CYCOTIAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H16N4O3S
Molecular Weight	308.356
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(N(CC1=C(N)N=C(C)N=C1)C=O)=C2CCOC(=O)S2

InChI

InChIKey=LLJDJQYGZBQFIF-DHZHZOJOSA-N

InChI=1S/C13H16N4O3S/c1-8(11-3-4-20-13(19)21-11)17(7-18)6-10-5-15-9(2)16-12(10)14/h5,7H,3-4,6H2,1-2H3,(H2,14,15,16)/b11-8+

HIDE SMILES / InChI

Molecular Formula	C13H16N4O3S
Molecular Weight	308.356
Charge	0
Count

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

Description
Sources: http://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/119923/1/14_0767.pdf
Curator's Comment: description was created based on several sources, including, http://www.drugfuture.com/mt/thiamine-nitrate.pdf

Cycotiamine is a derivative of tiamine that was developed in Japan and used for the treatment of neurogenic bladder.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Neurogenic bladder 6 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5751425	Palliative		Approved 8583	COMETAMIN Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671197#sid=170465848	inconclusive [IC50 43.6486 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=170465848	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170465848	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671196#sid=170465848	yes [IC50 13.8029 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671201#sid=170465848	yes [IC50 15.4871 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671200#sid=170465848

PubMed

Title	Date	PubMed
[Clinical effects of cycothiamine (Cometamin) on neurogenic bladder: cystometric study].	1968-10	5751425

Patents

Sample Use Guides

In Vivo Use Guide

900 to 3,700 mg given by intravenous administration.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:26:08 GMT 2025` Edited by `admin` on `Wed Apr 02 08:26:08 GMT 2025`
Record UNII	FT8753F8R9
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CYCOTIAMINE

Official Name

English

CYCOTHIAMIN(E)

Preferred Name

English

N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-N-(1-(2-OXO-1,3-OXATHIAN-4-YLIDENE)ETHYL)FORMAMIDE

Systematic Name

English

CYCOTIAMINE [MART.]

Common Name

English

cycotiamine [INN]

Common Name

English

COMMETAMIN

Brand Name

English

CYCLOCARBOTHIAMINE

Common Name

English

Cycotiamine [WHO-DD]

Common Name

English

CYCOTIAMINE [JAN]

Common Name

English

CYCOTHIAMIN(E) [MI]

Common Name

English

CARBOTHIAMINE

Common Name

English

COMETAMINE

Brand Name

English

N-(1-(2-OXO-1,3-OXATHIAN-4-YLIDENE)ETHYL)-N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45812