5-fluoromethylornithine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5-fluoromethylornithine : An ornithine derivative in which one of the hydrogens at position 5 is replaced by a fluoromethyl group. It is an irreversible inhibitor of ornithine aminotransferase. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID Source	ID
PubMed CID	119351
CHEBI ID	195324
SCHEMBL ID	2940605
MeSH ID	M0160669

Synonyms (14)

Synonym
5-fluoromethylornithine
5-fmorn
2,5-diamino-6-fluorohexanoic acid
5fmorn
CHEBI:195324
116292-10-5
5-amino-6-fluoronorleucine
norleucine, 5-amino-6-fluoro-
SCHEMBL2940605
6-fluoro-2,5-diaminohexanoic acid
DTXSID60921989
norleucine,5-amino-6-fluoro-(9ci)
EN300-191171
2,5-diamino-6-fluorohexanoicacid

Research Excerpts

Dosage Studied

Excerpt	Relevance	Reference
" It is, however, obvious that both in rats and mice the severity of symptoms depends not only on dose and dosing schedule of TAA, but also on strain and body weight (age)."	( Effects of inhibition of ornithine aminotransferase on thioacetamide-induced hepatogenic encephalopathy. Grauffel, C; Knödgen, B; Sarhan, S; Seiler, N, 1993)	0.29

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

Role	Description
EC 2.6.1.13 (ornithine aminotransferase) inhibitor	An EC 2.6.1.* (transaminase) inhibitor that interferes with the action of ornithine aminotransferase (EC 2.6.1.13).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

Class	Description
ornithine derivative	A non-proteinogenic amino acid derivative resulting from reaction of ornithine at the amino group, the carboxy group, or the side-chain amino group, or from the replacement of any hydrogen of ornithine by a heteroatom. The definition normally excludes peptides containing ornithine residues.
organofluorine compound	An organofluorine compound is a compound containing at least one carbon-fluorine bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (22)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (9.09)	18.7374
1990's	14 (63.64)	18.2507
2000's	4 (18.18)	29.6817
2010's	2 (9.09)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	17.27 (24.57)
Research Supply Index	3.14 (2.92)
Research Growth Index	5.22 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (17.27)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (4.55%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	21 (95.45%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.38	2	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	4.47	7	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
carnitine [no description available]	1.98	1	amino-acid betaine	human metabolite; mouse metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	1.98	1	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
putrescine [no description available]	3.08	5	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
spermidine [no description available]	2.41	2	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	2.41	2	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	3.78	3	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2.4	2	alpha-amino acid; fluoroamino acid	trypanocidal drug
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	2.38	2	organic heterobicyclic compound; organonitrogen heterocyclic compound
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	5.53	22	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.4	2	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	1.98	1	mercaptopropanoic acid	algal metabolite
thiazoles [no description available]	2.44	2	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.39	2	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.98	1	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	1.98	1	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	2	1	ammonium salt; inorganic chloride	ferroptosis inhibitor
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.43	2	benzenes; phenyl acetates
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.44	2	organic bromide salt	colorimetric reagent; dye
2-aminobicyclo(2,2,1)heptane-2-carboxylic acid 2-aminobicyclo(2,2,1)heptane-2-carboxylic acid: amino acid analog; releases insulin; RN given refers to unlabeled cpd without isomeric designation	2.01	1	monoterpenoid
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.4	2	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
carnosine polaprezinc: stimulates bone growth	1.98	1	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	1.98	1	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
canaline canaline: structure	6.97	1	amino acid zwitterion; non-proteinogenic L-alpha-amino acid	antimetabolite; antineoplastic agent; phytogenic insecticide; plant metabolite
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.43	2	acetate salt; ammonium salt	buffer; food acidity regulator
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	1.99	1	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	8.78	3	thiocarboxamide	hepatotoxic agent
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	1.98	1	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist

Condition	Relationship Strength	Studies
Hyperammonemia Elevated level of AMMONIA in the blood. It is a sign of defective CATABOLISM of AMINO ACIDS or ammonia to UREA.	3.37	2
Gyrate Atrophy Progressive, autosomal recessive, diffuse atrophy of the choroid, pigment epithelium, and sensory retina that begins in childhood.	2.92	4
Inborn Errors of Metabolism [description not available]	1.98	1
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	1.98	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	1.98	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.38	2
Coma A profound state of unconsciousness associated with depressed cerebral activity from which the individual cannot be aroused. Coma generally occurs when there is dysfunction or injury involving both cerebral hemispheres or the brain stem RETICULAR FORMATION.	1.98	1
Convulsive Generalized Seizure Disorder [description not available]	1.98	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	1.98	1
Absence Seizure [description not available]	1.98	1
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	1.98	1
Encephalopathy, Hepatic [description not available]	1.98	1
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	1.98	1
Hepatocellular Carcinoma [description not available]	1.99	1
Cancer of Liver [description not available]	1.99	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.99	1
Liver Neoplasms Tumors or cancer of the LIVER.	1.99	1
Deficiency Disease, Ornithine Carbamoyltransferase [description not available]	2	1
Amino Acid Metabolism Disorders, Inborn [description not available]	2	1
Ornithine Carbamoyltransferase Deficiency Disease An inherited urea cycle disorder associated with deficiency of the enzyme ORNITHINE CARBAMOYLTRANSFERASE, transmitted as an X-linked trait and featuring elevations of amino acids and ammonia in the serum. Clinical features, which are more prominent in males, include seizures, behavioral alterations, episodic vomiting, lethargy, and coma. (Menkes, Textbook of Child Neurology, 5th ed, pp49-50)	2	1
Chorioretinitis Inflammation of the choroid in which the sensory retina becomes edematous and opaque. The inflammatory cells and exudate may burst through the sensory retina to cloud the vitreous body.	2.92	1
Acute Liver Injury, Drug-Induced [description not available]	1.98	1
Bleeding [description not available]	1.98	1
Liver Dysfunction [description not available]	1.98	1
Hemorrhage Bleeding or escape of blood from a vessel.	1.98	1
Liver Diseases Pathological processes of the LIVER.	1.98	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	1.98	1
EHS Tumor [description not available]	1.97	1

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