MERTANSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H48ClN3O10S
Molecular Weight	738.288
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H]1\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C(=C2)N(C)C(=O)C[C@H](OC(=O)[C@H](C)N(C)C(=O)CCS)[C@]3(C)O[C@H]3[C@H](C)[C@@H]4C[C@@]1(O)NC(=O)O4

InChI

InChIKey=ANZJBCHSOXCCRQ-FKUXLPTCSA-N

InChI=1S/C35H48ClN3O10S/c1-19-10-9-11-26(46-8)35(44)18-25(47-33(43)37-35)20(2)31-34(4,49-31)27(48-32(42)21(3)38(5)28(40)12-13-50)17-29(41)39(6)23-15-22(14-19)16-24(45-7)30(23)36/h9-11,15-16,20-21,25-27,31,44,50H,12-14,17-18H2,1-8H3,(H,37,43)/b11-9+,19-10+/t20-,21+,25+,26-,27+,31+,34+,35+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C35H48ClN3O10S
Molecular Weight	738.288
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20937594

Mertansine (Maytansine) is a 19–member ansa macrolide structure attached to a chlorinated benzenering. It was originally isolated from the shrub Maytenus ovatus. Mertansine (DM1) is a tubulin inhibitor, it inhibits the assembly of microtubules by binding to tubulin, with a linker structure can create an antibody-drug conjugate (ADC). Mertansine is a potent microtubule-targeted compound that induces mitotic arrest and kills tumor cells at sub-nanomolar concentrations. The antimitotic effect of maytansine has been attributed to its ability to inhibit microtubule assembly by binding to tubulin with a KD of ~ 1 umol/L, at or near the vinblastine-binding site. Experimental ADCs with the SPP-DM1 design include lorvotuzumab mertansine. DM1 can also be linked to an antibody using the SMCC (4-(3-mercapto-2,5-dioxo-1-pyrrolidinylmethyl)-cylohexanecarboxylic acid) linker, in which case the International Nonproprietary Name of the conjugate formed contains the word emtansine. DM1 and its attachment via these linkers result from ImmunoGen Inc research. Trastuzumab emtansine (T-DM1) is an anti-HER2/neu antibody-drug conjugate.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20937594	Inhibitor 8504		0.86 µM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Leukemia 72 Sources: https://clinicaltrials.gov/ct2/show/NCT02420873 http://adisinsight.springer.com/drugs/800008504	Primary	Phase II 1147	Unknown Approved Use Unknown
Solid tumors 147 Sources: https://clinicaltrials.gov/ct2/show/NCT02452554 http://adisinsight.springer.com/drugs/800008504	Primary	Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://clinicaltrials.gov/ct2/show/NCT01745965	Primary	Phase II 1147	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 supressor 22 inhibitor 2252	supressor 19 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A4 98 CYP3A5 136 UGT1A6 136 UGT1A1 246 CYP2C8 1057 UGT1A9 148 UGT1A3 89 UGT2B7 197 P-gp 1741	CYP3A4/5 91 CYP1A2 1197 CYP2B6 776 CYP2C8 810 P-gp 2052 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
UGT1A4 100	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	no [IC50 >2.5 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25048520/	no
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	no
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	no
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	no
CYP2C8 1117	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.0321 uM]
CYP2B6 1160	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.0368 uM]
UGT1A9 155	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.0541 uM]
CYP1A2 2333	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.0937 uM]
CYP3A4 2633	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.16 uM]
CYP2C9 2497	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.5784 uM]
UGT1A1 303	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 0.8567 uM]
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [IC50 4.3 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/ \| https://pubmed.ncbi.nlm.nih.gov/25048520/	yes [Ki 11 uM]
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes [Ki 13.5 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/ \| https://pubmed.ncbi.nlm.nih.gov/25048520/	yes [Ki 14 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/ \| https://pubmed.ncbi.nlm.nih.gov/25048520/	yes [Ki 3.4 uM]
CYP2C19 2141	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes
CYP3A5 201	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25048520/	yes
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32131538/	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22752008/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22752008/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22752008/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22752008/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22752008/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22752008/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25048520/	yes
CYP3A4/5 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25048520/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25048520/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/24035823/

Sourcing

Vendor/Aggregator	ID	URL
AbovChem LLC	HY-19792	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-19792
eMolecules	93428809	https://orderbb.emolecules.com/search/#?query=93428809

PubMed

Title	Date	PubMed
Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules.	2010-10	20937594

Patents

Sample Use Guides

In Vivo Use Guide

Leukemia treatment: Lorvotuzumab mertansine (IMGN901) administered intravenously at a dose of 100 mg/m2 on Day 1 and 8 of a 21-day cycle.

Route of Administration: Intravenous

In Vitro Use Guide

Under the experimental conditions used, the half maximal concentration for inhibition of microtubule assembly for Mertansine (Maytansine) was 1 ± 0.02 umol/L; for S-methyl DM1, 4 ± 0.1 umol/L; and for S-methyl DM4, 1.7 ± 0.4 umol/L. Maytansine showed nearly complete inhibition of microtubule polymerization at 3 umol/L.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:20 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:20 GMT 2025`
Record UNII	DDZ29HGH0E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MERTANSINE

Common Name

English

DM-1

Preferred Name

English

MAYTANSINE, N2'-DEACETYL-N2'-(3-MERCAPTO-1-OXOPROPYL)-

Common Name

English

DM1

Common Name

English

N2'-DEACETYL-N2'-(3-MERCAPTO-1-OXOPROPYL)-MAYTANSINE

Common Name

English

MAYTANSINOID DM1 [MI]

Common Name

English

MAYTANSINOID DM 1

Common Name

English

N2'-DEACETYL-N2'-(3-MERCAPTO-1-OXOPROPYL)-MAYTANSINE, L-

Common Name

English

Code System Code Type Description

SMS_ID

300000053364