NICOTINYL MALEATE

US Previously Marketed

First approved in 1949

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H7NO.C4H4O4
Molecular Weight	225.198
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCC1=CN=CC=C1.OC(=O)\C=C/C(O)=O

InChI

InChIKey=RFZPTICEDBOFHH-BTJKTKAUSA-N

InChI=1S/C6H7NO.C4H4O4/c8-5-6-2-1-3-7-4-6;5-3(6)1-2-4(7)8/h1-4,8H,5H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13383231 | https://www.ncbi.nlm.nih.gov/pubmed/5621227 | https://www.ncbi.nlm.nih.gov/pubmed/5860388

Nicotinyl alcohol is a direct-acting vasolidator, that may decrease the blood pressure and it is a cholesterol-lowering agent. Nicotinyl alcohol as a tartrate salt led to the efficiency improvements in patients with intermittent claudication. In addition, nicotinyl alcohol alone or associated with other drugs was studied in the treatment of radicular syndromes; and was shown, that the effect had not been due to mechanical compression.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intermittent claudication 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13383231	Primary		Not Provided 504	ronicol Approved Use Unknown
Radicular syndromes 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5398437	Primary		Not Provided 504	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	Other AEs: Increased appetite, Skin rash... Other AEs: Increased appetite (15%) Skin rash (36%) Itching (37%) Flushing (68%) Nausea (50%) Abdominal pain (15%) Sources: https://pubmed.ncbi.nlm.nih.gov/222145/

AEs

AE	Significance	Dose	Population
Abdominal pain	15%	600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/
Increased appetite	15%	600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/
Skin rash	36%	600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/
Itching	37%	600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/
Nausea	50%	600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/
Flushing	68%	600 mg 2 times / day steady, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: steady Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/222145/	unhealthy, 30 - 66 years n = 20 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: 30 - 66 years Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/222145/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO22409	https://www.001chemical.com/chem/100-55-0
3B Scientific (Wuhan) Corp	3B3-010708	http://www.3bsc.com/index/pro_info.php?id=33201
AA Blocks	AA00004J	http://www.aablocks.com/goods/Goods/detail?id=AA00004J
AEchem Scientific Corp., USA	AE045319	http://www.aechemsc.com/info_products/AE045319.php
AHH Chemical co.,ltd	MT-22014	http://www.ahhchemical.com/product/MT-22014.html
AK Scientific, Inc. (AKSCI)	71601	http://www.aksci.com/item_detail.php?cat=71601
Aaron Chemicals	AR0000WB	http://www.aaronchem.com/100-55-0
AbMole Bioscience	M5363	http://www.abmole.com/products/3-pyridinemethanol.html
Acadechem	ACDS-028471	http://www.acadechemical.com/product/103170
Accela ChemBio Inc	SY001086	http://www.accelachem.com/cn/search.html?keyword=SY001086&attname=GoodsCode
Achemica	ACMC-1C7ZK	http://www.achemica.com/prodinfo/?id=59873
Achemo Scientific Limited	AC-13420	http://www.achemo.com/search/?Keyword= 100-55-0
Achemtek	0104-017426	http://www.achemtek.com/100-55-0
Acros Organics	AC132005000	https://www.fishersci.com/shop/products/3-hydroxymethyl-pyridine-98-acros-organics-2/AC132005000
Acros Organics	AC132000050	https://www.fishersci.com/shop/products/3-hydroxymethyl-pyridine-98-acros-organics/AC132000050
Acros Organics	AC132001000	https://www.fishersci.com/shop/products/3-hydroxymethyl-pyridine-98-acros-organics/AC132001000
Alfa Aesar	A10381	https://www.alfa.com/en/catalog/A10381/
Alfa Chemistry	744221-34-9	https://www.alfa-chemistry.com/cas_744221-34-9.htm
Alichem	24007806	http://www.alichem.com/en/products/100-55-0.html
Allbio Pharm Co., Ltd	AD12516	http://www.allbiopharm.com/product/n/AD12516
Angene	AGN-PC-07Y4V7	http://www.angenechemical.com/productshow/AGN-PC-07Y4V7.html
Anward	ANW-14316	http://www.anward.com/pro_result/13038
Ark Pharm	AK-46173	http://www.arkpharminc.com/products/100-55-0.html
Aurora Fine Chemicals LLC	A00.156.740	http://online.aurorafinechemicals.com/info?ID=A00.156.740
Aurum Pharmatech LLC	M-6218	http://www.Aurumpharmatech.com/Product/ProductDetails/M_6218
BLD Pharm	BD89112	http://www.bldpharm.com/products/100-55-0.html
BioChemPartner	BCP20084	http://www.biochempartner.com/100-55-0-BCP20084
BioSynth	W-108954	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-108954.html
BioSynth	J-650089	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-650089.html
Boerchem	BC209311	http://www.boerchem.com/?product_35498.html
Capot Chemical	11736	http://www.capotchem.com/en/11736.htm
Capot Chemical	PubChem11736	http://www.capotchem.com/en/11736.htm
Chem Scene	CS-4356	http://www.chemscene.com/100-55-0.html
ChemMol	1202882	http://www.chemmol.com/chemmol/1202882.html
ChemMol	2100215	http://www.chemmol.com/chemmol/2100215.html
ChemMol	30104754	http://www.chemmol.com/chemmol/30104754.html
ChemMol	44003613	http://www.chemmol.com/chemmol/44003613.html
ChemMol	49417869	http://www.chemmol.com/chemmol/49417869.html
ChemReagents	817441	http://www.chemreagents.com/Product/Product.asp?ProductID=817441
Chemenu	CM102582	http://www.chemenu.com/products/CM102582
Chemspace	CSSB00000212025	https://chem-space.com/CSSB00000212025
Clearsynth	CS-T-60967	https://www.clearsynth.com/en/CST60967.html
Debye Scientific	DB-012725	http://www.debyesci.com/cas_100-55-0.html
Finetech	FT-0674210	http://www.finetechnology-ind.com/prod/detail/pub/1189493-62-6.html
Finetech	FT-0674186	http://www.finetechnology-ind.com/prod/detail/pub/258854-74-9.html
FondChemical	FDB-3102	http://www.fondchemical.com/cpshow_cid_8_pid_2376.html
Glentham Life Sciences	GK4076	http://www.glentham.com/products/product/GK4076/
Hairui	ENJL01103	http://www.hairuichem.com/en/product/100-55-0.html
Lab Network	LN00004460	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00004460
MIC Scientific	HC150097	http://www.michemical.com/mkdetail.php?id=614
Matrix Scientific	119313	https://www.matrixscientific.com/119313.html
MedChem Express	HY-B0893	http://www.medchemexpress.com/3-Pyridinemethanol.html
Molcore	CS22409	https://www.molcore.com/product/100-55-0
MuseChem	I000091	https://www.musechem.com/product/I000091.html
Oakwood	208628	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=89627&ExtHyperLink=1
Parchem	32720	http://www.parchem.com/chemical-supplier-distributor/3-Piperidine-methanol-022720.aspx
Parchem	31701	http://www.parchem.com/chemical-supplier-distributor/3-pyridinemethanol-021701.aspx
R&D Chemicals	FS011361	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=579
Renno Tech	RP00469	http://www.rennotech.com/product_show.asp?id=6860
Shanghai Send Pharmaceutical Technology Co., Ltd	send36076	http://shsendpharm.com/
Sigma-Aldrich	P66807_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/p66807?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	43045_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/43045?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	V900526_VETEC	https://www.sigmaaldrich.com/catalog/product/vetec/v900526?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S012814	http://www.sinfoobiotech.com/product/1016212
TCI (Tokyo Chemical Industry)	P0555	http://www.tcichemicals.com/eshop/en/us/commodity/P0555/index.html
THE BioTek	bt-253009	https://www.thebiotek.com/product/inhibitors/bt-253009
Vesino Industrial Co Ltd	VZ27242	http://www.vsnchem.com/goto/product/40219/
VladaChem	VL275315-100G	https://www.vladachem.com/product.php?products=100-55-0
Yuhao Chemical	HL1274	http://www.chemyuhao.com/100-55-0.html
abcr GmbH	AB469464	http://www.abcr.com/shop/en/AB469464
abcr GmbH	AB121175	http://www.abcr.de/shop/en/AB121175
eNovation Chemicals	D383143	http://www.enovationchem.com/productDetails.asp?productID=D383143
eNovation Chemicals	D404346	https://www.enovationchem.com/ProductDetails.asp?ProductID=D404346
eNovation Chemicals	D552480	https://www.enovationchem.com/ProductDetails.asp?ProductID=D552480
iChemical	EBD1837862	http://www.ichemical.com/products/100-55-0.html
mcule	MCULE-4350730997	https://mcule.com/MCULE-4350730997/

PubMed

Title	Date	PubMed
Importance of free fatty acids as a determinant of myocardial oxygen consumption and myocardial ischemic injury during norepinephrine infusion in dogs.	1974 May	4825226
Enzymatic oxidation of NADP+ to its 4-oxo derivative is a side-reaction displayed only by the adrenodoxin reductase type of ferredoxin-NADP+ reductases.	2007 Aug	17635583
Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress.	2009 Mar 16	18845131

Patents

Sample Use Guides

In Vivo Use Guide

25 mg tablet 4 times a daily

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

NICOTINYL MALEATE

Systematic Name

English

Nicotinyl maleate [WHO-DD]

Common Name

English

3-PYRIDINEMETHANOL, (2Z)-2-BUTENEDIOATE (1:1) (SALT)

Systematic Name

English

Code System Code Type Description

FDA UNII

EX8S2926D7