CHEBI:4670 - dobutamine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name dobutamine
ChEBI ID CHEBI:4670
Definition A catecholamine that is 4-(3-aminobutyl)phenol in which one of the hydrogens attached to the nitrogen is substituted by a 2-(3,4-dihydroxyphenyl)ethyl group. A β1-adrenergic receptor agonist that has cardiac stimulant action without evoking vasoconstriction or tachycardia, it is used as the hydrochloride to increase the contractility of the heart in the management of acute heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:184505, CHEBI:554519
Supplier Information ChemicalBook:CB2684343, eMolecules:509516, ZINC000000085378
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Folate, also known as vitamin B9 and folacin, is one of the B vitamins. Manufactured folic acid, which is converted into folate by the body, is used as a dietary supplement and in food fortification as it is more stable during processing and storage. Folate is required for the body to make DNA and RNA and metabolise amino acids necessary for cell division and maturation of blood cells. As the human body cannot make folate, it is required in the diet, making it an essential nutrient. It occurs naturally in many foods. The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements. Folate in the form of folic acid is used to treat anemia caused by folate deficiency. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby. NTDs include anencephaly and spina bifida, among other defects. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs. More than 80 countries use either mandatory or voluntary fortification of certain foods with folic acid as a measure to decrease the rate of NTDs. Long-term supplementation with relatively large amounts of folic acid is associated with a small reduction in the risk of stroke and an increased risk of prostate cancer. There are concerns that large amounts of supplemental folic acid can hide vitamin B12 deficiency. Not consuming enough folate can lead to folate deficiency. This may result in a type of anemia in which red blood cells become abnormally large. Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair. Folate deficiency in children may develop within a month of poor dietary intake. In adults, normal total body folate is between 10 and 30 mg with about half of this amount stored in the liver and the remainder in blood and body tissues. In plasma, the natural folate range is 150 to 450 nM. Folate was discovered between 1931 and 1943. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 65th most commonly prescribed medication in the United States, with more than 10 million prescriptions. The term "folic" is from the Latin word folium (which means leaf) because it was found in dark-green leafy vegetables.
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Formula C18H23NO3
Net Charge 0
Average Mass 301.38010
Monoisotopic Mass 301.16779
InChI InChI=1S/C18H23NO3/c1-13(2-3-14-4-7-16(20)8-5-14)19-11-10-15-6-9-17(21)18(22)12-15/h4-9,12-13,19-22H,2-3,10-11H2,1H3
InChIKey JRWZLRBJNMZMFE-UHFFFAOYSA-N
SMILES CC(CCc1ccc(O)cc1)NCCc1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
beta-adrenergic agonist
An agent that selectively binds to and activates beta-adrenergic receptors.
molecular messenger

(via monoamine molecular messenger )
Application(s): cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
beta-adrenergic agonist
An agent that selectively binds to and activates beta-adrenergic receptors.
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ChEBI Ontology
Outgoing dobutamine (CHEBI:4670) has role β-adrenergic agonist (CHEBI:35522)
dobutamine (CHEBI:4670) has role cardiotonic drug (CHEBI:38147)
dobutamine (CHEBI:4670) has role sympathomimetic agent (CHEBI:35524)
dobutamine (CHEBI:4670) is a catecholamine (CHEBI:33567)
dobutamine (CHEBI:4670) is a secondary amine (CHEBI:32863)
Incoming dobutamine hydrochloride (CHEBI:4671) has part dobutamine (CHEBI:4670)
(R)-dobutamine (CHEBI:59804) is a dobutamine (CHEBI:4670)
(S)-dobutamine (CHEBI:59805) is a dobutamine (CHEBI:4670)
IUPAC Name
4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
INNs Sources
dobutamina ChemIDplus
dobutamine WHO MedNet
dobutamine ChemIDplus
dobutaminum ChemIDplus
Synonyms Sources
(±)-4-(2-((3-(p-hydroxyphenyl)-1-methylpropyl)amino)ethyl)pyrocatechol ChemIDplus
3,4-dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-β-phenylethylamine ChEBI
4-{2-[3-(4-Hydroxy-phenyl)-1-methyl-propylamino]-ethyl}-benzene-1,2-diol ChEMBL
DL-dobutamine ChEBI
DOBUTAMINE ChEMBL
Dobutamine KEGG COMPOUND
rac-dobutamine ChEBI
racemic-dobutamine ChemIDplus
Manual Xrefs Databases
937 DrugCentral
C06967 KEGG COMPOUND
D03879 KEGG DRUG
DB00841 DrugBank
DE2317710 Patent
Dobutamine Wikipedia
HMDB0014979 HMDB
LSM-1807 LINCS
US3987200 Patent
View more database links
Registry Numbers Types Sources
2946389 Reaxys Registry Number Reaxys
34368-04-2 CAS Registry Number KEGG COMPOUND
34368-04-2 CAS Registry Number ChemIDplus
Citations Types Sources
11280019 PubMed citation Europe PMC
11950781 PubMed citation Europe PMC
18323735 PubMed citation Europe PMC
22537238 PubMed citation Europe PMC
Last Modified
22 February 2017