl-2 19 Target ID: CHEMBL4860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22195752	Inhibitor 8504		0.22 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Small-cell lung cancer 41 Sources: http://adisinsight.springer.com/drugs/800013657 https://clinicaltrials.gov/ct2/show/NCT01563601	Primary	Phase III 665	Unknown Approved Use Unknown
Hodgkin's lymphoma 33 Sources: http://adisinsight.springer.com/drugs/800013657 https://clinicaltrials.gov/ct2/show/NCT00359892	Primary	Phase II 1147	Unknown Approved Use Unknown
Leukemia 72 Sources: http://adisinsight.springer.com/drugs/800013657 https://clinicaltrials.gov/ct2/show/NCT00918931	Primary	Phase II 1147	Unknown Approved Use Unknown
Myelofibrosis 15 Sources: https://clinicaltrials.gov/ct2/show/NCT00360035	Primary	Phase II 1147	Unknown Approved Use Unknown
Systemic mastocytosis 2 Sources: http://adisinsight.springer.com/drugs/800013657 https://clinicaltrials.gov/ct2/show/NCT00918931	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
92.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18931344	40 mg/m² 1 times / 3 weeks multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
155 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	28 mg/m² 1 times / week multiple, intravenous dose: 28 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
27.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	1.25 mg/m² 1 times / week multiple, intravenous dose: 1.25 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
33.46 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	7 mg/m² 1 times / week multiple, intravenous dose: 7 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
114.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	20 mg/m² 1 times / week multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
277 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18931344	40 mg/m² 1 times / 3 weeks multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
599 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	28 mg/m² 1 times / week multiple, intravenous dose: 28 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
34.37 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	1.25 mg/m² 1 times / week multiple, intravenous dose: 1.25 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
55.01 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	7 mg/m² 1 times / week multiple, intravenous dose: 7 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
401 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	20 mg/m² 1 times / week multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
59.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18931344	40 mg/m² 1 times / 3 weeks multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	28 mg/m² 1 times / week multiple, intravenous dose: 28 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11.66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	1.25 mg/m² 1 times / week multiple, intravenous dose: 1.25 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
45.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	7 mg/m² 1 times / week multiple, intravenous dose: 7 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
28.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20538761	20 mg/m² 1 times / week multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	OBATOCLAX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
60 mg 1 times / day multiple, intravenous Highest studied dose Dose: 60 mg, 1 times / day Route: intravenous Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25285531	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25285531	Sources: https://pubmed.ncbi.nlm.nih.gov/25285531
20 mg 1 times / day multiple, intravenous MTD Dose: 20 mg, 1 times / day Route: intravenous Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25285531	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25285531	Sources: https://pubmed.ncbi.nlm.nih.gov/25285531
1.25 mg/m2 1 times / week multiple, intravenous MTD Dose: 1.25 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 1.25 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	Sources: https://pubmed.ncbi.nlm.nih.gov/20538761
20 mg/m2 1 times / week multiple, intravenous MTD Dose: 20 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 20 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	Sources: https://pubmed.ncbi.nlm.nih.gov/20538761
30 mg 1 times / day multiple, intravenous Studied dose Dose: 30 mg, 1 times / day Route: intravenous Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25285531	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25285531	DLT: Somnolence, Confusion... Other AEs: Dizziness, Mood alteration NOS... Dose limiting toxicities: Somnolence (grade 3, 33.3%) Confusion (grade 3, 33.3%) Ataxia (grade 3, 33.3%) Other AEs: Dizziness (grade 1-2, 33.3%) Mood alteration NOS (grade 1-2, 33.3%) Speech disorder (grade 1-2, 33.3%) Confusion (grade 1, 33.3%) Ataxia (grade 1-2, 33.3%) Euphoria (grade 1-2, 66.7%) Somnolence (grade 1, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/25285531
28 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 28 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 28 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	DLT: Somnolence, Tonic clonic movements... Dose limiting toxicities: Somnolence (grade 3, 16.7%) Tonic clonic movements (grade 3, 16.7%) Coordination abnormal (grade 3, 33.3%) Dizziness (16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/20538761
7 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 7 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 7 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20538761	DLT: Coordination abnormal... Dose limiting toxicities: Coordination abnormal (33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/20538761

AEs

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY572578	https://www.001chemical.com/chem/803712-67-6
Ambinter	Amb22520492	http://www.ambinter.com/reference/22520492
BioChemPartner	BCP20625	http://www.biochempartner.com/803712-67-6-BCP20625
BOC Sciences	803712-67-6	https://www.bocsci.com/obatoclax-cas-803712-67-6-item-91078.html
Boerchem	BC203251	http://www.boerchem.com/?product_34136.html
Chem Scene	CS-0025474	http://www.chemscene.com/803712-67-6.html
ChemMol	44001449	http://www.chemmol.com/chemmol/44001449.html
Chemspace	CSSB00102513633	https://chem-space.com/CSSB00102513633
MedChem Express	HY-10969A	https://www.medchemexpress.com/obatoclax-1.html
Molcore	MC572578	https://www.molcore.com/product/803712-67-6
Smolecule	S864937	https://www.smolecule.com/products/s864937
Synblock Inc	SB16622	http://www.synblock.com/product/803712-67-6.html

PubMed

Title	Date	PubMed
Obatoclax mesylate : pharmacology and potential for therapy of hematological neoplasms.	2012-03	22324354
Phase I dose finding studies of obatoclax (GX15-070), a small molecule pan-BCL-2 family antagonist, in patients with advanced solid tumors or lymphoma.	2010-08-01	20538761
Small molecule obatoclax (GX15-070) antagonizes MCL-1 and overcomes MCL-1-mediated resistance to apoptosis.	2007-12-04	18040043

Patents

Sample Use Guides

In Vivo Use Guide

30 mg by vein over 3 hours Days 1-3, 14-day cycle

Route of Administration: Intravenous

In Vitro Use Guide

Obatoclax completely inhibits Bak recovery of Mcl-1 at 5 uM in SK-Mel5 cells and overcomes resistance to ABT-373-induced apoptosis conferred by Mcl-1 in KB/Bcl-2 cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:24 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:24 GMT 2025`
Record UNII	39200FJ43J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OBATOCLAX MESILATE

Preferred Name

English

OBATOCLAX MESYLATE

Official Name

English

2-[2-[(3,5-Dimethyl-1H-pyrrol-2-yl)methylidene]-3-methoxy-2H-pyrrol-5-yl]-1H-indole monomethanesulfonate

Systematic Name

English

1H-INDOLE, 2-(2-((3,5-DIMETHYL-1H-PYRROL-2-YL)METHYLENE)-3-METHOXY-2H-PYRROL-5-YL), MONOMETHANESULPHONATE

Common Name

English

Obatoclax mesilate [WHO-DD]

Common Name

English

OBATOCLAX MESYLATE [USAN]

Common Name

English

1H-INDOLE, 2-(2-((3,5-DIMETHYL-1H-PYRROL-2-YL)METHYLENE)-3-METHOXY-2H-PYRROL-5-YL), MONOMETHANESULFONATE

Common Name

English

2-(2-((3,5-DIMETHYL-1H-PYRROL-2-YL)METHYLIDENE)-3-METHOXY-2H-PYRROL-5-YL)-1H-INDOLE MONOMETHANESULPHONATE

Systematic Name

English

GX-15-070MS

Code

English

GX15-070MS

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

232106