THIOCOLCHICINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H25NO5S
Molecular Weight	415.503
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C(OC)=C2C(CC[C@H](NC(C)=O)C3=CC(=O)C(SC)=CC=C23)=C1

InChI

InChIKey=CMEGANPVAXDBPL-INIZCTEOSA-N

InChI=1S/C22H25NO5S/c1-12(24)23-16-8-6-13-10-18(26-2)21(27-3)22(28-4)20(13)14-7-9-19(29-5)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H25NO5S
Molecular Weight	415.503
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9474240 | https://www.ncbi.nlm.nih.gov/pubmed/2191947
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15588720

Thiocolchicine is a colchicine-derivative used in the therapy of some diseases and extensively studied in the field of oncological research as antimitotic agent. It is tubulin polymerization and microtubule assembly inhibitor and axonal cytoskeleton modulator; apoptosis inducer. Thiocolchicine-dimers were shown to be potent topoisomerase I inhibitors. Thiocolchicine is a potential antitumor agent.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9459025 \| https://www.ncbi.nlm.nih.gov/pubmed/2191947 \| https://www.ncbi.nlm.nih.gov/pubmed/9083485 \| https://www.ncbi.nlm.nih.gov/pubmed/2735908	Inhibitor 8297	0.65 µM [IC50]
DNA topoisomerase I 59 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15588720	Inhibitor 8297	5.2 µM [IC50]
MDA-MB-231 1 Target ID: CHEMBL400 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10602712	Inhibitor 8297	0.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10602712	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Anti-AIDS agents, 3. Inhibitory effects of colchicine derivatives on HIV replication in H9 lymphocyte cells.	1991 Mar-Apr	1919593
Cyclic pifithrin-alpha sensitizes wild type p53 tumor cells to antimicrotubule agent-induced apoptosis.	2008 Jun	18516295

Patents

Sample Use Guides

In Vivo Use Guide

for the treatment of Peyronie's Disease: 2mL injection containing 4mg of thiocolchicine, injected using a 0.3x8mm needle in many punctures into the plaque. Thiocolchicine 4mg or verapamil 5mg were given in 7 injections (once a week)

Route of Administration: Other

In Vitro Use Guide

At concentrations from 1 nM to 100 uM, Thiocolchicine inhibited cancer cell proliferation

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:16:35 GMT 2023` Edited by `admin` on `Sat Dec 16 08:16:35 GMT 2023`
Record UNII	47541468FI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOCOLCHICINE

Common Name

English

THIOCOLCHICINE [MI]

Common Name

English

ACETAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-1,2,3-TRIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-7-YL)-

Systematic Name

English

10-DEMETHOXY-10-(METHYLTHIO)COLCHICINE

Common Name

English

NSC-186301

Code

English

COLCHICINE, 10-THIO-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67421