CYCOTIAMINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H16N4O3S.ClH
Molecular Weight	344.817
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=TWKGUAZLHNQNQW-YGCVIUNWSA-N

InChI=1S/C13H16N4O3S.ClH/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);1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
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 `Mon Mar 31 21:29:30 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:30 GMT 2025`
Record UNII	D91A3111VY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYCOTIAMINE HYDROCHLORIDE

Common Name

English

CYCOTHIAMIN HYDROCHLORIDE

Preferred Name

English

CYCOTHIAMINE HYDROCHLORIDE

Common Name

English

CYCOTIAMINE HYDROCHLORIDE [JAN]

Common Name

English

Cycotiamine hydrochloride [WHO-DD]

Common Name

English

O,S-CYCLOCARBOTHIAMINE HYDROCHLORIDE

Common Name

English

CYCOTHIAMIN HYDROCHLORIDE [MI]

Common Name

English

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

Common Name

English

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

Systematic Name

English

Code System Code Type Description

CAS

19488-19-8