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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

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

Molecular Formula	C10H12N2O
Molecular Weight	176.2151
Charge	0
Count

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

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 2752	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 2752	495.0 µM [EC50]
Neuronal acetylcholine receptor protein alpha-7 subunit 78 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23087643	Agonist 2752	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 33 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 22 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
Systemic nicotine exposure in tobacco harvesters.	2001-08-02	11480503
Osteogenic protein-1 overcomes the inhibitory effect of nicotine on posterolateral lumbar fusion.	2001-08-01	11474350
The effect of tobacco smoke, nicotine, and cotinine on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL).	2001-07-25	11423342
An integrated approach to prenatal smoking cessation interventions.	2001-07-17	11452662
Correlation between nicotine-induced inhibition of hematopoiesis and decreased CD44 expression on bone marrow stromal cells.	2001-07-15	11435297
Prevalence of nicotine consumption in drug deaths.	2001-07-15	11390141
Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus.	2001-07-06	11430869
High-performance liquid chromatographic determination of pyridostigmine bromide, nicotine, and their metabolites in rat plasma and urine.	2001-07	11471991
A simple high-pressure liquid chromatography cotinine assay: validation of smoking status in pregnant women.	2001-07	11471874
Single-dose pharmacokinetics of bupropion in adolescents: effects of smoking status and gender.	2001-07	11452710
Oltipraz chemoprevention trial in Qidong, People's Republic of China: results of urine genotoxicity assays as related to smoking habits.	2001-07	11440963
Saliva cotinine as indicator of cigarette smoking in pregnant women.	2001-07	11440610
Trends in the smoking habits of young adults with diabetes.	2001-07	11423599
Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography.	2001-06-15	11417874
A prospective study of insulin-like growth factor-I, IGF-binding proteins-1, -2 and -3 and lung cancer risk in women.	2001-06-15	11351312
Cost effectiveness of computer tailored and non-tailored smoking cessation letters in general practice: randomised controlled trial.	2001-06-09	11397745
Cluster randomised controlled trial to compare three methods of promoting secondary prevention of coronary heart disease in primary care.	2001-06-02	11387182
Regional cerebral blood flow effects of nicotine in overnight abstinent smokers.	2001-06-01	11377408
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.	2001-06	11434509
Gender differences in autoantibodies to oxidative DNA base damage in cigarette smokers.	2001-06	11401914
Individual differences in urinary cotinine levels in Japanese smokers: relation to genetic polymorphism of drug-metabolizing enzymes.	2001-06	11401907
Biomarkers of polycyclic aromatic hydrocarbon-DNA damage and cigarette smoke exposures in paired maternal and newborn blood samples as a measure of differential susceptibility.	2001-06	11401906
Dose-years as an improved index of cumulative tobacco smoke exposure.	2001-06	11399126
Heavily smoking women who cannot quit in pregnancy: evidence of pharmacokinetic predisposition.	2001-06	11360023
CYP1B1 expression in human lung.	2001-06	11353763
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.	2001-06	11353760
Effect of cigarette smoking on levels of bioavailable testosterone in healthy men.	2001-06	11352783
Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures.	2001-05-31	11377240
Measures of maternal tobacco exposure and infant birth weight at term.	2001-05-15	11384951
Drop in cotinine levels signals less smoke exposure, experts say.	2001-05-02	11333281
Cotinine binding to nicotinic acetylcholine receptors in bovine chromaffin cell and rat brain membranes.	2001-05	11403732
CDC unveils body burden.	2001-05	11401773
Lung cancer due to passive smoking--a review.	2001-05	11401014
Household smoking and bronchial hyperresponsiveness in children with asthma.	2001-05	11392364
Effects of smoking cessation and nicotine substitution on systemic eicosanoid production in man.	2001-05	11383717
Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines.	2001-05	11368554
Science is changing! 300 chemicals and each chemical will have a fingerprint.	2001-05	11368053
Metropolitan home living conditions associated with indoor endotoxin levels.	2001-05	11344344
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.	2001-04-25	11339282
[Prevalence of cannabis and tobacco use in patients attending a methadone center. Evaluation by urinary biomarkers].	2001-04	11435993
Determination of coumarin metabolism in Turkish population.	2001-04	11393269
Accuracy of self-reported cigarette smoking among pregnant women in the 1990s.	2001-04	11383579
Infant exposure to environmental tobacco smoke: a prevalence study in Australia.	2001-04	11357908
Rebuttal to: Passive smoking adversely affects the haemostasis/fibrinolytic parameters in healthy non-smoker offspring of healthy smokers.	2001-04	11341523
Effectiveness of a high school smoking cessation program.	2001-04	11335771
Smoking reduction in smokers compliant to a smoking cessation trial with nicotine patch.	2001-02	11407211
Assessment of prenatal smoke exposure by determining nicotine and its metabolites in maternal and neonatal urine.	2001-01	11339618
Urine test for the assessment of smoking status.	2001	11440208
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.	2001	11339881
Personal exposures to PM(2.5) and polycyclic aromatic hydrocarbons and their relationship to environmental tobacco smoke at two locations in Greece.	2000-08-14	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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:04 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:04 GMT 2025`
Record UNII	6ZAF060BHS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COTININE FUMARATE [MI]

Preferred Name

English

COTININE FUMARATE

Official 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