COTININE FUMARATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C10H12N2O.C4H4O4
Molecular Weight	468.5023
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CN1[C@@H](CCC1=O)C2=CN=CC=C2.CN3[C@@H](CCC3=O)C4=CN=CC=C4

InChI

InChIKey=NXHGVNVRWLOZDF-SZYUIZJOSA-N

InChI=1S/2C10H12N2O.C4H4O4/c2*1-12-9(4-5-10(12)13)8-3-2-6-11-7-8;5-3(6)1-2-4(7)8/h2*2-3,6-7,9H,4-5H2,1H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*9-;/m00./s1

HIDE SMILES / InChI

Description
Sources: https://www.cdc.gov/biomonitoring/pdf/Cotinine_FactSheet.pdf
Curator's Comment: description was created based on several sources, including: https://cancercontrol.cancer.gov/brp/tcrb/monographs/7/m7_7.pdf | https://www.ncbi.nlm.nih.gov/pubmed/26972290

Cotinine is a product formed after the chemical nicotine enters the body. Measuring cotinine in people’s blood is the most reliable way to determine exposure to nicotine for both smokers and nonsmokers exposed to environmental tobacco smoke. Cotinine is safe, non-addictive and has pharmacokinetic properties adequate for therapeutic use. Research has shown that cotinine has antipsychotic, anxiolytic, and antidepressant properties and modulates the serotonergic, cholinergic and dopaminergic systems. Cotinine behaves as a positive allosteric modulator of the nicotinic acetylcholine receptors and has anti-inflammatory effects. Cotinine is under investigation as an agent for the treatment of depression, PTSD, schizophrenia, Alzheimer's disease and Parkinson's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nicotinic acetylcholine receptors alpha3/alpha6/beta2 (Saimiri sciureus) 3 Target ID: Nicotinic acetylcholine receptors alpha3/alpha6/beta2 (Saimiri sciureus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18305015	Agonist 2678	236.0 µM [EC50]
Nicotinic acetylcholine receptors alpha4/beta2 (Saimiri sciureus) 3 Target ID: Nicotinic acetylcholine receptors alpha4/beta2 (Saimiri sciureus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18305015	Agonist 2678	495.0 µM [EC50]
Neuronal acetylcholine receptor protein alpha-7 subunit 77 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23087643	Agonist 2678	175.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Chronic stress 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24713149	Palliative	Preclinical	Unknown Approved Use Unknown
Nicotine dependence 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/998055 https://www.ncbi.nlm.nih.gov/pubmed/832462 https://www.ncbi.nlm.nih.gov/pubmed/1780420 https://cancercontrol.cancer.gov/brp/tcrb/monographs/7/m7_7.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Post-traumatic stress disorder 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22137886 https://www.ncbi.nlm.nih.gov/pubmed/26166610	Palliative	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.	2001	11339881
[Prevalence of cannabis and tobacco use in patients attending a methadone center. Evaluation by urinary biomarkers].	2001 Apr	11435993
Accuracy of self-reported cigarette smoking among pregnant women in the 1990s.	2001 Apr	11383579
Infant exposure to environmental tobacco smoke: a prevalence study in Australia.	2001 Apr	11357908
Rebuttal to: Passive smoking adversely affects the haemostasis/fibrinolytic parameters in healthy non-smoker offspring of healthy smokers.	2001 Apr	11341523
Effectiveness of a high school smoking cessation program.	2001 Apr	11335771
Smoking status, reading level, and knowledge of tobacco effects among low-income pregnant women.	2001 Apr	11304092
Novel liquid chromatographic-tandem mass spectrometric methods using silica columns and aqueous-organic mobile phases for quantitative analysis of polar ionic analytes in biological fluids.	2001 Apr 25	11339282
Two behavioral treatments for smoking reduction: a pilot study.	2001 Feb	11260813
Determinants of environmental tobacco smoke in a population of Puerto Rican children.	2001 Feb	11260812
Postpartum smoking behaviors and immune response in mothers of term and preterm infants.	2001 Feb	11260581
Association of smoking with serum and dietary levels of antioxidants in adults: NHANES III, 1988-1994.	2001 Feb	11211635
[Smoking in adolescents, saliva cotinine concentrations and respiratory disease].	2001 Feb	11181206
Application of planar chromatography to the determination of cotinine in urine of active and passive smoking pregnant women.	2001 Feb	11180301
Assessment of prenatal smoke exposure by determining nicotine and its metabolites in maternal and neonatal urine.	2001 Jan	11339618
Tobacco hypersensitivity and environmental tobacco smoke exposure in a pediatric population.	2001 Jan	11206241
Evaluation of the effect of passive smoking on otitis media in children by an objective method: urinary cotinine analysis.	2001 Jan	11192887
Pharmacokinetics of nicotine in healthy elderly people.	2001 Jan	11180039
Nicotine yield from machine-smoked cigarettes and nicotine intakes in smokers: evidence from a representative population survey.	2001 Jan 17	11208883
High-performance liquid chromatographic determination of pyridostigmine bromide, nicotine, and their metabolites in rat plasma and urine.	2001 Jul	11471991
Trends in the smoking habits of young adults with diabetes.	2001 Jul	11423599
Prevalence of nicotine consumption in drug deaths.	2001 Jul 15	11390141
The effect of tobacco smoke, nicotine, and cotinine on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL).	2001 Jul 25	11423342
Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus.	2001 Jul 6	11430869
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.	2001 Jun	11434509
Gender differences in autoantibodies to oxidative DNA base damage in cigarette smokers.	2001 Jun	11401914
Biomarkers of polycyclic aromatic hydrocarbon-DNA damage and cigarette smoke exposures in paired maternal and newborn blood samples as a measure of differential susceptibility.	2001 Jun	11401906
Dose-years as an improved index of cumulative tobacco smoke exposure.	2001 Jun	11399126
Heavily smoking women who cannot quit in pregnancy: evidence of pharmacokinetic predisposition.	2001 Jun	11360023
CYP1B1 expression in human lung.	2001 Jun	11353763
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.	2001 Jun	11353760
Effect of cigarette smoking on levels of bioavailable testosterone in healthy men.	2001 Jun	11352783
Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography.	2001 Jun 15	11417874
Cluster randomised controlled trial to compare three methods of promoting secondary prevention of coronary heart disease in primary care.	2001 Jun 2	11387182
Cost effectiveness of computer tailored and non-tailored smoking cessation letters in general practice: randomised controlled trial.	2001 Jun 9	11397745
Nicotine metabolism and CYP2D6 phenotype in smokers.	2001 Mar	11303596
Nicotine and cotinine adducts of a melanin intermediate demonstrated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001 Mar	11258976
Exposure to cold and draught, alcohol consumption, and the NS-phenotype are associated with chronic bronchitis: an epidemiological investigation of 3387 men aged 53-75 years: the Copenhagen Male Study.	2001 Mar	11171928
Red wine polyphenols, in the absence of alcohol, reduce lipid peroxidative stress in smoking subjects.	2001 Mar 15	11295361
Cotinine binding to nicotinic acetylcholine receptors in bovine chromaffin cell and rat brain membranes.	2001 May	11403732
CDC unveils body burden.	2001 May	11401773
Effects of smoking cessation and nicotine substitution on systemic eicosanoid production in man.	2001 May	11383717
Metropolitan home living conditions associated with indoor endotoxin levels.	2001 May	11344344
Adaptation of an enzyme immunoassay to assess urinary cotinine in nonsmokers exposed to tobacco smoke.	2001 May	11325906
Accumulation of nicotine and its metabolites in rat brain after intermittent or continuous peripheral administration of [2'-(14)C]nicotine.	2001 May	11302929
Measures of maternal tobacco exposure and infant birth weight at term.	2001 May 15	11384951
Drop in cotinine levels signals less smoke exposure, experts say.	2001 May 2	11333281
In vitro effects of nicotine on mitochondrial respiration and superoxide anion generation.	2001 May 4	11325348
Systemic nicotine exposure in tobacco harvesters.	2001 May-Jun	11480503
Personal exposures to PM(2.5) and polycyclic aromatic hydrocarbons and their relationship to environmental tobacco smoke at two locations in Greece.	2001 May-Jun	11477515

Patents

Sample Use Guides

In Vivo Use Guide

Mouse: 5 mg/kg during 37 days

Route of Administration: Oral

In Vitro Use Guide

High (190 ug/ml) concentration of Cotinine significantly altered all the sperm kinetic variables in relation to the time of incubation (forward motility, velocity, linearity and beat cross-frequency). Despite the impact seen on these parameters, there was still 30% forward motility after 24 h of incubation.

Name

Type

Language

COTININE FUMARATE

Official Name

English

COTININE FUMARATE [MI]

Common Name

English

COTININE FUMARATE [USAN]

Common Name

English

1-METHYL-5-(3-PYRIDINYL)-2-PYRROLIDINONE FUMARATE

Systematic Name

English

N-METHYL-2-(3-PYRIDYL)-5-PYRROLIDONE FUMARATE

Systematic Name

English

(-)-1-METHYL-5-(3-PYRIDYL)-2-PYRROLIDINONE FUMARATE (2:1)

Systematic Name

English

2-PYRROLIDINONE, 1-METHYL-5-(3-PYRIDINYL)-, (S)-, (E)-2-BUTENEDIOATE (2:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73579