INCYCLINIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H17NO7
Molecular Weight	371.3408
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=C(O)C[C@@H]2C[C@@H]3CC4=C(C(O)=CC=C4)C(=O)C3=C(O)[C@]2(O)C1=O

InChI

InChIKey=ZXFCRFYULUUSDW-OWXODZSWSA-N

InChI=1S/C19H17NO7/c20-18(26)14-11(22)6-9-5-8-4-7-2-1-3-10(21)12(7)15(23)13(8)16(24)19(9,27)17(14)25/h1-3,8-9,21-22,24,27H,4-6H2,(H2,20,26)/t8-,9-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H17NO7
Molecular Weight	371.3408
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23469077 | https://www.ncbi.nlm.nih.gov/pubmed/16152604 | https://www.ncbi.nlm.nih.gov/pubmed/25502932 | https://clinicaltrials.gov/ct2/show/NCT00020683 | https://clinicaltrials.gov/ct2/show/NCT00001683

Iincyclinide, also known as CMT-3 and COL-3, is an MMP inhibitor and a chemically-modified tetracycline with potential antineoplastic activity patented by Chas. Pfizer & Co. Incyclinide has been shown to experimentally suppress prostate cancer, colon adenocarcinoma and melanoma invasiveness in cell culture. Incyclinide is an especially effective inhibitor of the growth and viability of filamentous fungi. Unfortunately, in clinical trials, Iincyclinide failed to demonstrate efficacy in Lymphoma, Melanoma, Renal Cell Carcinoma, and some other tumors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Matrix metalloproteinase 14 6 Target ID: CHEMBL3869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11172680	Inhibitor 8504
Matrix metalloproteinase 9 20 Target ID: CHEMBL321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16242193	Inhibitor 8504

PubMed

Title	Date	PubMed
Chemically modified tetracyclines induce apoptosis in cultured mast cells.	2005-10	16039551
Chemically modified tetracycline (CMT)-3 inhibits histamine release and cytokine production in mast cells: possible involvement of protein kinase C.	2005-07	16134060
Effect of chemically modified tetracycline on transforming growth factor-beta1 and caspase-3 activation in liver of septic rats.	2005-07	16003065
Cyclooxygenase-2 inhibitor celecoxib augments chemotherapeutic drug-induced apoptosis by enhancing activation of caspase-3 and -9 in prostate cancer cells.	2005-06-20	15688368
Role of chemically modified tetracycline on TNF-alpha and mitogen-activated protein kinases in sepsis.	2004-11	15489642
A nonantibiotic chemically modified tetracycline (CMT-3) inhibits intimal thickening.	2003-10	14507662
Inhibition of cell proliferation, invasion, tumor growth and metastasis by an oral non-antimicrobial tetracycline analog (COL-3) in a metastatic prostate cancer model.	2002-03-10	11857423
Reversible sideroblastic anemia associated with the tetracycline analogue COL-3.	2001-05	11279658
Cytotoxic activity and inhibition of tumor cell invasion by derivatives of a chemically modified tetracycline CMT-3 (COL-3).	2001-02	11172682
CMT-3, a non-antimicrobial tetracycline (TC), inhibits MT1-MMP activity: relevance to cancer.	2001-02	11172680

Patents

Sample Use Guides

In Vivo Use Guide

50 mg/day and 100 mg/day

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:22:52 GMT 2025` Edited by `admin` on `Mon Mar 31 21:22:52 GMT 2025`
Record UNII	21G64WZQ4I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INCYCLINIDE

Official Name

English

(4aS,5aR,12aS)-3,10,12,12a-Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Preferred Name

English

NSC-683551

Code

English

METASTAT

Brand Name

English

2-NAPHTHACENECARBOXAMIDE, 1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-, (4AS,5AR,12AS)-

Common Name

English

INCYCLINIDE [USAN]

Common Name

English

incyclinide [INN]

Common Name

English

COL-3

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1970